Journal articles: 'Quinoxaline'

1

Soleymani, Mousa, and Mahdieh Chegeni. "The Chemistry and Applications of the Quinoxaline Compounds." Current Organic Chemistry 23, no. 17 (November 2, 2019): 1789–827. http://dx.doi.org/10.2174/1385272823666190926094348.

Full text

Abstract:

The quinoxaline derivatives are beneficial compounds because of their various medicinal and industrial applications. They are well-known for application in organic light emitting devices, polymers and pharmaceutical agents. The quinoxaline-containing polymers are applicable in optical devices due to their thermal stability and low band gap. There are many reported procedures for the synthesis of bis- and polyquinoxalines and quinoxaline-containing macrocycles. The quinoxaline-based compounds as fascinating structures are important subjects of interest in either basic or applied sciences. This review summarizes the latest progresses related to the quinoxalines, quinoxaline-containing macrocycles, and bis- and poly quinoxalines, including the synthesis, functionalization and modification methods and applications of these compounds.

APA, Harvard, Vancouver, ISO, and other styles

2

El-Sawy, Eslam, Fatma Bassyouni, Sherifa Abu-Bakr, Hanaa Rady, and Mohamed Abdlla. "Synthesis and biological activity of some new 1-benzyl and 1-benzoyl-3-heterocyclic indole derivatives." Acta Pharmaceutica 60, no. 1 (March 1, 2010): 55–71. http://dx.doi.org/10.2478/v10007-010-0004-0.

Full text

Abstract:

Synthesis and biological activity of some new 1-benzyl and 1-benzoyl-3-heterocyclic indole derivativesStarting from 1-benzyl- (2a) and 1-benzoyl-3-bromoacetyl indoles (2b) new heterocyclic, 2-thioxoimidazolidine (4a, b), imidazolidine-2,4-dione (5a, b), pyrano(2,3-d)imida-zole (8a, band9a, b), 2-substituted quinoxaline (11a, b-17a, b) and triazolo(4,3-a)quinoxaline derivatives (18a, band19a, b) were synthesized and evaluated for their antimicrobial and anticancer activities. Antimicrobial activity screening performed with concentrations of 0.88, 0.44 and 0.22 μg mm-2showed that 3-(1-substituted indol-3-yl)quinoxalin-2(1H)ones (11a, b) and 2-(4-methyl piperazin-1-yl)-3-(1-substituted indol-3-yl) quinoxalines (15a, b) were the most active of all the tested compounds towardsP. aeruginosa, B. cereusandS. aureuscompared to the reference drugs cefotaxime and piperacillin, while 2-chloro-3-(1-substituted indol-3-yl)quinoxalines (12a, b) were the most active against C.albicanscompared to the reference drug nystatin. On the other hand, 2-chloro-3-(1-benzyl indol-3-yl) quinoxaline12adisplay potent efficacy against ovarian cancer xenografts in nude mice with tumor growth suppression of 100.0 ± 0.3 %.

APA, Harvard, Vancouver, ISO, and other styles

3

Wu, Degui, Jian Zhang, Jianhai Cui, Wei Zhang, and Yunkui Liu. "AgNO2-mediated direct nitration of the quinoxaline tertiary benzylic C–H bond and direct conversion of 2-methyl quinoxalines into related nitriles." Chem. Commun. 50, no. 74 (2014): 10857–60. http://dx.doi.org/10.1039/c4cc01327a.

Full text

Abstract:

A unique method for AgNO₂-mediated direct nitration of the quinoxaline tertiary C–H bond and direct conversion of 2-methyl quinoxalines into 2-quinoxaline nitriles under oxidative conditions has been developed.

APA, Harvard, Vancouver, ISO, and other styles

4

Kasatkina, Svetlana O., Ekaterina E. Stepanova, Maksim V. Dmitriev, Ivan G. Mokrushin, and Andrey N. Maslivets. "Synthesis of pyrimido[1,6-a]quinoxalines via intermolecular trapping of thermally generated acyl(quinoxalin-2-yl)ketenes by Schiff bases." Beilstein Journal of Organic Chemistry 14 (July 11, 2018): 1734–42. http://dx.doi.org/10.3762/bjoc.14.147.

Full text

Abstract:

Acyl(quinoxalin-2-yl)ketenes generated by thermal decarbonylation of 3-acylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones react regioselectively with Schiff bases under solvent-free conditions to form pyrimido[1,6-a]quinoxaline derivatives in good yields.

APA, Harvard, Vancouver, ISO, and other styles

5

Chaouiki, Abdelkarim, Maryam Chafiq, Mohamed Rbaa, Hassane Lgaz, Rachid Salghi, Brahim Lakhrissi, Ismat H. Ali, Sheerin Masroor, and Youngjae Cho. "New 8-Hydroxyquinoline-Bearing Quinoxaline Derivatives as Effective Corrosion Inhibitors for Mild Steel in HCl: Electrochemical and Computational Investigations." Coatings 10, no. 9 (August 21, 2020): 811. http://dx.doi.org/10.3390/coatings10090811.

Full text

Abstract:

There has been substantial research undertaken on the role of green synthesized corrosion inhibitors as a substantial approach to inhibit the corrosion of metals and their alloys in acidic environments. Herein, electrochemical studies, surface characterization, and theoretical modeling were adopted to investigate the corrosion inhibition proprieties of novel synthesized quinoxaline derivatives bearing 8-Hydroxyquinoline, namely 1-((8-hydroxyquinolin-5-yl) methyl)-3,6-dimethylquinoxalin-2(1H)-one (Q1) and 1-((8-hydroxyquinolin-5-yl)methyl) quinoxalin-2(1H)-one (Q2) on mild steel corrosion in 1 mol/L HCl solution. The principal finding of this research was that both inhibitors acted as good corrosion inhibitors with Q1 having the highest performance (96% at 5 × 10−3 mol/L). Electrochemical results obtained via potentiodynamic polarization (PDP) and electrochemical impedance spectroscopy (EIS) techniques demonstrated that quinoxaline compounds belonged to mixed-type inhibitors; their presence significantly increased the polarization resistance, preventing simultaneously anodic and cathodic reactions. Further, experimental results provided preliminary insights about the interactions mode between studied molecules and the mild steel surface, which followed the Langmuir adsorption model, and physical and chemical interactions assisted their inhibition mechanism. Besides, SEM analyses confirmed the existence of protective film on the metal surface after the addition of 5 × 10−3 mol/L of quinoxalines. In addition, the temperature and immersion time effects on inhibition performances of quinoxalines were investigated to evaluate their performances in different operating conditions. Besides, Density Functional Theory (DFT) and molecular dynamics (MD) simulations were carried out to explore the most reactive sites of quinoxaline inhibitors and their interaction mechanism. Theoretical results revealed that the inhibitor molecule with additional electron-donating functional group strongly interacted with the steel surface.

APA, Harvard, Vancouver, ISO, and other styles

6

Ruiz, Diego M., Juan C. Autino, Nancy Quaranta, Patricia G. Vázquez, and Gustavo P. Romanelli. "An Efficient Protocol for the Synthesis of Quinoxaline Derivatives at Room Temperature Using Recyclable Alumina-Supported Heteropolyoxometalates." Scientific World Journal 2012 (2012): 1–8. http://dx.doi.org/10.1100/2012/174784.

Full text

Abstract:

We report a suitable quinoxaline synthesis using molybdophosphovanadates supported on commercial alumina cylinders as catalysts. These catalysts were prepared by incipient wetness impregnation. The catalytic test was performed under different reaction conditions in order to know the performance of the synthesized catalysts. The method shows high yields of quinoxaline derivatives under heterogeneous conditions. Quinoxaline formation was obtained using benzyl,o-phenylenediamine, and toluene as reaction solvent at room temperature. The CuH2PMo11VO40supported on alumina showed higher activity in the tested reaction. Finally, various quinoxalines were prepared under mild conditions and with excellent yields.

APA, Harvard, Vancouver, ISO, and other styles

7

Rifhat Bibi, Rifhat Bibi, Muhammad Yaseen Muhammad Yaseen, Haseen Ahmad Haseen Ahmad, Ismat Ullah Khan Ismat Ullah Khan, Shaista Parveen Shaista Parveen, and Abbas Hassan Abbas Hassan. "Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction." Journal of the chemical society of pakistan 43, no. 1 (2021): 95. http://dx.doi.org/10.52568/000550.

Full text

Abstract:

Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety of important biological potencies. Palladium catalyzed cross coupling process provided an effective synthetic practice for the synthesis of alkyne derivatives of quinoxaline. Vareity of terminal alkynes were coupled with 2-(4-bromophenyl)quinoxaline under optimized conditions for Sonogashira reaction, affording alkyne substituted quinoxaline derivatives in high yields. The optimized reaction conditions for coupling of range of terminal alkyne with quinoxaline basic core render this process significant for designing of medicinally interesting precursors.

APA, Harvard, Vancouver, ISO, and other styles

8

Rifhat Bibi, Rifhat Bibi, Muhammad Yaseen Muhammad Yaseen, Haseen Ahmad Haseen Ahmad, Ismat Ullah Khan Ismat Ullah Khan, Shaista Parveen Shaista Parveen, and Abbas Hassan Abbas Hassan. "Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction." Journal of the chemical society of pakistan 43, no. 1 (2021): 95. http://dx.doi.org/10.52568/000550/jcsp/43.01.2021.

Full text

Abstract:

Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety of important biological potencies. Palladium catalyzed cross coupling process provided an effective synthetic practice for the synthesis of alkyne derivatives of quinoxaline. Vareity of terminal alkynes were coupled with 2-(4-bromophenyl)quinoxaline under optimized conditions for Sonogashira reaction, affording alkyne substituted quinoxaline derivatives in high yields. The optimized reaction conditions for coupling of range of terminal alkyne with quinoxaline basic core render this process significant for designing of medicinally interesting precursors.

APA, Harvard, Vancouver, ISO, and other styles

9

Rifhat Bibi, Rifhat Bibi, Muhammad Yaseen Muhammad Yaseen, Haseen Ahmad Haseen Ahmad, Ismat Ullah Khan Ismat Ullah Khan, Shaista Parveen Shaista Parveen, and Abbas Hassan Abbas Hassan. "Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction." Journal of the chemical society of pakistan 43, no. 1 (2021): 95. http://dx.doi.org/10.52568/000009.

Full text

Abstract:

Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety of important biological potencies. Palladium catalyzed cross coupling process provided an effective synthetic practice for the synthesis of alkyne derivatives of quinoxaline. Vareity of terminal alkynes were coupled with 2-(4-bromophenyl)quinoxaline under optimized conditions for Sonogashira reaction, affording alkyne substituted quinoxaline derivatives in high yields. The optimized reaction conditions for coupling of range of terminal alkyne with quinoxaline basic core render this process significant for designing of medicinally interesting precursors.

APA, Harvard, Vancouver, ISO, and other styles

10

Zayed, Mohamed F. "Chemistry, Synthesis, and Structure Activity Relationship of Anticancer Quinoxalines." Chemistry 5, no. 4 (November 14, 2023): 2566–87. http://dx.doi.org/10.3390/chemistry5040166.

Full text

Abstract:

Quinoxaline is a fused heterocycle system of a benzene ring and pyrazine ring. It has earned considerable attention due to its importance in the field of medicinal chemistry. The system is of extensive importance due to its comprehensive array of biological activities. Quinoxaline derivatives have been used as anticancer, anticonvulsant, anti-inflammatory, antidiabetic, antioxidant, antibacterial, anti-TB, antimalarial, antiviral, anti-HIV, and many other uses. Variously substituted quinoxalines are significant therapeutic agents in the pharmaceutical industry. This review spotlights on the chemistry, physiochemical characters, synthesis, pharmaceutical products, and medicinal chemistry of various anticancer quinoxaline derivatives that were developed in the last period. It covers the period from 2016 to 2023.

APA, Harvard, Vancouver, ISO, and other styles

11

Irfan, Ali, Sajjad Ahmad, Saddam Hussain, Fozia Batool, Haseeba Riaz, Rehman Zafar, Katarzyna Kotwica-Mojzych, and Mariusz Mojzych. "Recent Updates on the Synthesis of Bioactive Quinoxaline-Containing Sulfonamides." Applied Sciences 11, no. 12 (June 19, 2021): 5702. http://dx.doi.org/10.3390/app11125702.

Full text

Abstract:

Quinoxaline is a privileged pharmacophore that has broad-spectrum applications in the fields of medicine, pharmacology and pharmaceutics. Similarly, the sulfonamide moiety is of considerable interest in medicinal chemistry, as it exhibits a wide range of pharmacological activities. Therefore, the therapeutic potential and biomedical applications of quinoxalines have been enhanced by incorporation of the sulfonamide group into their chemical framework. The present review surveyed the literature on the preparation, biological activities and structure-activity relationship (SAR) of quinoxaline sulfonamide derivatives due to their broad range of biomedical activities, such as diuretic, antibacterial, antifungal, neuropharmacological, antileishmanial, anti-inflammatory, anti-tumor and anticancer action. The current biological diagnostic findings in this literature review suggest that quinoxaline-linked sulfonamide hybrids are capable of being established as lead compounds; modifications on quinoxaline sulfonamide derivatives may give rise to advanced therapeutic agents against a wide variety of diseases.

APA, Harvard, Vancouver, ISO, and other styles

12

Khatoon, Hena, and Emilia Abdulmalek. "Novel Synthetic Routes to Prepare Biologically Active Quinoxalines and Their Derivatives: A Synthetic Review for the Last Two Decades." Molecules 26, no. 4 (February 18, 2021): 1055. http://dx.doi.org/10.3390/molecules26041055.

Full text

Abstract:

Quinoxalines, a class of N-heterocyclic compounds, are important biological agents, and a significant amount of research activity has been directed towards this class. They have several prominent pharmacological effects like antifungal, antibacterial, antiviral, and antimicrobial. Quinoxaline derivatives have diverse therapeutic uses and have become the crucial component in drugs used to treat cancerous cells, AIDS, plant viruses, schizophrenia, certifying them a great future in medicinal chemistry. Due to the current pandemic situation caused by SARS-COVID 19, it has become essential to synthesize drugs to combat deadly pathogens (bacteria, fungi, viruses) for now and near future. Since quinoxalines is an essential moiety to treat infectious diseases, numerous synthetic routes have been developed by researchers, with a prime focus on green chemistry and cost-effective methods. This review paper highlights the various synthetic routes to prepare quinoxaline and its derivatives, covering the literature for the last two decades. A total of 31 schemes have been explained using the green chemistry approach, cost-effective methods, and quinoxaline derivatives’ therapeutic uses.

APA, Harvard, Vancouver, ISO, and other styles

13

Viji, Mayavan, Manjunatha Vishwanath, Jaeuk Sim, Yunjeong Park, Chanhyun Jung, Seohu Lee, Heesoon Lee, Kiho Lee, and Jae-Kyung Jung. "α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other N-heterocycles via decarboxylative oxidative annulation reaction." RSC Advances 10, no. 61 (2020): 37202–8. http://dx.doi.org/10.1039/d0ra07093a.

Full text

APA, Harvard, Vancouver, ISO, and other styles

14

Ou, Zhongping, Wenbo E, Jianguo Shao, Paul L. Burn, Craig S. Sheehan, Robin Walton, Karl M. Kadish, and Maxwell J. Crossley. "Electrochemical and spectroelectrochemical properties of building blocks for molecular arrays: reactions of quinoxalino[2,3-b]porphyrins containing metal(II) ions." Journal of Porphyrins and Phthalocyanines 09, no. 02 (February 2005): 142–51. http://dx.doi.org/10.1142/s1088424605000216.

Full text

Abstract:

Quinoxalino[2,3-b]porphyrins are laterally-extended porphyrins with aromatic ring systems fused to the β,β'-positions of a pyrrolic ring of the macrocycle. They are building blocks for coplanar laterally-extended oligoporphyrins with applications in molecular electronics. The electrochemistry and spectroelectrochemistry of four such quinoxalinoporphyrins containing metal(II) ions and one free-base quinoxalinoporphyrin dissolved in nonaqueous media have been investigated and the data are compared to that seen for the same derivatives of the parent macrocycle lacking the fused quinoxaline ring. The investigated compounds are represented as (P)M and (PQ)M, where P = 5 ,10,15,20-tetrakis(3,5-di-tert-butylphenyl)porphyrin, PQ = 5,10,15,20-tetrakis(3,5-di-tert-butylphenyl)quinoxalino[2,3-b]porphyrin and M = 2 H , Zn , Cu , Ni or Pd . The complexes all undergo two ring-centered reductions and one or two ring-centered oxidations in PhCN , CH 2 Cl 2, pyridine or THF . Additional redox reactions are also seen for the quinoxaline group in THF . The fusion of an electroactive quinoxaline group to the porphyrin macrocycle results in an 80 to 270 mV shift of E 1/2 towards easier reductions and the appearance of a third reduction which is assigned as a quinoxaline-centered redox process. The average HOMO-LUMO gap for the ( P ) M and ( PQ ) M derivatives is 2.26 ± 0.09 V and 2.14 ± 0.08 V , respectively. Both values are smaller than the average separation of 2.33 ± 0.13 V for the corresponding derivatives of tetraphenylporphyrin. The electrochemistry and UV-visible spectroelectrochemcal data indicate that moderate communication exists between the quinoxaline unit and the porphyrin π-ring system.

APA, Harvard, Vancouver, ISO, and other styles

15

Montana, Marc, Vincent Montero, Omar Khoumeri, and Patrice Vanelle. "Quinoxaline Derivatives as Antiviral Agents: A Systematic Review." Molecules 25, no. 12 (June 16, 2020): 2784. http://dx.doi.org/10.3390/molecules25122784.

Full text

Abstract:

Background: In recent decades, several viruses have jumped from animals to humans, triggering sizable outbreaks. The current unprecedent outbreak SARS-COV-2 is prompting a search for new cost-effective therapies to combat this deadly pathogen. Suitably functionalized polysubstituted quinoxalines show very interesting biological properties (antiviral, anticancer, and antileishmanial), ensuring them a bright future in medicinal chemistry. Objectives: Focusing on the promising development of new quinoxaline derivatives as antiviral drugs, this review forms part of our program on the anti-infectious activity of quinoxaline derivatives. Methods: Study compiles and discusses recently published studies concerning the therapeutic potential of the antiviral activity of quinoxaline derivatives, covering the literature between 2010 and 2020. Results: A final total of 20 studies included in this review. Conclusions: This review points to a growing interest in the development of compounds bearing a quinoxaline moiety for antiviral treatment. This promising moiety with different molecular targets warrants further investigation, which may well yield even more encouraging results regarding this scaffold.

APA, Harvard, Vancouver, ISO, and other styles

16

Liu, Yali, Yu Wei, Zhen Yang, Yang Li, Yan Liu, and Ping Liu. "Highly selective C3–H iodination of pyrrolo[1,2-a]quinoxalines." Organic & Biomolecular Chemistry 19, no. 23 (2021): 5191–96. http://dx.doi.org/10.1039/d1ob00759a.

Full text

APA, Harvard, Vancouver, ISO, and other styles

17

Goswami, Shyamaprosad, Shampa Chakraborty, Avijit Kumar Das, Abhishek Manna, Aditya Bhattacharyya, Ching Kheng Quah, and Hoong-Kun Fun. "Selective colorimetric and ratiometric probe for Ni(ii) in quinoxaline matrix with the single crystal X-ray structure." RSC Adv. 4, no. 40 (2014): 20922–26. http://dx.doi.org/10.1039/c4ra00594e.

Full text

Abstract:

A quinoxaline based colorimetric nickel sensor,HQAP[2-(quinoxalin-2-ylmethyleneamine)phenol] with high selectivity and sensitivity toward Ni²⁺ions is shown to have potential for practical use.

APA, Harvard, Vancouver, ISO, and other styles

18

EI-Bendary, E. R., F. E. Goda, A. R. Maarouf, and F. A. Badria. "Synthesis and antimicrobial evaluation of 3-hydrazino-quinoxaline derivatives and their cyclic analoaues." Scientia Pharmaceutica 72, no. 2 (June 11, 2004): 175–85. http://dx.doi.org/10.3797/scipharm.aut-04-15.

Full text

Abstract:

A series of quinoxaline derivatives has been synthesized by reacting 3-hydrazinoquinoxalines 1a,b with many bifunctional reagents. Reaction of 1a,b with chloroacetyl chloride and ethyl chloroacetate afforded 1-chloromethyl[1,2,4]tnazoIo[4,3-a]quinoxalines 2a,b and dihydro[1,2,4]triazino[4,3-a]quinoxalin-2-ones 3a,b respectively. Condensation of 1a,b with ethyl acetoacetate and acetylacetone yielded 2-quinoxalinylhydrazonobutanoates 4a,b and 2-quinoxalinylhydrazono-2-pentanones 5a,b respectively. Cyclization of 5a,b gave 3,5-dimethylpyrazolylquinoxalines 6a,b. Moreover, reaction of compounds 2a,b with N-phenyl piperazine derivatives afforded 4-(4-Arylpiperazin-1-yl)-1-[(4-arylpiperazin-1-yl) methyl)]triazoloquinoxalines 7a−e. The prepared compounds were screened for in vitro antibacterial and antifungal activities. None of the tested compounds showed significant activity towards Pseudomonas aeruginosa. However, remarkable activities were noticed for compounds 5a and 5b against Eschenchia coli. Staphylococcus aureus and Candida albicans. Compounds 6a and 6b lacked any antimicrobial activities against the tested microorganisms.

APA, Harvard, Vancouver, ISO, and other styles

19

Kamal, Ahmed, Korrapati Suresh Babu, Shaikh Faazil, S. M. Ali Hussaini, and Anver Basha Shaik. "l-Proline mediated synthesis of quinoxalines; evaluation of cytotoxic and antimicrobial activity." RSC Adv. 4, no. 86 (2014): 46369–77. http://dx.doi.org/10.1039/c4ra08615e.

Full text

Abstract:

A simple, greener and highly efficient method for the synthesis of functionalized quinoxalines has been developed employing l-proline as a catalyst in water. The newly synthesized quinoxaline–sulphonamide conjugates exhibited significant cytotoxic and antimicrobial activities.

APA, Harvard, Vancouver, ISO, and other styles

20

Li, Yuwen, Mei Qiu, Yubin Bai, Shaoqi Qu, and Zhihui Hao. "Improved synthesis of quinocetone and its two desoxymetabolites." Journal of the Serbian Chemical Society 83, no. 3 (2018): 265–70. http://dx.doi.org/10.2298/jsc170614118l.

Full text

Abstract:

Oxidation of o-nitroaniline with sodium hypochlorite afforded benzofurazan oxide in 96 % yield, and treatment of benzofurazan oxide with acetylacetone in the presence of triethylamine gave 2-acetyl-3-methyl-quinoxaline- -1,4-dioxide in 94 % yield. Finally, condensation of 2-acetyl-3-methyl-quinoxaline- 1,4-dioxide with benzaldehyde using 4-(dimethylamino)pyridinium acetate as a catalyst led to quinocetone in 95 % yield. Subsequently, reduction of the synthesized quinocetone with sodium dithionite resulted in two deoxy derivatives, 1-(3-methyl-4-oxido-2-quinoxalinyl)-3-phenyl-2-propen-1-one and 1-(3-methyl-2-quinoxalinyl)-3-phenyl-2-propen-1-one in 88.5 and 92 % yield, respectively. Furthermore, the synthesized quinocetone, and its deoxy derivatives were characterized by 1H-NMR, 13C-NMR and elemental analysis.

APA, Harvard, Vancouver, ISO, and other styles

21

Kovrizhina, Anastasia R., Elizaveta I. Samorodova, and Andrei I. Khlebnikov. "11H-Indeno[1,2-b]quinoxalin-11-one 2-(4-ethylbenzylidene)hydrazone." Molbank 2021, no. 4 (November 23, 2021): M1299. http://dx.doi.org/10.3390/m1299.

Full text

Abstract:

11H-Indeno[1,2-b]quinoxaline derivatives present an important type of nitrogen-containing heterocyclic compound that are useful intermediate products in organic synthesis and have potential pharmaceutical applications. A new 11H-indeno[1,2-b]quinoxalin-11-one-2-(4-ethylbenzylidene)hydrazone (compound 3) was synthesized. Compound 3 is the first example of an azine derivative based on the 11H-indeno[1,2-b]quinoxaline system. The Z,E-isomerism of compound 3 was investigated by DFT calculations. Bioavailability was evaluated in silico using ADME predictions. According to the ADME results, compound 3 is potentially highly bioavailable and has potential to be used for the treatment of neuroinflammation and ischemia–reperfusion injury.

APA, Harvard, Vancouver, ISO, and other styles

22

Mamedov, Vakhid A. "Recent advances in the synthesis of benzimidazol(on)es via rearrangements of quinoxalin(on)es." RSC Advances 6, no. 48 (2016): 42132–72. http://dx.doi.org/10.1039/c6ra03907c.

Full text

Abstract:

The review describes all the quinoxaline-benzimidazole rearrangements as a whole and the new quinoxalinone-benzimidazol(on)e rearrangements in particular when exposed to nucleophilic rearrangements which can be used for the synthesis of various biheterocyclic motifs.

APA, Harvard, Vancouver, ISO, and other styles

23

Gavernet, Luciana, Pablo Hernan Palestro, and Luis Bruno-Blanch. "Docking Applied to the Study of Inhibitors of c-Met Kinase." ISRN Physical Chemistry 2012 (December 13, 2012): 1–5. http://dx.doi.org/10.5402/2012/391897.

Full text

Abstract:

Quinoxaline derivatives were studied as inhibitors of c-Met kinase, a receptor associated with high tumor grade and poor prognosis in a number of human cancers. In this paper we used docking methodologies to predict the binding conformation of a set of quinoxalines and to explain the differences of biological activities previously reported.

APA, Harvard, Vancouver, ISO, and other styles

24

Patinote, Cindy, Sandy Raevens, Amélie Baumann, Eloise Pellegrin, Pierre-Antoine Bonnet, and Carine Deleuze-Masquéfa. "[1,2,4]triazolo[4,3-a]quinoxaline as Novel Scaffold in the Imiqualines Family: Candidates with Cytotoxic Activities on Melanoma Cell Lines." Molecules 28, no. 14 (July 18, 2023): 5478. http://dx.doi.org/10.3390/molecules28145478.

Full text

Abstract:

Cutaneous melanoma is one of the most aggressive human cancers and is the deadliest form of skin cancer, essentially due to metastases. Novel therapies are always required, since cutaneous melanoma develop resistance to oncogenic pathway inhibition treatment. The Imiqualine family is composed of heterocycles diversely substituted around imidazo[1,2-a]quinoxaline, imidazo[1,2-a]pyrazine, imidazo[1,5-a]quinoxaline, and pyrazolo[1,5-a]quinoxaline scaffolds, which display interesting activities on a panel of cancer cell lines, especially melanoma cell lines. We have designed and prepared novel compounds based on the [1,2,4]triazolo[4,3-a]quinoxaline scaffold through a common synthetic route, using 1-chloro-2-hydrazinoquinoxaline and an appropriate aldehyde. Cyclization is ensured by an oxidation-reduction mechanism using chloranil. The substituents on positions 1 and 8 were chosen based on previous structure–activity relationship (SAR) studies conducted within our heterocyclic Imiqualine family. Physicochemical parameters of all compounds have also been predicted. A375 melanoma cell line viability has been evaluated for 16 compounds. Among them, three novel [1,2,4]triazolo[4,3-a]quinoxalines display cytotoxic activities. Compounds 16a and 16b demonstrate relative activities in the micromolar range (respectively, 3158 nM and 3527 nM). Compound 17a shows the best EC50 of the novel series (365 nM), even if EAPB02303 remains the lead of the entire Imiqualine family (3 nM).

APA, Harvard, Vancouver, ISO, and other styles

25

Bowroju, Suresh Kuarm, Hanumaiah Marumamula, and Rajitha Bavanthula. "One-pot protocol for the synthesis of quinoxalines from styrenes, o-phenylenediamine and benzo[c][1,2,5]thiadiazole-4,5-diamine using triiodoisocyanuric acid." Organic Communications 14, no. 1 (March 26, 2021): 48–57. http://dx.doi.org/10.25135/acg.oc.93.2009.1800.

Full text

Abstract:

Triiodoisocyanuric acid (TICA) controlled one-pot and easy-operational protocol has been developed for the synthesis of substituted phenylquinoxalines (3a-3i) and phenyl-[1,2,5]thiadiazolo[3,4-f]quinoxaline (5a-5f) from styrenes with o-phenylenediamine and benzo[c][1,2,5]thiadiazole-4,5-diamine respectively. The reaction involves co-bromination and oxidation for the formation of an a-bromo ketone as an intermediate in the presence of triiodoisocyanuric acid, followed by condensation with the o-phenylenediamine and benzo[c][1,2,5]thiadiazole-4,5-diamine for the formation of phenylquinoxalines (3a-3i) and phenyl-[1,2,5]thiadiazolo[3,4-f]quinoxaline (5a-5f) in 55-79% yield. This protocol environmentally benign and economically viable. Substituted quinoxalines were obtained in good to excellent yields with wide substrate scope and functional-group tolerance.

APA, Harvard, Vancouver, ISO, and other styles

26

Lima, Rafaely N., Jaqueline R. Gonçalves, Valdenizia R. Silva, Luciano de S. Santos, Daniel P. Bezerra, Milena B. P. Soares, Andrei Leitão, and André L. M. Porto. "Antioxidant, Antitumor and Bactericidal Activities of Ethyl Gallate Quinoxalines." Current Bioactive Compounds 16, no. 6 (October 2, 2020): 900–910. http://dx.doi.org/10.2174/1573407215666190318144105.

Full text

Abstract:

Background: Quinoxaline, a fused heterocycle of benzene and pyrazine rings are becoming recognized as a potent class of anti-cancer compounds, such as, in a wide array of pharmacological activities. Methods: We evaluate the three gallate quinoxalines (G-A1, G-A2, and G-A3) as c-Met kinase inhibitors using a docking study, in vitro anticancer potential measurements, antioxidant and bactericidal activities. Results: The docking study showed hydrogen bond linkage of quinoxalines with amino acids at active site of c-Met kinase structures, indicating a possible cancer inhibition cell proliferation. Therefore, the three quinoxalines were analyzed against four in vitro cancer cell lines, and G-A1 demonstrated cytotoxicity against HL-60 and HCT116 cell lines (IC50= 9.55 and IC50= 16.67 μmol L-1, respectively). In HepG2 and MCF-7 cells, the IC50 were 22.48 and 33.42 μmol L-1, respectively. For G-A2 and G-A3, cytotoxic activity ranged from 61.22 to >101.21 μmol L-1. Potent antioxidant activities were also obtained for G-A2>G-A1>G-A3 (IC50= 4.5-8.4 μmol L-1 and AAI= 8.8-17.8). Six different Bacillius strains showed growth inhibition (11.33 to 13.33 mm) in the presence of quinoxaline G-A1 (500 μg). Conclusion: The present work showed the biological potential of quinoxalines G-A1, G-A2 and G-A3 in inhibiting four cancer cells proliferation, in addition to a very strong antioxidant activity.

APA, Harvard, Vancouver, ISO, and other styles

27

Piltan, Mohammad. "One-Pot Synthesis of Thiazolo[3,4-a]Quinoxalines from 1,2-Diamines, Aryl Isothiocyanates and Ethyl Bromopyruvate." Journal of Chemical Research 41, no. 12 (December 2017): 712–14. http://dx.doi.org/10.3184/174751917x15127369231305.

Full text

Abstract:

Some hitherto unreported thiazolo[3,4- a]quinoxaline derivatives have been synthesised in excellent yields via a one-pot, three-component reaction of benzene-1,2-diamines, ethyl bromopyruvate and aryl isothiocyanates in MeCN, for the first time. The protocol avoids the use of any catalysts or chromatographic separations and provides a wide range of novel thiazolo[3,4- a]quinoxalines.

APA, Harvard, Vancouver, ISO, and other styles

28

Hossain, MM, MM Hossain, MH Muhib, MR Mia, S. Kumar, and SA Wadud. "In vitro antioxidant potential study of some synthetic quinoxalines." Bangladesh Medical Research Council Bulletin 38, no. 2 (December 9, 2012): 47–50. http://dx.doi.org/10.3329/bmrcb.v38i2.12880.

Full text

Abstract:

In continuation of our study the in vitro antioxidant activity of some novel quinoxaline derivatives was investigated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) method with respect to ascorbic acid. To determine the antioxidant activity, a number of substituted indoxyls (3A-G), cyclic ketones (2A-G), and quinoxalines (1A-G) were synthesized by both microwave and conventional heating methods. The present findings revealed that some quinoxalines and their precursors (1D, 1F, 1G and 2E) exhibited a marked scavenging effect on DPPH radical. DOI: http://dx.doi.org/10.3329/bmrcb.v38i2.12880 Bangladesh Med Res Counc Bull 2012; 38: 47-50

APA, Harvard, Vancouver, ISO, and other styles

29

Yan, Rulong, and Xin Guan. "Copper-Catalyzed Synthesis of Alkyl-Substituted Pyrrolo[1,2-a]quinoxalines from 2-(1H-Pyrrol-1-yl)anilines and Alkylboronic Acids." Synlett 31, no. 04 (January 17, 2020): 359–62. http://dx.doi.org/10.1055/s-0037-1610743.

Full text

Abstract:

A radical pathway for the construction of pyrrolo[1,2-a]quinoxalines by using 2-(1H-pyrrol-1-yl)anilines and alkylboronic acids has been developed. Features of this process include Cu catalysis, readily accessible starting materials, and simple operations. Alkylboronic acids are used for the construction of pyrrolo[1,2-a]quinoxaline derivatives, and the desired products are obtained in moderate yields.

APA, Harvard, Vancouver, ISO, and other styles

30

Ho, Tuan Hoang. "Iron(III) promoted oxidative annulation of benzylic C-H bonds in (α-amino)arylacetic acids for synthesis of 4-aryl pyrrolo[1,2-a]quinoxalines." Ministry of Science and Technology, Vietnam 65, no. 4 (December 15, 2023): 11–13. http://dx.doi.org/10.31276/vjste.65(4).11-13.

Full text

Abstract:

Using amino acids for synthesis of heterocycles is a synthetically promising field. However, developing the practical methods for transformations of amino acids into heterocycles is still challenging. Given that alpha amino acids are abundant or easily prepared, herein we report a method for annulation of benzylic C-H bonds in derivatives of 2-phenylglycine with 1-(2-nitroaryl)pyrroles. The reactions proceeded well in the presence of iron(III) acetylacetonate catalyst and potassium carbonate base. Scope of pyrrolo[1,2-a]quinoxalines was studied. Regardless of electronic properties of substituents, the pyrrolo[1,2-a]quinoxaline de-rivatives were successfully isolated, as yields varied from 42% to 52%. Pyrrolo[1,2-a]quinoxalines substituted with heterocycles at C4 positions as pyridine and thiophene were competent substrates. Reaction mechanism was proposed to start with a decar-boxylative/deaminative sequence of 2-phenylglycine to afford benzaldehyde. The iron catalyst was presumed to facilitate the re-duction of 1-(2-nitroaryl)pyrroles to furnish the corresponding aniline. Imine condensation followed by cyclisation and oxidation would yield the pyrrolo[1,2-a]quinoxaline. Our method would offer a convenient tactic to transform abundant alpha amino acids into synthetically useful heterocycles.

APA, Harvard, Vancouver, ISO, and other styles

31

Azizian, Javad, Shahab Zomorodbakhsh, Mahdieh Entezari, and Hossein Anaraki-Ardakani. "Functionalization of Carboxylated Multi-Wall Nanotubes with Derivatives ofN1-(11H-Indeno[1,2-b]quinoxalin-11-ylidene)benzene-1,4-diamine." Journal of Chemistry 2013 (2013): 1–7. http://dx.doi.org/10.1155/2013/917970.

Full text

Abstract:

Quinoxaline derivatives are compounds with pharmaceutical applications. In this study, derivatives ofN1-(11H-indeno[1,2-b]quinoxalin-11-ylidene)benzene-1,4-diamine were synthesized and attached to carboxylated multi-wall nanotubes (MWNT–COOH). Functionalized carbon nanotubes were characterized by scanning electron microscopy (SEM) to study the shape of structures, transmission electron microscopy (TEM), fast Fourier transform infrared (FT-IR), Raman spectroscopy, and elemental analysis.

APA, Harvard, Vancouver, ISO, and other styles

32

Tang, Xiang-Ying, Yue-fa Gong, and Heng-rui Huo. "Metal-Free Synthesis of Pyrrolo[1,2-a]quinoxalines Mediated by TEMPO Oxoammonium Salts." Synthesis 50, no. 14 (June 13, 2018): 2727–40. http://dx.doi.org/10.1055/s-0037-1610131.

Full text

Abstract:

We herein describe a novel TEMPO oxoammonium salt initiated Pictet–Spengler reaction of imines, generated in situ from carbonyl compounds and pyrrole- or indole-containing substrates, to afford 4,5-dihydropyrrolo[1,2-a]quinoxalines or 5,6-dihydroindolo[1,2-a]quinoxalines in good to excellent yields. Moreover, a one-pot synthesis of a biologically important quinoxaline is achieved via a cyclization–dehydrogenation process using one equivalent of the oxoammonium salt.

APA, Harvard, Vancouver, ISO, and other styles

33

Nhari, Laila M., Elham N. Bifari, Aisha R. Al-Marhabi, Huda A. Al-Ghamdi, Sameera N. Al-Ghamdi, Fatimah A. M. Al-Zahrani, Khalid O. Al-Footy, and Reda M. El-Shishtawy. "Synthesis of Novel Key Chromophoric Intermediates via C-C Coupling Reactions." Catalysts 12, no. 10 (October 21, 2022): 1292. http://dx.doi.org/10.3390/catal12101292.

Full text

Abstract:

The fundamentals of Pd-catalyzed Csp2−Csp2 Miyaura borylation, Suzuki cross-coupling, and Stille cross-coupling reactions for a variety of borylated precursors based on phenothiazine (PTZ), phenoxazine (POZ), carbazole (Cz), and quinoxaline (QX) units have been explored. Three palladium-based catalysts were chosen for this study: Pd(PPh3)4, Pd(PPh3)2Cl2, and Pd(dppf)Cl2, applying different reaction conditions. Around 16 desired chromophores were successfully designed and synthesized using C-C cross-coupling reactions in moderate to excellent yields, including PTZ, POZ, and Cz units coupled with QX, indolinium iodide, thienyl, phenyl, or triphenylamine moieties. Additionally, PTZ, POZ, and Cz have been employed in synthesizing various pinacol boronate ester derivatives in good to moderate yields. Interestingly, Pd(dppf)Cl2 was found to be the best catalyst for borylation, and C-C cross-coupling reactions occurred in as little as 30 min, with an excellent yield exceeding 98%. Pd(PPh3)4 and Pd(PPh3)2Cl2 catalyzed the reaction to obtain the desired products in moderate to good yields after a long time (20–24 h). On the other hand, the Suzuki-Miyaura cross-coupling between N-(2-methyl)hexyl carbazole pinacol boronate ester derivative 10c and three halogenated quinoxaline derivatives—4-(3-(5-bromothiophen-2-yl)quinoxalin-2-yl)benzaldehyde (27), 4-(5-(3-(5-bromothiophen-2-yl)quinoxalin-2-yl)thiophen-2-yl)benzaldehyde (30), and 4-(3-chloroquinoxalin-2-yl)benzaldehyde (25) catalyzed by Pd(PPh3)4—afforded three carbazole-quinoxaline chromophores (28, 30, and 31, respectively) in 2–3 h, with good to excellent yields reaching 86%. The electron-deficient QX couplers proved to be coupled efficiently using the Stille coupling reaction, which involves the coupling between electron-rich orgaostannane and electron-deficient halide. The synthesized precursors and desired chromophores were characterized by FTIR, 1H-NMR, 13C-NMR, and HRMS.

APA, Harvard, Vancouver, ISO, and other styles

34

Yao, Hua, Sen Lin, Xiaoyang Zhong, Bingqing Wang, Zhaohua Yan, and Feng Xiong. "H2O2-Promoted Alkylation of Quinoxalin-2(1H)-ones with Styrenes and Dimethyl Sulfoxide." Synlett 32, no. 12 (May 12, 2021): 1213–18. http://dx.doi.org/10.1055/a-1507-6499.

Full text

Abstract:

AbstractA hydrogen peroxide (H2O2)-mediated quinoxaline-2(1H)-ones hydrocarbylation reaction has been reported. The reaction is achieved through the difunctionalization of styrene. In this transformation, methyl radical resulting from dimethyl sulfoxide firstly attacks styrenes to provide alkyl radicals which then undergo alkylation at the C3 position of quinoxalin-2(1H)-one. A green, convenient, and simple protocol for the synthesis of 3-alkylquinoxalin-2(1H)-ones was provided.

APA, Harvard, Vancouver, ISO, and other styles

35

Montero, Vincent, Marc Montana, Omar Khoumeri, Florian Correard, Marie-Anne Estève, and Patrice Vanelle. "Synthesis, In Vitro Antiproliferative Activity, and In Silico Evaluation of Novel Oxiranyl-Quinoxaline Derivatives." Pharmaceuticals 15, no. 7 (June 23, 2022): 781. http://dx.doi.org/10.3390/ph15070781.

Full text

Abstract:

The quinoxaline core is a promising scaffold in medicinal chemistry. Multiple quinoxaline derivatives, such as the topoisomerase IIβ inhibitor XK-469 and the tissue transglutaminase 2 inhibitor GK-13, have been evaluated for their antiproliferative activity. Previous work reported that quinoxaline derivatives bearing an oxirane ring present antiproliferative properties against neuroblastoma cell lines SK-N-SH and IMR-32. Likewise, quinoxalines with an arylethynyl group displayed promising antineoplastic properties against glioblastoma and lung cancer cell lines, U87-MG and A549 respectively. Here, 40 new quinoxaline derivatives bearing an oxirane ring were synthesized using a tetrakis(dimethylamino)ethylene (TDAE) strategy and a Sonogashira cross-coupling reaction. Each reaction with TDAE furnished a pair of diastereoisomers cis and trans. These new compounds formed two series according to the substitution of position 2 on the quinoxaline core, with chlorine or phenylacetylene respectively. Each of these isomers was evaluated for antiproliferative activity against neuroblastoma cell lines SK-N-SH and IMR-32 by MTT assay. All cell viability assay results were analyzed using R programming, as well as a statistical comparison between groups of compounds. Our evaluation showed no difference in drug sensitivity between the two neuroblastoma cell lines. Moreover, trans derivatives were observed to display better activities than cis derivatives, leading us to conclude that stereochemistry plays an important role in the antiproliferative activity of these compounds. Further support for this hypothesis is provided by the lack of improvement in antineoplastic activity following the addition of the phenylacetylene moiety, probably due to steric hindrance. As a result, compounds with nitrofuran substituents from the TDAE series demonstrated the highest antiproliferative activity with IC50 = 2.49 ± 1.33 μM and IC50 = 3.96 ± 2.03 μM for compound 11a and IC50 = 5.3 ± 2.12 μM and IC50 = 7.12 ± 1.59 μM for compound 11b against SK-N-SH and IMR-32, respectively. Furthermore, an in silico study was carried out to evaluate the mechanism of action of our lead compounds and predict their pharmacokinetic properties.

APA, Harvard, Vancouver, ISO, and other styles

36

Nicolescu, Alina, Emilian Georgescu, Florea Dumitrascu, Florentina Georgescu, Florina Teodorescu, Constantin Draghici, Mino R. Caira, and Calin Deleanu. "Exocyclic Enamines of Pyrrolo[1,2-a]quinoxalines Generated by 1,3-dipolar Cycloaddition Reactions of Benzimidazolium Ylides to Activated Alkynes." Revista de Chimie 71, no. 3 (January 1, 2001): 197–209. http://dx.doi.org/10.37358/rc.20.3.7989.

Full text

Abstract:

The reactions of N-acetonylbenzimidazolium chlorides with various activated alkynes, in the presence of bases, led under mild conditions to a mixture of pyrrolo[1,2-a]benzimidazoles (3), 4-methylene-pyrrolo[1,2-a]quinoxaline derivatives (4) and pyrrolo[1,2-a]quinoxalin-4-one derivatives (5). The exocyclic enamine derivatives 4 have been fully characterized by multinuclear NMR spectroscopy and X-ray crystallography. A mechanism rationalizing the formation of the enamine derivatives is proposed.

APA, Harvard, Vancouver, ISO, and other styles

37

Guillon, Jean, Solène Savrimoutou, Sandra Rubio, Stéphane Moreau, Noël Pinaud, Mathieu Marchivie, and Vanessa Desplat. "1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one: Synthesis, Crystal Structure and Anti-Leukemic Activity." Molbank 2020, no. 1 (January 29, 2020): M1113. http://dx.doi.org/10.3390/m1113.

Full text

Abstract:

1-Phenyl-8-[[4-(pyrrolo[1,2-a]quinoxalin-4-yl)phenyl]methyl]-1,3,8-triazaspiro[4.5]decan-4-one has been successfully synthesized via a multi-step pathway starting from 2-nitroaniline. Structure characterization of this original pyrrolo[1,2-a]quinoxaline derivative was achieved by FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This title compound shows interesting cytotoxic potential against several human leukemia cell lines (K562, HL60, and U937 cells).

APA, Harvard, Vancouver, ISO, and other styles

38

Rahman, Faiz-Ur, Yong-sheng Li, Ioannis D. Petsalakis, Giannoula Theodorakopoulos, Julius Rebek, and Yang Yu. "Recognition with metallo cavitands." Proceedings of the National Academy of Sciences 116, no. 36 (August 19, 2019): 17648–53. http://dx.doi.org/10.1073/pnas.1909154116.

Full text

Abstract:

We describe here the effects of metal complexation on the molecular recognition behavior of cavitands with quinoxaline walls. The nitrogen atoms of the quinoxalines are near the upper rim of the vase-like shape and treatment with Pd(II) gave 2:1 metal:cavitand derivatives. Characterization by 1H, 13C NMR spectroscopy, HR ESI-MS, and computations showed that the metals bridged adjacent quinoxaline panels and gave cavitands with C2v symmetry. Both water-soluble and organic-soluble versions were prepared and their host/guest complexes with alkanes, alcohols, acids, and diols (up to C12) were studied by 1H NMR spectroscopy. Analysis of the binding behavior indicated that the metals rigidified the walls of the receptive vase conformation and enhanced the binding of hydrophobic and even water-soluble guests, compared to related cavitands reported previously. The results demonstrated that the conformational dynamics of the cavitand were slowed by the coordination of Pd(II) and stabilized the host’s complexes.

APA, Harvard, Vancouver, ISO, and other styles

39

Kathrotiya, Haresh G., Sagar P. Gami, and Yogesh T. Naliapara. "An Efficient and Clean Synthesis of Thiophenyl Thiazole Depended Novel Triazolo[4,3-a]Quinoxaline Derivatives." International Letters of Chemistry, Physics and Astronomy 51 (May 2015): 125–34. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.51.125.

Full text

Abstract:

A simple and efficient approach for the synthesis of thiophenyl thiazole based triazolo [4,3-a] quinoxaline derivatives is described. In this methodology, 3-hydrazinyl-N-(4-(thiophen-2-yl) thiazol-2-yl) quinoxalin-2-amine derivatives treated with various aromatic aldehyde to form Schiff base which on treatment with iodobenzene diacetate in dichloromethane at room temperature to furnish title compounds. The synthesized compounds were characterized by 1H NMR, 13C NMR, FT-IR, elemental analysis, and mass spectral data

APA, Harvard, Vancouver, ISO, and other styles

40

Kathrotiya, Haresh G., Sagar P. Gami, and Yogesh T. Naliapara. "An Efficient and Clean Synthesis of Thiophenyl Thiazole Depended Novel Triazolo[4,3-<i>a</i>]Quinoxaline Derivatives." International Letters of Chemistry, Physics and Astronomy 51 (May 15, 2015): 125–34. http://dx.doi.org/10.56431/p-flw9zc.

Full text

Abstract:

A simple and efficient approach for the synthesis of thiophenyl thiazole based triazolo [4,3-a] quinoxaline derivatives is described. In this methodology, 3-hydrazinyl-N-(4-(thiophen-2-yl) thiazol-2-yl) quinoxalin-2-amine derivatives treated with various aromatic aldehyde to form Schiff base which on treatment with iodobenzene diacetate in dichloromethane at room temperature to furnish title compounds. The synthesized compounds were characterized by 1H NMR, 13C NMR, FT-IR, elemental analysis, and mass spectral data

APA, Harvard, Vancouver, ISO, and other styles

41

Guillon, Jean, Solène Savrimoutou, Sandra Albenque-Rubio, Noël Pinaud, Nina Fillová, Stéphane Moreau, Virginie Baylot, and Vanessa Desplat. "Synthesis, Crystal Structure and Anti-Leukemic Activity of (E)-Pyrrolo[1,2-a]quinoxalin-4-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one." Molbank 2023, no. 3 (July 8, 2023): M1691. http://dx.doi.org/10.3390/m1691.

Full text

Abstract:

(E)-Pyrrolo[1,2-a]quinoxalin-4-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one was designed then synthesized using a multi-step pathway starting from commercially available 2-nitroaniline. Structure characterization of this original substituted pyrrolo[1,2-a]quinoxaline compound was achieved by using FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This new pyrroloquinoxaline shows interesting cytotoxic potential against different human leukemia cell lines (MV4-11, K562, MOLM14 and Jurkat cells).

APA, Harvard, Vancouver, ISO, and other styles

42

Vicente, Esther, Raquel Villar, Asunción Burguete, Beatriz Solano, Silvia Pérez-Silanes, Ignacio Aldana, Joseph A. Maddry, et al. "Efficacy of Quinoxaline-2-Carboxylate 1,4-Di-N-Oxide Derivatives in Experimental Tuberculosis." Antimicrobial Agents and Chemotherapy 52, no. 9 (July 14, 2008): 3321–26. http://dx.doi.org/10.1128/aac.00379-08.

Full text

Abstract:

ABSTRACT This study extends earlier reports regarding the in vitro efficacies of the 1,4-di-N-oxide quinoxaline derivatives against Mycobacterium tuberculosis and has led to the discovery of a derivative with in vivo efficacy in the mouse model of tuberculosis. Quinoxaline-2-carboxylate 1,4-di-N-oxide derivatives were tested in vitro against a broad panel of single-drug-resistant M. tuberculosis strains. The susceptibilities of these strains to some compounds were comparable to those of strain H37Rv, as indicated by the ratios of MICs for resistant and nonresistant strains, supporting the premise that 1,4-di-N-oxide quinoxaline derivatives have a novel mode of action unrelated to those of the currently used antitubercular drugs. Specific derivatives were further evaluated in a series of in vivo assays, including evaluations of the maximum tolerated doses, the levels of oral bioavailability, and the efficacies in a low-dose aerosol model of tuberculosis in mice. One compound, ethyl 7-chloro-3-methylquinoxaline-2-carboxylate 1,4-dioxide, was found to be (i) active in reducing CFU counts in both the lungs and spleens of infected mice following oral administration, (ii) active against PA-824-resistant Mycobacterium bovis, indicating that the pathway of bioreduction/activation is different from that of PA-824 (a bioreduced nitroimidazole that is in clinical trials), and (iii) very active against nonreplicating bacteria adapted to low-oxygen conditions. These data indicate that 1,4-di-N-oxide quinoxalines hold promise for the treatment of tuberculosis.

APA, Harvard, Vancouver, ISO, and other styles

43

Guillon, Jean, Solène Savrimoutou, Sandra Albenque-Rubio, Noël Pinaud, Stéphane Moreau, and Vanessa Desplat. "Synthesis, Crystal Structure and Anti-Leukemic Activity of 1,3-Dihydro-1-{1-[4-(4-phenylpyrrolo[1,2-a]quinoxalin-3-yl)benzyl]piperidin-4-yl}-2H-benzimidazol-2-one." Molbank 2022, no. 1 (February 9, 2022): M1333. http://dx.doi.org/10.3390/m1333.

Full text

Abstract:

1,3-Dihydro-1-{1-[4-(4-phenylpyrrolo[1,2-a]quinoxalin-3-yl)benzyl]piperidin-4-yl}-2H-benzimidazol-2-one has been synthesized through a multi-step pathway starting from commercially available 2-nitroaniline. A structure characterization of this new substituted pyrrolo[1,2-a]quinoxaline compound was achieved by using FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This new pyrroloquinoxaline derivative shows an interesting cytotoxic potential against several human leukemia cell lines (HL60, K562 and U937 cells).

APA, Harvard, Vancouver, ISO, and other styles

44

Alswah, Mohamed, Adel Ghiaty, Ahmed El-Morsy, and Kamal El-Gamal. "Synthesis and Biological Evaluation of Some [1,2,4]Triazolo[4,3-a]quinoxaline Derivatives as Novel Anticonvulsant Agents." ISRN Organic Chemistry 2013 (September 12, 2013): 1–7. http://dx.doi.org/10.1155/2013/587054.

Full text

Abstract:

2-([1,2,4]Triazolo[4,3-a]quinoxalin-4-ylthio)acetic acid hydrazide (10) was used as a precursor for the syntheses of novel quinoxaline derivatives with potential anticonvulsant properties. The newly synthesized compounds have been characterized by IR, 1H NMR, and mass spectral data followed by elemental analysis. The anticonvulsant evaluation was carried out for eleven of the synthesized compounds using metrazol induced convulsions model and phenobarbitone sodium as a standard. Among this set of tested compounds, two of them (14, and 15b) showed the best anticonvulsant activities.

APA, Harvard, Vancouver, ISO, and other styles

45

Gomes, Ligia Rebelo, John Nicolson Low, Ana S. M. C. Rodrigues, James L. Wardell, Marcus V. N. de Souza, Thais C. M. Noguiera, and Alessandra C. Pinheiro. "Comparison of the structure of (E)-2-(2-benzylidenehydrazinylidene)quinoxaline with those of its chloro- and bromobenzylidene analogues." Acta Crystallographica Section C Crystal Structure Communications 69, no. 8 (July 13, 2013): 920–26. http://dx.doi.org/10.1107/s0108270113015370.

Full text

Abstract:

(E)-2-(2-Benzylidenehydrazinylidene)quinoxaline, C15H12N4, crystallized with two molecules in the asymmetric unit. The structures of six halogen derivatives of this compound were also investigated: (E)-2-[2-(2-chlorobenzylidene)hydrazinylidene]quinoxaline, C15H11ClN4; (E)-2-[2-(3-chlorobenzylidene)hydrazinylidene]quinoxaline, C15H11ClN4; (E)-2-[2-(4-chlorobenzylidene)hydrazinylidene]quinoxaline, C15H11ClN4; (E)-2-[2-(2-bromobenzylidene)hydrazinylidene]quinoxaline, C15H11BrN4; (E)-2-[2-(3-bromobenzylidene)hydrazinylidene]quinoxaline, C15H11BrN4; (E)-2-[2-(4-bromobenzylidene)hydrazinylidene]quinoxaline, C15H11BrN4. The 3-Cl and 3-Br compounds are isomorphous, as are the 4-Cl and 4-Br compounds. In all of these compounds, it was found that the supramolecular structures are governed by similar predominant patterns,viz.strong intermolecular N—H...N(pyrazine) hydrogen bonds supplemented by weak C—H...N(pyrazine) hydrogen-bond interactions in the 2- and 3-halo compounds and by C—H...Cl/Br interactions in the 4-halo compounds. In all compounds, there are π–π stacking interactions.

APA, Harvard, Vancouver, ISO, and other styles

46

Hou, Yong, Mohammad Yaser Masoomi, Minoo Bagheri, Ali Morsali, and Sang Woo Joo. "Two reversible transformable mercury(ii) coordination polymers as efficient adsorbents for removal of dibenzothiophene." RSC Advances 5, no. 99 (2015): 81356–61. http://dx.doi.org/10.1039/c5ra12686j.

Full text

Abstract:

Three new compounds of Hg(ii) have been synthesized, [Hg(quinoxaline)₂(NO₂)₂] (1), [Hg₃(μ-quinoxaline)₂(μ-SCN)₆]n (2) and [Hg(μ-quinoxaline)(μ-CN)₂]n (3) through the reaction between a quinoxaline ligand and mercury(ii) salts.

APA, Harvard, Vancouver, ISO, and other styles

47

Sibiya, Mixo, Lerato Raphoko, Dikgale Mangokoana, Raymond Makola, Winston Nxumalo, and Thabe Matsebatlela. "Induction of Cell Death in Human A549 Cells Using 3-(Quinoxaline-3-yl) Prop-2-ynyl Methanosulphonate and 3-(Quinoxaline-3-yl) Prop-2-yn-1-ol." Molecules 24, no. 3 (January 23, 2019): 407. http://dx.doi.org/10.3390/molecules24030407.

Full text

Abstract:

Despite major advancements in the development of various chemotherapeutic agents, treatment for lung cancer remains costly, ineffective, toxic to normal non-cancerous cells, and still hampered by a high level of remissions. A novel cohort of quinoxaline derivatives designed to possess a wide spectrum of biological activities was synthesized with promising targeted and selective anticancer drug activity. Hence, this study was aimed at determining in vitro anticancer activity effects of a newly synthesized class of 3-(quinoxaline-3-yl) prop-2-ynyl quinoxaline derivatives on A549 lung cancer cells. An assessment of the quinoxaline derivatives ferric reducing power, free radical scavenging activity, cytotoxic activity, and ability to induce reactive oxygen species (ROS) production was performed using the Ferric Reducing Antioxidant Power (FRAP), 2,2-diphenyl-1-picryl-hydrazyl (DPPH), 3-[4,5-dimethylthiazole-2-yl]-2,5-diphenyltetrazolium bromide (MTT) and 2’,7’-dichlorodihydrofluorescein diacetate (H2DCFDA) assays, respectively. The ability of the quinoxaline derivatives to induce apoptosis in A549 cells was assessed using the Acridine Orange/Ethidium Bromide (AO/EB) and Annexin V-FITC/Dead Cell Assay. Of the four quinoxaline derivatives tested, 3-(quinoxaline-3-yl) prop-2-ynyl methanosulphate (LA-39B) and 3-(quinoxaline-3-yl) prop-2-yn-1-ol (LA-55) displayed a dose-dependent reducing power, free-radical scavenging activity, inhibition of cell viability, and stimulation of ROS production which was accompanied by induction of apoptosis in A549 lung cancer cells. None of the quinoxaline derivatives induced cell death or ROS production in non-cancerous Raw 267.4 macrophage cells. Cytotoxicity was observed in A549 lung cancer, HeLa cervical cancer, and MCF-7 breast cancer cells albeit inhibition was more pronounced in A549 cells. The results of the study suggest that 3-(quinoxaline-3-yl) prop-2-ynyl methanosulphate and 3-(quinoxaline-3-yl) prop-2-yn-1-ol induce apoptotic cell death in A549 lung cancer cells.

APA, Harvard, Vancouver, ISO, and other styles

48

Iazzetti, Antonia, Giancarlo Fabrizi, Antonella Goggiamani, Federico Marrone, Alessio Sferrazza, and Karim Ullah. "Synthesis of Functionalized 3H-pyrrolo-[1,2,3-de] Quinoxalines via Gold-Catalyzed Intramolecular Hydroamination of Alkynes." Molecules 28, no. 15 (August 2, 2023): 5831. http://dx.doi.org/10.3390/molecules28155831.

Full text

Abstract:

A gold-catalyzed protocol to obtain functionalized 3H-pyrrolo [1,2,3-de] quinoxalines from suitable substituted N-alkynyl indoles has been proposed. The mild reaction conditions were revealed to be compatible with different functional groups, including halogen, alkoxyl, cyano, ketone, and ester, allowing the isolation of title compounds with yields from good to high. A reaction mechanism has been proposed, and theoretical calculations have been provided to rationalize the final step of the hypothesized reaction mechanism. As quinoxaline-containing polycyclic compounds, this class of molecules may represent a valuable template in medicinal chemistry and material science.

APA, Harvard, Vancouver, ISO, and other styles

49

Matušina, Zbyněk, Radomíra Olbřímková, Hana Votavová, Josef Neumann, Martin Hradilek, Milan Souček, Petr Maloň, Milan Kodíček, and Ivan Stibor. "Linear Heptapeptides Containing DNA-Intercalators. Synthesis and Interaction with DNA." Collection of Czechoslovak Chemical Communications 64, no. 9 (1999): 1419–32. http://dx.doi.org/10.1135/cccc19991419.

Full text

Abstract:

Five peptides of general structure X-Ser-Pro-Thr-Ser-Pro-Ser-Y (X = Tyr, quinoxaline- 2-carbonyl, acridine-9-carbonyl, Y = Tyr, (quinoxalin-2-yl)amino) were prepared using standard solid-phase peptide synthesis technique. Their interaction with DNA (calf thymus DNA and plasmids pUC9, p∆NS and pGEMEX) was studied using UV and CD spectroscopy, sedimentation analysis and agarose gel electrophoresis after treatment with topoisomerase I. In contrast to earlier findings (Suzuki M.: Nature 1990, 344, 562) intercalation into DNA structure has not been proved for any compound studied.

APA, Harvard, Vancouver, ISO, and other styles

50

Ghorab, Mostafa, Fatma Ragab, Helmy Heiba, Marwa El-Gazzar, and Mostafa El-Gazzar. "Synthesis, in vitro anticancer screening and radiosensitizing evaluation of some new 4-[3-(substituted)thioureido]-N-(quinoxalin-2-yl)-benzenesulfonamide derivatives." Acta Pharmaceutica 61, no. 4 (December 1, 2011): 415–25. http://dx.doi.org/10.2478/v10007-011-0040-4.

Full text

Abstract:

Synthesis, in vitro anticancer screening and radiosensitizing evaluation of some new 4-[3-(substituted)thioureido]-N-(quinoxalin-2-yl)-benzenesulfonamide derivatives Sulfonamides and quinoxaline derivatives possess many types of biological activities and have been recently reported to show substantial antitumor activity. This paper reports the synthesis of novel thioureido sulfaquinoxaline derivatives. All the newly synthesized compounds were evaluated for their in vitro anticancer activity against a human liver cell line (HEPG2) and showed higher activity than the reference drug doxorubicin. 4-(3-(4-Ethylbenzoate) thioureido)-N-(quinoxalin-2-yl)benzenesulfonamide (9) (IC50 = 15.6 μmol L-1), N-(pyridin-2-yl)-4-(3-(4-(N-quinoxalin-2-yl-sulfamoyl)phenyl)thioureido)benzenesulfonamide (10) (IC50 = 26.8 μmol L-1) and N-(quinoxalin-2-yl)-4-(3-(4-(N-thiazol-2-ylsulfamoyl)phenyl)thioureido)benzenesulfonamide (11) (IC50 = 24.4 μmol L-1) were the most potent compared to doxorubicin (IC50 = 71.8 μmol L-1). The most potent compounds 9, 10 and 11 were evaluated as radiosensitizing agents by subjecting the compounds to γ-irradiation (8 kGy).

APA, Harvard, Vancouver, ISO, and other styles

Journal articles on the topic 'Quinoxaline'

Create a spot-on reference in APA, MLA, Chicago, Harvard, and other styles