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Journal articles on the topic 'Pyrazolone derivatives'

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Author: Grafiati

Published: 18 May 2024

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1

Abd-Ella, Aly A., Saoud A. Metwally, Mokhtar A. Abd ul-Malik, Yasser A. El-Ossaily, Fathy M. Abd Elrazek, Safwat A. Aref, Youssra A. Naffea, and Shaban A. A. Abdel-Raheem. "A review on recent advances for the synthesis of bioactive pyrazolinone and pyrazolidinedione derivatives." Current Chemistry Letters 11, no. 2 (2022): 157–72. http://dx.doi.org/10.5267/j.ccl.2022.2.004.

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Oxo derivatives of pyrazolines and pyrazolidines are important heterocyclic compounds due to their unique biological activities and have been widely applied in pharmaceutical and agromedical fields. In this review, we provide an account of some recent advances in the field of pyrazolone chemistry, specifically on the reported synthesis methods of pyrazolinone (3-oxo-1,2-dihydropyrazole) and 3,5-pyrzolidinediones (3,5-dioxotetrahydropyrazoles) derivatives.

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2

Edrees, Mastoura M. "Synthesis of 4-hydrazinopyrazolo[3,4-d]pyrimidines and their Reactions with Carbonyl Compounds." Journal of Chemical Research 37, no. 1 (January 2013): 6–10. http://dx.doi.org/10.3184/174751912x13543818811749.

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Synthesis of a new 4-hydrazinopyrazolo[3,4- d]pyrimidine was achieved via heating (4,6-dithioxo-1 H-pyrazolo[3,4- d] pyrimidin-3-yl)acetonitrile with hydrazine hydrate. Reactions of the latter product with thiophene-2-carbaldehyde and ethyl hydrazonoacetoacetate analogues afforded the corresponding hydrazone and pyrazole derivatives, respectively. Similarly, condensation of 2-[6-(benzylsulfanyl)-4-hydrazino-1 H-pyrazolo[3,4- d]pyrimidin-3-yl]acetonitrile with thiophene-2-carbaldehyde and ethyl hydrazonoacetoacetate analogues gave the respective hydrazone and pyrazolone derivatives. Alkylation reactions of 2-[4,6-bis(benzylsulfanyl)-1 H-pyrazolo[3,4- d]pyrimidin-3-yl]acetonitrile with arylamines gave the respective 4-( N-arylamino)-6-benzylsulfanylpyrazolo[3,4- d]pyrimidine derivatives.

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3

Gil-Ordóñez, Marta, Camille Aubry, Cristopher Niño, Alicia Maestro, and José M. Andrés. "Squaramide-Catalyzed Asymmetric Mannich Reaction between 1,3-Dicarbonyl Compounds and Pyrazolinone Ketimines: A Pathway to Enantioenriched 4-Pyrazolyl- and 4-Isoxazolyl-4-aminopyrazolone Derivatives." Molecules 27, no. 20 (October 17, 2022): 6983. http://dx.doi.org/10.3390/molecules27206983.

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A series of N-Boc ketimines derived from pyrazolin-5-ones have been used as electrophiles in enantioselective Mannich reactions with different 1,3-dicarbonyl compounds. This method provides a direct pathway to access the 4-amino-5-pyrazolone derivatives bearing a quaternary substituted stereocenter and containing two privileged structure motifs, the β-diketone and pyrazolinone substructures. The adducts were obtained in excellent yields (up to 90%) and enantioselectivities (up to 94:6 er) by employing a very low loading of 2 mol% of a quinine-derived bifunctional squaramide as an organocatalyst for a wide range of substrates. In addition, the utility of the obtained products was demonstrated through one step transformations to enantioenriched diheterocyclic systems (4-pyrazolyl-pyrazolone and 4-isoxazolyl-pyrazolone), potentially promising candidates for drug discovery.

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4

Gediz Erturk, Aliye, and Hilal Omerustaoglu. "Synthesis and Cytotoxic Evaluation of Some Substituted 5-Pyrazolones and Their Urea Derivatives." Molecules 25, no. 4 (February 18, 2020): 900. http://dx.doi.org/10.3390/molecules25040900.

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In this paper, a series of new substituted-5-pyrazolones were first synthesized, then formulated by the Vilsmeier–Haack reaction to obtain substituted-4-carbaldehyde-5-pyrazolones. In the final step, when urea was reacted with formulated pyrazolones, we found that, instead of the C=N bond in azomethine form, the compounds tautomerized to form a series of novel pyrazole-4-ylidenemethylurea structures. The structures of these compounds were elucidated by FTIR, 1H, 13C NMR, LC-MS/MS, and elemental analysis methods. The cytotoxic and antioxidant effects of substituted 5-pyrazolones and their pyrazolone-urea derivatives were investigated in metastatic A431 and noncancerous HaCaT human keratinocytes by a mitochondrial activity test. The effects of the compounds on the migration of cancerous and noncancerous cell lines were investigated by using a cell scratch assay. The General Linear Model, Statistical Package for Social Sciences (SPSS v26) was used to determine if there was a statistically significant difference between the control and the treatment groups. Four of the nine compounds showed an antioxidant effect. All 5-pyrazolone-urea compounds showed higher toxicity (p < 0.05) in cancerous A431 cells compared to noncancerous cells at all time points. All compounds also showed a biphasic hormetic effect. Four of the nine compounds inhibited cell migration.

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5

Pattan, S. R., P. A. Chavan, R. A. Muluk, S. S. Dengale, S. V. Hiremath, K. D. Pansare, S. S. Vetal, and J. S. Pattan. "SYNTHESIS AND BIOLOGICAL EVALUATION OF SOME HETEROCYCLES CONTAINING OXADIAZOLE AND PYRAZOLE RING FOR ANTI-BACTERIAL, ANTI-FUNGAL AND ANTI-TUBERCULAR ACTIVITIES." INDIAN DRUGS 49, no. 03 (March 28, 2012): 18–24. http://dx.doi.org/10.53879/id.49.03.p0018.

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1, 3, 4-oxadiazoles were synthesized by treating pyrazine-2-carbohydrazide with CS2 and alc. KOH and their derivatives were prepared by using R-Cl compounds. pyrazolones were synthesized by treatingpyrazine-2-carbohydrazide with ethyl acetoacetate. The derivatives of pyrazolone were prepared by refluxing pyrazolone with formaldehyde and different substituted secondary amines. All the synthesized compounds were characterized by IR, 1H-NMR and elemental analysis and evaluated for antibacterial, antifungal and antitubercular activities.

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6

Yang, Kai, Xiaoze Bao, Ye Yao, Jingping Qu, and Baomin Wang. "Iodine-mediated cross-dehydrogenative coupling of pyrazolones and alkenes." Organic & Biomolecular Chemistry 16, no. 34 (2018): 6275–83. http://dx.doi.org/10.1039/c8ob01645c.

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7

Brogden, Rex N. "Pyrazolone Derivatives." Drugs 32, Supplement 4 (1986): 60–70. http://dx.doi.org/10.2165/00003495-198600324-00006.

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8

Manojkumar, Parameswaran, Thengungal Ravi, and Gopalakrishnan Subbuchettiar. "Synthesis of coumarin heterocyclic derivatives with antioxidant activity and in vitro cytotoxic activity against tumour cells." Acta Pharmaceutica 59, no. 2 (June 1, 2009): 159–70. http://dx.doi.org/10.2478/v10007-009-0018-7.

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Synthesis of coumarin heterocyclic derivatives with antioxidant activity andin vitrocytotoxic activity against tumour cellsThe aim of the present work was to synthesise coumarinyl heterocycles and to elucidate the potential role of these compounds as antioxidants and cytotoxic agents against Dalton's lymphoma ascites tumour cells (DLA) and Ehrlich ascites carcinoma cells (EAC). The synthesis of coumarin derivatives containing pyrazole, pyrazolone, thiazolidin-4-one, 5-carboxymethyl-4-thiazolidinone and 3-acetyl-1,3,4-oxadiazole ring is reported. 4-Methylcoumarinyl-7-oxyacetic acid hydrazide (1) reacted with arylazopropanes or hydrazono-3-oxobutyrate derivatives to form pyrazole (3a-c) and pyrazolone derivatives (5a-c). Heterocyclisation of Schiff's bases of 1 with thioglycolic acid, thiomalic acid or acetic anhydride afforded novel heterocyclic derivatives 4-thiazolidinones (7a-c), 5-carboxymethyl-4-thiazolidinones (8a-c) and oxadiazoles (9a-c), respectively. Some of the compounds showed promising antioxidant activityin vitroand cytotoxic activity against DLA cells and EAC cells.

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9

Zhang, Wande, Shah Nawaz, Yue Huang, Wenjing Gong, Xingfu Wei, Jingping Qu, and Baomin Wang. "C-4 benzofuranylation of pyrazolones by a metal-free catalyzed indirect heteroarylation strategy." Organic & Biomolecular Chemistry 19, no. 46 (2021): 10215–22. http://dx.doi.org/10.1039/d1ob01920a.

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A metal-free catalyzed indirect heteroarylation of pyrazolones with 2-(3-hydroxy-3,3-diarylprop-1-yn-1-yl)phenols has been developed, delivering a wide range of novel 4-benzofuran-substituted pyrazolone derivatives.

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10

Bao, Xiaoze, Xingyue Wang, Jin-Miao Tian, Xinyi Ye, Baomin Wang, and Hong Wang. "Recent advances in the applications of pyrazolone derivatives in enantioselective synthesis." Organic & Biomolecular Chemistry 20, no. 12 (2022): 2370–86. http://dx.doi.org/10.1039/d1ob02426d.

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11

Namera, Dipti L., Khushal M. Kapadiya, Mitesh M. Chhatrola, and Umed C. Bhoya. "Microwave Assisted Synthesis of some Novel Sulphonamide Bearing Pyrazolone Core Structure." International Letters of Chemistry, Physics and Astronomy 30 (March 2014): 116–26. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.30.116.

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We have described some novel Sulphonamide bearing pyrazoline derivatives synthesized by conventional method as well as microwave assisted method of synthesis. The reaction of 4-(3-methyl-5-oxo-4,5-dihydro-1-H-pyrazol-1-yl)benzenesulphonamide with substituted benzaldehyde in the presence of Methanol as solvent and piperidine as catalyst, generated a series of substituted pyrazolone derivatives 4a-m. The structures of all synthesized compounds are well characterized by Mass spectroscopy, FT-IR, 1H NMR and elemental analysis. After obtaining experimental data regarding the yield and the time taken for the synthesis by both the approaches, convenient and microwave assisted method, it was ascertained that the microwave assisted method is more suitable for synthesis of pyrazolone derivatives 4a-m.

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12

Namera, Dipti L., Khushal M. Kapadiya, Mitesh M. Chhatrola, and Umed C. Bhoya. "Microwave Assisted Synthesis of some Novel Sulphonamide Bearing Pyrazolone Core Structure." International Letters of Chemistry, Physics and Astronomy 30 (March 12, 2014): 116–26. http://dx.doi.org/10.56431/p-d7mgbf.

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We have described some novel Sulphonamide bearing pyrazoline derivatives synthesized by conventional method as well as microwave assisted method of synthesis. The reaction of 4-(3-methyl-5-oxo-4,5-dihydro-1-H-pyrazol-1-yl)benzenesulphonamide with substituted benzaldehyde in the presence of Methanol as solvent and piperidine as catalyst, generated a series of substituted pyrazolone derivatives 4a-m. The structures of all synthesized compounds are well characterized by Mass spectroscopy, FT-IR, 1H NMR and elemental analysis. After obtaining experimental data regarding the yield and the time taken for the synthesis by both the approaches, convenient and microwave assisted method, it was ascertained that the microwave assisted method is more suitable for synthesis of pyrazolone derivatives 4a-m.

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13

Gadhave, Anil, Shashikant Kuchekar, and Bhausaheb Karale. "Ultrasonication-Induced Synthesis and Antimicrobial Evaluation of Some Multifluorinated Pyrazolone Derivatives." Journal of Chemistry 2013 (2013): 1–9. http://dx.doi.org/10.1155/2013/741953.

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A series of novel fluorine containing pyrazole-pyrazolone (4a–j) and chromone-pyrazolone (5a–i) was synthesized from multifluorinated pyrazolone by the Knoevenagel condensation reaction. All compounds were synthesized by conventional heating as well as ultrasound irradiation technique. It was found that ultrasonication method was more efficient than conventional heating method. The newly synthesized compounds were subjected forin vitroantimicrobial screening against four bacterial pathogens, namely,Staphylococcus aureus, Streptococcus pyogenes, Escherichia coli,andPseudomonas aeruginosaand three fungal pathogensCandida albicans, Aspergillus niger,andAspergillus clavatus, using broth microdilution (MIC) method (CLSI guidelines). Among them, some compounds exhibited promising antibacterial activity against the tested strains. All synthesized compounds were characterized by IR,1H-NMR, mass, and elemental analysis.

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14

Abdel Hafez, Ali A. "Synthesis of Some Heterocyclic Sulfones Related to Quinolinol." Collection of Czechoslovak Chemical Communications 58, no. 9 (1993): 2222–26. http://dx.doi.org/10.1135/cccc19932222.

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It is well known that pyrazolone derivatives possess antifungal and antibacterial activities. Pyrazole and isoxazole derivatives are widely used in medicinal chemistry. In continuation of our work on the synthesis of heterocycles containing the quinoline moiety we synthesized different heterocyclic sulfones related to quinolinol.

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15

Zaiter, Jamila, Hanane Achibat, Ouafa Amiri, Abderrafia Hafid, Mostafa Khouili, El Mostapha Rakib, Cláudia M. B. Neves, et al. "An easy synthetic access to new pyrazole spiro derivatives from 3-amino-1-phenyl-2-pyrazolin-5-one." New Journal of Chemistry 39, no. 9 (2015): 6738–41. http://dx.doi.org/10.1039/c5nj01306b.

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16

El-Ossaily, Yasser A., Nuha M. M. Alanazi, Ibrahim O. Althobaiti, Hamud A. Altaleb, Nayef S. Al-Muailkel, Mohamed Y. El-Sayed, Modather F. Hussein, et al. "Multicomponent approach to the synthesis and spectral characterization of some 3,5-pyrazolididione derivatives and evaluation as anti-inflammatory agents." Current Chemistry Letters 13, no. 1 (2024): 127–40. http://dx.doi.org/10.5267/j.ccl.2023.8.003.

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Pyrazolones are a class of heterocyclic compounds that contain a pyrazole ring fused to a ketone group. Recent scientific research has focused extensively on the potential anti-inflammatory properties of pyrazolone compounds due to their diverse pharmacological effects in alleviating inflammation and reducing fever. This motivated us to focus on the preparation of these derivatives in a simple and eco-friendly manner. A convenient new green methodology was modified for the preparation of 1-phenyl-3,5-pyrazolidinedione by the sonicated MCR of diethyl malonate, phenylhydrazine, and a catalytic amount imidazole as homogenous organic catalyst in water green solvent in a good yield. On the other hand, some of 4-arylidinepyrazolidinedione derivatives are prepared in the same manner via the treatment of a mixture of diethyl malonate, phenylhydrazine, aromatic aldehydes, and a catalytic amount of imidazole in an aqueous medium. Our target synthesized pyrazolidinediones were elucidated via elemental and several spectral analyses. Due to the importance of pyrazolidinediones in the field of treating inflammation and relieving pain, a number of prepared compounds were chosen to test their efficacy as anti-inflammatory agents using carrageenan-induced foot edema in rats and compare the results with indomethacin, the standard drug. We found that the majority of derivatives yield promising results spanning from good to wonderful, so derivatives (15k, 15b, 15h, 15a, and 15j) yield the best results while derivative (15i) yields an average result. As for the derivative (15f), it yields the lowest results compared to the standard drug. This is due to the difference in the structural composition of these derivatives, which increases the likelihood of their use as anti-inflammatory derivatives.

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17

Yuan, Huijun, Yao Li, Hanhui Zhao, Zhihong Yang, Xin Li, and Wenjun Li. "Asymmetric synthesis of atropisomeric pyrazole via an enantioselective reaction of azonaphthalene with pyrazolone." Chemical Communications 55, no. 84 (2019): 12715–18. http://dx.doi.org/10.1039/c9cc06360a.

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The first catalytic asymmetric reaction of azonaphthalene with pyrazolone has been established. A wide range of axially chiral pyrazole derivatives have been achieved in good yields (68–99%) with excellent enantioselectivities (83–98% ee) by utilizing chiral phosphoric acid as a catalyst.

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18

A. Almehizia, Abdulrahman, Ahmad M. Naglah, Amer A. Zen, Tamer K. Khatab, and Ashraf S. Hassan. "TCS/ZnCl2 as a controlled reagent for the Michael addition and heterocyclic cyclization based on the phenyl pyrazolone scaffold with docking validation as a Covid-19 protease inhibitor." Bulletin of the Chemical Society of Ethiopia 38, no. 4 (April 30, 2024): 1119–27. http://dx.doi.org/10.4314/bcse.v38i4.24.

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TCS/ZnCl2 is presented as a new catalyst for achieving the Michael addition adduct 5a-g by the reaction of phenyl pyrazolone 4 as the Michael donor and arylidene derivatives 3a-g as the Michael acceptor. The one-pot multi-component reaction of the same fragments' scaffolds as aldehydes 1a-g, malononitrile (2), and phenyl pyrazolone 4 with the same catalyst gives pyrano[2,3-c]pyrazole derivatives 6a-g as final products. The prepared compounds undergo docking validation as COVID-19 protease inhibitors and are compared with hydroxychloroquine as a reference drug. KEY WORDS: Pyranopyrazole, multi-component reactions, TCS/ZnCl2 catalyst, COVID-19, the energy score, hydroxychloroquine Bull. Chem. Soc. Ethiop. 2024, 38(4), 1119-1127. DOI: https://dx.doi.org/10.4314/bcse.v38i4.24

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19

Li, Jun-Hua, and Da-Ming Du. "Enantioselective synthesis of chiral heterocycles containing both chroman and pyrazolone derivatives catalysed by a chiral squaramide." Organic & Biomolecular Chemistry 13, no. 20 (2015): 5636–45. http://dx.doi.org/10.1039/c4ob02653e.

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An efficient chiral squaramide-catalysed enantioselective Michael addition of pyrazolin-5-ones to 3-nitro-2H-chromenes afforded chiral heterocycles containing both chroman and pyrazolone derivatives in high to excellent yields (up to 98%) with high enantioselectivities (up to 96%) under very low catalyst loading (0.2 mol%).

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20

Hamama, Wafaa S., Mohamed A. Ismail, Hana’a A. Al-Saman, and Hanafi H. Zoorob. "Convenient Selective Synthesis of Substituted Pyrido[2,3-d]pyrimidones and Annulated Derivatives." Zeitschrift für Naturforschung B 62, no. 1 (January 1, 2007): 104–10. http://dx.doi.org/10.1515/znb-2007-0115.

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The reaction of 6-aminouracil (1) with the appropriate α,β -unsaturated ketones, gave the corresponding pyrido[2,3-d]pyrimidin-2,4-diones 3, 6, 8 and 10, respectively. Treatment of 1 with salicylaldehyde, 6-carboethoxy-3,5-diphenyl-2-cyclohexenone (13) or 2,6- bis(phenylmethylidene)cyclohexanone (15) afforded the corresponding pyrimido[4,5-d]quinoline- 2,4-diones 12, 14 and 16, respectively. Furthermore, a pyrido[2,3-d]pyrimidine incorporating 3,2’- bis(quinoline) derivative 18 was synthesized. Annulation of pyrido[2,3-d]pyrimidine with pyrazole or imidazole moieties was achieved via reaction of 1 with benzylidene derivatives of pyrazolone, imidazolone or 3-carboethoxycoumarin (23) to give 21, 22 and 24, respectively.

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21

Hassan, Alaa A., Yusria R. Ibrahim, and Ahmed M. Shawky. "Reactions of Substituted Carbohydrazides with Electron-poor Olefins." Zeitschrift für Naturforschung B 63, no. 8 (August 1, 2008): 998–1004. http://dx.doi.org/10.1515/znb-2008-0813.

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Substituted carbohydrazides 1a - e reacted with ethenetetracarbonitrile (2) in dimethylformamide with formation of diacylhydrazines 4a - e and 5-amino-1-substiuted pyrazole-3,3,4-tricarbonitriles 5a - e. On the other hand, 1a-c reacted with diethyl (E)-2,3-dicyanobutenedioate (3) to give oxadiazinone and pyrazolone derivatives 12a - e and 13a - e, respectively.

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22

Leleu-Chavain, Natascha, Romain Regnault, Hania Ahouari, Raphaël Le Biannic, Mostafa Kouach, Frédérique Klupsch, Romain Magnez, et al. "Antioxidant Properties and Aldehyde Reactivity of PD-L1 Targeted Aryl-Pyrazolone Anticancer Agents." Molecules 27, no. 10 (May 21, 2022): 3316. http://dx.doi.org/10.3390/molecules27103316.

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Small molecules targeting the PD-1/PD-L1 checkpoint are actively searched to complement the anticancer arsenal. Different molecular scaffolds have been reported, including phenyl-pyrazolone derivatives which potently inhibit binding of PD-L1 to PD-1. These molecules are structurally close to antioxidant drug edaravone (EDA) used to treat amyotrophic lateral sclerosis. For this reason, we investigated the capacity of five PD-L1-binding phenyl-pyrazolone compounds (1–5) to scavenge the formation of oxygen free radicals using electron spin resonance spectroscopy with DPPH/DMPO probes. In addition, the reactivity of the compounds toward the oxidized base 5-formyluracil (5fU) was assessed using chromatography coupled to mass spectrometry and photodiode array detectors. The data revealed that the phenyl-pyrazolone derivatives display antioxidant properties and exhibit a variable reactivity toward 5fU. Compound 2 with a N-dichlorophenyl-pyrazolone moiety cumulates the three properties, being a potent PD-L1 binder, a robust antioxidant and an aldehyde-reactive compound. On the opposite, the adamantane derivative 5 is a potent PD-L1 binding with a reduced antioxidant potential and no aldehyde reactivity. The nature of the substituent on the phenyl-pyrazolone core modulates the antioxidant capacity and reactivity toward aromatic aldehydes. The molecular signature of the compound can be adapted at will, to confer additional properties to these PD-L1 binders.

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23

Cho, Joungmo, Venkata Subbaiah Sadu, Yohan Han, Yunsoo Bae, Hwajeong Lee, and Kee-In Lee. "Structural Requirements of 1-(2-Pyridinyl)-5-pyrazolones for Disproportionation of Boronic Acids." Molecules 26, no. 22 (November 11, 2021): 6814. http://dx.doi.org/10.3390/molecules26226814.

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We observed an unusual formation of four-coordinate boron(III) complexes from the reaction of 1-(2-pyridinyl)-5-pyrazolone derivatives with arylboronic acids in the basic media. The exact mechanism is not clear; however, the use of unprotected boronic acid and the presence of a bidentate ligand appeared to be the key structural requirements for the transformation. The results suggest that base-promoted disproportionation of arylboronic acid with the assistance of the [N,O]-bidentate ligation of 1-(2-pyridinyl)-5-pyrazolone should take place and facilitate the formation of pyrazole diarylborinate. Experiments to obtain a deeper understanding of its mechanism are currently underway.

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24

Mahajan, Suruchi, Pankaj Chauhan, Uğur Kaya, Kristina Deckers, Kari Rissanen, and Dieter Enders. "Enantioselective synthesis of pyrazolone α-aminonitrile derivatives via an organocatalytic Strecker reaction." Chemical Communications 53, no. 49 (2017): 6633–36. http://dx.doi.org/10.1039/c7cc02874a.

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A highly enantioselective organocatalytic Strecker reaction of pyrazolone-derived ketimines with TMSCN has been developed providing an efficient entry to pyrazolone α-aminonitrile derivatives with a tetra-substituted stereocenter.

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25

Shyshkina, Olena O., Volodymyr V. Medviediev, Oleg V. Shishkin, Andrii I. Kysil, and Yulian M. Volovenko. "Unexpected synthesis of pyrazolone derivatives." Tetrahedron 71, no. 8 (February 2015): 1283–86. http://dx.doi.org/10.1016/j.tet.2014.12.082.

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26

Achuthanandhan, Jyothi, and Baskar Lakshmanan. "Docking studies of tetra substituted pyrazolone derivatives as potential antiviral agents." JOURNAL OF PHARMACEUTICAL CHEMISTRY 5, no. 2 (December 20, 2018): 5–8. http://dx.doi.org/10.14805/jphchem.2018.art103.

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In an attempt to find potential antiviral agents, a series of pyrazolones (PA1-PA6& PC1-PC6) were designed and evaluated for their DENVNS5 (RNA-dependent RNA polymerase) inhibitory activity. Molecular docking studies of all the designed compounds into the binding site of DENVNS5 (PDB Code: 4C11) were performed to gain a comprehensive understanding into rational binding modes. These compounds were also screened for in silico drug-likeliness properties on the basis of the absorption, distribution, metabolism and excretion (ADME) prediction. Among all the synthesized compounds, analogue PA6showed superior inhibitory activity against RNA dependent RNA polymerase. SAR study indicated that the presence of an electron withdrawing substitution on pyrazolone derivatives significantly improves its binding interaction with the protein.Results of ADME prediction revealed that most of these compounds showed in silico drug-likeliness.

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27

Parveen, Mehtab, Shaista Azaz, Ali Mohammed Malla, Faheem Ahmad, Musheer Ahmad, and Mayank Gupta. "An SiO2/ZnBr2 mediated expeditious approach to 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one derivatives in water under microwave irradiation." RSC Advances 6, no. 1 (2016): 148–62. http://dx.doi.org/10.1039/c5ra21146h.

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28

Ahmed, Badie, and Jasim Abdullah. "Ultrasound Assisted Synthesis Of Pyrazolone Derivatives." JOURNAL OF EDUCATION AND SCIENCE 26, no. 5 (December 1, 2013): 57–63. http://dx.doi.org/10.33899/edusj.2013.163055.

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29

Pavlov, P. T., A. F. Goleneva, A. E. Lesnov, and T. S. Prokhorova. "Biological activity of some pyrazolone derivatives." Pharmaceutical Chemistry Journal 32, no. 7 (July 1998): 370–72. http://dx.doi.org/10.1007/bf02645994.

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30

Ishihara, Yoshimi, Takeyuki Ito, Hiroshi Saito, and Jiro Takano. "Reaction of acridine with pyrazolone derivatives." Journal of Heterocyclic Chemistry 42, no. 5 (July 2005): 963–67. http://dx.doi.org/10.1002/jhet.5570420533.

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31

Zonouz, Adeleh Moshtaghi, Masoumeh Beiranvand, Rahim Mohammad-Rezaei, and Soheila Naderi. "Green and Efficient Synthesis of Fluorescent Bis(pyrazolyl)methanes in Choline Chloride/Urea Deep Eutectic Solvent." Letters in Organic Chemistry 17, no. 7 (July 7, 2020): 548–54. http://dx.doi.org/10.2174/1570178617666191111121813.

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A series of pyrazole-based heteroaromatic compounds were synthesized by the reaction of 3-methyl-5-pyrazolone and aromatic aldehydes in Choline chloride/urea DES as a green solvent. This simple and green procedure has advantages such as easy operation, short reaction times, efficient yields, low cost and minimum use of hazardous solvents and catalysts. The structure of compounds was determined by IR, 1H and 13C NMR spectra, and the crystal structure of 4a was confirmed using X-ray crystallographic analysis. The optical properties of Pyrazole derivatives 4a-g have also been studied with UV/vis and fluorescence spectroscopy. All of these pyrazole-containing heteroaromatic compounds displayed maximum emission peak from 340 to 360 nm.

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32

Kashinath, Dhurke, Kota Sathish, and Sakkani Nagaraju. "Synthesis of Spiro Pyrazolone-Oxindole and Bicyclic Pyrazolone Derivatives via Solvent-Dependent Regioselective Aza-1,4/1,6-Michael and Intramolecular Cycloaddition under Catalyst-Free Conditions." SynOpen 05, no. 02 (April 13, 2021): 123–33. http://dx.doi.org/10.1055/a-1480-9837.

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AbstractA solvent-dependent, highly regioselective [3+2]-cycloaddition reaction of isoxazole-styrenes and azomethine imines under catalyst-free conditions is reported, furnishing a library of pyrazolone–spirooxindole hybrids. Good regioselectivity for the isomeric structures was achieved by the reaction of isoxazole-styrene and azomethine imine in different solvents and temperatures. The developed method was extended for the synthesis of tri-substituted dinitrogen-fused pyrazolones by using a 1,6-Michael addition reaction. Furthermore, the isoxazole moiety was converted into a carboxylic acid as a model study via ring opening.

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33

Guo, Jixi, Yucai Zhang, Dianzeng Jia, Mingxi Guo, and Yinhua Li. "Design and synthesis of reversible solid-state photochromic pyrazolones by introducing a pyridine ring." Photochemical & Photobiological Sciences 15, no. 10 (2016): 1222–26. http://dx.doi.org/10.1039/c6pp00119j.

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34

Wang, Jun, Guan-Cheng Xu, Yan-Ping Zhang, Hua-Ying Luo, Jin-Yao Li, Li Zhang, and Dian-Zeng Jia. "Copper(ii) complexes with 4-acyl pyrazolone derivatives and diimine coligands: synthesis, structural characterization, DNA binding and antitumor activity." New Journal of Chemistry 43, no. 6 (2019): 2529–39. http://dx.doi.org/10.1039/c8nj02695e.

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35

Deyab, M. A., A. S. Fouda, M. M. Osman, and S. Abdel-Fattah. "Mitigation of acid corrosion on carbon steel by novel pyrazolone derivatives." RSC Advances 7, no. 71 (2017): 45232–40. http://dx.doi.org/10.1039/c7ra08761f.

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36

Ao, Chaoqun, Jingjing Huang, Xinfang Xu, Shikun Jia, Zhenghui Kang, and Wenhao Hu. "A Rh-catalyzed three-component reaction for the diastereoselective synthesis of pyrazolone derivatives with contiguous quaternary stereocenters." Organic & Biomolecular Chemistry 18, no. 18 (2020): 3466–70. http://dx.doi.org/10.1039/d0ob00482k.

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Efficient approach for the facile construction of polyfunctionalized pyrazolone derivatives bearing two contiguous quaternary stereocenters in good yields with high regioselectivities and excellent diastereoselectivities.

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37

Marzouk, Magda Ismail, Galal Hosni Sayed, Mohamed Said Abd ElHalim, and Salma Yehia Mansour. "Synthesis and characterization of novel pyrazolone derivatives." European Journal of Chemistry 5, no. 1 (March 31, 2014): 24–32. http://dx.doi.org/10.5155/eurjchem.5.1.24-32.870.

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38

Radini, Ibrahim. "Design, Synthesis, and Antimicrobial Evaluation of Novel Pyrazoles and Pyrazolyl 1,3,4-Thiadiazine Derivatives." Molecules 23, no. 9 (August 21, 2018): 2092. http://dx.doi.org/10.3390/molecules23092092.

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A novel series of pyrazolyl 1,3,4-thiadiazines 5a–c, 8a–c, 12, 15a–c, 17a–c, and 20 was prepared from the reaction of pyrazole-1-carbothiohydrazide 1a,b with 2-oxo-N′-arylpropanehydrazonoyl chloride, 2-chloro-2-(2-arylhydrazono)acetate, and 3-bromoacetylcoumarin. Moreover, the regioselective reaction of 5-pyrazolone-1-carbothiohydrazide 1a with 4-substituted diazonium salts and 4-(dimethylamino)benzaldehyde gave the corresponding hydrazones 21a–c and 22. The newly prepared compounds were characterized by spectroscopy and elemental analysis. Many new synthesized compounds showed considerable antimicrobial activity against tested microorganisms. Hydrazones 21a–c and 22 showed remarkable antibacterial and antifungal activities. 4-(2-(p-tolyl)hydrazineylidene)-pyrazole-1-carbothiohydrazide 21a displayed the highest antibacterial and antifungal activities with minimum inhibitory concentration (MIC) values lower than standard drugs chloramphenicol and clotrimazole, in the range of 62.5–125 and 2.9–7.8 µg/mL, respectively.

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De Crescentini, L., F. R. Perrulli, G. Favi, S. Santeusanio, G. Giorgi, O. A. Attanasi, and F. Mantellini. "Reactions of 1,2-diaza-1,3-butadienes with propargyl alcohol as an approach to novel bi-heterocyclic systems." Organic & Biomolecular Chemistry 14, no. 37 (2016): 8674–78. http://dx.doi.org/10.1039/c6ob01595f.

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Starting from easily available 1,2-diaza-1,3-dienes and propargyl alcohol, spyro-bicyclic systems, through 2,3-Wittig rearrangement, and pyrazolone–triazole derivatives, through a typical “click reaction”, are obtained.

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Li, Jun-Hua, and Da-Ming Du. "Correction: Enantioselective synthesis of chiral heterocycles containing both chroman and pyrazolone derivatives catalysed by a chiral squaramide." Organic & Biomolecular Chemistry 13, no. 26 (2015): 7337. http://dx.doi.org/10.1039/c5ob90099a.

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Correction for ‘Enantioselective synthesis of chiral heterocycles containing both chroman and pyrazolone derivatives catalysed by a chiral squaramide’ by Jun-Hua Li, et al., Org. Biomol. Chem., 2015, 13, 5636–5645.

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MOHAMMAD, Abeer Essa, Munther Abduljaleel MUHAMMAD-ALI, and Ekhlas Qanber JASIM. "SYNTHESIS, DOCKING STUDY, AND BIOLOGICAL EVALUATION OF 4-AMINOANTIPYRINE-ISONIAZID DERIVATIVES AS A HYBRID ANTIBACTERIAL AND ANALGESIC AGENTS." Periódico Tchê Química 19, no. 42 (October 11, 2022): 12–28. http://dx.doi.org/10.52571/ptq.v19.n42.2022.02_munther_pgs_12_28.pdf.

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Background: 4-aminoantipyrine is one of the pyrazolone derivatives, it has been exposed to a large range of biological activities as an antimicrobial, analgesic, antiviral, anti-inflammatory, and anticancer compound. One of the important derivatives is the hybrid pyrazolone which includes two organic or inorganic drugs attached to give new pharmaceutical agents which may be the same or different activity from the original drugs. Aim: This research aimed to synthesize novel compounds derived from 4-aminoantipyrine and test their biological activity. Methods: Synthesis of 4-aminoantipyrine derivatives, which contain structurally two heterocyclic moieties, pyrazolone with oxadiazole, triazole, or tetrazole rings. The structures of the compounds were identified by 1H-NMR and FT-IR spectroscopy. The in vitro, developed compounds were screened for their analgesic activity and antibacterial activity against medically important gram (+) and gram (-) bacterial strains. Results: The antibacterial evaluation tests showed that some compounds gave good activity and others had no activity. The analgesic activity referred that the synthesized compounds had promising potency. The free binding energy (S) of the compounds with the protein 6B73 were ?4.90 to ?8.76 kcal/mol, whereas free energy (S) with the protein 5C1M gave ?4.94 to ?9.21 kcal/mol. Discussion: Among the tested compounds, it was found that compounds 1a, 4b, and 5a had more potent antibacterial activity. The analgesic activity showed that compounds 1b, 4b, and 5a gave the best activity using hot plate methods compared with the standard drug. On the other hand, compounds 1a, 4b, and 5b gave good activity using the writhing test method. Conclusions: Potent, good, or moderate analgesic and antibacterial agents were synthesized using simple and high-yield chemical reactions. The chemical reactions include the synthesis of hybrid antibacterial and analgesic agents using pyrazolone compounds.

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Regnault, Romain, Frédérique Klupsch, Hassiba El-Bouazzati, Romain Magnez, Raphaël Le Biannic, Natascha Leleu-Chavain, Hania Ahouari, et al. "Novel PD-L1-Targeted Phenyl-Pyrazolone Derivatives with Antioxidant Properties." Molecules 28, no. 8 (April 15, 2023): 3491. http://dx.doi.org/10.3390/molecules28083491.

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Orally-active anticancer small molecules targeting the PD-1/PD-L1 immune checkpoint are actively searched. Phenyl-pyrazolone derivatives with a high affinity for PD-L1 have been designed and characterized. In addition, the phenyl-pyrazolone unit acts as a scavenger of oxygen free radicals, providing antioxidant effects. The mechanism is known for the drug edaravone (1) which is also an aldehyde-reactive molecule. The present study reports the synthesis and functional characterization of new molecules (2–5) with an improved anti-PD-L1 activity. The leading fluorinated molecule 5 emerges as a potent checkpoint inhibitor, avidly binding to PD-L1, inducing its dimerization, blocking PD-1/PD-L1 signaling mediated by phosphatase SHP-2 and reactivating the proliferation of CTLL-2 cells in the presence of PD-L1. In parallel, the compound maintains a significant antioxidant activity, characterized using electron paramagnetic resonance (EPR)-based free radical scavenging assays with the probes DPPH and DMPO. The aldehyde reactivity of the molecules was investigated using 4-hydroxynonenal (4-HNE), which is a major lipid peroxidation product. The formation of drug-HNE adducts, monitored by high resolution mass spectrometry (HRMS), was clearly identified and compared for each compound. The study leads to the selection of compound 5 and the dichlorophenyl-pyrazolone unit as a scaffold for the design of small molecule PD-L1 inhibitors endowed with antioxidant properties.

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Sun, Bing-Bing, Jun-Bo Chen, Jun-Qi Zhang, Xiao-Peng Yang, Hao-Peng Lv, Zheng Wang, and Xing-Wang Wang. "Organo-catalyzed asymmetric cascade annulation reaction for the construction of bi-spirocyclic pyrazolone and oxindole derivatives." Organic Chemistry Frontiers 7, no. 5 (2020): 796–809. http://dx.doi.org/10.1039/d0qo00001a.

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Organo-catalyzed tandem reaction between β,γ-unsaturated α-ketoesters and α-arylidene pyrazolinones was developed, and it provided chiral bi-spirocyclic pyrazolone and oxindole derivatives in high yields with good to excellent stereoselectivity.

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Arora, Kishor. "In-Silico QSAR Studies of Some Pyrazolone Compounds." European Journal of Advanced Chemistry Research 4, no. 4 (October 18, 2023): 1–8. http://dx.doi.org/10.24018/ejchem.2023.4.4.148.

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In-silico studies are fascinating the workers/scientists working in the field of drugs designing. The present paper includes QSAR studies related to some novel substituted pyrazolone derivatives. A series of seven pyrazolone compounds is taken for these studies. All the compounds were evaluated for antimicrobial activity against six different microbes viz. bacterial and fungal microbes. Their reported antimicrobial activities were used for Quantitative Structure Activity Relationship (QSAR) studies. The correlation between different computed molecular descriptor of the compounds with their reported biological activities has also been studied and reported in the paper.

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45

El-Mahdy, Kamelia. "Synthesis of Some New Tetracyclic Pyrimidine Derivatives Using Exocyclic α,β-Unsaturated Ketone and Evaluation of Their Antitumor Activities." JOURNAL OF ADVANCES IN CHEMISTRY 12, no. 8 (May 1, 2016): 311–17. http://dx.doi.org/10.24297/jac.v12i8.2840.

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Thiazolopyrimidine 2 was obtained from the reaction of dihydropyrimidinone with chloroacetic acid and benzaldehyde. Thiazolopyrimidine 2 containing an α,β-unsaturated ketonic function [-CH=CH-CO-] has been used as a component of Michael addition with an equimolar amount of dinucleophiles to give a series of novel tetracyclic pyrimidine derivatives. Treatment of thiazolopyrimidine 2 with uracil, aminotriazole, cyanoacetic acid hydrazide, o-phenylenediamine or diaminopyridine afforded the corresponding pyridopyrimidine, triazolopyrimidine, pyrazolone, benzodiazepine and triazepine derivative, respectively. The detailed synthesis, spectroscopic data, and antitumor activity for synthesized compounds were reported.

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46

El-Mahdy, Kamelia. "Synthesis of Some New Tetracyclic Pyrimidine Derivatives Using Exocyclic α,β-Unsaturated Ketone and Evaluation of Their Antitumor Activities." JOURNAL OF ADVANCES IN CHEMISTRY 4, no. 1 (April 19, 2008): 311–17. http://dx.doi.org/10.24297/jac.v4i1.960.

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Thiazolopyrimidine 2 was obtained from the reaction of dihydropyrimidinone with chloroacetic acid and benzaldehyde. Thiazolopyrimidine 2 containing an α,β-unsaturated ketonic function [-CH=CH-CO-] has been used as a component of Michael addition with an equimolar amount of dinucleophiles to give a series of novel tetracyclic pyrimidine derivatives. Treatment of thiazolopyrimidine 2 with uracil, aminotriazole, cyanoacetic acid hydrazide, o-phenylenediamine or diaminopyridine afforded the corresponding pyridopyrimidine, triazolopyrimidine, pyrazolone, benzodiazepine and triazepine derivative, respectively. The detailed synthesis, spectroscopic data, and antitumor activity for synthesized compounds were reported.

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47

Ashtekar, Harsha, Prarambh S. R. Dwivedi, Natasha Aggarwal, Zeena Fernandes, and Nimmy Varghese. "In-silico Validation of Pyrazolone Derivatives as the Potent Scaff old for Modulating Protein Abnormalities Associated with Parkinson’s Disease." INTERNATIONAL JOURNAL OF DRUG DELIVERY TECHNOLOGY 13, no. 01 (March 25, 2023): 1–9. http://dx.doi.org/10.25258/ijddt.13.1.01.

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Aim: We explored pyrazolone derivatives for anti-Parkinson’s activity using in-silico tools to identify novel lead hits against Parkinson’s disease. Background: Parkinson’s disease is the most predominant neuronal degenerative disorder, caused by protein aggregation and dopamine imbalance. The available therapeutic agents on prolonged exposure lead to severe adverse eff ects and provide only symptomatic relief. Therefore, it is a need for novel drug molecules that would modulate the disease condition. Objectives: To identify novel hit molecule for a sequence of molecules designed using pyrazolone as a parent moiety by computer-aided drug design techniques. Materials and Methods: Derivatives are generated by various substituted functional groups and further, pharmacokinetic profi le, the biological spectrum, adverse drug eff ect, molecular docking, molecular dynamic, and MMPBSA evaluation was performed. Results: Thirty-four compounds follow a pharmacokinetic profi le. 15 compounds were predicted to possess a positive central nervous system activity score. The compounds C13, C12, C14, A1, C9, and C7 possessed the highest binding affi nity of -7.81, -3.15, -8.49, -3.43, -6.09, and -2.77 kcal/mol with various targets involved in Parkinson’s disease. Compound C13 exhibit ed highest binding score of -9.78 kcal/mol formono amino oxidase-B. Conclusion: From our investigations, we hope that novel substituted pyrazolone derivatives can act as an assuring virtual hit molecule for developing anti-Parkinson’s agents. These predictions obtained via in-silico techniques could aid the development of pharmacological inhibitors for Parkinson’s disease.

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Yoon, Sanghyun, Byunghun Choi, Md Morshedur Rahman, Santosh Kumar, Shekh Md Mamun Kabir, and Joonseok Koh. "Dyeing of Polyester with 4-Fluorosulfonylphenylazo-5-pyrazolone Disperse Dyes and Application of Environment-Friendly Aftertreatment for Their High Color Fastness." Materials 12, no. 24 (December 14, 2019): 4209. http://dx.doi.org/10.3390/ma12244209.

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Dyeing and fastness properties of a series of 4-fluorosulfonylphenylazo-5-pyrazolone dyes on polyester were investigated in this study. The 4-nitrophenylazo-5-pyrazolone dyes were also synthesized to compare their dyeing and fastness properties on polyester with those of fluorosulfonyl-substituted analogues. The substantivity of 4-arylazo-5-pyrazolone derivatives containing a p-fluorosulfonyl group in the diazo component was lower than that of their nitro analogues which have a higher extinction coefficient and higher affinity because of the polar nitro group. They showed relatively hypsochromic color and lower chroma on polyester compared with their nitro analogues because of the relatively weaker electron-accepting power of the fluorosulfonyl group compared to the nitro group. Disperse dyeing of polyester with 4-fluorosulfonylphenylazo-5-pyrazolone disperse dyes achieved high color fastness and reduces the adverse environmental impact of the dyeing process by providing the option of performing alkali clearing instead of reductive clearing, which has high biological oxygen demand when discharged into the dyeing effluent and generates carcinogenic aromatic amines.

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Pégurier, Cécile, Philippe Collart, Pierre Danhaive, Sabine Defays, Michel Gillard, Frédéric Gilson, Thierry Kogej, et al. "Pyrazolone methylamino piperidine derivatives as novel CCR3 antagonists." Bioorganic & Medicinal Chemistry Letters 17, no. 15 (August 2007): 4228–31. http://dx.doi.org/10.1016/j.bmcl.2007.05.035.

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Wang, Jin-Jun, Bing-Zhu Yin, Gui-Ji Jiang, and Kimiaki Imafuku. "Synthesis of isochroman-fused pyrazolone and pyrimidine derivatives." Journal of Heterocyclic Chemistry 27, no. 5 (July 1990): 1181–84. http://dx.doi.org/10.1002/jhet.5570270504.

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