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Journal articles on the topic 'Quinazoline-4(3H)-ones'

Author: Grafiati

Published: 18 May 2024

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1

Widiyana, Anita Puspa. "COMPUTATION DESIGN OF QUINAZOLINE-4(3H)-ON DERIVATIVES AS CYCLOOXYGENASE-2 (COX-2) INHIBITOR." Jurnal Farmasi Sains dan Praktis 7, no. 2 (November 1, 2021): 163–70. http://dx.doi.org/10.31603/pharmacy.v7i2.4827.

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The 3-(benzylideneamino)-2-(2,4-dichlorophenyl)-quinazoline-4(3H)-ones (BDCQ) are compounds developed as anticancer drugs and quinazolines. The activity and bioavailability of BDCQ derivatives as anticancer compounds that inhibit COX-2 can be predicted by computer programs and online servers. Substituents are added at positions 2 and 3 to the quinazoline-4(3H)-on ring, such as -H, -NO2, -OCH3, -N(CH3)2, -SO2NH2, -OH, and –OCH3. QSAR as COX-2 inhibitor analysis was performed by SPSS Ver. 21 software. Lipinski’s rule of five for determining bioavailability is performed by an online server at http://ilab.acdlabs.com. The best QSAR equation used to predict the COX-2 inhibitors from these compounds is RS-pred = 0.372 Log P + 0.014 MR + 0.979 Etot – 4.859, with n= 12, R = 0.998; SE = 0.356, F = 805.252 and sig = 0.001. Six compounds were predicted to have good oral bioavailability, such as 3-(benzylideneamino)-2-(2,4-dichlorophenyl)quinazoline-4(3H)-one, 2-(2,4-dichlorophenyl)-3-((2-nitrobenzylidene)amino)quinazoline-4(3H)-one, 2-(2,4-dichlorophenyl)-3-((3-nitrobenzylidene)amino)quinazoline-4(3H)-one, 2-(2,4-dichlorophenyl)-3-((2-methoxybenzilidene)amino)quinazoline-4(3H)-one, 2-(2,4-dichlorophenyl)-3-((3-methoxybenzylidene)amino)quinazolin-4(3H)-one, and 2-(((2-(2,4-dichlorophenyl)-4-oxoquinazolin-3(4H)-yl)imino)methyl)- benzenesulfonamide. This research can be used as an in vitro and in vivo study for BDCQ derivatives as anticancer drugs.

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2

Appani, Ramgopal, Baburao Bhukya, and Kiran Gangarapu. "Synthesis and Antibacterial Activity of 3-(Substituted)-2-(4-oxo-2-phenylquinazolin-3(4H)-ylamino)quinazolin-4(3H)-one." Scientifica 2016 (2016): 1–5. http://dx.doi.org/10.1155/2016/1249201.

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A series of novel 3-(substituted)-2-(substituted quinazolinylamino)quinazolin-4(3H)-ones were synthesized by the reaction of 3-(substituted)-2-hydrazino-quinazoline-4(3H)-ones with 2-phenyl-3,1-benzoxazin-4-one. The starting materials 3-(substituted)-2-hydrazino-quinazolin-4(3H)-ones were synthesized from various primary amines by a multistep synthesis. All the title compounds were tested for their antibacterial activity using ciprofloxacin as reference standard. Compounds 3-(4-fluorophenyl)-2-(4-oxo-2-phenylquinazolin-3(4H)-ylamino)quinazolin-4(3H)-one (9a) and 3-(4-chlorophenyl)-2-(4-oxo-2-phenylquinazolin-3(4H)-ylamino)quinazolin-4(3H)-one (9h) emerged as the most active compounds of the series. These compounds have shown most potent antibacterial activity against the tested organisms ofProteus vulgarisandBacillus subtilishaving zone of inhibition values of 1.1 cm and 1.4 cm for compound9a1.2 cm and 1.0 cm for compound9h, respectively.

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3

Špirková, Katarína, and Štefan Stankovský. "Annelation to the Quinazoline Ring. Preparation of Some Substituted 2H-Imidazo- and 2,3-Dihydropyrimido[1,2-c]quinazolines." Collection of Czechoslovak Chemical Communications 61, no. 6 (1996): 957–61. http://dx.doi.org/10.1135/cccc19960957.

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Preparation of some substituted 2H-imidazo[1,2-c]quinazolin-3-ones (2a-2f) and 2,3-dihydropyrimido[1,2-c]quinazolin-4-ones (3a-3c) by reaction of corresponding 3H-quinazoline-4-thiones (1a-1d) with amino acid esters is described. IR, 1H NMR and 13C NMR spectra of the compounds synthesized are presented.

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4

Tiwari, Abhishek R., and Bhalchandra M. Bhanage. "Transition-metal free synthesis of quinazolinones via tandem cyclization of 2-halobenzoic acids with amidines." RSC Advances 5, no. 70 (2015): 57235–39. http://dx.doi.org/10.1039/c5ra11159e.

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5

Peter Osarodion Osarumwense, Mary Olire Edema, and Cyril Odianosen Usifoh. "Synthesis and antibacterial activities of quinazolin-4(3h)-one, 2-methyl-4(3h)-quinazolinone and 2–phenyl-4(3h)-quinazolinone." International Journal of Biological and Pharmaceutical Sciences Archive 1, no. 2 (April 30, 2021): 077–84. http://dx.doi.org/10.30574/ijbpsa.2021.1.2.0027.

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Background: Quinazoline and quinazolinone scaffolds represent an important class of biologically active nitrogen heterocyclic compounds. Many marketed drugs are based on these moieties. A diverse range of molecules with quinazoline/quinazolinone moieties have been reported to exhibit broad spectrum of biological activities Objective: This study is aimed at the synthesis of these quinazolinone derivatives, quinazolin-4(3H)-One, 2-Methyl-4(3H)-quinazolinone and 2–Phenyl-4(3H)-quinazolin-4(3H)–one and evaluate them for their antibacterial activities. Method: The consolidation of 2-amino-methyl-4-methoxybenzoate with acetic anhydride produced the cyclic compound 2-methyl-4, 5-disubstituted-1, 3-benzo-oxazine-4-one which also produce a novel 2,3-disubstituted quinazolin-4 ones via the reaction with hydrazine hydrate. The quinazolinone derivatives quinazolin-4(3H)-One, 2-Methyl-4(3H)-quinazolinone and 2–Phenyl-4(3H)-quinazolin-4(3H)–one were evaluated pharmacologically for their in vivo analgesic activities by acetic acid induced writhing in mice. The compounds synthesized were assuredly validated by means of Infrared, Nuclear Magnetic Resonance (1H and 13C), Gas Chromatography Mass Spectrophotometer and Elemental analysis. The synthesized compounds were tested for their antibacterial activity.Compounds 1,2 and 3 showed significant antibacterial activities. Discussion: Compound 1 was identified by the absence of methyl group and the presence of methyl group for compound 2. The test analysed compounds exhibited significant antibacterial activities. The compounds synthesized exhibited promising antibacterial activities against the tested organisms. Conclusion: The compounds have high antibacterial activities. Compound 2 has a higher activity compared to Compound 1 and 3. Compound 2 has a higher antibacterial against Escherichia coli, Klebsiella pneumonia and Pseudomonas aeuriginosa

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6

Oluwaseye, Adedirin, A. UZAIRU, G. A. SHALLANGWA, and S. E. ABECHI. "QSAR STUDIES ON DERIVATIVES OF QUINAZOLINE-4(3H)-ONES WITH ANTICONVULSANT ACTIVITIES." Journal of Engineering and Exact Sciences 4, no. 2 (July 4, 2018): 0255–64. http://dx.doi.org/10.18540/jcecvl4iss2pp0255-0264.

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7

Srivastav, Manish, MD Salahuddin, and S. M. Shantakumar. "Synthesis and Anti-inflammatory Activity of Some Novel 3-(6-Substituted-1, 3-benzothiazole-2-yl)-2-[{(4-substituted phenyl) amino} methyl] quinazolines-4 (3H)-ones." E-Journal of Chemistry 6, no. 4 (2009): 1055–62. http://dx.doi.org/10.1155/2009/507052.

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A series of novel 3-(6-substituted-1, 3-benzothiazole-2-yl)-2-[{(4-substituted phenyl) amino} methyl] quinazolines-4(3H)-ones were synthesized by treating 2-(chloromethyl)-3-(6-substituted-1, 3-benzothiazole-2-yl) quinazoline-4-(3H)-one (IIa-d) with various substituted amine. The compounds (IIa-d) prepared by treating 2-[(chloroacetyl) amino] benzoic acid with different 2-amino-6-substituted benzothiazole. Elemental analysis, IR,1HNMR and mass spectral data confirmed the structure of the newly synthesized compounds. Synthesized quinazolines-4-one derivative were investigated for their anti-inflammatory and antibacterial activity.

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8

Wright, William B., Andrew S. Tomcufcik, Peter S. Chan, Joseph W. Marsico, and Jeffery B. Press. "Thromboxane synthetase inhibitors and antihypertensive agents. 4. N-[(1H-imidazol-1-yl)alkyl] derivatives of quinazoline-2,4(1H,3H)-diones, quinazolin-4(3H)-ones, and 1,2,3-benzotriazin-4(3H)-ones." Journal of Medicinal Chemistry 30, no. 12 (December 1987): 2277–83. http://dx.doi.org/10.1021/jm00395a016.

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9

Barlaam, Bernard, Craig S. Harris, Jonathan Lecoq, and Ha Thi Hoang Nguyen. "Preparation of 6-aminoquinazolin-4(3H)-ones via direct SNAr on the quinazoline ring." Tetrahedron 68, no. 2 (January 2012): 534–43. http://dx.doi.org/10.1016/j.tet.2011.11.008.

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10

Naidu, P. Paradesi, Akula Raghunadh, K. Raghavendra Rao, Ramamohan Mekala, J. Moses Babu, B. R. Rao, V. Siddaiah, and Manojit Pal. "Urea/Thiourea as Ammonia Surrogate: A Catalyst-Free Synthesis of 2-Substituted 2,3-Dihydroquinazolin-4(1H)-ones/Quinazoline-4(3H)-ones." Synthetic Communications 44, no. 10 (April 29, 2014): 1475–82. http://dx.doi.org/10.1080/00397911.2013.862551.

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11

Kumar, Ashok, Pratibha Sharma, Prerna Kumari, and Bhagwan Lal Kalal. "Exploration of antimicrobial and antioxidant potential of newly synthesized 2,3-disubstituted quinazoline-4(3H)-ones." Bioorganic & Medicinal Chemistry Letters 21, no. 14 (July 2011): 4353–57. http://dx.doi.org/10.1016/j.bmcl.2011.05.031.

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12

Tashrifi, Zahra, Mohammad Mohammadi-Khanaposhtani, Mahmood Biglar, Bagher Larijani, and Mohammad Mahdavi. "Isatoic Anhydride: A Fascinating and Basic Molecule for the Synthesis of Substituted Quinazolinones and Benzo di/triazepines." Current Organic Chemistry 23, no. 10 (August 16, 2019): 1090–130. http://dx.doi.org/10.2174/1385272823666190701142930.

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This review article is focused on the synthesis of compounds with quinazolinones and benzo di/triazepine scaffolds. These invaluable derivatives are of great interest in medicinal and pharmaceutical studies because of their important biological properties. Quinazolinones have diverse applications due to their antibacterial, analgesic, antiinflammatory, antifungal, antimalarial, antihypertensive, CNS depressant, anticonvulsant, antihistaminic, antiparkinsonism, antiviraland and anticancer activities. On the other hand, pharmacological properties of benzodiazepines include antianxiety, anticancer, anticonvulsant, antagonists of cholecystokinin receptors (CCK), antileishmanial, sleep-inducing muscle relaxant and several other useful and interesting properties. As an example, three main categories of drugs, namely anxiolytics, sedative hypnotics (sleep inducers) and anticonvulsants are constructed by 1,4-benzodiazepines. Finally, benzotriazepines are believed to possess various pharmacological properties such as antipsychotic and antitumor activities. Hence, this review is divided into three major sections, considering quinazolinones, benzodiazepines and benzotriazepines. In the first section, we take a brief look at various approaches towards synthesis of substituted quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones. Also in this section, we try to give an overview of the synthetic routes and strategies recently reported for the generation of various classes of substituted 4(3H)-quinazolinones and 2,3-dihydroquinazolin-4(1H)-ones. Accordingly, quinazolin-4(3H)-ones, were subdivided into three major classes: 2-substituted, 3-substituted and 2,3-disubstituted-quinazolinones. 2,3- dihydroquinazolin-4(1H)-ones also were subdivided into six sub-categories: 2-monosubstituted, 2,2- disubstituted, 2,3-disubstituted, 1,2,3-trisubstituted, 2,2,3-trisubstituted 2,3-dihydroquinazolin-4(1H)-ones and boron-containing quinazoline-4(1H)-ones. In the other two sections, we cover the literature related to synthesis of benzo di/triazepine. The most recent developments are highlighted with a special emphasis on new synthetic routes based on isatoic anhydride as starting material.

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13

Beutner, Gregory, William Wertjes, Sloan Ayers, Qi Gao, and Eric Simmons. "A Divergent Nickel-Catalyzed Synthesis of Quinazolinediones and Benzoxazinone Imines." Synthesis 50, no. 22 (May 17, 2018): 4453–61. http://dx.doi.org/10.1055/s-0037-1610140.

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During exploration of the nickel(0)-catalyzed reaction of isocyanates and isatoic anhydrides, it was found that changes in the substitution pattern of the isocyanate led to constitutionally isomeric quinazolinediones [quinazoline-2,4(1H,3H)-diones] or benzoxazinone imines [2-imino-1,2-dihydro-4H-3,1-benzoxazin-4-ones]. Ligand and solvent screening experiments allowed for identification of conditions that could lead to each constitutional isomer in good to excellent levels of selectivity and yield. Comprehensive characterization of the previously poorly characterized benzoxazinone imines is also provided.

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14

Kut, D. Zh, M. M. Kut, M. Yг Onysko, and V. G. Lendel. "Electrophilic cyclization of propargyl thioethers of 3-methyl(phenyl)-2-(prop-2-yn-1-ylthio)-7-(trifluoromethyl)quinazolin-4(3H)-ones by tellurium tetrahalides." Voprosy Khimii i Khimicheskoi Tekhnologii, no. 6 (December 2021): 40–44. http://dx.doi.org/10.32434/0321-4095-2021-139-6-40-44.

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The paper presents the results of the study of the process of electrophilic intramolecular cyclization of 3-methyl(phenyl)-2-(prop-2-yn-1-ylthio)-7-(trifluoromethyl)quinazolin-4(3H)-ones by tellurium tetrahalides. 3-Methyl(phenyl)-2-(prop-2-yn-1-ylthio)-7-(trifluoromethyl)quinazolin-4(3H)-ones were prepared by the alkylation of the corresponding thions with propargyl bromide in an alkaline alcohol medium. It is found that the interaction of propargyl thioethers of 3-substituted 2-thioxo-7-(trifluoromethyl)-2,3-dihydroquinazolin-4(1H)-ones with tellurium tetrahalides, which were obtained in situ from tellurium dioxide and six equivalents of corresponding concentrated hydrohalic acid, leads to the formation of halides of angular 4-methyl(phenyl)-5-oxo-1-((trihalotellanyl)methylidene)-8-(trifluoromethyl)-1,2,4,5-tetrahydrothiazolo[3,2-a]quinazolin-10-iums. The most optimal conditions for the tellurium-induced electrophilic heterocyclization of propargyl thioethers with tellurium terahalides are the use of glacial acetic acid as a solvent and stirring of the reaction mixture at room temperature for 24 hours. It is found that the electrophilic cyclization of 3-methyl(phenyl)-2-(prop-2-yn-1-ylthio)-7-(trifluoromethyl)quinazolin-4(3H)-ones by tellurium tetrahalides occurs stereoselectively with the formation of one configurational isomer. The influence of the nature of halogen in the electrophilic reagent and the substituent in position 3 of quinazoline is examined and it is found that these factors do not affect the regioselectivity of the electrophilic intramolecular cyclization process. As a result of the conducted study, potentially biologically active salts of tellurofunctionalized thiazolinoquinazolines of angular structure were received.

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15

Prabhakar, B., P. Lingaiah, and K. Laxma Reddy. "ESR and other spectral studies on copper(II) complexes with 2,3-disubstituted quinazoline-(3H)-4-ones." Polyhedron 9, no. 6 (January 1990): 805–11. http://dx.doi.org/10.1016/s0277-5387(00)81345-5.

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16

Kalogirou, Andreas S., Andreas Kourtellaris, and Panayiotis A. Koutentis. "Synthesis and Reactivity of 3′,5′-Dichloro-1H -spiro(quinazoline-2,4′-[1,2,6]thiadiazin)-4(3H )-ones." European Journal of Organic Chemistry 2019, no. 31-32 (June 7, 2019): 5462–74. http://dx.doi.org/10.1002/ejoc.201900576.

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17

Naidu, P. Paradesi, Akula Raghunadh, K. Raghavendra Rao, Ramamohan Mekala, J. Moses Babu, B. R. Rao, V. Siddaiah, and Manojit Pal. "ChemInform Abstract: Urea/Thiourea as Ammonia Surrogate: A Catalyst-Free Synthesis of 2-Substituted 2,3-Dihydroquinazolin-4(1H)-ones/Quinazoline-4(3H)-ones." ChemInform 45, no. 43 (October 10, 2014): no. http://dx.doi.org/10.1002/chin.201443172.

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18

Prabhakar, B., P. Lingaiah, and K. Laxma Reddy. "Synthesis and spectral studies on Co (II) and Ni (II) complexes with polyfunctional quinazoline-(3H)-4-ones." Proceedings / Indian Academy of Sciences 103, no. 5 (October 1991): 599–605. http://dx.doi.org/10.1007/bf02841060.

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19

Kulkarni, RS, NK Sathish, AA Kempwade, and SA Kavatagimath. "Synthesis and Evaluation of Novel Quinazolin-4-(3h)-one Analogues for their Anti-Inflammatory Activity." INTERNATIONAL JOURNAL OF PHARMACEUTICAL QUALITY ASSURANCE 14, no. 04 (December 25, 2023): 933–41. http://dx.doi.org/10.25258/ijpqa.14.4.20.

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New 2, 3-disubstituted quinazolin-4-(3H)ones was conceived and synthesized through the substitution of various primary amines at the 3-position and a range of aldehydes at the 2-position. These compounds were characterized using elemental analysis, IR spectroscopy, 1H NMR spectroscopy and MS. Subsequently, the anti-inflammatory activity of these newly developed quinazoline derivatives was investigated by in-vitro protein denaturation method. In-vitro studies revealed that compounds QB1, QB2, QB4, QB8, QB9, QF1, QF3, QF4, QF8 and QF10 have significant anti-inflammatory potential. In-vivo anti-inflammatory properties of QB2 and QF8 were tested in carrageenan-induced paw edema. Research findings demonstrated that compounds QB2 and QF8 have significant anti-inflammatory properties.

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20

Singh, Shiv Dev, Arvind Kumar, Firoz Babar, Neetu Sachan, and Arun Kumar Sharma. "Synthesis of Novel 3(N,N-dialkylamino)alkyl/phenyl Substituted Thieno [2,3-d]pyrimidinones as H1-Anti-Histaminic and Antimicrobial Agents." Current Bioactive Compounds 15, no. 1 (February 6, 2019): 63–70. http://dx.doi.org/10.2174/1573407214666180226130957.

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Background: Thienopyrimidines are the bioisoster of quinazoline and unlike quinazoline exist in three isomeric forms corresponding to the three possible types annulation of thiophene to the pyrimidine ring viz thieno[2,3-d] pyrimidine, thieno[3,2-d] pyrimidine and thieno[3,4-d]pyrimidine. Heterocyclic containing the thienopyrimidinone moiety exhibits various pronounced activities such as anti-hypertensive, analgesic and anti-inflammatory, antiviral, platelet aggregation inhibitory, antiprotozoal bronchodilatory, phosphodiesterase inhibitory, antihistaminic, antipsychotic and antimicrobial activity. Objective: Synthesis of novel 3(N,N-dialkylamino)alkyl/phenyl substituted thieno[2,3-d]pyrimidinones as H1-anti-histaminic and antimicrobial agents. Methods: A series of 3-[(N,N-dialkylamino)alkyl/phenyl]-2-(1H)thioxo-5,6,7,8-tetrahydrobenzo(b) thieno(2,3-d)pyrimidine-4(3H)-ones[4a-d], their oxo analogous [5a-d] and 3-[(N,N-dialkylamino)alkyl]- 2-chlorophenyl-5,6,7,8-tetrahydrobenzo(b)thieno(2,3-d)pyrimidine- 4 (3H)-ones[6a-d]derivative were synthesized from 2-amino-4,5,6,7-tetrahydrobenzo(b)thiophene-3-carboxylic acid by nucleophilic substitution of different N,N-dialkyl alkylene/phenylene diamines on activated 3-acylchloride moiety followed by cyclocondensation with carbon disulfide and ethanolic potassium hydroxide to get [4a-d] and in second reaction by condensation with 4-chlorobenzoyl chloride to get [6a-d] by single pot novel innovative route. The oxo analogous [5a-d] were prepared by treating derivatives [4a-d] with potassium permagnate in ethanolic KOH. The synthesized compound were evaluated for H1-antihistaminic and antimicrobial activities. Results: All synthesized compounds exhibited significant H1-antihistaminic activity by in vitro and in vivo screening methods and data were verified analytically and statistically. The compound 4a, 4b, 5a and 5b showed significant H1-antihistaminiic activity than the reference standard chlorpheniramine maleate. The compound 6d, 6c, 5c and 4c exhibited significant antimicrobial activity.

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Thuy, Linh Bui Thi, Phuoc Le Thien, Hien Dang Chi, Hai Ha Pham Thi, and Cong Nguyen Tien. "Synthesis and antibacterial activities of some novel hybrid compounds based on 2‐mercapto‐3‐arylquinazolin‐4(3H)‐one scaffold bearing specific coumarin." Vietnam Journal of Chemistry 61, S2 (November 2023): 131–36. http://dx.doi.org/10.1002/vjch.202300093.

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AbstractTwo series of novel hybrid compounds, in which a variety of 2‐mercapto‐3‐arylquinazolin‐4(3H)‐ones (3a‐d)/6‐bromo‐2‐mercapto‐3‐phenylquinazolin‐4(3H)‐one (9) act as fundamental moieties are incorporated in particular 3‐(2‐bromoacetyl)‐2H‐chromen‐2‐one (4) or 2‐chloro‐N‐(2‐oxo‐2H‐chromen‐3‐yl)acetamide (5) via alkylation of the thiol group in quinazolin‐4(3H)‐one ring, were synthesized. The key intermediates (3a‐d) and (9) were prepared by the reaction of anthranilic acid (1)/2‐amino‐5‐bromobenzoic acid (8) with carbon disulfide and appropriate aromatic amines in an alkaline medium. These compounds’ structures were confirmed by comparing their physical characteristics and spectral data to the earlier ones. Ten novel products (6a‐d, 7a‐d, 10, 11) were synthesized and the structures were determined by their IR, 1H‐NMR, 13C‐NMR and HR‐MS spectral data. Subsequently, their antimicrobial activities were estimated in vitro test against four bacterial strains including P. aeruginosa NRRL B‐14781 and E. coli NRRL B‐409 (Gram‐negative), B. cereus ATCC 10876 and L. monocytogenes ATCC 13932 (Gram‐positive), by agar well diffusion assay. The outcome showed that all hybrid compounds have potential inhibition of tested Gram‐negative bacteria. Compound (6d) revealed remarkable antibacterial effects on P. aeruginosa and E. coli growth. Besides, compounds (6a), (7a), (7d) and (10) have also inhibitory effects on B. cereus strain at tested concentrations. The compounds mentioned above contain the 3‐chlorophenyl/phenyl substituent at position 3 in the quinazoline ring.

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Sulthana M.T, Chitra K, and Alagarsamy V. "Synthesis of novel 4-oxo-N-(4-oxo-3-substituted-3,4-dihydroquinazolin-2-yl amino)-2-phenylquinazoline-3(4H)-carboxamidines as AntiHIV, antitubercular and antibacterial agents." International Journal of Research in Pharmaceutical Sciences 10, no. 3 (July 19, 2019): 2186–92. http://dx.doi.org/10.26452/ijrps.v10i3.1449.

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A series of novel 4-oxo-N-(4-oxo-3-substituted-3,4-dihydroquinazolin-2-yl amino)-2-phenylquinazoline-3(4H)-carboxamidines are prepared from methyl 4-oxo-2-phenylquinazoline-3(4H)-carbthioimidate & 3-(substituted)-2-hydrazino-quinazoline-4(3H)-ones. The starting material 4-oxo-2-phenylquinazoline-3(4H)-carbthioimidates were prepared from anthranilic acid while the 3-(substituted)-2-hydrazino-quinazolin-4(3H)-one was prepared from a range of 1° amines using multistep preparation. Entire synthesized analogues were screened for their antitubercular, anti-HIV and antibacterial activity. Among the series, N-(3-(4-nitrophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl amino)-4-oxo-2-phenylquinazoline-3(4H)-carboxamidine (BQC7) and N-(3-(4-chlorophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl amino)-4-oxo-2-phenylquinazoline-3(4H)-carboxamidine (BQC9) showed most potent activity against S. epidermidis, S. aureus & B. subtilis with the MIC of 3 µg/mL. The compound BQC7 displayed the antitubercular potency at 12.5 µg/mL and anti-HIV activity at 8.53 µg/mL against HIV1 and HIV2. Thus, these derivatives are useful in the development of novel antitubercular & antiHIV agents. The results obtained from this study confirm that the synthesized and biologically evaluated quinazolines showed promising antimicrobial, antitubercular and anti-HIV activities and are new scaffolds for antimicrobial activity.

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El-Messery, Shahenda M., Ghada S. Hassan, Mahmoud N. Nagi, El-Sayed E. Habib, Sarah T. Al-Rashood, and Hussein I. El-Subbagh. "Synthesis, biological evaluation and molecular modeling study of some new methoxylated 2-benzylthio-quinazoline-4( 3H )-ones as nonclassical antifolates." Bioorganic & Medicinal Chemistry Letters 26, no. 19 (October 2016): 4815–23. http://dx.doi.org/10.1016/j.bmcl.2016.08.022.

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24

Jatav, Varsha, Sushil Kashaw, and Pradeep Mishra. "Synthesis, antibacterial and antifungal activity of some novel 3-[5-(4-substituted phenyl) 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones." Medicinal Chemistry Research 17, no. 2-7 (December 14, 2007): 169–81. http://dx.doi.org/10.1007/s00044-007-9047-2.

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Jatav, Varsha, Pradeep Mishra, Sushil Kashaw, and J. P. Stables. "Synthesis and CNS depressant activity of some novel 3-[5-substituted 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones." European Journal of Medicinal Chemistry 43, no. 1 (January 2008): 135–41. http://dx.doi.org/10.1016/j.ejmech.2007.02.004.

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Jatav, Varsha, Pradeep Mishra, Sushil Kashaw, and J. P. Stables. "CNS depressant and anticonvulsant activities of some novel 3-[5-substituted 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones." European Journal of Medicinal Chemistry 43, no. 9 (September 2008): 1945–54. http://dx.doi.org/10.1016/j.ejmech.2007.12.003.

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El-Azab, Adel S., Nasr Y. Khalil, and Alaa A. M. Abdel-Aziz. "Remarkable Conversion of 2-Thioxo-2,3-dihydroquinazolin-4(1H)-ones into the Corresponding Quinazoline-2,4(1H,3H)-diones: Spectroscopic Analysis and X-Ray Crystallography." Journal of Chemistry 2021 (April 2, 2021): 1–8. http://dx.doi.org/10.1155/2021/6612177.

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A simple and efficient new synthetic method to obtain 3-substituted quinazolin-2,4-diones 9–16 by the reaction of 3-substituted 2-thioxo-quinazolin-4-ones 1–8 with sodamide under mild conditions was presented. The structure of the newly synthesized compounds was determined by infrared spectroscopy, UV-visible spectroscopy, nuclear magnetic resonance, and single-crystal X-ray crystallographic analysis. The crystal structure of 6-methyl-3-phenylquinazoline-2,4(1H,3H)-dione (11) [C15H12N2O2: MF = 252.27, triclinic, P-1, a = 7.8495 (13) Å, b = 12.456 (2) Å, c = 13.350 (2) Å, α = 103.322 (3)°, β = 90.002 (3)°, γ = 102.671 (4)°, V = 1237.5 (3) Å3, Z = 4, R = 0.0592, wR = 0.1699, S = 1.039] was determined. In the crystal cell, two identical conformers of compound 11 were found connected by intramolecular hydrogen bonds, responsible for the favourable occurrence of these two independent molecules.

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Patil, Avinash, Swastika Ganguly, and Sanjay Surana. "Synthesis and antiulcer activity of 2-[5-substituted-1-H-benzo(d) imidazol-2-yl sulfinyl]methyl-3-substituted quinazoline-4-(3H) ones." Journal of Chemical Sciences 122, no. 3 (May 2010): 443–50. http://dx.doi.org/10.1007/s12039-010-0052-5.

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29

Kashaw, Sushil. "P2-396: Synthesis, characterization and anti-Alzheimer's screening of new bioactive 3-[5-substituted 1,3,4-thiadiazole -2 yl]-2- styryl Quinazoline-4(3H)-ones." Alzheimer's & Dementia 8, no. 4S_Part_11 (July 2012): P401—P402. http://dx.doi.org/10.1016/j.jalz.2012.05.1106.

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30

Gheshlaghi, Saman Zare, Ali Ebrahimi, Zeinab Faghih, Zahra Faghih, Asiyeh Shahraki, and Leila Emami. "Azole-methyl-3-(4-phenoxyphenyl) quinazolin-4(3H) ones, novel quinazoline-azole hybrid scaffolds, as new potent anticancer agents: Design, synthesis, biological evaluation, molecular dynamic simulation and theoretical approach." Tetrahedron 147 (October 2023): 133650. http://dx.doi.org/10.1016/j.tet.2023.133650.

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31

Prasad, Malavattu G., C. Vijaya Lakshmi, Naresh K. Katari, Sreekantha B. Jonnalagadda, and Manojit Pal. "Lemon Juice Mediated Synthesis of 3-Substituted Quinazolin-4(3H)-Ones and their Pharmacological Evaluation." Anti-Cancer Agents in Medicinal Chemistry 19, no. 16 (January 23, 2020): 2001–9. http://dx.doi.org/10.2174/1871520619666190723151909.

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Background: Compounds containing the quinazoline-4(3H)-one framework constitute an important class of fused N-heterocycles that are found in more than 200 naturally occurring alkaloids. These compounds also show a diverse range of pharmacological activities including antitumor properties. This prompted us to explore a series of quinazolin-4-(3H)-one derivatives having no substituent at C-2 as potential cytotoxic agents. Objective: The objective of this study was to synthesize and evaluate 3-substituted quinazolin-4(3H)-one derivatives for their potential cytotoxic properties. Methods: A convenient method has been developed for the rapid synthesis of this class of compounds under a mild and non-hazardous reaction condition in good yields. The methodology involved a three-component reaction employing isatoic anhydride, amines and glyoxylic acid as reactants in the presence of lemon juice in PEG- 400 at room temperature (25-30ºC) under ultrasound irradiation. All the synthesized compounds were screened via an MTT assay for their potential cytotoxic properties in vitro using the cancerous cell lines e.g. A549, A2780, HepG2, K562, MCF-7 and HCT-116 and a non-cancerous HEK293 cell line. Results: Several compounds such as 3a, 3b, 3d, 3e and 3f showed promising growth inhibition against these cancer cell lines but no significant effects on HEK293 cell line. The IC50 values of these compounds were comparable to doxorubicin whereas 3f significantly induced apoptosis in MCF-7 cells that also was comparable to doxorubicin. Conclusion: An ultrasound-assisted MCR facilitated by lemon juice has been developed to synthesize 3- substituted quinazolin-4(3H)-one derivatives that could act as potential anticancer agents.

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Маркосян, А. И., А. C. Айвазян, С. А. Габриелян, М. Ю. Дангян, and А. Г. Аракелян. "Синтез и антибактериальная активность производных 3-аллил-5,5-диметил-2-тиоксо-2,3,5,6-тетрагидробензо[h]хиназолин-4(1H)-она." Chemical Journal of Armenia, November 9, 2023, 228–38. http://dx.doi.org/10.54503/0515-9628-2023.76.3-228.

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Alkylation of 3-allyl-5,5-dimethyl-2-thioxo-2,3,5,6-tetrahyd-robenzo[h]quinazo-line-4(1H)-one (thioxobenzoquinazoline) was alkylated in an alkaline medium with halides of various structures, resulting in the formation of 2-sulfanylsubstituted 3-allyl-5,5-dimethyl-5,6-dihydrobenzo[h]quinazolin-4(3H)-ones. The condensation of thioxobenzohquinazoline with hydrazine hydrate yielded 3-allyl-2-hydrazinyl-5,5-dimethyl-5,6-dihydroben-zo[h]quinazoline-4(3H)-one. However, analogous reactions with 2-ethanolamine and 3-propanolamine proceeded anomalously, resulting in the formation of 2-(2-hydroxyethyl)amino-5,5-dimethyl-5,6-dihydroben-zo[h]quinazoline-4(3H)-one and 2-(3-hydroxypropyl)amino-5,5-dimethyl-5,6-dihydro-benzo[h]quinazoline-4(3H)-one, respectively. Interaction of the mentioned thioxoben-zohquinazoline with benzylamine occurs through intramolecular cyclization, forming 6,6,10-trimethyl-9,10-dihydro-5H-benzo[h]thiazolo[2,3-b]quinazoline-7(6H)-one. The antibacterial properties of the synthesized compounds were studied against both Gram-positive and Gram-negative microorganisms. The research results revealed that the investigated compounds possess antibacterial activity.

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O'Brien, Nicholas, Jayne Gilbert, Adam McCluskey, and Jennette Sakoff. "2,3-Dihydroquinazolin-4(1H)-ones and Quinazolin-4(3H)-ones as Broad-Spectrum Cytotoxic Agents and Impact on Tubulin Polymerisation." RSC Medicinal Chemistry, 2024. http://dx.doi.org/10.1039/d3md00600j.

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Tubulin plays a central role in mitosis and has been the target of multiple anticancer drugs, including paclitaxel. Herein two separate families of 2,3-dihydroquinazoline-4(1H)-ones and quinazoline-4(3H) ones, comprising 57 compounds...

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Mai, Jiexiong, Ziwei Huang, Shaohuan Lv, Quan Chen, Rongrong Chen, Feng Xie, Jun Wang, and Bin Li. "Visible light-induced cascade N-alkylation/amidation reaction of quinazolin-4(3H)-ones and related N-heterocycles." Organic & Biomolecular Chemistry, 2023. http://dx.doi.org/10.1039/d2ob02226e.

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An efficient and visible light-promoted cascade N-alkylation/amidation of quinazolin-4(3H)-ones with benzyl halides with an important role of K2CO3 has been described for the first time to provide a convenient access to quinazoline-2,4(1H,3H)-diones.

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35

Kumar Tiwary, Bipransh, Kiran Pradhan, Ashis Kumar Nanda, and Ranadhir Chakraborty. "Implication of Quinazoline-4(3H)-ones in Medicinal Chemistry: A Brief Review." Journal of Chemical Biology & Therapeutics 01, no. 02 (2016). http://dx.doi.org/10.4172/2572-0406.1000104.

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36

Stepakov, Alexander V., Alexander S. Filatov, Anna G. Larina, Mikhail L. Petrov, and Vitali M. Boitsov. "Synthesis of Quinolino[1,2-c]quinazolin-6-one Derivatives via Formal (4+2)-Cycloaddition of Alkenes to Quinazolinе-Derived N-Acyliminium Cations: An Experimental and Theoretical Study." Synthesis, January 31, 2022. http://dx.doi.org/10.1055/a-1755-2061.

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Abstract3-Aryl-4-hydroxy-1-methyl-3,4-dihydroquinazolin-2(1H)-ones were synthesized by reduction of 3-aryl-1-methylquinazoline-2,4(1H,3H)-diones with sodium triethylborohydride and studied as precursors of N-acyliminium cations that were expected to be trapped with various alkenes as (4+2)-cycloadducts. Unsubstituted 3-aryl-4-hydroxy-1-methyl-3,4-dihydroquinazolin-2(1H)-ones in the presence of BF3·Et2O failed to produce the desired cycloadducts probably due to a homooligomerization reaction involving N-acyliminium intermediates. To prevent this side reaction, we found it necessary to introduce substituents at both positions C6 and C8 of the quinazoline ring and C4′ of the 3-phenyl substituent. Utilizing bromine atoms as substituents at C6 and C8, N-acyliminium cations generated from 3-aryl-6,8-dibromo-4-hydroxy-1-methyl-3,4-dihydroquinazolin-2(1H)-ones in the presence of BF3·Et2O smoothly reacted with such alkenes as indene, acenaphthylene, styrene, α-methylstyrene to give new quinolino[1,2-c]quinazolin-6-one derivatives with high regio- and stereoselectivity. Density functional theory calculations were performed at the M06-2x/cc-pVDZ level to obtain an insight into the mechanism of the (4+2)-cycloaddition reaction of quinazoline-derived N-acyliminium cations to alkenes.

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Zahran, Sally S., Fatma A. Ragab, Marwa G. El-Gazzar, Aiten M. Soliman, Walaa R. Mahmoud, and Mostafa M. Ghorab. "Antiproliferative, antiangiogenic and apoptotic effect of new hybrids of quinazoline-4(3H)-ones and sulfachloropyridazine." European Journal of Medicinal Chemistry, November 2022, 114912. http://dx.doi.org/10.1016/j.ejmech.2022.114912.

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38

Маркосян, А. И., А. С. Багдасарян, А. С. Айвазян, С. А. Габриелян, М. Ю. Дангян, and А. Г. Аракелян. "Синтез превращения 5,5-Диметил-3-пропил-2-тиоксо-2,3,5,6-тетрагидробензо[h]хиназолин-4(1H)-она и антибактериальные свойства полученых соединений." Chemical Journal of Armenia, December 26, 2022, 294–303. http://dx.doi.org/10.54503/0515-9628-2022.75.3-294.

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На базе этил 1-амино-3,3-диметил-3,4-дигидронафталин-2-карбоксилата (аминоэфир) разработан метод синтеза 5,5-диметил-3-пропил-2-тиоксо-2,3,5,6-тетрагидробензо[h]хиназолин-4(1H)-она (тиоксобензохиназолин), который в щелочной среде алкилирован галогенидами различного строения, что привело к получению 2-алкилтио-5,5-диметил-3-пропил-5,6-дигидро-бензо[h]хиназолин-4(3H)-онам. Конденсацией тиоксобензохиназолина с гидразин гидратом и 2-этаноламином синтезированы 2-гидразинил-5,5-диметил-3-пропил-5,6-дигидро-бензо[h]хиназолин-4(3H)-он и 2-[(2-гид-роксиэтил)амино]-5,5-диметил-3-пропил-5,6-дигидробензо[h]хиназолин-4(3H)-он, соответственно. Изучены антибактериальные свойства синтезированных соединений. В результате исследований установлено, что изученные соединения обладают слабой или умеренной антибактериальной активностью. 1-Ամինո-3,3-դիմեթիլ-3,4-դիհիդրոնավթալին-2-կարբօքսիլատի (ամինոէսթեր) հիման վրա մշակվել է 5,5-դիմեթիլ-3-պրոպիլ-2-թիօքսո-2,3,5,6-տետրահիդրոբեն-զո[h]խինազոլին-4(1H)-ոնի (թիօքսոբենզոխինազոլին) սինթեզի եղանակ։ Վերջինս հիմնային միջավայրում ալկիլացվել է տարբեր կառուցվածքների հալոգենիդներով, ինչը բերել է 2-ալկիլթիո-5,5-դիմեթիլ-3-պրոպիլ-5,6-դիհիդրոբենզո[h] խինազոլին-4(3H)-ոնների։ Թիօքսոբենզոխինազոլինի կոնդենսումով 2-էթանոլամինի հետ սինթեզվել է 2-(2-հիդրօքսիէթիլամինո)-5,5-դիմեթիլ-3-պրոպիլ-5,6-դի-հիդրոբեն-զո[h]խինազոլին-4(3H)-ոն։ Ուսումնասիրվել են սինթեզված միացությունների հակամանրէային հատկությունները: Կենսաբանական հետազոտությունների արդյունքում պարզվել է, որ միացություններն ունեն թույլից չափավոր հակամանրէային ակտիվություն։ 1-Amino-3,3-dimethyl-3,4-dihydro-naphthalene-2-carboxylate (aminoether) in the medium of low-boiling alcohols (methanol, ethanol, isopropanol) was reacted with propyl isothiocyanate. It was found that the best yields were obtained when the reaction was carried out at the boiling point of the solvent. When the reaction is carried out for 18-20 hours, the formed ethyl 3,3-dimethyl-1-(3-propylthioureido)-3,4-dihydronaphthalene-2-carboxylate under the reaction conditions is partially cyclized to 5,5-dimethyl-3-propyl-2-thioxo-2,3,5,6-tetrahydrobenzo[h]quinazoline-4(1H)-one (thioxobenzoquinazoline) in a 1:1 ratio. To increase the yield of thioxobenzoquinazoline, the resulting mixture was treated with a solution of caustic potash, which led to the production of thioxoquinazoline with a yield of 40%. The alkylation of thioxobenzoquinazoline in the presence of caustic potash with halides of various structures in absolute ethanol led to 2-alkylthio-5,5-dimethyl-3-propyl-5,6-dihydro-benzo[h]quinazoline-4(3H)-ones with yields of 48-83%. As a result of condensation of thioxobenzoquinazoline with 2-aminoethanol in excess of the amine, 2-(2-hydroxyethylamino)-5,5-dimethyl-3-propyl-5,6- dihydroben-zo[h]quinazoline-4(3H)-one was synthesized. The antibacterial activity of the compounds was studied by ―diffusion in agar‖ at a microbial load of 20 million microbial bodies per 1 ml of medium. Gram-positive staphylococci (St. Aureus 209p, Bac.subtilis) and gram-negative rods (Sh. Flexneri 6858, E. coli 0-55) were used as test objects. As a result of the research, it was found that the studied compounds had weak or moderate antibacterial activity.

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39

WRIGHT, W. B. JUN, A. S. TOMCUFCIK, P. S. CHAN, J. W. MARSICO, and J. B. PRESS. "ChemInform Abstract: Thromboxane Synthetase Inhibitors and Antihypertensive Agents. Part 4. N-((1H-Imidazol-1-yl)alkyl) Derivatives of Quinazoline-2,4(1H,3H)-diones (III), Quinazolin-4(3H)-ones (V), and 1,2,3-Benzotriazin-4(3H)-ones (VII)." ChemInform 19, no. 24 (June 14, 1988). http://dx.doi.org/10.1002/chin.198824237.

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40

Markosyan, A. I., A. S. Ayvazyan, S. H. Gabrielyan, S. S. Mamyan, F. H. Arsenyan, A. S. Safaryan, and H. H. Arakelyan. "Synthesis and Antibacterial and Antitumor Activity of 2-Sulfanyl-Substituted 3H-Spiro[Benzo[H]Quinazoline-5,1′-Cycloheptane]-4(6H)-Ones." Pharmaceutical Chemistry Journal, December 7, 2022. http://dx.doi.org/10.1007/s11094-022-02774-0.

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41

Sengupta, Devashish, Ranjan Kumar Das, Debdulal Sharma, and Subrata Paul. "Microwave-assisted Synthesis of 3-amino-2-phenylquinazolin-4(3H)-one (QH) and 4-oxo-2-phenylquinazoline-3(4H)-carbothioamide (QTh)." Current Microwave Chemistry 10 (May 16, 2023). http://dx.doi.org/10.2174/2213335610666230516165046.

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Background: Microwave synthesis has developed as a powerful tool for the cost-effective and greener synthesis of organic molecules, including quinazolines. Irradiation with microwave leads to the excitation of molecules and equitable distribution of thermal energy in a much shorter time than conventional synthesis. This results in shorter reaction time and, more often than not, higher efficiency. Objective: The primary objective of the work presented in this article was to prepare hydrazine hydrate or thiourea derivative of quinazolines through microwave synthesis as small-molecule scaffolds for further need-based functionalisation, isolation, and characterisation. We, herein, report the synthesis of two quinazolinone derivatives of thiourea and hydrazine, 3-amino-2-phenylquinazolin-4(3H)-one (QH) and 4-oxo-2-phenylquinazoline-3(4H)-carbothioamide (QTh), respectively. Method: A multi-step synthetic strategy starting from anthranilic acid was employed to synthesise the small molecule quinazolinones 3-amino-2-phenylquinazolin-4(3H)-one (QH) and 4-oxo-2-phenylquinazoline-3(4H)-carbothioamide (QTh). The compounds were synthesised by reacting hydrazine and thiourea with 2-benzamidobenzoyl chloride in DMF under microwave irradiation (800 W at 135 °C for 4 min) in the presence of potassium carbonate. The acid chloride was prepared by chlorination of 2-benzamidobenzoic acid, which in turn was synthesised from anthranilic acid by benzoylation. This method is an efficient alternative approach to synthesising quinazolinones from benzoxazin-4-ones. Results: We have successfully synthesised, isolated, and characterised the quinazolinone derivative QH (yield: 81%) and QTh (yield: 85%). The structures of the compounds were established through spectroscopic techniques. Theoretical optimisation of the structures was also achieved using DFT. The HOMO-LUMO difference for QH and QTh was calculated to be 4.60 and 4.47 eV, respectively. Conclusion: The reported protocol is advantageous over conventional methods of quinazoline synthesis from benzoxazin-4-ones. The time required for the reaction is much less (4 min) as compared to the usual requirements of reflux (> 4 h); the higher energy gap of QTh indicates greater stability than that of QH. Keywords: 3-amino-2-phenylquinazolin-4(3H)-one (QH), 4-oxo-2-phenylquinazoline-3(4H)-carbothioamide (QTh), HOMO-LUMO, DMF, microwave irradiation.

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42

Jatav, Varsha, Pradeep Mishra, Sushil Kashaw, and J. P. Stables. "ChemInform Abstract: Synthesis and CNS Depressant Activity of Some Novel 3-[5-Substituted 1,3,4-Thiadiazole-2-yl]-2-styryl Quinazoline-4(3H)-ones." ChemInform 39, no. 21 (May 20, 2008). http://dx.doi.org/10.1002/chin.200821160.

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El-Subbagh, Hussein I., and Mohamed A. Sabry. "2-Substituted-mercapto-quinazolin-4(3H)-ones as DHFR inhibitors." Mini-Reviews in Medicinal Chemistry 21 (March 4, 2021). http://dx.doi.org/10.2174/1389557521666210304105736.

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: Antifolates are a class of drugs used as antibacterial, antiparasitic, and anticancer agents. This review focuses on 2-substituted-mercapto-quinazolin-4(3H)-one analogues as dihydrofolate reductase (DHFR) inhibitors. Several research efforts have concluded a structural model for this class of 2-thio-quinazoline derivatives to get compounds with remarkable biological activity. The pattern and orientation of the -system substitutions with regard to the quinazoline nucleus manipulate the activity. The application of the obtained model criteria produced compounds 18, 20, and 21, which proved to be 4-8 times more active than the reference drug methotrexate (MTX, 1).

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Dutta, Nilakshi, Bidyutjyoti Dutta, Apurba Dutta, Bipul Sarma, and Diganta Sarma. "Room temperature ligand free Cu2O-H2O2 catalyzed tandem oxidative synthesis of quinazolin-4(3H)-one and quinazoline derivatives." Organic & Biomolecular Chemistry, 2023. http://dx.doi.org/10.1039/d2ob02085h.

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An efficient and simple copper catalytic system has been developed for synthesis of medicinally important 2-phenylquinazoline-4(3H)-ones from 2-aminobenzonitrile and benzyl alcohol, additionally 2-phenylquinazolines from 2-aminobenzylamine and benzaldehyde. Mild oxidant H2O2...

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45

Darwish, K., and O. Dakhil. "A Review on Methods of Synthesis of Quinazolines and (4H)-3,1-Quinazolin-4-ones." Libyan Journal of Science &Technology 5, no. 2 (September 18, 2022). http://dx.doi.org/10.37376/ljst.v5i2.2267.

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The main objectives of organic and medicinal chemistry are the design, synthesis and production of molecules having valuable human therapeutic effects. There are numerous biologically active molecules with six-membered rings, containing two heteroatoms. The development of research on biological activity of quinazoline compounds started with the synthesis of 2-methyl-3-phenylquinazolin-4(3H)-one that was later on approved to have has soporific and sedative action. This biological importance encouraged scientists to develop various new synthetic pathways of novel products. This review may cover and explain most of the old and recent synthetic methods of quinazolines and quinazolinones over more than a century.

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TOKALI, Feyzi Sinan. "Synthesis and Structural Characterization of Novel 2-Aminomethyl Quinazolin-4(3H)-ones as Organic Building Blocks." Sakarya University Journal of Science, September 29, 2022. http://dx.doi.org/10.16984/saufenbilder.1085086.

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Quinazoline and quinazolinone derivatives display an extensive application in organic and pharmaceutical chemistry, and they have been used as natural and synthetic materials for medicinal chemistry purposes. Here I reported an investigation of a new series of quinazolin-4(3H)-one ring derivatives. In this context, starting from the methyl anthranilate, six quinazolinone derivatives (4a-f) with various aminomethyl moieties at position 2 were synthesized with good yields (89-80%). The structures of the novel compounds were identified using NMR Spectroscopy (1H NMR - 13C NMR). The data obtained from the all spectra clearly identify the structures of the compounds.

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Devidas, Amrutkar Rakesh, and Mahendra Sing Ranawat. "Microwave Assisted Synthesis And Molecular Docking Studies Of Some 4 - (3h)-Quinazolinone Derivatives As Inhibitors Of Human Gamma-Aminobutyric Acid Receptor, The Gaba (A)R-Beta3 Homopentamer." Medicinal Chemistry 16 (December 16, 2019). http://dx.doi.org/10.2174/1573406416666191216121442.

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Background: Quinazolines and quinazolinones constitute a major class of biologically active molecules both from natural and synthetic sources. The quinazolinone moiety is an important pharmacophore showing many types of pharmacological activities as shown in recent exhaustive review on the chemistry of 2-heteroaryl & heteroalkyl-4-quinazolinones4-quinazolinones are the formal condensation products of anthranilic acid and amides, and they can also be prepared in this fashion through the Niementowski quinazolinone synthesis, named after it’s discoverer Stefan Niementowski. Quinazoline and condensed Quinazoline exhibit potent central nervous system (CNS) activities like anti-anxiety, analgesic, anti-inflammatory [10] and anticonvulsant [11]. Quinazolin-4-ones with 2, 3-disubstitution is reported to possess significant analgesic, anti-inflammatory and anticonvulsant activities Methods: To expand these views and application profiles, efforts have been developed for the synthesis of a new class of quinazolinone by incorporating different amines into synthesized benzoxazinone ring by replacing O atom in the ring. Up to now, a great number of various procedures have been proposed for the synthesis of quinazolin-4-ones in the past few years [16]. Using microwave radiation, this reaction could be easily and rapidly performed in very good yields, providing a large quantity of various 3-substituted-2- propyl-quinazolin-4-one derivatives which can be employed as useful bioactive compounds. We report a facile and efficient method for the synthesis of 3-substituted-2-propyl-quinazolin-4-one by the condensation reaction of Anthranilic acid or Halogen substituted anthranilic acid or methyl anthranilate, butanoic anhydride with various amines. we also reports a drug/ligand or receptor/protein interactions by identifying the suitable active sites in human gamma-aminobutyric acid receptor, the gaba (a)r-beta3 homopentamer human gamma-aminobutyric acid receptor, the gaba (a)r-beta3 homopentamer protein. Results: We are pleased to find that the reaction provided of 3-alkyl/aryl-2-alkyl-quinazolin-4-one gives good yield as well as good quality of product by using MW. All the synthesized compounds were subjected to grid-based molecular docking studies. The results shows that compound 4t have good affinity to the active site residue of human gamma-aminobutyric acid receptor, the gaba (a)r-beta3 homopentamer. Conclusion: The Microwave irradiation for synthesis of the title compounds offers reduction in reaction time, operation simplicity, cleaner reaction, easy work up and improved yields. The procedure clearly highlights the advantages of Green Chemistry. The data reported in this article may be a helpful guide for the medicinal chemists who are working in this area. The Protein-Ligand interaction plays a significant role in structural based drug designing. In the Present work we have docked the ligand, 2, 3-disubstituted quinazolinone with the proteins that are used as the target for GABA-A receptor.

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Abdullahi, Sagiru Hamza, Adamu Uzairu, Gideon Adamu Shallangwa, Sani Uba, and Abdullahi Bello Umar. "Ligand-based drug design of quinazolin-4(3H)-ones as breast cancer inhibitors using QSAR modeling, molecular docking, and pharmacological profiling." Journal of the Egyptian National Cancer Institute 35, no. 1 (August 7, 2023). http://dx.doi.org/10.1186/s43046-023-00182-3.

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Abstract Background Breast cancer is the most common tumor among females globally. Its prevalence is growing around the world, and it is alleged to be the leading cause of cancer death. Approved anti-breast cancer drugs display several side effects and resistance during the early treatment stage. Hence, there is a need for the development of more effective and safer drugs. This research was aimed at designing more potent quinazolin-4(3H)-one molecules as breast cancer inhibitors using a ligand-based design approach, studying their modes of interaction with the target enzyme using molecular docking simulation, and predicting their pharmacological properties. Methods The QSAR model was developed using a series of quinazoline-4(3H)-one derivatives by utilizing Material Studio v8.0 software and validated both internally and externally. Applicability domain virtual screening was utilized in selecting the template molecule, which was structurally modified to design more potent molecules. The inhibitive capacities of the design molecules were predicted using the developed model. Furthermore, molecular docking was performed with the EGFR target active site residues, which were obtained from the protein data bank online server (PDB ID: 2ITO) using Molegro Virtual Docker (MVD) software. SwissADME and pkCSM online sites were utilized in predicting the pharmacological properties of the designed molecules. Results Four QSAR models were generated, and the first model was selected due to its excellent internal and external statistical parameters as follows: R2 = 0.919, R2adj = 0.898, Q2cv = 0.819, and R2pred = 0.7907. The robustness of the model was also confirmed by the result of the Y-scrambling test performed with cR2p = 0.7049. The selected model was employed to design seven molecules, with compound 4 (pIC50 = 5.18) adopted as the template. All the designed compounds exhibit better activities ranging from pIC50 = 5.43 to 5.91 compared to the template and Doruxybucin (pIC50 = 5.35). The results of molecular docking revealed better binding with the EGFR target compared with the template and Doruxybucin. The designed compounds exhibit encouraging therapeutic applicability, as evidenced by the findings of pharmacological property prediction. Conclusions The designed derivatives could be utilized as novel anti-breast cancer agents.

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