- Design and synthesis of new benzylidene-quinazolinone hybrids as potential anti-diabetic agents: In vitro α-glucosidase inhibition, and docking studies
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A novel series of benzylidene-quinazolinone hybrids 8a,b and 10a-n were designed, synthesized, and evaluated for their in vitro α-glucosidase inhibitory effect aiming to discover efficient anti-diabetic agents. The synthesized compounds were assessed for their in vivo anti-hyperglycemic activities against STZ-induced hyperglycemic rats. Five compounds (10m, 10f, 10c, 10d and 8b) demonstrated potent activities with percent reduction in blood glucose levels of 43.07, 40.14, 39.83, 37.04 and 36.16, respectively. The most active members were further evaluated in vitro for their α-glucosidase inhibitory binding affinities. Among them, Compound 10m containing 4-hydroxybenzylidene moiety and compound 10f with 4-chlorobenzylidene moiety connected to the acetohydrazide demonstrated the most potent inhibitory activities towards α-glucosidase with IC50 values of 561 and 610 μM, respectively. Molecular docking study was performed in order to understand the molecular interactions between the molecule and enzyme.
- Ayyad, Rezk R.,Ibrahim, Albaraa,Khalifa, Mohamed M.,Mansour, Ahmed M.,Sakr, Helmy M.
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- Practical approach to 2-thioxo-2,3-dihydroquinazolin-4(1H)-one via dithiocarbamate–anthranilic acid reaction
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A practical and straightforward protocol has been developed for the preparation of 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives from dithiocarbamate chemistry. The method involves the reaction of anthranilic acid derivatives (2-aminobenzoic acid, 2-aminobenzamide and isatoic anhydride) with various dithiocarbamate derivatives using ethanol as solvent. The main advantages of this protocol include practical simplicity, good to high yields, and ease of product isolation, purification and cheapness of the solvent.
- Azizi, Najmedin,Edrisi, Mahtab
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p. 109 - 112
(2017/01/13)
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- A convenient and efficient synthesis of 2-thioxoquinazolinone derivatives via microwave irradiation
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The synthesis of 2-thioxoquinazolinone derivatives was achieved by condensation of isatoic anhydride, primary amine, and carbon disulfide under microwave irradiation. This convenient and efficient method affords the desired products with good to excellent yields. Satisfactory infrared spectroscopy, 1H NMR, and high-resolution mass spectrometry (electrospray ionization) spectra were obtained for all compounds described.
- Liu, Weiwei,Zhang, Qiang,Gong, Feng,Cao, Zhiling,Huo, Yunfeng
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p. 317 - 321
(2015/03/30)
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- Development of 2-thioxoquinazoline-4-one derivatives as dual and selective inhibitors of dynamin-related protein 1 (Drp1) and puromycin-sensitive aminopeptidase (PSA)
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An established inhibitor ot dynamin-related protein 1 (Drp1), 3-(2,4-dichloro-5-methoxyphenyl)- 2- thioxoquinazoline-4-one (mdivi-1), was recently reported also to show potent puromycin-sensitive aminopeptidase (PSA)-inhibitory activity. Herein, we report structural development of mdivi-1 derivatives and structure-activity relationship (SAR) analysis of the synthesized compounds, as well as the structurally related PSA-specific inhibitor 3-(2,6-diethylphenyl)quinazoline-2,4-dione (PAQ-22), with the aim of identifying key structural features for inhibitory activity in order to develop selective inhibitors of Drpl, which is a potential target for treatment of Huntington's disease. Among the synthesized compounds, 3-(4-chloro3methoxyphenyl)-2-thioxoquinazoline-4-one 10g) exhibited more potent Drpl-inhibitory activity than mdivi-1 with high selectivity for Drpl over PSA.
- Numadate, Akiyoshi,Mita, Yusuke,Matsumoto, Yotaro,Fujii, Shinya,Hashimoto, Yuichi
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p. 979 - 988
(2015/02/19)
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- Synthesis and analgesic, anti-inflammatory activities of 3-(3-methoxyphenyl)-2-substituted amino-quinazolin-4 (3H)-ones
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A variety of novel 3-(3-methoxyphenyl)-2- substituted amino-quinazolin- 4(3H)-ones were synthesized by reacting the amino group of 2-hydrazino-3-(3- methoxyphenyl)- quinazolin-4(3H)-one with a variety of aldehydes and ketones. The starting material 2-hydrazino-3-(3- methoxyphenyl)-quinazolin-4(3H)-one was synthesized from 3-methoxy aniline. The title compounds were investigated for analgesic, anti-inflammatory, and ulcerogenic behavior. Among these the compound 2-(1-methyl butylidene- hydrazino)-3-(3-methoxyphenyl)-3H-quinazolin-4-one (AS3) emerged as the most active compound for the analgesic activity, while the compound 2-(1-ethyl propylidene- hydrazino)-3-(3-methyoxyphenyl)-3H-quinazolin- 4- one (AS2) showed most potent anti-inflammatory activity of the series and these compounds are moderately more potent when compared to the reference standard diclofenac sodium. Interestingly the test compounds showed only mild ulcerogenic potential when compared to acetylsalicylic acid. Springer Science+Business Media, LLC 2010.
- Alagarsamy,Gopinath,Parthiban,Subba Rao,Murali,Raja Solomon
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p. 946 - 954
(2012/05/04)
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- 4-(3-Methoxyphenyl)-1-substituted-4H-[1,2,4]triazolo[4,3-a] quinazolin-5-ones: New class of H1-antihistaminic agents
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A series of 1-substituted-4-(3-methoxyphenyl)-4H-[1,2,4]triazolo[4,3-a] quinazolin-5-ones were synthesized by the cyclization of 2-hydrazino-3-(3- methoxyphenyl)-3H-quinazolin-4-one with various electrophile. The starting material 2-hydrazino-3-(3-methoxy
- Alagarsamy, Veerachamy,Sharma,Parthiban,Hanish Singh,Thirusenthil Murugan,Raja Solomon
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experimental part
p. 5 - 9
(2010/04/05)
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- Heterocycles as cholecystokinin (CCK) ligands
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Novel quinazolinone derivatives with good binding affinity for the CCK-A and CCK-B receptors, pharmaceutical compositions containing them and methods of using them are taught. The compounds are useful agents to suppress appetite, reduce gastric acid secre
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Page/Page column 23
(2008/06/13)
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