Synthesis and evaluation of fused pyrimidine derivatives as anti-inflammatory, antiproliferative and antimicrobial agents

Vachala, Seekarajapuram Dinakaran and Keloth, Kothari Srinivasan and Peralam Yegneswaran, Prakash (2012) Synthesis and evaluation of fused pyrimidine derivatives as anti-inflammatory, antiproliferative and antimicrobial agents. Medicinal Chemistry Research, 21 (10). pp. 2998-3005. ISSN 1054-2523

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Abstract

In this study, condensation of 2-amino-5-chlorobenzoic acid with benzoyl chloride afforded 2-benzamido-5- chloro benzoic acid which on cyclization with different primary amines yielded the corresponding 6-chloro-2-phenyl- 3-substituted quinazolin-4(3H)-ones (V1–V8). The reaction was monitored by thin layer chromatographic analysis. The structure of the synthesized compounds was confirmed by spectral studies and elemental analysis. All these compounds were screened for their anti-inflammatory, antiproliferative and antimicrobial activities. Anti-inflammatory activity was done by rat paw oedema method. Compounds V6 and V5 showed a good percentage inhibition of inflammation at the 2nd and the 3rd h, respectively. Antiproliferative activity was carried out byMTT assay againstChang liver,Hep2 andHeLa cell lines. Compounds V1, V5 and V8 showed antiproliferative activity at low concentrations. The minimum inhibitory concentrations (MIC) of the synthesized compounds against Pseudomonas aeruginosa, Staphylococcus aureus, Escherichia coli, Candida albicans and Aspergillus flavus was studied by microdilution assay. Compound V4 was found to be a potent antimicrobial agent against the organisms tested. Further, itwas selected for time kill study. These data revealed that the compounds containing chloro- and/or fluoro-substituted phenyl ring or N,N-dimethyl ethyl substitutions in the quinazolin-4(3H)-ones led to increase of their biological activities.

Item Type: Article
Uncontrolled Keywords: 4(3H)-Quinazolinone �Minimum inhibitory concentration � Time kill study �Anti-inflammatory � Antiproliferative � MTT assay
Subjects: Medicine > KMC Manipal > Microbiology
Pharmacy > MCOPS Manipal > Pharmaceutical Chemistry
Depositing User: KMC Manipal
Date Deposited: 23 Nov 2012 10:54
Last Modified: 14 Dec 2015 14:29
URI: http://eprints.manipal.edu/id/eprint/77630

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