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Research Article

4-(4-Morpholinophenyl)-6-arylpyrimidin-2-amines: synthesis, spectral analysis, and in vitro microbiological evaluation

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Pages 347-353 | Received 29 Mar 2009, Accepted 01 Jun 2009, Published online: 29 Oct 2009
 

Abstract

Compounds 4-(4-morpholinophenyl)-6-phenylpyrimidin-2-amine 20, 4-(4-methoxyphenyl)-6-(4-morpholinophenyl)pyrimidin-2-amine 23, 4-(4-bromophenyl)-6-(4-morpholinophenyl)pyrimidin-2-amine 25, 4-(3-chlorophenyl)-6-(4-morpholinophenyl) pyrimidin-2-amine 27, and 4-(3-fluorophenyl)-6-(4-morpholinophenyl)pyrimidin-2-amine 28 exerted excellent antibacterial activity against V. cholerae. Compounds 4-(4-chlorophenyl)-6-(4-morpholinophenyl)pyrimidin-2-amine 22, 25, 4-(4-morpholinophenyl)-6-(3-nitrophenyl)pyrimidin-2-amine 26, and 28, which contained electron-withdrawing chloro, bromo, nitro, and fluoro functional groups, respectively, at the para/meta position of the phenyl ring attached to the pyrimidine ring promoted much activity against S. aureus. Compounds 4-(4-fluorophenyl)-6-(4-morpholinophenyl)pyrimidin-2-amine 24 and 25 (against β-hemolytic Streptococcus) and compound 28 (against S. felxneri) showed pronounced activity. Compounds 26 and 28 (against K. pneumoniae) and compounds 24, 25, and 28 (against P. aeruginosa) exerted strong antibacterial activity. Compounds 22 and 25 promoted much antifungal activity against A. flavus, while compounds 24 and 25 registered maximum activity against Mucor. Compounds 23 (against C. albicans) and 27 and 28 (against Rhizopus) promoted good activity.

Acknowledgments

The authors are thankful to the NMR Research Center, Indian Institute of Science, Bangalore for recording spectra.

Declaration of interest: One of the authors (V.K.) is grateful to the Council of Scientific and Industrial Research (CSIR), New Delhi, Republic of India for providing financial support in the form of a CSIR-Senior Research Fellowship (SRF) in Organic Chemistry. Another author (J.T.) wishes to thank the Annamalai University authorities for providing financial support in the form of a Research Fellowship.

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