4-(4-morpholinophenyl)-6-arylpyrimidin-2-amines: synthesis, spectral analysis, and in vitro microbiological evaluation.
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 beta-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.
Thanusu
J
J
Department of Chemistry, Annamalai University, Annamalainagar, Tamil Nadu, India.
Kanagarajan
V
V
Gopalakrishnan
M
M
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D015195:Drug Design; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000588:Amines; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D011743:Pyrimidines; C030986:pyrimidine