Synthesis of N-{[5-aryl/alkyl-1,3,4-oxadiazol-2-yl]methyl}pyridin-2-amine as Antimicrobial and Anticancer Agents

Abstract

A new series of oxadiazole analogues were synthesized starting from 2-aminopyridine. The compounds were characterized by infrared (IR), nuclear magnetic resonance (NMR) and mass spectral analyses followed by their antiproliferative and antimicrobial activities. Three compounds were tested for in vitro antiproliferative activity against NCI-60 human cell lines of nine different panels including leukemia, non-small lung cancer, colon cancer, CNS cancer, melanoma, ovarian cancer, renal cancer, prostate cancer, and breast cancer according to the National Cancer Institute (NCI US) Protocol at 10 µM. The compounds N-{[5-(4-Chlorophenyl)-1,3,4-oxadiazol-2-yl]methyl}pyridin-2-amine (5c), N-{[5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl}pyridin-2-amine (5f) and N-{[5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl}pyridin-2-amine (5g) showed anticancer with higher selectivity towards HOP-92 (Non-Small Cell Lung Cancer) and showed percent growth inhibition of 34.14, 35.29 and 31.59 at 10 µM concentration in single dose assay. N-{[5-(4-Fluorophenyl)-1,3,4-oxadiazol-2-yl]methyl}pyridin-2-amine (5b) showed maximum antibacterial activity with minimum inhibitory concentration (MIC) of 4-8 µg/mL, while N-{[5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl}pyridin-2-amine (5f) showed maximum antifungal activity with MIC 4 µg/mL.