Antimicrobial and antiurease activities of newly synthesized morpholine derivatives containing an azole nucleus

作者：Bektas Hakan^*; Ceylan Sule; Demirbas Neslihan; Alpay Karaoglu Sengul; Sokmen Bahar Bilgin

来源：Medicinal Chemistry Research, 2013, 22(8): 3629-3639.

DOI：10.1007/s00044-012-0318-1

• Morpholine
• 1,2,4-Triazole
• 1,3,4-Oxadiazole
• Mannich base
• Antimicrobial activity
• Antiurease activity

2-[6-(Morpholin-4-yl)pyridin-3-ylamino]acetohydrazide (4) was obtained starting from 6-morpholin-4-ylpyridin-3-amine (2) via the formation of ester (3) and then converted to the corresponding Schiff bases (5, 6) with the reaction with aromatic aldehydes. The carbothioamide (9), obtained from the reaction of hydrazide with phenylisothiocyanate, was converted to the corresponding 1,2,4-triazole (11) and 1,3,4-thiadiazole (12) derivatives by the treatment with NaOH or H2SO4, respectively. The cyclocondenzation of 9 with 4-chlorophenacyl bromide or ethyl bromoacetate produced the corresponding 1,3-thiazole (10) or 1,3-thiazolidine derivatives (13), respectively. Antimicrobial and antiurease activities of newly synthesized compounds were investigated. Some of them were found to be active on M. smegmatis, and they displayed activity toward C. albicans and S. cerevisiae in high concentration. Compound 10 proved to be the most potent showing an enzyme inhibition activity with an IC50 = 2.37 +/- A 0.19 mu M.

• 出版日期2013-8