Synthesis, antimicrobial and cytotoxic activity of novel azetidine-2-one derivatives of 1H-benzimidazole

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• 作者：Malleshappa Noolvi^a ; ^{mnoolvi@yahoo.co.uk" class="auth_mail} ; Suresh Agrawal^a ; Harun Patel^a ; ^{hpatel_38@yahoo.com" class="auth_mail} ; Aravind Badiger^b ; Monika Gaba^a ; Azit Zambre^c
• 关键词：Antibacterial activity ; Cytotoxic activity ; Schiff bases ; 2-Amino benzimidazole
• 刊名：Arabian Journal of Chemistry
• 出版年：April, 2014
• 年：2014
• 卷：7
• 期：2
• 页码：219-226
• 全文大小：776 K

文摘

A series of 1-methyl-N-[(substituted-phenylmethylidene)-1H-benzimidazol-2-amines (4a-4g) were prepared via the formation of 1-methyl-1H-benzimidazol-2-amine (3), which was prepared by the cycloaddition of o-phenylenediamine (1) with cyanogen bromide in the presence of aqueous base followed by N-methylation with methyl iodide in the presence of anhydrous potassium carbonate in dry acetonitrile. Moreover, the four-membered 尾-lactam ring was introduced by the cycloaddition of 4a-4g and chloroacetyl chloride in the presence of triethylamine catalyst to give 3-chloro-1-(1-methyl-1H-benzimidazol-2-yl)-(4鈥?substituted)-phenylazetidin-2-one 5a-5g. A total of 14 compounds were synthesized and characterized by IR, ¹H NMR, ¹³C NMR and Mass spectral technique, in addition they were evaluated for anti-bacterial and cytotoxic properties. Among the chemicals tested 4a, 4b, 5a, 5b, 5g exhibited good antibacterial activity and 5f, 5g shown good cytotoxic activity in vitro.