One-pot, four-component synthesis of novel cytotoxic agents 1-(5-aryl-1,3,4-oxadiazol-2-yl)-1-(1H-pyrrol-2-yl)methanamines

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• 作者：Ali Ramazani^a ; ^{aliramazani@gmail.com" class="auth_mail} ; Mehdi Khoobi^b ; Azar Torkaman^a ; Fatemeh Zeinali Nasrabadi^c ; Hamid Forootanfar^d ; Mojtaba Shakibaie^d ; Mandana Jafari^d ; Alieh Ameri^d ; Saeed Emami^e ; Mohammad Ali Faramarzi^f ; Alireza Foroumadi^b ; Abbas Shafiee^b ; ^{ashafiee@ams.ac.ir" class="auth_mail}
• 关键词：Anti-cancer agents ; Cytotoxic activity ; 1 ; 3 ; 4-Oxadiazole ; Aza-Wittig reaction ; Multi-component reactions
• 刊名：European Journal of Medicinal Chemistry
• 出版年：6 May, 2014
• 年：2014
• 卷：78
• 期：Complete
• 页码：151-156
• 全文大小：305 K

文摘

A series of N-benzyl-1-(5-aryl-1,3,4-oxadiazol-2-yl)-1-(1H-pyrrol-2-yl)methanamines were synthesized via one-pot reaction of appropriate benzylamine, pyrrole-2-carbaldehyde, (N-isocyanimino)triphenylphosphorane, and a carboxylic acid. The anti-tumor potential of title compounds was tested against several cancer cell lines by using MTT assay. Some tested compounds including 5e, 5p and 5q exhibited comparable or better cytotoxic activity against A549, HT29 or HT1080聽cells in comparison to the reference drug doxorubicin. Also, the cytotoxic activity of compounds 5d and 5n against MCF-7 was better than that of doxorubicin. Compound 5n with IC₅₀ value of 4.3聽渭M was 4-fold more potent than doxorubicin. The structure-activity relationship study revealed that the introduction of halogen atoms on both 5-phenyl ring and N-benzyl part improved the cytotoxic activity against all tested cell lines.