Synthesis, antibacterial activity and cytotoxicity of new fused pyrazolo[1,5-a]pyrimidine and pyrazolo[5,1-c][1,2,4]triazine derivatives from new 5-aminopyrazoles

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• 作者：Wedad M. Al-Adiwish^a ; ^{we80dad@yahoo.com} ; M.I.M. Tahir^b ; ^{mibrahim@science.upm.edu.my} ; A. Siti-Noor-Adnalizawati^c ; ^{adnaliza@yahoo.com} ; Siti Farah Hashim^c ; ^{farah_samura@yahoo.com} ; Nazlina Ibrahim^c ; ^{nazlina@ukm.my} ; W.A. Yaacob^a ; ^{wanyaa@ukm.my}
• 关键词：5-Aminopyrazoles ; Pyrazolo[1 ; 5-a]pyrimidines ; Pyrazolo[5 ; 1-c][1 ; 2 ; 4]triazines ; ¦Á ; ¦Á-Dicyanoketene-S ; S- and N ; S-acetals ; Antibacterial activity ; Cytotoxicity
• 刊名：European Journal of Medicinal Chemistry
• 出版年：2013
• 出版时间：June, 2013
• 年：2013
• 卷：64
• 期：Complete
• 页码：464-476
• 全文大小：1435 K

文摘

New 5-aminopyrazoles 2a-c were prepared in high yields from the reaction of known ¦Á,¦Á-dicyanoketene-N,S-acetals 1a-c with hydrazine hydrate under reflux in ethanol. These compounds were utilized as intermediates to synthesize pyrazolo[1,5-a]-pyrimidines 3a-c, 4a-d, 5a-c, and 6a-c, as well as pyrazolo[5,1-c][1,2,4]triazines 7a-c and 8a-c, by the reaction of 2-[bis(methylthio)methylene]malononitrile, ¦Á,¦Á-dicyanoketene-N,S-acetals 1a-b, acetylacetone, acetoacetanilide as well as acetylacetone, and malononitrile, respectively. Furthermore, cyclization of 2a-c with pentan-2,5-dione yielded the corresponding 5-pyrrolylpyrazoles 9a-c. Moreover, fusion of 2a-c with acetic anhydride resulted in the corresponding 1-acetyl-1H-pyrazoles 10a-c. The antibacterial activity and cytotoxicity against Vero cells of several selected compounds are also reported.