Hassan Ashraf S, Hafez Taghrid S, Osman Souad A
Department of Organometallic and Organometalloid Chemistry, National Research Centre, El-Buhoth St, Cairo, Doki, Egypt.
Sci Pharm. 2014 Oct 24;83(1):27-39. doi: 10.3797/scipharm.1409-14. Print 2015 Jan-Mar.
5-Amino-N-aryl-3-[(4-methoxyphenyl)amino]-1H-pyrazole-4-carboxamides 4a-c were synthesized by the reaction of N-(aryl)-2-cyano-3-[(4-methoxyphenyl)amino]-3-(methylthio)acrylamides 3a-c with hydrazine hydrate in ethanol. The reaction of 5-amino-N-aryl-1H-pyrazoles 4a-c with acetylacetone 5 or 2-(4-methoxybenzylidene)malononitrile 8 yielded the pyrazolo[1,5-a]pyrimidine derivatives 7a-c and 10a-c, respectively. The structures of the synthesized compounds were established based on elemental analysis and spectral data (IR, MS, (1)H-NMR, and (13)C-NMR). Representative examples of the new synthesized products were screened for their in vitro cytotoxic activity against Ehrlich Ascites Carcinoma (EAC) cells.
通过N-(芳基)-2-氰基-3-[(4-甲氧基苯基)氨基]-3-(甲硫基)丙烯酰胺3a-c与水合肼在乙醇中反应合成了5-氨基-N-芳基-3-[(4-甲氧基苯基)氨基]-1H-吡唑-4-甲酰胺4a-c。5-氨基-N-芳基-1H-吡唑4a-c与乙酰丙酮5或2-(4-甲氧基亚苄基)丙二腈8反应,分别生成吡唑并[1,5-a]嘧啶衍生物7a-c和10a-c。基于元素分析和光谱数据(红外光谱、质谱、¹H-核磁共振和¹³C-核磁共振)确定了合成化合物的结构。对新合成产物的代表性实例进行了针对艾氏腹水癌(EAC)细胞的体外细胞毒性活性筛选。