Synthesis and biological evaluation of novel ethyl 2-amino-6-ferrocenyl-1,6-dihydropyrimidine-5-carboxylates and ethyl 2-amino-6-ferrocenylpyrimidine-5-carboxylates

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• 作者：Elena I. Klimova^a ; ^{eiklimova@yahoo.com.mx} ; Jessica J. Sanchez Garcí ; a^a ; Tatiana Klimova^a ; Teresa Ramí ; rez Apan^b ; Eduardo A. Vá ; zquez Ló ; pez^a ; Marcos Flores-Alamo^a ; Marcos Martí ; nez Garcí ; a^b
• 关键词：Ferrocene ; Ferrocenyl-1 ; 6-dihydropyrimidines ; Ferrocenylpyrimidines ; Oxidation ; Antitumor activity ; Macrophages
• 刊名：Journal of Organometallic Chemistry
• 出版年：2012
• 期刊代码：64_0022328x
• 类别：ch
• 出版时间：15 June, 2012
• 卷：708-709
• 期：Complete
• 页码：37-45
• 文件大小：681 K

摘要

Reactions of ethyl 2-acyl-3-ferrocenylacrylates (acyl聽=聽acetyl, benzoyl, p-nitrobenzoyl) with guanidine and 1,1-dimethylguanidine furnish ethyl 2-amino-6-ferrocenyl-4-methyl(aryl)-1,6-dihydropyrimidine-5-carboxylates. Their oxidative dehydrogenation with PhI(OAc)₂ results in the corresponding ethyl 2-amino-6-ferrocenyl-4-methyl(aryl)pyrimidine-5-carboxylates. The structures of the synthesized compounds were established on the basis of the data from ¹H and ¹³C NMR spectroscopy and confirmed by X-ray diffraction analysis. All compounds were tested in聽vitro against six human tumor cell lines U-251, PC-3,K-562, HCT-15, MCF-7 and SKLU-1 to assess their in聽vitro antitumor activity. The results suggest biological specificity towards PC-3 and K-562 cells for compounds 4a-c at doses 50聽渭M, which are lower than cis-platin IC₅₀^'s in the two cell lines. Additionally, peritoneal mouse macrophages (M鈭? were also evaluated for compounds 4a-f and 5a-f.