期刊
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
卷 56, 期 3, 页码 465-475出版社
MAIK NAUKA/INTERPERIODICA/SPRINGER
DOI: 10.1134/S1070428020030161
关键词
pyrimidine; pyrazole; isoxazole; cyanopyridine
New diaryl-substituted pyridine, pyrimidine, pyrazole, and isoxazole derivatives bearing biphenyl-4-yl and 4-(dimethylamino)phenyl substituents have been prepared by the reaction of 1-(1,1 '-biphenyl-4-yl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one with different nitrogen nucleophiles such as urea, thiourea, guanidine hydrochloride, semicarbazide hydrochloride, thiosemicarbazide, and hydroxylamine hydrochloride. Nicotinonitrile derivative has been synthesized by one-pot reaction of 4-acetylbiphenyl, 4-(dimethylamino)benzaldehyde, and malononitrile in the presence of ammonium acetate under microwave irradiation, and subsequent treatment with hydrazine hydrate gave 4,6-diaryl-1H-pyrazolo[3,4-b]pyridin-3-amine. The behavior of 4,6-diarylpyrimidin-2-amine toward carbon electrophiles has been investigated by reacting it with p-toluenesulfonyl chloride, acetyl chloride, ethyl acetoacetate, ethyl cyanoacetate, and nitrous acid to afford the corresponding N-substituted derivatives. 3,5-Diaryl-4,5-dihydro-1H-pyrazole-1-carboxamide reacted with p-toluenesulfonyl chloride and phenylhydrazine to produceN-tosyl carboxamide and carbohydrazonamide derivatives, respectively. Treatment of analogous pyrazole-1-carbothioamide with phenyl isothiocyanate, p-toluenesulfonyl chloride, and chloroacetyl chloride affordedN-(phenylcarbamothioyl), N-tosyl, and aminoacetamide derivatives, respectively. All the synthesized compounds were characterized by(1)H NMR, IR, and mass spectra and elemental analyses. Some of the newly synthesized compounds were evaluated for theirin vitro cytotoxic activity against HePG-2 and MCF-7 cell lines. 4-(1,1 '-Biphenyl-4-yl)-6-[4-(dimethylamino)phenyl]-5,6-dihydropyrimidine-2(1H)-thione and 4-[5-(1,1 '-biphenyl-4-yl)-4,5-dihydro-1,2-oxazol-3-yl]-N,N-dimethylaniline displayed a promising growth inhibitory effect toward the two cell lines in comparison with the standard drug doxorubicin.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据