S. Y. Mansour, G. Sayed, S. A. Al-halim
Mar 1, 2020
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Journal
Russian Journal of Organic Chemistry
Abstract
Abstract 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-1 H -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-1 H -pyrazole-1-carboxamide reacted with p -toluenesulfonyl chloride and phenylhydrazine to produce N -tosyl carboxamide and carbohydrazonamide derivatives, respectively. Treatment of analogous pyrazole-1-carbothioamide with phenyl isothiocyanate, p -toluenesulfonyl chloride, and chloroacetyl chloride afforded N -(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 their in 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(1 H )-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.