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Molecules 2016, 21(1), 30; doi:10.3390/molecules21010030

Synthesis and Cytotoxic Effect of Some Novel 1,2-Dihydropyridin-3-carbonitrile and Nicotinonitrile Derivatives

1
Department of Chemistry, College of Science, Taibah University, Al-Madinah Al-Monawarah 1343, Saudi Arabia
2
Department of Photochemistry, National Research Centre, Dokki, Cairo 12622, Egypt
3
Department of Chemistry, College of Science, King Khalid University, Abha 9004, Saudi Arabia
4
Department of Pharmaceutical Chemistry, College of Pharmacy, Helwan University, Ain Helwan, Cairo 11795, Egypt
*
Author to whom correspondence should be addressed.
Academic Editors: Derek J. McPhee and Bimal K. Banik
Received: 9 November 2015 / Revised: 15 December 2015 / Accepted: 22 December 2015 / Published: 31 December 2015
(This article belongs to the Section Bioorganic Chemistry)
View Full-Text   |   Download PDF [1068 KB, uploaded 31 December 2015]   |  

Abstract

1-(2,4-Dichlorophenyl)-3-(4-fluorophenyl)propen-1-one (1) was prepared and reacted with an active methylene compound (ethyl cyanoacetate) in the presence of ammonium acetate to give the corresponding cyanopyridone 2. Compound 2 reacted with hydrazine hydrate, malononitrile, ethyl bromoacetate and phosphorous oxychloride to afford compounds 4 and 711, respectively. The 2-chloropyridine derivative 11 reacted with different primary amines, namely benzyl amine, piperonyl amine, 1-phenylethyl amine, and/or the secondary amines 2-methyl-pipridine and morpholine to give the corresponding derivatives 1215. Hydrazinolysis of chloropyridine derivative 11 with hydrazine hydrate afforded the corresponding hydrazino derivative 17. Condensation of compound 17 with ethyl acetoacetate, acetylacetone, isatin and different aldehydes gave the corresponding derivatives 1821. Some of newly synthesized compounds were screened for cytotoxic activity against three tumor cell lines. The results indicated that compounds 8 and 16 showed the best results, exhibiting the highest inhibitory effects towards the three tumor cell lines, which were higher than that of the reference doxorubicin and these compounds were non-cytotoxic towards normal cells (IC50 values > 100 μg/mL). View Full-Text
Keywords: nicotinonitrile; 4-fluorophenylpyridine; acetohydrazide; chloropyridine; cytotoxicity nicotinonitrile; 4-fluorophenylpyridine; acetohydrazide; chloropyridine; cytotoxicity
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M. Flefel, E.; S. Abbas, H.-A.; E. Abdel Mageid, R.; A. Zaghary, W. Synthesis and Cytotoxic Effect of Some Novel 1,2-Dihydropyridin-3-carbonitrile and Nicotinonitrile Derivatives. Molecules 2016, 21, 30.

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