Novel synthesis of nicotinamide derivatives of cytotoxic properties

Bioorganic & Medicinal Chemistry
Adel S GirgisFlora F Barsoum

Abstract

A variety of 2-substituted-4,6-diaryl-3-pyridinecarboxamides 5 were synthesized through aromatic nucleophilic substitution reaction of secondary amines with 2-bromo analogues 4. The latter were obtained via bromination of 2-cyano-3,5-diaryl-5-oxo-N-substituted pentamides 3 in glacial acetic acid. Moreover, pentamide derivatives 3 were prepared through base-catalyzed Michael addition of cyanacetanilides 2 with 1,3-diaryl-2-propen-1-ones 1. Otherwise, reaction of 2-bromo-3-pyridinecarboxamides 4 with primary aromatic amines in refluxing pyridine afforded the corresponding 2-(arylamino)-3-pyridinecarboxamides 6 besides the unexpected 2-unsubstituted amino analogues 7. Antitumor properties of the synthesized pyridinecarboxamides utilizing 59 different human tumor cell lines, representing leukemia, melanoma, and cancers of the lung, colon, brain, ovary, breast, prostate as well as kidney, were screened. Many of the tested compounds show considerable in vitro antitumor properties especially 5c and 7a, which reveal moderate activities against most of the used human tumor cell lines. It has also been achieved that, all the tested nicotinamide derivatives reveal promising antitumor properties against MDA-MB-231/ATCC (breast cancer).

References

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Citations

Dec 3, 2014·European Journal of Medicinal Chemistry·Adel S GirgisAlan R Katritzky
Apr 28, 2011·Acta Crystallographica. Section E, Structure Reports Online·Mehmet AkkurtOrhan Büyükgüngör
Jul 15, 2011·Acta Crystallographica. Section E, Structure Reports Online·Mehmet AkkurtOrhan Büyükgüngör
Jul 15, 2011·Acta Crystallographica. Section E, Structure Reports Online·S RanjithA K Mohanakrishnan
Aug 13, 2011·Acta Crystallographica. Section E, Structure Reports Online·S RanjithK Pitchumani
Mar 1, 2012·European Journal of Medicinal Chemistry·Adel S GirgisAlan R Katritzky
Sep 17, 2010·European Journal of Medicinal Chemistry·Alan R KatritzkyIva Stoyanova-Slavova
Oct 14, 2008·Nuclear Medicine and Biology·Xiang LiuAndrew Katsifis
Aug 20, 2015·The Journal of Organic Chemistry·Huanfeng JiangWanqing Wu
Oct 3, 2012·Journal of Enzyme Inhibition and Medicinal Chemistry·Abdel-Sattar S Hamad ElgazwyNasser S M Ismail
May 20, 2015·Organic & Biomolecular Chemistry·Adel S GirgisAlan R Katritzky
Aug 11, 2015·Organic & Biomolecular Chemistry·Mohamed A IbrahimAlan R Katritzky
Mar 16, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tamara SiberDajana Gašo-Sokač
Sep 16, 2006·Bioorganic & Medicinal Chemistry·Adel S Girgis, Mohey Ellithey
Feb 18, 2014·Journal of Chemical Information and Modeling·Polina V OliferenkoAlan R Katritzky

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