Synthesis, characterization, industrial application and anticancer activity of new N-mustard substituted coumarin derivatives
Citation
A Barasara, M Pandya, D Purohit "Synthesis, characterization, industrial application and anticancer activity of new N-mustard substituted coumarin derivatives", International Journal of Engineering Trends and Technology (IJETT), V47(6),344-348 May 2017. ISSN:2231-5381. www.ijettjournal.org. published by seventh sense research group
Abstract
A series of N-mustard Substituted-coumarin have been synthesized characterized and evaluated for their in vitro cytotoxicity and anticancer activity against PC-3 human cancer cell lines. The methodology involves nucleophilic substitution of readily accessible 3-Cyano-4-chloro coumarin with ethanol amine further on chlorination gives substituted 4-(bis(2-chloroethyl)amino)-2-oxo-2H-chromene-3-carbonitrile derivatives. Among these compounds screened, three compounds (ASW-2g, ASW-2f and ASW-2e) showed GI50 range from 80 to 95 ?g/ml. All synthesized compounds were characterized by IR, NMR and Mass spectral analysis and screened for anticancer activity using PC-3 cell line. All the compounds showed moderate to good anticancer activity.
References
1. Kramer, B. S., Gohagan, J. K. & Prorok, P. C. Cancer screening: theory and practice. (CRC Press, 1999).
2. Kohn, K. W., Hartley, J. A. & Mattes, W. B. Mechanisms of DNA sequence selective alkylation of guanine-N7 positions by nitrogen mustards. Nucleic Acids Res.1987,15, 10531–10549
3. Millard, J. T., Raucher, S. & Hopkins, P. B. Mechlorethamine Cross-Links Deoxy guanosine Residues. J. Am. Chem. Soc.1990,2459–2460
4. (a).M.Stahmann, T. Wolff, K. Link, J. Am.Chem.Soc.,1943,65,2285.(b).E.Renk. W. Stoll, Prog.Drug.Res.,1968,14,226.(c).F.Kazmier,Mayo Clinic. Proc.,1974,49,918.(d).S.Moran, Crop. Protect.,2001,20,529.
5. J.Hinmann, H. Hoeksema, E. Carbon, W. Jackson, J. Am. Chem.Soc.,1956,78,1072.
6. A. Bourinbaiar, X. Tan, R. Nagomy, Acta Virol.,1993,37,241.
7. I.Kostava, Curr. Med. Chem.- Anti Cancer Agents, 2005,5,29.
8. P. Laurin, M. Klich, C. Dupis-Hamelin, P. Mauvais, P. Lassaigne, A. Bonnefoy, B.Musicki,Bioorg. Med.Chem. Lett.,1999,9,2079.
9. V. Trapov, E. Perfanov, L. Smirnov, Khim.-Farm. Zh.,1996,30,20.
10. G. Raskob, P. Comp, G. Pineo, R. Hull, In Anticoagulant: Physiologic, Pathologic band Pharmacologic, D. Green, Ed.6, Eds.;CRC Press, Boca Raton,1994,231.
11. S. Pillai, S. Menon, L. Mitscher, C. Pillai, D. Shankel, J. Nat. Prod.,1999,62,1358.
12. W.Gao, W. Hou, M. Chang, Y. Cui, Y. Li, X. wang, L. Tang and S. Sun; Farming ZhuanliShenqingGongkaiShuomingshu, CN101220016,2008.
Keywords
4-chloro-3-cyano coumarin, Aniline mustard, Anticancer activity, Nucleophilic substitution, Spectral analysis.