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A Novel Route for the Synthesis of Recemic 4-(Coumaryl) Alanines and Their Antimicrobial Activity
Corresponding Author(s) : Raviraj A. Kusanur
Asian Journal of Chemistry,
Vol. 26 No. 4 (2014): Vol 26 Issue 4
Abstract
4-Bromomethyl coumarins (3) when reacted with diethyl acetamidomalonate (4) in presence of sodium hydride afforded the intermediate compounds 5. Compounds 5 on hydrolysis with 48 % HBr resulted in hydrobromide salt of corresponding alanine derivatives (6). Free alanines (7) were obtained by neutralizing with ammonia solution. The resulting alanine derivatives (7) were characterised by IR, NMR and mass spectroscopic techniques and further screened for their antimicrobial activity.
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- C.G. Bradshaw, K. Ceszkowski, G. Turcatti, I.J.M. Beresford and A. Chollet, J. Med. Chem., 37, 1991 (1994); doi:10.1021/jm00039a012.
- G. Turcatti, H. Vogel and A. Chollet, Biochemistry, 34, 3972 (1995); doi:10.1021/bi00012a015.
- B. Liu and E. Wilson, Eur. J. Immunol., 40, 186 (2010); doi:10.1002/eji.200939819.
- M. Stanchev, S. Tabakova, G. Videnov, E. Golovinsky and G. Jung, Arch. Pharm. (Weinheim), 332, 297 (1999); doi:10.1002/(SICI)1521-4184(19999)332:9<297::AID-ARDP297>3.0.CO;2-#.
- M. Kulkarni, G. Kulkarni, C.-H. Lin and C.-M. Sun, Curr. Med. Chem., 13, 2795 (2006); doi:10.2174/092986706778521968.
- A.M.E. Naggar, M.H. El-Gammal and B.A. El-Tawil, Acta Chir. Acad. Sci. Hung., 89, 279 (1976).
- A. Burger and G.E. Ullyot, J. Org. Chem., 12, 342 (1947); doi:10.1021/jo01166a021.
- B.B. Dey and Y. Shankaranarayana, J. Indian Chem. Soc., 11, 687 (1934).
- R.A. Kusanur, M.V. Kulkarni, G.M. Kulkarni, S.K. Nayak, T.N. Guru Row, K. Ganesan and C.-M. Sun, J. Heterocycl. Chem., 47, 91 (2010); doi:10.1002/jhet.273.
- C.N.R. Rao, Chemical Applications of IR spectroscopy, Academic Press, New York, p. 256 (1963).
- E. Casman, Am. J. Clin. Pathol., 17, 281 (1947).
References
C.G. Bradshaw, K. Ceszkowski, G. Turcatti, I.J.M. Beresford and A. Chollet, J. Med. Chem., 37, 1991 (1994); doi:10.1021/jm00039a012.
G. Turcatti, H. Vogel and A. Chollet, Biochemistry, 34, 3972 (1995); doi:10.1021/bi00012a015.
B. Liu and E. Wilson, Eur. J. Immunol., 40, 186 (2010); doi:10.1002/eji.200939819.
M. Stanchev, S. Tabakova, G. Videnov, E. Golovinsky and G. Jung, Arch. Pharm. (Weinheim), 332, 297 (1999); doi:10.1002/(SICI)1521-4184(19999)332:9<297::AID-ARDP297>3.0.CO;2-#.
M. Kulkarni, G. Kulkarni, C.-H. Lin and C.-M. Sun, Curr. Med. Chem., 13, 2795 (2006); doi:10.2174/092986706778521968.
A.M.E. Naggar, M.H. El-Gammal and B.A. El-Tawil, Acta Chir. Acad. Sci. Hung., 89, 279 (1976).
A. Burger and G.E. Ullyot, J. Org. Chem., 12, 342 (1947); doi:10.1021/jo01166a021.
B.B. Dey and Y. Shankaranarayana, J. Indian Chem. Soc., 11, 687 (1934).
R.A. Kusanur, M.V. Kulkarni, G.M. Kulkarni, S.K. Nayak, T.N. Guru Row, K. Ganesan and C.-M. Sun, J. Heterocycl. Chem., 47, 91 (2010); doi:10.1002/jhet.273.
C.N.R. Rao, Chemical Applications of IR spectroscopy, Academic Press, New York, p. 256 (1963).
E. Casman, Am. J. Clin. Pathol., 17, 281 (1947).