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South African Journal of Chemistry

On-line version ISSN 1996-840X
Print version ISSN 0379-4350

S.Afr.j.chem. (Online) vol.61  Durban  2008

 

RESEARCH ARTICLE

 

Synthesis and antioxidant activity of 3,3'-diselanediylbis (N,N-disubstituted indolizine-1-carboxamide) and derivatives

 

 

Chandrashekhar Narajji; Manohar D. Karvekar*; A. Kumar Das

Department of Pharmaceutical Chemistry, Krupanidhi College of Pharmacy, 5 Sarjapur Road, Koramangala, Bangalore, 560 034, India

 

 


ABSTRACT

A series of novel diselenides 5a-e were synthesized from α-haloketones, α-picoline alkenes and various secondary amines under a dry nitrogen atmosphere. The structures of these compounds were established by means of their spectral data and they were screened for scavenging activity against 1,1-diphenyl-2-picryl-hydrazyl (DPPH.). The results of this research showed that two of these compounds (5e and 5d) exhibited reasonable antioxidant activity. The intermediate, methyl 5-methylindolizine-1-carboxylate was prepared by condensation of methyl acrylate with 1-(carboxymethyl)-2-methylpyridinium halide, which was prepared from a-picoline and chloroacetic acid by using the Tschischibabin reaction.

Keywords: Antioxidants, diselenides, indolizine, free radical scavenger, 1,1-DPPH


 

 

Full text available only in pdf format.

 

Acknowledgements

The authors sincerely thank the management and staff of Krupanidhi College of Pharmacy for their dedicated collaboration and devotion.

 

References

1 P.C. Hsu and Y.L. Guo, Toxicology, 2002,180, 33-44.         [ Links ]

2 H. Kimura, T. Sawada, S. Oshima, K. Kozawa, T. Ishioka and M. Kato, Curr. Drug Targets Imflamm. Allergy, 2005, 4, 489-495.         [ Links ]

3 R. Ramirez, J. Carracedo, R. Jimenaz, A. Canela, E. Herrera, P. Aljama and M.A. Blasco, J. Biol. Chem, 2003, 278, 836-842.         [ Links ]

4 J.F. Long, P.K. Dutta and B.D.Hogg, Environ. Health Perspect, 1997, 105, 706-711.         [ Links ]

5 N.T.T. Huong, K. Matsumoto, R. Kasai, K. Yamasaki and W. Watanabe, Biol. Pharm. Bull., 1998, 21, 978-981.         [ Links ]

6 H. Haraguchi, H. Ishikawa and I. Kubo, Planta Med., 1997, 63, 213-215.         [ Links ]

7 T.C.J. Stadtman, Biol. Chem., 1991, 266, 16257-16260.         [ Links ]

8 F. Ursini, in Oxidative Processes and Antioxidants, Paoletti, R. (ed.), Raven Press, New York, NY, USA, 1994, pp. 25-31.         [ Links ]

9 J.T. Rotruck, A.L. Pope, H.E. Ganther, A.B. Swanson, D.G. Hafeman and W.G. Hoekstra, Science, 1973, 179, 588-590.         [ Links ]

10 L. Flohe,W.A. Gunzler and H.H. Schock, FEBS Lett., 1973, 32,132-134.         [ Links ]

11 M.J. Berry, L. Banu and P.R. Larsen, Nature, 1991, 349, 438-440.         [ Links ]

12 J.C. Boyington, VN. Gladyshev, S.V Khangulov, T.C. Stadtman and P.D. Sun, Science, 1997, 275, 1305-1308.         [ Links ]

13 R. Ladenstein, O. Epp, K. Bartels, A. Jones, R. Huber and A. Wendel, J. Mol. Biol., 1979, 134, 199-218.         [ Links ]

14 O. Epp, R. Ladenstein and A. Wendel, Eur. J. Biochem., 1983, 133, 51-69.         [ Links ]

15 H.J. Reich and C.P. Jasperse, J. Am. Chem. Soc., 1987, 109, 5549-5551.         [ Links ]

16 S.R. Wilson, P.A. Zucker, R.R.C. Huang and A. Spector, J. Am. Chem. Soc., 1989, 111, 5936-5939.         [ Links ]

17 M. Iwaoka and S. Tomoda, J. Am. Chem. Soc., 1994, 116, 2557-2561.         [ Links ]

18 L. Engman, C. Andersson, R. Morgenstern, I.A. Cotgreave, C.M. Andersson and A. Hallberg, Tetrahedron, 1994, 50, 2929-2938.         [ Links ]

19 J. Chaudiere, J.C. Yadan, I. Erdelmeier, L.C. Tailhan and M. Moutet, in Oxidative Processes and Antioxidants, (Paoletti, R., ed.), Raven Press, New York, NY, USA, 1994, pp. 165-184.         [ Links ]

20 K.S. Bani and G. Mugesh, J. Am. Chem. Soc., 2005, 127, 11477-11485.         [ Links ]

21 C. Narajji, M.D. Karvekar and A.K. Das, Indian J. Pharm. Sci., 2007, 69, 344-351.         [ Links ]

22 L. Zhang, F. Liang, L. Sun, Y. Hu and H. Hu, Synthesis, 2000, 1733-1737.         [ Links ]

23 S. Kumazawa, M. Taniguchi, Y. Suzuki, M. Shimura, M. Kwon and T. Nakayama, J. Agric. Food Chem., 2002, 50, 373-377.         [ Links ]

24 G. Mugesh, A. Panda, H.B. Singh, N.S. Punekar and R.J. Butcher, Acta Pharmacol. Sin., 2004, 25, 666-671.         [ Links ]

25 S. Olgen, and T. Çoban, Biol. Pharm. Bull., 2003, 26, 736-738.         [ Links ]

26 G. Mugesh, A. Panda, H.B. Singh, N.S. Punekar and R.J. Butcher, Chem. Commun., 1998, 2227-2228.         [ Links ]

27 R. Zhao and A. Holmgren, J. Biol. Chem., 2002, 277, 39456-39462.         [ Links ]

 

 

Received 10 September 2007
Revised 13 March 2008
Accepted 2 April 2008

 

 

* To whom correspondence should be addressed. E-mail: ch_pharmacy@rediffmail.com

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