Synthesis and antibacterial activity of benzotriazole substituted acridines

International Journal of Biological Chemistry

Volumn 5, Issue 3, 2011, Pages 193-199

  Singh, Narinder Pal ^a   Kumar, Rajesh ^a   Prasad, Deo Nandan ^a   Sharma, Sarita ^b   Silakari, Om ^c  

^a Shivalik College of Pharmacy   (India)

^b Global College of Pharmacy   (India)

^c PUNJABI UNIVERSITY   (India)

Author keywords

1H NMR; Acridine; Antibacterial activity; Benzotriazole; Cyclization; O phenylenediamine

Indexed keywords

EID: 84863401221     PISSN: 1819155X     EISSN: 21522561     Source Type: Journal    
DOI: 10.3923/ijbc.2011.193.199     Document Type: Article

References (19)

1. Albert, A. and B. Ritchie, 1955. 9-Aminoacridine. Org. Syntheses, 3: 53-56.
2. Cope, H., R. Mutter, W. Heal, C. Pascoe, P. Brown, S. Pratt and B. Chen, 2006. Synthesis and SAR study of acridine, 2-methylquinoline and 2-phenylquinazoline analogues as anti-prion agents. Eur. J. Med. Chem., 41: 1124-1143.
3. Cremieux, A., J. Chevalier, D. Sharples, H. Berny and A.M. Galy et al., 1995. Antimicrobial activity of 9-oxo and 9-thio acridines: Correlation with intercalation into DNA and effects on macromolecular biosynthesis. Res. Microbiol., 146: 73-83.
4. Demeunynck, M., 2004. Antitumour acridines. Expert Opin. Ther. Patents, 14: 55-70
5. Desbois, N., M. Gardette, J. Papon, P. Labarre and A. Maisonial et al., 2008. Design, synthesis and preliminary biological evaluation of acridine compounds as potential agents for a combined targeted chemo-radionuclide therapy approach to melanoma. Bioorg. Med. Chem., 16: 7671-7690.
6. Dubey, A., S.K. Srivastava and S.D. Srivastava, 2011. Conventional and microwave assisted synthesis of 2-oxo-4-substituted aryl-azetidine derivatives of benzotriazole: A new class of biological compounds. Bioorg. Med. Chem. Lett., 21: 569-573.
7. Gamage, S.A., J.A. Spicer, G.J. At well, G.J. Finlay, B.C. Baguley and W.A. Denny, 1999. Structure activity relationships for substituted bis (acridine-4-carboxamides): A new class of anticancer agents. J. Med. Chem., 42: 2383-2393.
8. Goodell, J.R., A.V. Ougolkov, H. Hiasa, H. Kaur, R. Remmel, D.D. Billadeau and D.M. Ferguson, 2008. Acridine-based agents with topoisomerase II activity inhibit cancer cell proliferation and induce apoptosis. J. Med. Chem., 51: 179-182.
9. Kapuriya, N., K. Kapuriya, X. Zhang, T.C. Chou and R. Kakadiya et al., 2008. Synthesis and biological activity of stable and potent antitumor agents, aniline nitrogen mustards linked to 9-anilinoacridines via a urea linkage. Bioorg. Med. Chem., 16: 5413-5423.
10. Kumar, A., K. Srivastva, S.K. Kumar, S.K. Pun and P.M.S. Chauhan, 2009. Synthesis of 9-anilinoacridines triazines as new class of hybrid antimalarial agents. Bioorg. Med. Chem. Lett., 19: 6996-6999.
11. Ma, Z., L. Rao and U. Bierbach, 2009. Replacement of a thiourea-s with an amidine-NH donor group in a platinum-acridine antitumor compound reduces the metal's reactivity with cysteine sulfur. J. Med. Chem., 52: 3424-3427.
12. Parajuli, R. and C. Medhi, 2004. Basicities of some 9-substituted acridine-4-carboxamides: A density functional theory (DFT) calculation. J. Chem. Sci., 116: 235-241.
13. Rastogi, K., J.Y. Chang, W.Y. Pan, C.H. Chen, T.C. Chan, L.T. Chen and T.L Su, 2002. Antitumor AHMA linked to DNA minor groove binding agent: Synthesis and biological evaluation. J. Med. Chem., 45: 4485-4493.
14. Sondhi, S.M., N. Singh, A.M. Lahoti, K. Bajaj, A. Kumar, O. Lozach, L. Meijer, 2005.Synthesis of Acridinyl-thiazolino derivatives and their evaluation for Anti-inflammatory, analgesic and kinase inhibition activities. Bioorg. Med. Chem., 13: 4291-4299.
15. Spicer, J.A., S.A. Gamage, G.J. Atwell, G.J. Finlay, B.C. Baguley and W.A. Denny, 1997. Structure-activity relationships for Acridine-substituted analogues of the mixed topoisomerase I/II inhibitor N-[2-(Dimethyl amino) ethyl) acridine] acridine-4-carboxamide. J. Med. Chem., 40: 1919-1929.
16. Su, T.L., Y.W. Lin, T.C.Chou, X. Zhang, V.A. Bachenkov and C.H. Chen, 2006. Potent antitumor 9-anilinoacridines and acridines bearing an alkylating N-mustard residue on the acridine chromophore: Synthesis and biological activity. J. Med. Chem., 49: 3710-3718.
17. Swamy, S.N., Basappa, G. Sarala, B.S. Priya, S.L. Gaonkar, J.S. Prasad and K.S. Rangappa, 2006. Microwave-assisted synthesis of N-alkylated benzotriazole derivatives: Antimicrobial studies. Bioorg. Med. Chem. Lett., 16: 999-1004.
18. Venugopala, K.N., G.K. Rao and P.N.S. Pai, 2007. Synthesis and pharmacological study of some novel schiff bases of 4-hydroxy 6-carboxhydrazino benzothiophene analogs. J. Pharmacol. Toxico., 2: 248-255.
19. Wainwright, M., 2001. Acridine-A neglected antibacterial chromophore. J. Antimicrob. Chemother., 47: 1-13.