Design, synthesis and SAR exploration of hybrid 4-chlorophenylthiazolyl-s- triazine as potential antimicrobial agents

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 27, Issue 2, 2012, Pages 281-293

  Gahtori, Prashant ^a   Ghosh, Surajit K ^a  

^a DIBRUGARH UNIVERSITY   (India)

Author keywords

MIC; Molinspiration; Osiris; s Triazine; Substituent effect; Synthesis

Indexed keywords

4 CHLOROPHENYLTHIAZOLYL S TRIAZINE; ANTIINFECTIVE AGENT; NITROGEN; NUCLEOPHILE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; GRAM NEGATIVE AEROBIC RODS AND COCCI; GRAM POSITIVE BACTERIUM; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ANIMALS; ANTI-INFECTIVE AGENTS; ARTEMIA; BACTERIA; DRUG DESIGN; LARVA; MICROBIAL SENSITIVITY TESTS; STRUCTURE-ACTIVITY RELATIONSHIP; SURVIVAL RATE; TRIAZINES;

NEGIBACTERIA; OSIRIS; POSIBACTERIA;

EID: 84857445783     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2011.587418     Document Type: Article

References (27)

1. News and analysis. Antibacterial and antifungal drug discovery challenge. Nature Biotechnology 2000;18:IT24-IT26.
2. Cassell GH. Emergent antibiotic resistance: health risks and economic impact. Fems Immunol Med Microbiol 1997;18:271-274. (Pubitemid 27397499)
3. Donadio S, Mafoli S, Monciardini P, Sosio M, Jabes D. Antibiotic discovery in the twenty-frst century: current trends and future perspectives. J Antibiot 2010;63:423-430.
4. Critically important antibacterial agents for human medicine for risk management strategies of non-human use, a report of a WHO working group consultation. Canberra, Australia: February. 2005, pp. 15-18.
5. Melato S, Prosperi D, Coghi P, Basilico B, Monti D. A combinatorial approach to 2,4,6-trisubstituted triazines with potent antimalarial activity: combining conventional synthesis and microwave-assistance. Chem Med Chem 2008;3:873-876.
6. Agarwal A, Srivastava K, Puri SK, Chauhan PMS. Syntheses of 2,4,6-trisubstituted triazines as antimalarial agents. Bioorg Med Chem Lett 2005;15:531-533. (Pubitemid 40143120)
7. Baliani A, Bueno GJ, Stewart ML, Yardley V, Brun R, Barrett MP et al. Design and synthesis of a series of melamine-based nitroheterocycles with activity against Trypanosomatid parasites. J Med Chem 2005;48:5570-5579. (Pubitemid 41209254)
8. Garaj V, Puccetti L, Fasolis G, Winum JY, Montero JL, Scozzafava A, Vullo D, Innocenti A, Supuran CT. Carbonic anhydrase inhibitors: novel sulfonamides incorporating 1,3,5-triazine moieties as inhibitors of the cytosolic and tumour-associated carbonic anhydrase isozymes I, II and IX. Bioorg Med Chem Lett 2005;15:3102-3108. (Pubitemid 40755204)
9. Carta F, Garaj V, Maresca A, Wagner J, Avvaru B, Robbins A, Scozzafava A, McKenna R, Supuran CT. Sulfonamides incorporating 1,3,5-triazine moieties selectively and potently inhibit carbonic anhydrase transmembrane isoforms IX, XII and XIV over cytosolic isoforms I and II: solution and X-ray crystallographic studies. Bioorg Med Chem Lett. 2011;19:3105-3119.
10. Xiong YZ, Chen FE, Balzarini J, De Clercq E, Pannecouque C. Non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 11: structural modulations of diaryltriazines with potent anti-HIV activity. Eur J Med Chem 2008;43:1230-1236. (Pubitemid 351734548)
11. Zhou C, Min J, Liu Z, Young Z, Deshazer H, Gao T, Chang YT, Kallenbach R. Synthesis and biological evaluation of novel 1,3,5-triazine derivatives as antimicrobial agents. Bioorg Med Chem Lett 2008;18:1308-1311. (Pubitemid 351226548)
12. Srinivas K, Srinivas U, Bhanuprakash K, Harakishore K, Murthy USN, Rao VJ. Synthesis and antibacterial activity of various substituted triazines. Eur J Med Chem 2006;41:1240-1246. (Pubitemid 44666218)
13. Singh UP, Singh RK, Bhat HR, Subhaschandra YP, Kumar V, Kumawat MK, Gahtori P. Synthesis and antibacterial evaluation of series of novel tri-substituted-s-triazine derivatives. Med Chem Res 2010.
14. Gahtori P, Das A, Bhatt H. Synthesis and antibacterial assessment of N-[4-(4-substituted phenyl)-1,3-thiazol-2-yl]-1,3,5-triazin-2-amine. Indian J Pharm Sci 2009;71:79-82.
15. Gahtori P, Singh A, Ghosh SK, Das A, Archana U. Synthesis of some substituted phenylthiazolyl 1,3,5-triazine derivatives. Asian J Chem 2010;23:1189-1192.
16. Hernandes MZ, Cavalcanti SM, Moreira DR, de Azevedo Junior WF, Leite AC. Halogen atoms in the modern medicinal chemistry: hints for the drug design. Curr Drug Targets 2010;11:303-314.
17. Truston JT, Dudley JR, Kaiser DW, Henbleikner I, Schaefer FC, Holm-Hensen D. Cyanuric chloride derivatives. I. Aminochloro-s-triazines. J Am Chem Soc 1951;73:2981-2983.
18. European Committee for Antimicrobial Susceptibility Testing (EUCAST) of the European Society of Clinical Microbiology and Infectious Diseases (ESCMID). EUCAST Defnitive Document E.DEF 2.1, August 2000: Determination of antimicrobial susceptibility test breakpoints. Clin Microbiol Infect 2000;6:509-515.
19. Chaudhary MI, Tomsen WJ. Bioassay techniques for drug development. Harwood Academic Publishers, 2001, pp. 9.
20. Richards WG. Computer-aided drug design. Pure Appl Chem 1994;66:1589-1596.
21. Dalafave DS. Design of druglike small molecules for possible inhibition of antiapoptotic BCL-2, BCL-W, and BFL-1 proteins. Biomed Eng Comput Biol 2010;2:11-21.
22. Ertl P, Rohde B, Selzer P. Fast calculation of molecular polar surface area (PSA) as a sum of fragment-based contributions and its application to the prediction of drug transport properties. J Med Chem 2000;43:3714-3717.
23. Mannhold R, Poda GI, Ostermann C, Tetko IV. Calculation of molecular lipophilicity: State-of-the-art and comparison of log P methods on more than 96,000 compounds. J Pharm Sci 2009;98:861-893.
24. Siegal G, Ab E, Schultz J. Integration of fragment screening and library design. Drug Discov Today 2007;12:1032-1039. (Pubitemid 350180558)
25. Fox JL. Te business of developing antibacterials. Nat Biotechnol 2006;24:1521-1528.
26. Kim S, Lee J. Folate-targeted drug-delivery systems prepared by nano-comminution. Drug Dev Ind Pharm 2011;37:131-138.
27. Lombardino JG, Lowe JA. A guide to drug discovery: Te role of the medicinal chemist in drug discovery-then and now. Nat Rev Drug Discovery 2004;3:853-862. (Pubitemid 39405946)