Design, Synthesis, Antibacterial Activity, and Molecular Docking Studies of Novel Hybrid 1,3-Thiazine-1,3,5-Triazine Derivatives as Potential Bacterial Translation Inhibitor

Chemical Biology and Drug Design

Volumn 80, Issue 4, 2012, Pages 572-583

  Singh, Udaya P ^a   Pathak, Manish ^a   Dubey, Vaibhav ^a   Bhat, Hans R ^a   Gahtori, Prashant ^b   Singh, Ramendra K ^c  

^a SAM HIGGINBOTTOM UNIVERSITY OF AGRICULTURE   (India)

^b UTTARAKHAND TECHNICAL UNIVERSITY   (India)

^c UNIVERSITY OF ALLAHABAD   (India)

Author keywords

1,3,5 Triazine; 1,3 thiazine; Antibacterial; Docking; Translation inhibition

Indexed keywords

2N [4,6 BIS(4 NITROPHENYL) 6H 1,3 THIAZIN 2 YL] N4,N6 BIS(3 NITROPHENYL) 1,3,5 TRIAZINE 2,4,6 TRIAMINE; 4 [2 (4,6 BIS(3 NITROPHENYLAMINO) 1,3,5 TRIAZIN 2 YLAMINO) 6 (2 NITROPHENYL) 6H 1,3 THIAZIN 4 YL]PHENOL; ANTIINFECTIVE AGENT; BACTERIAL RNA; LEVOFLOXACIN; RNA 16S; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BINDING AFFINITY; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; ESCHERICHIA COLI; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

ANTI-BACTERIAL AGENTS; BACTERIA; BACTERIAL INFECTIONS; HUMANS; MOLECULAR DOCKING SIMULATION; PROTEIN BIOSYNTHESIS; THIAZINES; TRIAZINES;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; NEGIBACTERIA; POSIBACTERIA;

EID: 84866600436     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2012.01430.x     Document Type: Article

References (23)

1. Active Bacterial Core Surveillance (ABCs). Report emerging infections program network Streptococcus pneumoniae, (2008) available at: http://www.cdc.gov/abcs/reports-findings/survreports/spneu08.pdf.
2. ECDC/EMEA Joint Technical Report. The bacterial challenge: time to react. (2009) EMEA/576176/2009.
3. Roberts R.R., Hota B., Ahmad I., Scott R.D. 2nd, Foster S.D., Abbasi F., Schabowski S., Kampe L.M., Ciavarella G.G., Supino M., Naples J., Cordell R., Levy S.B., Weinstein R.A. (2009) Hospital and societal costs of antimicrobial-resistant infections in a Chicago teaching hospital: implications for antibiotic stewardship. Clin Infect Dis;49:1175-1184.
4. Singh U.P., Singh R.K., Bhat H.R., Subhashchandra Y.P., Kumar V., Kumawat M.K., Gahtori P. (2011) Synthesis and antibacterial evaluation of series of novel tri-substituted-s-triazine derivatives. Med Chem Res;20:1603-1610.
5. Singh U.P., Bhat H.R., Gahtori P. (2012) Antifungal activity, SAR and physicochemical correlation of some clubbed thiazole-1, 3, 5-triazine derivatives. J Mycol Med;22:134-141.
6. Gahtori P., Ghosh S.K., Singh B., Singh U.P., Bhat H.R., Uppal A. (2011) Synthesis, SAR and antibacterial activity of hybrid chloro, dichloro-phenylthiazolyl-s-triazines. Saudi Pharm J;20:35-43.
7. Hermann T. (2005) Drugs targeting the ribosome. Curr Opin Struct Biol;15:355-366.
8. Zhou Y., Sun Z., Froelich J.M., Hermann T., Wall D. (2006) Structure-activity relationships of novel antibacterial translation inhibitors: 3, 5-diamino-piperidinyl triazines. Bioorg Med Chem Lett;16:5451-5456.
9. Zhou Y., Gregor V.E., Sun Z., Ayida B.K., Winters G.C., Murphy D., Simonsen K.B., Vourloumis D., Fish S., Froelich J.M., Wall D., Hermann T. (2005) Structure-guided discovery of novel aminoglycoside mimetics as antibacterial translation inhibitors. Antimicrob Agents Chemother;49:4942-4949.
10. Zhou C., Min J., Liu Z., Young A., Deshazer H., Gao T., Chang Y.T., Kallenbach N.R. (2008) Synthesis and biological evaluation of novel 1, 3, 5-triazine derivatives as antimicrobial agents. Bioorg Med Chem Lett;18:1308-1311.
11. Gahtori P., Ghosh S.K. (2012) Design, synthesis and SAR exploration of hybrid 4-chlorophenylthiazolyl-s-triazine as potential antimicrobial agents. J Enzyme Inhib Med Chem;27:281-293.
12. Chen H., Lyne P.D., Giordanetto F., Lovell T., Li J. (2006) On evaluating molecular-docking methods for pose prediction and enrichment factors. J Chem Inf Model;46:401-415.
13. Gallivan J.P., Dougherty D.A. (1999) Cation-pi interactions in structural biology. Proc Natl Acad Sci U S A;96:9459-9464.
14. Wang R., Lu Y., Wang S.J. (2003) Comparative evaluation of 11 scoring functions for molecular docking. J Med Chem;46:2287-2303.
15. Gehlhaar D.K., Verkhivker G.M., Rejto P.A., Sherman C.J., Fogel D.B., Fogel L.J., Freer S.T. (1995) Molecular recognition of the inhibitor AG-1343 by HIV-1 protease: conformationally flexible docking by evolutionary programming. Chem Biol;2:317-324.
16. Gehlhaar D.K., Bouzida D., Rejto P.A., Parrill L., Rami Reddy M. (1999) Series title: ACS symposium series, 719. Washington, DC.: American Chemical Society; pp. 292-311.
17. Muegge I., Martin Y.C. (1999) A general and fast scoring function for protein-ligand interactions: a simplified potential approach. J Med Chem;42:791-804.
18. Brooks B.R., Bruccoleri R.E., Olafson B.D., States D.J., Swaminathan S., Karplus M. (1983) CHARMM: a program for macromolecular energy, minimization, and dynamics calculations. J Comput Chem;4:187-217.
19. Momany F.A., Rone R. (1992) Validation of the general purpose QUANTA ®3.2/CHARMm® force field. J Comput Chem;13:888-990.
20. Venkatachalam C.M., Jiang X., Oldfield T., Waldman M. (2003) LigandFit: a novel method for the shape-directed rapid docking of ligands to protein active sites. J Mol Graph Model;21:289-307.
21. Mayo S.L., Olafson B.D., Goddard W.A. III (1990) DREIDING: a generic force field for molecular simulations. J Phys Chem;94:8897-8909.
22. National Committee for Clinical Laboratory Standards (1982) Standard Methods for Dilution Antimicrobial Susceptibility Test for Bacteria Which Grows Aerobically. Villanova: NCCLS;p. 242.
23. Lalitha M.K. (2004) Manual on Antimicrobial Susceptibility Testing (Under the auspices of Indian Association of Medical Microbiologists). Vellore, India: C.M.C.