QSAR and docking studies on chalcone derivatives for antitubercular activity against M.tuberculosis H37Rv

Journal of Chemometrics

Volumn 28, Issue 6, 2014, Pages 499-507

  Yadav, Dharmendra Kumar ^a   Ahmad, Imran ^a   Shukla, Aparna ^a   Khan, Feroz ^a   Negi, Arvind Singh ^a   Gupta, Atul ^a  

^a CSIR CENTRAL INSTITUTE OF MEDICINAL AND AROMATIC PLANTS   (India)

Author keywords

ADMET; Chalcones; Docking; Enoyl reductase; QSAR

Indexed keywords

ANTIBIOTICS; BINDING ENERGY; COMPUTATIONAL CHEMISTRY; METABOLISM; MOLECULAR GRAPHICS; MOLECULAR ORBITALS; PHYSIOLOGY; STRUCTURAL DESIGN; STRUCTURE (COMPOSITION); TUBES (COMPONENTS);

ADMET; ANTITUBERCULAR ACTIVITIES; CHALCONE DERIVATIVES; CHALCONES; DOCKING; DOCKING STUDIES; ENOYL REDUCTASE; M. TUBERCULOSIS; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP STUDIES;

TOXICITY;

EID: 84902120028     PISSN: 08869383     EISSN: 1099128X     Source Type: Journal    
DOI: 10.1002/cem.2606     Document Type: Article

References (32)

1. Koul A, Arnoult E, Lounis N, Guillemont J, Andries K. The challenge of new drug discovery for tuberculosis. Nature 2011; 7331: 483-490.
2. WHO Global tuberculosis report, 2013 (http://www.who.int/tb/publications/global_report/en/index.html).
3. Dipti G, Jyotsna JM. Resistant TB: newer drugs and community approach. Recent Pat. Antiinfect Drug Discov. 2011; 6: 27-37.
4. Zheng M, Jin H, Fu L, Xu J, Wang B, Zhao W, Zhu H, Li P, Lu Y, Li Q. A comparative study on the activities of six combination regimens against multidrug-resistant Mycobacterium tuberculosis infection in BALB/c mice. J. Chemother. 2013; 25: 81-6.
5. Murray PR, Rosenthal KS, Pfaller MA. Medical Microbiology (5th edn). Elsevier, Mosby: Philadelphia, PA, 2005.
6. Figueroa M, Cruz RI, Cruz RB, Byeb R, Navarrete A, Mata R. Constituents, biological activities and quality control parameters of the crude extract and essential oil from Arracacia tolucensis var. multifida. J. Ethnopharmacol. 2007; 113: 125-131.
7. Bukhari SN, Franzblau SG, Jantan I, Jasamai M. Current prospects of synthetic curcumin analogs and chalcone derivatives against Mycobacterium tuberculosis. Med. Chem. 2013; 9: 897-903.
8. Khunt RC, Khedkar VM, Coutinho EC. Synthesis and 3D-QSAR analysis of 2-chloroquinoline derivatives as H37 RV MTB inhibitors. Chem. Biol. Drug Des. 2013; 82: 669-84.
9. Mata R, Morales I, Perez O, Rivero-Cruz I, Acevedo L, Enriquez-Mendoza I, Bye R, Franzblau S, Timmermann B. Antimycobacterial compounds from Piper sanctum. J. Nat. Prod. 2004; 67: 1961-1968.
10. Ahmad I, Thakur JP, Chanda D, Saikia D, Khan F, Dixit S, Kumar A, Konwar R, Negi AS, Gupta A. Amide derivatives of 2, 3-diarylacrylophenone as estrogen receptor binding ligands. Bioorg. Med. Chem. Lett. 2013; 23: 1322-1325.
11. Yadav DK, Khan F. QSAR, docking and ADMET studies of camptothecin derivatives as inhibitors of DNA topoisomerase-I. J. Chemom. 2013; 27: 21-33.
12. Yadav DK, Kalani K, Khan F, Srivastava SK. QSAR and docking based semi-synthesis and in vitro evaluation of 18β-glycyrrhetinic acid derivatives against human lung cancer cell line A-549. Med. Chem. 2013; 9: 1073-84.
13. Collins L, Franzblau SG. Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob. Agents Chemother. 1997; 41: 1004-9.
14. Morris RP, Nguyen L, Gatfield J, Visconti K, Nguyen K, Schnappinger D, Ehrt S, Liu Y, Heifets L, Pieters J, Schoolnik G, Thompson CJ. Ancestral antibiotic resistance in Mycobacterium tuberculosis. Proc. Natl. Acad. Sci. 2005; 102: 12200-5.
15. Piddock LJ, Ricci V. Accumulation of five fluoroquinolones by Mycobacterium tuberculosis H37Rv. J. Antimicrob. Chemother. 2001; 48: 787-91.
16. Gautam R, Saklani A, Jachak SM. Indian medicinal plants as a source of antimycobacterial agents. J. Ethnopharmacol. 2007; 110: 200-34.
17. Akihisa T, Franzblau SG, Ukiya M, Okuda H, Zhang F, Yasukawa K, Suzuki T, Kimura Y. Antitubercular activity of triterpenoids from Asteraceae flowers. Biol. Pharm. Bull. 2005; 28: 158-60.
18. Sandra M, Newton CL, Colin WW. A review of antimycobacterial natural products. Phytother. Res. 2000; 14: 303-322.
19. Fenlon CH, Cynamon MH. Comparative in vitro activities of ciprofloxacin and other 4-quinolones against Mycobacterium tuberculosis and Mycobacterium intracellulare. Antimicrob. Agents Chemother. 1986; 29: 386-8.
20. Banfi E, Scialino G, Monti-Bragadin C. Development of a microdilution method to evaluate Mycobacterium tuberculosis drug susceptibility. J. Antimicrob. Chemother. 2003; 52: 796-800.
21. Wallace RJ, Jr. Nash DR, Steele LC, Steingrube V. Susceptibility testing of slowly growing mycobacteria by a microdilution MIC method with 7H9 broth. J. Clin. Microbiol. 1986; 24: 976-81.
22. Maurya A, Khan F, Bawankule DU, Yadav DK, Srivastava SK. QSAR, docking and in vivo studies for immunomodulatory activity of isolated triterpenoids from Eucalyptus tereticornis and Gentiana kurroo. Eur. J. Pharm. Sci. 2012; 47: 152-161.
23. Kumar S, Singh V, Tiwari M. QSAR modeling of the inhibition of reverse transcriptase enzyme with benzimidazolone analogs. Med. Chem. Res. 2011; 20: 1530-1541.
24. Kumar S. Singh V, Tiwari M. Quantitative structure activity relationship studies of sulfamide derivatives as carbonic anhydrase inhibitor: as antiglaucoma agents. J. Med. Chem. 2007; 3: 379-386.
25. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, Olson AJ. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J. Comput. Chem. 1998; 19: 1639-1662.
26. Seeliger D, de Groot BL. Ligand docking and binding site analysis with PyMOL and Autodock/Vina. J. Comput. Aided Mol. Des. 2010; 24: 417-22.
27. Yadav DK, Meena A, Srivastava A, Chanda D, Khan F, Chattopadhyay SK. Development of QSAR model for immunomodulatory activity of natural coumarinolignoids. Drug. Des. Devel. Ther. 2010; 4: 173-86.
28. Meena A, Yadav DK, Srivastava A, Khan F, Chanda D, Chattopadhyay SK. In silico exploration of anti-inflammatory activity of natural coumarinolignoids. Chem. Biol. Drug Des. 2011; 78: 567-79.
29. Yadav DK, Khan F, Negi AS. Pharmacophore modeling, molecular docking, QSAR, and in silico ADMET studies of gallic acid derivatives for immunomodulatory activity. J. Mol. Model. 2012; 18: 2513-25.
30. Saluja AK, Tiwari M, Kumar S. Ligand-based design, virtual screening, and ADME/T-based profiling on a dataset of 1, 3, 5-triazine-substituted benzene sulfonamides as carbonic anhydrase inhibitors. J. Chemom. DOI: 10.1002/cem.2579.
31. Kumar S, Tiwari M. Grid potential analysis, virtual screening studies and ADME/T profiling on N-arylsulfonylindoles as anti-HIV-1 agents. J. Chemom. 2013; 27: 143-154.
32. Yadav DK, Kalani K, Singh AK, Khan F, Srivastava SK, Pant AB. Design, synthesis and in vitro evaluation of 18β-glycyrrhetinic acid derivatives for anticancer activity against human breast cancer cell line MCF-7. Curr. Med. Chem. 2013. PMID: 24180274.