Click Chemistry Approach for Bis-Chromenyl Triazole Hybrids and Their Antitubercular Activity

Chemical Biology and Drug Design

Volumn 80, Issue 4, 2012, Pages 516-523

  Naik, Reshma J ^a   Kulkarni, Manohar V ^a   Sreedhara Ranganath Pai, K ^b   Nayak, Pawan G ^b  

^a KARNATAK UNIVERSITY   (India)

^b MANIPAL COLLEGE OF PHARMACEUTICAL SCIENCES   (India)

Author keywords

1,2,3 triazole; 2H chromen 2 one; Antibacterial; Antifungal; Antitubercular; Click reaction; Cytotoxic

Indexed keywords

1 [[4 [(4 METHYL 2 OXO 2H CHROMEN 7 YLOXY)METHYL] 1H 1,2,3 TRIAZOL 1 YL]METHYL]3H BENZO[F]CHROMEN 3 ONE; 3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; 4 [[4 [(4 METHYL 2 OXO 2H CHROMEN 7 YLOXY)METHYL] 1H 1,2,3 TRIAZOL 1 YL]METHYL]2H BENZO[H]CHROMEN 2 ONE; 4 METHYL 7 [[1 [(4 METHYL 2 OXO 2H CHROMEN 4 YL)METHYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY]2H CHROMEN 2 ONE; 4 METHYL 7 [[1 [(5,7 DIMETHYL 2 OXO 2H CHROMEN 4 YL)METHYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY]2H CHROMEN 2 ONE; 4 METHYL 7 [[1 [(6 BROMO 2 OXO 2H CHROMEN 4 YL)METHYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY]2H CHROMEN 2 ONE; 4 METHYL 7 [[1 [(6 CHLORO 2 OXO 2H CHROMEN 4 YL)METHYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY]2H CHROMEN 2 ONE; 4 METHYL 7 [[1 [(6 METHOXY 2 OXO 2H CHROMEN 4 YL)METHYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY]2H CHROMEN 2 ONE; 4 METHYL 7 [[1 [(6 METHYL 2 OXO 2H CHROMEN 4 YL)METHYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY]2H CHROMEN 2 ONE; 4 METHYL 7 [[1 [(7 CHLORO 2 OXO 2H CHROMEN 4 YL)METHYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY]2H CHROMEN 2 ONE; 4 METHYL 7 [[1 [(7 HYDROXY 2 OXO 2H CHROMEN 4 YL)METHYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY]2H CHROMEN 2 ONE; 4 METHYL 7 [[1 [(7 METHOXY 2 OXO 2H CHROMEN 4 YL)METHYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY]2H CHROMEN 2 ONE; 4 METHYL 7 [[1 [(7 METHYL 2 OXO 2H CHROMEN 4 YL)METHYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY]2H CHROMEN 2 ONE; 4 METHYL 7 [[1 [(7 METHYL 6,8 DINITRO 2 OXO 2H CHROMEN 4 YL)METHYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY]2H CHROMEN 2 ONE; 4 METHYL 7 [[1 [(7,8 DIMETHYL 2 OXO 2H CHROMEN 4 YL)METHYL] 1H 1,2,3 TRIAZOL 4 YL]METHOXY]2H CHROMEN 2 ONE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

AGAR GEL ELECTROPHORESIS; ANIMAL CELL; ARTICLE; ASPERGILLUS NIGER; ASSAY; CELL STRAIN V 79; CLICK CHEMISTRY; CONTROLLED STUDY; CYCLOADDITION; CYTOTOXICITY; DNA CLEAVAGE; ENTEROCOCCUS FAECALIS; ESCHERICHIA COLI; HUMAN; HUMAN CELL; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PRIORITY JOURNAL; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; ANTITUBERCULAR AGENTS; BACTERIA; CELL LINE; CHROMONES; CLICK CHEMISTRY; FUNGI; HUMANS; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES; TUBERCULOSIS;

BACTERIA (MICROORGANISMS); MYCOBACTERIUM TUBERCULOSIS; NEGIBACTERIA; POSIBACTERIA;

EID: 84866604365     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2012.01441.x     Document Type: Article

References (28)

1. Sunduru N., Sharma M., Chauhan P.M.S. (2010) Recent advances in the design and synthesis of Heterocycles as anti-tubercular agents. Future Med Chem;2:1469-1500.
2. Thomas K.D., Adhikari A.V., Chowdhury I.H., Sumesh E., Pal N.K. (2011) New quinolin-4-yl-1, 2, 3-triazoles carrying amides, sulphonamides and amidopiperazines as potential antitubercular agents. Eur J Med Chem;46:2503-2512.
3. Shiradkar S., Suresh Kumar G.V., Dasari V., Tatikonda S., Akula K.C., Shah R. (2007) Clubbed triazoles: a novel approach to antitubercular drugs. Eur J Med Chem;42:807-816.
4. Manvar A., Malde A., Verma J., Virsodia V., Mishra A., Upadhyay K., Acharya H., Coutinho E., Shah A. (2008) Synthesis, anti-tubercular activity and 3D-QSAR study of coumarin-4-acetic acid benzylidene hydrazides. Eur J Med Chem;43:2395-2403.
5. Manna K., Agrawal Y.K. (2010) Design, synthesis, and antitubercular evaluation of novel series of 3-benzofuran-5-aryl-1-pyrazolyl-pyridylmethanone and 3-benzofuran-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin analogs. Eur J Med Chem;45:3831-3839.
6. Karthikeyan S.V., Perumal S., Shetty K.N., Yogeeswari P., Sriram D. (2009) A microwave-assisted facile regioselective Fischer indole synthesis and antitubercular evaluation of novel 2-aryl-3, 4-dihydro-2H-thieno[3, 2-b]indoles. Bioorg Med Chem Lett;19:3006-3009.
7. Kulkarni M.V., Kulkarni G.M., Lin C.H., Sun C.M. (2006) Recent advances in coumarins and 1-azacoumarins as versatile biodynamic agents. Curr Med Chem;13:2795-2818.
8. Xu Z.Q., Barrow W.W., Suling W.J., Westbrook L., Barrow E., Lin Y.M., Flavin M.T. (2004) Anti-HIV natural product (+)-calanolide A is active against both drug-susceptible and drug-resistant strains of Mycobacterium tuberculosis. Bioorg Med Chem;12:1199-1207.
9. Cardoso S.H., Barreto M.B., Lourenco M.C.S., Henriques M.M.O., Candea A.L.P., Kaiser C.R., de Souza M.V.N. (2011) Antitubercular activity of new coumarins. Chem Biol Drug Des;77:489-493.
10. Lacy A., O'Kennedy R. (2004) Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer. Curr Pharm Des;10:3797-3811.
11. Shi Y., Zhou C.H. (2011) Synthesis and evaluation of a class of new coumarin triazole derivatives as potential antimicrobial agents. Bioorg Med Chem Lett;21:956-960.
12. Aparna V., Jeevan J., Ravi M., Desirajua G.R., Gopalakrishnan B. (2006) 3D-QSAR studies on antitubercular thymidine monophosphate kinase inhibitors based on different alignment methods. Bioorg Med Chem Lett;16:1014-1020.
13. Sivakumar K., Xie F., Cash B.M., Long S., Barnhill H.N., Wang Q. (2004) A fluorogenic 1, 3-dipolar cycloaddition reaction of 3-azidocoumarins and acetylenes. Org Lett;6:4603-4606.
14. Rostovtsev V.V., Green L.G., Fokin V.V., Sharpless K.B. (2002) A stepwise huisgen cycloaddition process: copper (I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew Chem Int Ed;41:2596-2599.
15. Zhang L., Chen X., Xue P., Sun H.H.Y., Williams I.D., Sharpless K.B., Fokin V.V., Jia G. (2005) Ruthenium-catalyzed cycloaddition of alkynes and organic azides. J Am Chem Soc;127:15998-15999.
16. Himo F., Lovell T., Hilgraf R., Rostovtsev V.V., Noodleman L., Sharpless K.B., Fokin V.V. (2005) Copper(I)-catalyzed synthesis of azoles DFT study predicts unprecedented reactivity and intermediates. J Am Chem Soc;127:210-216.
17. Sun S., Wu P. (2010) Mechanistic insights into Cu(I)-catalyzed azide-alkyne "click" cycloaddition monitored by real time infrared spectroscopy. J Phys Chem A;114:8331-8336.
18. Kusanur R.A., Kulkarni M.V., Kulkarni G.M., Nayak S.K., Guru Row T.N., Ganesan K., Sun C.M. (2010) Unusual anisotropic effects from 1, 3-dipolar cycloadducts of 4-azidomethyl coumarins. J Het Chem;47:91-97.
19. Kosiova I., Kovackova S., Kois P. (2007) Synthesis of coumarin-nucleoside conjugates via Huisgen 1, 3-dipolar cycloaddition. Tedrahedron;63:312-320.
20. Kulkarni M.V., Patil V.D. (1981) Studies on coumarins (Part I). Arch Pharm (Weinheim);314:708-711.
21. Basanagouda M., Kulkarni M.V. (2011) Novel one-pot synthesis for 2, 5-diaryl and 5-aryl-pyridazin-3(2h)-ones. Synth Commun;41:2569-2582.
22. Burger A., Ullyot G.E. (1947) Analgesic studies β-ethyl and β-isopropyl amine derivatives of pyridine and thiazole. J Org Chem;12:342-355.
23. Naik R.J., Kulkarni M.V. (2010) Fluorometric investigation of the interaction between nitrophenols and 7-hydroxy-4-azidomethylcoumarin. J Lumin;130:2065-2071.
24. Lourenco M.C.S., deSouza M.V.N., Pinheiro A.C., Ferreira M.L., Goncalves R.B., Nogneira T.C.M., Peralta M.A. (2007) Evaluation of anti-tubercular activity of nicotinic and isoniazid analogues. ARKIVOC;15:181-191.
25. Schwalbe R., Steele-Moore L., Goodwin A.C. (2007) Antimicrobial Susceptibility Testing Protocols. New York: Crc Press.
26. Manjula S.N., Kenganora M., Parihar V.K., Kumar S., Nayak P.G., Kumar N., Ranganath Pai K.S., Rao C.M. (2010) Antitumor and antioxidant activity of Polyalthia longifolia stem bark ethanol extract. Pharm Biol;48:690-696.
27. Sambrook J., Fritsch E.F., Maniatis T. (1989) Molecular Cloning: A Laboratory Manual. New York: Cold Spring Harbor Laboratory Press Cold.
28. Kulkarni M.V., Pujar B.J., Patil V.D. (1983) Studies on coumarins (Part- II). Arch Pharm (Weinheim);316:15-21.