'On water' assisted synthesis and biological evaluation of nitrogen and sulfur containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents

European Journal of Medicinal Chemistry

Volumn 45, Issue 6, 2010, Pages 2418-2426

  Tandon, Vishnu K ^a   Maurya, Hardesh K ^a   Verma, Manoj K ^a   Kumar, Rohitashw ^b   Shukla, Praveen K ^b  

^a UNIVERSITY OF LUCKNOW   (India)

^b CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

2,3 Dichloro 1,4 naphthoquinone; Antibacterial; Antifungal; Fluconazole; Green chemistry; On water; Quinone

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; 2 (3 CHLORO 1,4 DIOXO 1,4 DIHYDRONAPHTHALEN 2 YLTHIO)ACETIC ACID; 2 (ALLYLAMINO) 3 CHLORONAPHTHALENE 1,4 DIONE; 2 CHLORO 3 (2 MERCAPTOETHYLTHIO)NAPHTHALENE 1,4 DIONE; 2 CHLORO 3 (2 PHENYLHYDRAZINYL)NAPHTHALENE 1,4 DIONE; 2 CHLORO 3 (4 METHYLPIPERAZIN 1 YL)NAPHTHALENE 1,4 DIONE; 2 CHLORO 3 (PIPERIDIN 1 YL)NAPHTHALENE 1,4 DIONE; 2 CHLORO 3 (PYRROLIDIN 1 YL)NAPHTHALENE 1,4 DIONE; 2 CHLORO 3 MORPHOLINONAPHTHALENE 1,4 DIONE; 3 HYDROXY 4 METHYL 4H NAPHTHO[2,3 B][1,4]THIAZINE 5,10 DIONE; AMIKACIN; AMPHOTERICIN B; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; BICYCLO COMPOUND; FLUCONAZOLE; GENTAMICIN; GREEN FLUORESCENT PROTEIN; HETERO 1,4 NAPHTHOQUINONE DERIVATIVE; KANAMYCIN; MICONAZOLE; NITROGEN; NYSTATIN; SOLVENT; SULFUR; TOBRAMYCIN; UNCLASSIFIED DRUG; WATER;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; DRUG POTENCY; DRUG SYNTHESIS; PREVALENCE; TRICHOPHYTON MENTAGROPHYTES;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; BACTERIA; FUNGI; GREEN CHEMISTRY TECHNOLOGY; MICROBIAL SENSITIVITY TESTS; NAPHTHOQUINONES; NITROGEN; SULFUR; WATER;

EID: 77950866011     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.02.023     Document Type: Article

References (36)

1. Dallinger D., and Kappe C.O. Chem. Rev. 107 (2007) 2563-2591
2. Herrerias C.I., Yao X., Li Z., and Li C.-J. Chem. Rev. 107 (2007) 2546-2562
3. Li C.J., and Chen L. Chem. Soc. Rev. 35 (2006) 68-82
4. Rice L.B. Biochem. Pharmacol. 71 (2006) 991-995
5. Todar's Online Textbook of Bacteriology. http://www.textbookofbacteriology.net/
6. Peara S., and Patterson T.F. Clin. Infect. Dis. 35 (2002) 1073-1080
7. Kauffman C.A., Malani A.N., Easley C., and Kirkpatrick P. In: Kirkpatrick P.C. (Ed). Nature Reviews Drug Discovery vol. 6 (2007), Nature Publishing group, London 183-184
8. Kresse H., Belsey M.J., and Rouini H. In: Kirkpatrick P.C. (Ed). Nature Reviews Drug Discovery vol. 6 (2007), Nature Publishing group, London 19-20
9. Gutierrez P.l. Free Radical Biol. Med. 6 (1989) 405-445
10. Tudor G., Gutierrez P., Aguilera-Gutierrez A., and Ville E.A.S. Biochem. Pharmacol. 65 (2003) 1061-1075
11. Ganapaty S., Thomas P.S., Karagianis G., Waterman P.G., and Brun R. Phytochemistry 67 (2006) 1950-1956
12. Silva T.M.S., Camara C.S., Barbosa T.P., Soares A.Z., da Cunha L.C., Pinto A.C., and Vargas M.D. Bioorg. Med. Chem. 13 (2005) 193-196
13. Biot C., Bauer H., Schirmer R.H., and Davioud-Charret E. J. Med. Chem. 47 (2004) 5972-5983
14. Mantyla A., GarnierRautio J.T., Nevalainen T., Vepsalainen J., Koskinen A., Croft S.I., and Jarvinen T. J. Med. Chem. 47 (2004) 188-195
15. Tandon V.K., Maurya H.K., Tripathi A., ShivaKesva G.B., Shukla P.K., Srivastava A., and Panda D. Eur. J. Med. Chem. 44 (2009) 1086-1092
16. Tandon V.K., Maurya H.K., Yadav D.B., Tripathi A., Kumar M., and Shukla P.K. Bioorg. Med. Chem. Lett. 16 (2006) 5883-5887
17. Tandon V.K., Yadav D.B., Maurya H.K., Chaturvedi A.K., and Shukla P.K. Bioorg. Med. Chem. 14 (2006) 6120-6126
18. Tandon V.K., Yadav D.B., Singh R.V., Chaturvedi A.K., and Shukla P.K. Bioorg. Med. Chem. Lett. 15 (2005) 5324-5328
19. Tandon V.K., Yadav D.B., Singh R.V., Vaish M., Chaturvedi A.K., and Shukla P.K. Bioorg. Med. Chem. Lett. 15 (2005) 3463-3466
20. Tandon V.K., Chhor R.B., Singh R.V., Rai S., and Yadav D.B. Bioorg. Med. Chem. Lett. 14 (2004) 1079-1083
21. Tandon V.K., Singh R.B., and Yadav D.B. Bioorg. Med. Chem. Lett. 14 (2004) 2901-2904
22. Tandon V.K., Maurya H.K., Mishra N.N., and Shukla P.K. Eur. J. Med. Chem. 44 (2009) 3130-3137
23. Tandon V.K., and Maurya H.K. Tetrahedron Lett. 50 (2009) 5896-5902
24. Colwell C.A., and Mccall M. Science 101 (1945) 592-594
25. Hoffman-Ostenhof O. Science 105 (1947) 549-550
26. Bondi Jr. A., Dietz C.C., and Spaubling E.H. Science 103 (1946) 399-401
27. Becker H. Organicum (Practical Handbook of Organic Chemistry) (1973), Addison-Wesley, MA, USA 611
28. National Committee for Clinical Laboratory Standard. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeast, Approved Standard. Document M27-A (1997), National Committee for Clinical Laboratory Standards, Wayne, PA, USA
29. National Committee for Clinical Laboratory Standard. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Conidium Forming Filamentous Fungi: Proposed Standard. Document M38-P (1998), National Committee for Clinical Laboratory Standard, Wayne, PA, USA
30. Crystallographic data for the structure of Compound 4 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC765321 Copies of data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0) 1223 33603 or e-mail: deposit@ccdc.cam.ac.uk]. Each request should be accompanied by the complete citation of this publication.
31. Ryu C.-K., Jeong H.-J., Lee S.K., Kang H.-Y., Ko K.-M., Sun Y.-J., Song E.-H., Hur Y.H., and Lee C.-O. Arch. Pharm. Res. 23 (2000) 554-558
32. Clark N.G. Pestic. Sci. 15 (1984) 25-30
33. Ryu C.-K., Kang H.-Y., Yi Y.-J., Shin K.-H., and Lee B.H. Bioorg. Med. Chem. Lett. 10 (2000) 1589-1591
34. Ryu C.-K., Shim J.Y., Chae M.J., Choi L.H., Han J.-Y., Jung O.-J., Lee J.Y., and Jeong S.H. Eur. J. Med. Chem. 40 (2005) 438-444
35. Errante G., Motta G.L., Lagana C., Wittebolle V., Sarciron M.-É., and Barret R. Eur. J. Med. Chem. 41 (2006) 773-778
36. Ryu C.-K., Kang H.-Y., Lee S.-K., Nam K.A., Hong C.Y., Ko W.-G., and Lee B.-H. Bioorg. Med. Chem. Lett. 10 (2000) 461-464