Synthesis, antimicrobial and anti-inflammatory activities of some 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines bearing trichlorophenyl moiety

European Journal of Medicinal Chemistry

Volumn 43, Issue 4, 2008, Pages 808-815

  Karegoudar, Prakash ^b   Prasad, D Jagdeesh ^a   Ashok, Mithun ^a   Mahalinga, Manjathuru ^b   Poojary, Boja ^a   Holla, Bantwal Shivarama ^a  

^a MANGALORE UNIVERSITY   (India)

^b SeQuent Scientific Limited   (India)

Author keywords

Anti inflammatory; Antimicrobial screening; Triazolothiadiazines; Triazolothiadiazoles; Trichlorophenyl moiety

Indexed keywords

1,2,4 TRIAZOLO[3,4 B][1,3,4] THIADIAZOLE DERIVATIVE; 1,2,4 TRIAZOLO[3,4 B][1,3,4]THIADIAZINE DERIVATIVE; 3 (2,3,5 TRICHLOROPHENYL) 4 AMINO 1,2,4 TRIAZOLE 5 THIONE; 6 (3 AMIDO 4 HYDROXYPHENYL) 3 (2,3,5 TRICHLOROPHENYL) 7H [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZINE; 6 (3 BROMOPYRIDIN 4 YL) 3 (2,3,5 TRICHLOROPHENYL) [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZOLE; 6 (3,5 DICHLOROPHENYL) 3 (2,3,5 TRICHLOROPHENYL) [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZOLE; 6 (3,5 METHYLPHENYL) 3 (2,3,5 TRICHLOROPHENYL) [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZOLE; 6 (4 CHLOROPHENYL) 3 (2,3,5 TRICHLOROPHENYL) 7H [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZINE; 6 (4 METHOXYPHENYL) 3 (2,3,5 TRICHLOROPHENYL) 7H [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZINE; 6 (4 METHOXYPHENYL) 3 (2,3,5 TRICHLOROPHENYL) [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZOLE; 6 (4 METHYLPHENYL) 3 (2,3,5 TRICHLOROPHENYL) 7H [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZINE; 6 (4 METHYLPHENYL) 3 (2,3,5 TRICHLOROPHENYL) [1,2,4] TRIAZOLO[3,4 B][1,3,4]THIADIAZOLE; 6 (4 METHYLTHIOPHENYL) 3 (2,3,5 TRICHLOROPHENYL) 7H [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZINE; 6 (5 ISOQUINOLYL) 3 (2,3,5 TRICHLOROPHENYL) [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZOLE; 6 (5 QUINOLYL) 3 (2,3,5 TRICHLOROPHENYL) [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZOLE; 6 (BIPHENYL) 3 (2,3,5 TRICHLOROPHENYL) 7H [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZINE; 6 (PHENOXYMETHYL) 3 (2,3,5 TRICHLOROPHENYL) [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZOLE; 6 (PHENYL) 3 (2,3,5 TRICHLOROPHENYL) 7H [1,2,4] TRIAZOLO[3,4 B][1,3,4]THIADIAZINE; 6 (PHENYL) 3 (2,3,5 TRICHLOROPHENYL) [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZOLE; 6 (PHENYL) 3 (2,3,5 TRICHLOROPHENYL) [1,2,4]TRIAZOLO{3,4 B][1,3,4]THIADIAZOLE; 6 PYRIDIN 4 YL 3 (2,3,5 TRICHLOROPHENYL) [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZOLE; THIADIAZINE DERIVATIVE; THIADIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; RAT;

ANIMALS; ANTI-INFECTIVE AGENTS; ANTI-INFLAMMATORY AGENTS; BACTERIA; CARRAGEENAN; EDEMA; FUNGI; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; THIADIAZOLES;

EID: 41449111442     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2007.06.026     Document Type: Article

References (38)

1. Heindel N.D., and Reid J.R. J. Heterocycl. Chem. 17 (1980) 1087
2. Holla B.S., Kalluraya B., Sridhar K.R., Drake E., Thomas L.M., Bhandary K.K., and Levine M.S. Eur. J. Med. Chem. 29 (1994) 301
3. Mathew V., Keshavayya J., Vidya V.P., Acharya, and Reddy B.M. Eur. J. Med. Chem. 41 (2006) 1048
4. The Merck Index, Merck Co. Inc., twelfth ed., USA, 1996.
5. Haber J. Present status and perspectives on antimycoties with systematic effects. Cas. Lek. Cesk. 140 (2001) 596
6. Brucato A., Coppola A., Gianguzza S., and Provenzano P.M. Boll. Soc. Ital. Biol. Sper. 54 (1978) 1051
7. D.L. Coffen, R.I. Fryer, U.S. Patent, 3,849,434 1974;
8. Chem. Abstr., 82, 73044v, 1975.
9. M. Shiroki, T. Tahara, K. Araki, Jap. Patent 75100096, 1975;
10. Chem. Abstr., 84, 59588k, 1976.
11. Povelitsa F.D., and Gural A.G. Antibiotiki Moscow 18 (1973) 71
12. Chem. Abstr., 78, 93044, 1973.
13. Burch H.A., and Smith W.O. J. Med. Chem. 9 (1966) 405
14. Foroumadi A., Mansouri S., Kiani Z., and Rahmani A. Eur. J. Med. Chem. 38 (2003) 851
15. Ram V.J., Mishra L., Pandey N.H., Kushwaha D.S., Pieters L.A.C., and Vlietinck A.J. J. Heterocycl. Chem. 27 (1990) 351
16. Ergenc N., Ilhan E., and Ötük G. Pharmazie 47 (1992) 59
17. Holla B.S., Prasanna C.S., Poojary B., Rao K.S., and Sridhara. Indian J. Chem. 45B (2006) 2071
18. Mithun Ashok, and Shivarama Holla B. J. Pharmacol. Toxicol. 2 3 (2007) 256-263
19. Kalyoncuo{eth}lu N., Rollas S., Sür-Altiner D., Yegeno{eth}lu Y., and An{eth} O. Pharmazie 47 (1992) 796
20. Rollas S., Kalyoncuo{eth}lu N., Sür-Altiner D., and Yegeno{eth}lu Y. Pharmazie 48 (1993) 308
21. Mir I., Siddiqui M.T., and Comrie A. Tetrahedron 26 (1970) 5235
22. Rudnicka W., Foks H., Janowiec M., and Zwolska-Kwiek Z. Acta Pol. Pharm. 43 (1986) 523
23. Chem. Abstr., 108, 131695b, 1988.
24. Holla B.S., Veerendra B., Shivananda M.K., and Boja Poojary. Eur. J. Med. Chem. 38 (2003) 59
25. Duran A., Dogan H.N., and Rollas S. Farmaco 57 (2002) 559
26. Yale H.L., and Piala J.J. J. Med. Chem. 9 (1966) 42
27. Shah M.H., Mhasalkar M.Y., Palki M.V., Deliwala C.V., and Sheth U.K. J. Pharm. Sci. 58 (1969) 1398
28. Mhasalkar M.Y., Shah M.H., Nikam S.T., Anantanarayanan K.G., and Deliwala C.V. J. Med. Chem. 13 (1970) 672
29. J.M. Sprague, D.H. Pa, U.S. Patent 2,407,966, Sept. 17, 1946.
30. Barry A. Procedures and theoretical considerations for testing antimicrobial agents in agar media. In: Lorian (Ed). Antibiotics in Laboratory Medicine. fifth ed. (1991), Williams and Wilkins, Baltimore (MD, 1)
31. James MacLowry D., Jaqua Marry.J., and Selpak Sally.T. Appl. Microbiol. (July 1970) 46-53
32. Fenlon Christine.H., and Cynamon Michel.H. Antimicrob. Agents Chemother. 29 (1986) 386
33. Davis R., Markam A., and Balfour J.A. Drugs 51 6 (June 1996) 1019
34. Arthington-Skaggs B.A., Motley M., Warnock D.W., and Morrison C.J. J. Clin. Microbiol. (June 2000) 2254-2260
35. In: Verma R.S. (Ed). Antifungal Agents: Past, Present and Future Prospects (1998), National Academy Of Chemistry and Biology, Lucknow, India
36. winter C.A., Riseny E.A., and Nuss G.W. Proc. Soc. Exp. Biol. Med. 111 (1962) 544-546
37. Cox, Brian, Healy Patrick, Nobbs, Malcolm Stuart, Shah, Gira Panjabhai, U.S. Patent 6,465,461, Oct 15, 2002.
38. A. Sallmann, R. Pfisterb. U.S. Patent 3,558,690, 1971.