Synthesis, spectral characterization and biological evaluation of a novel series of 6-arylsubstituted-3-[2-(4-substitutedphenyl)propan-2-yl]-7H-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazines

European Journal of Medicinal Chemistry

Volumn 57, Issue , 2012, Pages 407-416

  Puthiyapurayil, Pushpan ^a,b   Poojary, Boja ^a   Chikkanna, Chandrashekhar ^c   Buridipad, Sunil Kumar ^d  

^a MANGALORE UNIVERSITY   (India)

^b SYNGENE INTERNATIONAL LTD   (India)

^c Department of Medicinal Chemistry   (India)

^d NET Pharmacy College   (India)

Author keywords

Anthelmintic activity; Antimicrobial activity; Ehrlich ascites carcinoma; MTT assay; Triazolothiadiazine

Indexed keywords

3 (2 PHENYLPROPAN 2 YL) 6 [4 (TRIFLUOROMETHOXY)PHENYL] 7H [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZINE; 3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; 3 [2 (4 BROMOPHENYL)PROPAN 2 YL] 6 (2,4 DICHLORO 5 FLUOROPHENYL) 7H [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZINE; 3 [2 (4 BROMOPHENYL)PROPAN 2 YL] 6 (3,4 DIFLUOROPHENYL) 7H [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZINE; 3 [2 (4 BROMOPHENYL)PROPAN 2 YL] 6 [4 (TRIFLUOROMETHOXY)PHENYL] 7H [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZINE; 3 [2 (4 CHLOROPHENYL)PROPAN 2 YL] 6 (2,4 DICHLORO 5 FLUOROPHENYL) 7H [1,2,4]TRIAZOLO [3,4 B][1,3,4]THIADIAZINE; 3 [2 (4 CHLOROPHENYL)PROPAN 2 YL] 6 (4 CHLORO 3 NITROPHENYL) 7H [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZINE; 3 [2 (4 CHLOROPHENYL)PROPAN 2 YL] 6 [4 (TRIFLUOROMETHOXY)PHENYL] 7H [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZINE; 3 [2 (4 CHLOROPHENYL)PROPAN 2 YL] 6 [4 (TRIFLUOROMETHOXY)PHENYL] 7H [1,2,4]TRIAZOLO[3,4 B]THIADIAZINE; 6 (2,4 DICHLORO 5 FLUOROPHENYL) 3 (2 PHENYLPROPAN 2 YL) 7H [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZINE; 6 (4 CHLORO 3 NITROPHENYL) 3 (2 PHENYLPROPAN 2 YL) 7H [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZINE; 6 (4 CHLORO 3 NITROPHENYL) 3 [2 (4 CHLOROPHENYL)PROPAN 2 YL] 7H [1,2,4]TRIAZOLO[3,4 B][1,3,4]THIADIAZINE; ANASTROZOLE; FLUCONAZOLE; ITRACONAZOLE; LETROZOLE; LORECLEZOLE; THIADIAZINE DERIVATIVE; TRIAZOLOTHIADIAZINE DERIVATIVE; TRYPAN BLUE; UNCLASSIFIED DRUG; VOROZOLE;

ANIMAL CELL; ANTHELMINTIC ACTIVITY; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CARBON NUCLEAR MAGNETIC RESONANCE; CELL STRAIN MCF 7; CONTROLLED STUDY; CYTOTOXICITY; DRUG EFFICACY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; IN VIVO STUDY; INFRARED SPECTROMETRY; LIQUID CHROMATOGRAPHY; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ANIMALS; ANTHELMINTICS; ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; CYTOTOXINS; FUNGI; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; OLIGOCHAETA; SPECTROPHOTOMETRY, INFRARED; THIADIAZINES; TRIAZOLES; TRYPAN BLUE;

EID: 84870055807     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.06.059     Document Type: Article

References (35)

1. N. Plant Drug Discovery Today 9 2004 328
2. H.M. Geysen Nat. Rev. Drug Discov. 2 2003 222
3. M. Kavallaris, N.M. Verrills, and B.T. Hill Drug. Resist. Update 4 2001 392
4. K.N. Gaind, B.N. Dhar, R.N. Chopra, and K.N. Kaul Indian J. Pharm. Sci. 27 1963 198
5. S.J. Sun, H.X. Lou, Y.H. Gao, P.H. Fan, B. Ma, W.Y. Ge, and X.N. Wang J. Pharm. Biomed. Anal. 34 2004 1117
6. M. Clemons, R.E. Coleman, and S. Verma Cancer Treat. Rev. 30 2004 325
7. G.A.R. Johnston Curr. Top. Med. Chem. 2 2002 903
8. N. Demirbas, A. Demirbas, S. Alpay Karaoglu, and E. Celik Arkivoc 1 2005 75
9. B.S. Holla, R. Gonsalves, and S. Shenoy Eur. J. Med. Chem. 35 2000 267
10. A. Shafiee, A. Sayadi, M.H. Roozbahni, A. Foroumadi, and F. Kamal Arch. Pharm. Med. Chem. 10 2002 495
11. S. Sharma, S. Gangal, A. Rauf, and M. Zahin Arch. Pharm. Chem. Life. Sci. 341 2008 714
12. N.N. Gulerman, H.N. Dogan, S. Rollas, C. Johnanssom, and C. Celik II Farmaco 56 2001 953
13. S. Papakonstantinou-Garoufalisa, N. Pouli, P. Marakos, and A. Chytyroglou-Ladas II Farmaco 57 2002 973
14. G. Turan-Zitouni, Z.A. Kaplacikli, M.T. Yildiz, P. Chevallet, and D. Kaya Eur. J. Med. Chem. 40 2005 607
15. A.R. Jalilian, S. Sattari, M. Bineshmarevasti, A. Shafiee, and M. Daneshtalab Arch. Pharm. Med. Chem. 333 2000 347
16. I. Kucukguzel, S.G. Kucukguzel, S. Rollas, and M. Kiraz Bioorg. Med. Chem. Lett. 11 2001 1703
17. L. Zahajska, V. Klimesova, J. Koci, K. Waisser, and J. Kaustova Arch. Pharm. Med. Chem. 337 2004 549
18. A. Foroumadi, Z. Kiani, and F. Soltani II Farmaco 58 2003 1073
19. G. Turan-Zitouni, M. Sivaci, F.S. Kilic, and K. Erol Eur. Med. Chem. 36 2001 685
20. B. Tozkoparan, E. Kupeli, E. Yesilada, and M. Ertan Bioorg. Med. Chem. 15 2007 1808
21. S.M. Rabea, N.A. El-Koussi, H.Y. Hassan, and T. Aboul-Fadi Arch. Pharm. Chem. Life. Sci. 339 2006 32
22. L. Labanuskas, E. Udrenaite, P. Gaidelis, and A. Brukstus II Farmaco 59 2004 255
23. M. Kritsanida, A. Mouroutsou, P. Marakos, N. Pouli, S. Papakonstantinou-Garoufalias, C. Pannecouque, M. Witvrouw, and E. DeClerc II Farmaco 57 2002 253
24. M.T. Abdel-Aal, W.A. El-Sayad, S.M. El-Kosy, and E.S.H. El-Ashry Arch. Pharm. Chem. Life. Sci. 341 2008 307
25. A. Varvaresou, T. Siatra-Papastaikoudi, A. Tsotinis, A. Tsantili-Kakouulidou, and A. Vamvakides II Farmaco 53 1998 320
26. A.P. Skoumbourdis, C.A. LeClair, E. Stefan, A.G. Turjanski, W. Maguire, S.A. Titus, R. Huang, D. S Auld, J. Inglese, C.P. Austin, S.W. Michnick, M. Xia, and C.J. Thomas Bioorg. Med. Chem. Lett. 19 2009 3686
27. Xavier Collin, Sauleau Armelle, and Joel Coulon Bioorg. Med. Chem. Lett. 13 2003 2601
28. P. Puthiyapurayil, B. Poojary, S. Kumar, and R. Hunnur J. Heterocycl. Chem. 48 2011 998
29. D.J. Brusick, Clifton, New Jersey (1984), p. 265.
30. T. Mossman J. Immunol. Methods 65 1983 55
31. B. Kalluraya, and S. Sreenivas IL Farmaco 53 1998 399
32. A.L. Bary Procedure for testing antimicrobial agents in agar media V.L. Corian, Antibiotics in Laboratory Medicine 1980 Williams and wilins Baltimore, MD 1 23
33. D. James, Mac Lowry, J.M. Jaqua, and T.S. Sally Appl. Microbiol. 20 1970 46
34. B.A. Arthington-Skaggs, M. Moltely, D.W. Warnock, and C.J. Morrison J. Clin. Microbiol. 38 2000 2254
35. T. Hama, and J.F. Hartwig Org. Lett. 10 2008 1549