Some biologically active oxovanadium(IV) complexes of triazole derived Schiff bases: Their synthesis, characterization and biological properties

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 25, Issue 5, 2010, Pages 599-607

  Chohan, Zahid H ^a   Sumrra, Sajjad H ^a  

^a BAHAUDDIN ZAKARIYA UNIVERSITY   (Pakistan)

Author keywords

Antibacterial; Antifungal; Oxovanadium(IV) complexes; Triazole Schiff base

Indexed keywords

OXOVANADIUM; SCHIFF BASE; TRIAZOLE; UNCLASSIFIED DRUG; VANADIUM;

ARTICLE; ASPERGILLUS FLAVUS; BACILLUS SUBTILIS; BACTERIAL STRAIN; CANDIDA ALBICANS; CANDIDA GLABRATA; CARBON NUCLEAR MAGNETIC RESONANCE; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; FUNGAL STRAIN; FUSARIUM SOLANI; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MICROSPORUM CANIS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; SALMONELLA TYPHI; SHIGELLA FLEXNERI; TRICHOPHYTON;

ANIMALS; ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; ARTEMIA; COORDINATION COMPLEXES; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; LETHAL DOSE 50; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICROBIAL SENSITIVITY TESTS; MITOSPORIC FUNGI; SCHIFF BASES; SPECTROPHOTOMETRY, INFRARED; TRIAZOLES; VANADATES;

ARTEMIA; BACTERIA (MICROORGANISMS); FUNGI; SALMONELLA TYPHI; STAPHYLOCOCCUS AUREUS;

EID: 77956015385     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756360903257884     Document Type: Article

References (59)

1. Sakurai H. A new concept: the use of vanadium complexes in the treatment of diabetes mellitus. Chem Rec 2002;2:237-248
2. Thompson KH, McNeill JH, Orvig C. Vanadium compounds as insulin mimics. Chem Rev 1999;99:2561-2572
3. Takino T, Yasui H, Yoshitake A, Hamajima Y, Matsushita R, Takada J, et al. A new halogenated antidiabetic vanadyl complex, bis(5-iodopicolinato) oxovanadium (IV): in vitro and in vivo insulinomimetic evaluations and metallokinetic analysis. J Bio Inorg Chem 2001;6:133-142
4. Butler A, Carrano CJ. Coordination chemistry of vanadium in biological systems. Coord Chem Rev 1991;109:61-105.
5. Sakurai H, Kojitane Y, Yoshikawa Y, Kawabe K, Yasui H. Antidiabetic vanadium (IV) and zinc (II) complexes. Coord Chem Rev 2002; 226:187-198
6. Xing YH, Aoki K, Bai FY. A new insulin-like vanadyl complex: synthesis and structure of V(IV)O(H2O)2 (2,6-pyridinedicarboxylate) E2H2O. J Coord Chem 2004;57:157-165
7. Thompson KH, Orvig C. Coordination chemistry of vanadium in metallopharmaceutical candidate compounds. Coord Chem Rev 2001;219-21:1033-1053
8. Haasnoot JG. Mononuclear, oligonuclear and polynuclear metal coordination compounds with 1,2,4-triazole derivatives as ligands. Coord Chem Rev 2000;200-2:131-185
9. Avaji PG, Patil SA, Badami PS. Synthesis, spectral, thermal, solid-state DC electrical conductivity and biological studies of Co(II) complexes with Schiff bases derived from 3-substituted-4-amino-5-hydrazino- 1,2,4-triazole and substituted salicylaldehydes. Transition Met Chem 2008;33:275-283
10. Singh K, Barwa MS, Tyagi P. Synthesis, characterization and biological studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes with bidentate Schiff bases derived by heterocyclic ketone. Eur J Med Chem 2006; 41:147-153
11. Badwaik VB, Aswar AS. Synthesis, characterization and biological studies of some Schiff base complexes. Russ J Coord Chem 2007; 33:755-760
12. Gulerman NN, Dogan HN, Rollas S, Johansson C, Celik C. Synthesis and structure elucidation of some new thioether derivatives of 1,2,4- triazoline-3-thiones and their antimicrobial activities. Farmaco 2001;56:953-958
13. Singh K, Singh DP, Barwa MS, Tyagi P. Some bivalent metal complexes of Schiff bases containing N and S donor atoms. J Enzyme Inhib Med Chem 2006;21:749-755
14. Bagihalli GB, Avaji PG, Patil SA, Badami PS. Synthesis, spectral characterization, in vitro antibacterial, antifungal and cytotoxic activities of Co(II), Ni(II) and Cu(II) complexes with 1,2,4-triazole Schiff bases. Eur J Med Chem 2008;43:2639-2649
15. Rezaei Z, Khabnadideh S, Pakshir K, Hossaini Z, Amiri F, Assadpour E. Design, synthesis and antifungal activity of triazole and benzotriazole derivatives. Eur J Med Chem 2008;xxx:1-4.
16. Reddy V, Patil S, Reddy T, Angadi SD. Synthesis, characterization and biological activities of Cu(II), Co(II), Ni(II), Mn(II) and Fe(III) complexes with Schiff base derived from 3-(4-chlorophenoxymethyl)-4-amino-5- mercapto-1,2,4-triazole. E-J Chem 2008;5:529-538
17. Serdar M, Gumrukcuoglu N, Karaoglu SA, Demirbas N. Synthesis of some novel 3,5-diaryl-1,2,4-triazole derivatives and investigation of their antimicrobial activities. Turk J Chem 2007;31:315-326
18. Ulusoy N, Gursoy A, Otuk G. Synthesis and antimicrobial activity of some 1,2,4-triazole-3-mercaptoacetic acid derivatives. Farmaco 2001;56:947-952
19. Demirba NS, Demirba AS, Alpay-Karaoglu, Elif EC. Synthesis and antimicrobial activities of some new [1,2,4]triazolo [3,4-b]thiadiazoles and [1,2,4]triazole [3,4-b][1,3,4]thiadiazines. ARKIVOC 2005;(i):75-91.
20. Demirbas N, Demirbas A, Karaoglu SA. Synthesis and biological activities of new 1,2,4-triazol-3-one derivatives. Russi J Bioorg Chem 2005;31:387-397
21. Bekircan O, Kahveci B, Kucuk M. Synthesis and anticancer evaluation of some new unsymmetrical 3,5-diaryl-4H-1,2,4-triazole derivatives. Turk J Chem 2006;30:29-40.
22. Holla BS, Veerendra B, Shivanada MK, Poojary B. Synthesis, characterization and anticancer activity studies on some Mannich bases derived from 1,2,4-triazoles. Eur J Med Chem 2003;38:759-767
23. Turan-Zitouni G, Kaplancikli ZA, Erol K, Kilic FS. Synthesis and analgesic activity of some triazoles and triazolothiadiazines. Farmaco 1999;54:218-223
24. Chen J, Sun XY, Chai KY, Lee JS, Song MS, Quan ZS. Synthesis and anticonvulsant evaluation of 4-(4-alkoxylphenyl)-3-ethyl-4H-1,2,4- triazoles as open-chain analogues of 7-alkoxyl-4,5-dihydro[1,2,4] triazolo[4,3-a]quinolines. Bioorg Med Chem 2007;15:6775-6781
25. Guo-Qiang H, Li-Li H, Song-Qiang X, Wen-Long H. Design, synthesis and antitumor activity of asymmetric bis(s-triazole Schiff-bases) bearing functionalized side-chain. Chin J Chem 2008;26:1145-1149
26. Invidiata FP, Grimaudo S, Giammanco P, Giammanco L. Synthesis and pharmacological properties of 6-substituted 3-(pyridine-4-yl)-1,2,4- triazole [3,4-b][1,3,4]thiadiazoles. Farmaco 1991;46:1489-1495
27. Bekircan O, Gumrukcuoglu N. Synthesis of some 3,5-diphenyl- 4H-1,2,4-triazole derivatives as antitumor agents. Indian J Chem 2005;44B:2107-2113
28. Monika W, Swatko-Ossor M, Mazur L, Rzaczynska Z, Siwek A. Synthesis, structure and investigations of tuberculosis inhibition activities of new 4-methyl-1-substituted-1H-1,2,4-triazoles-5(4H)-thione. J Hetrocyclic Chem 2008;45:1893-1896.
29. Kucukguzel I, Kucukguzel SG, Rollas S, Kirazb M. Some 3-thioxo/ alkylthio-1,2,4-triazoles with a substituted thiourea moiety as possible antimycobacterials. Biorg Med Chem Lett 2001;11:1703-1707
30. Klimesova V, Zahajska L, Waisser K, Kaustova J, Mollmann U. Synthesis and antimycobacterial activity of 1,2,4-triazole 3-benzylsulfanyl derivatives. Farmaco 2004;59:279-288
31. Dabak K, Sezer O, Akar A, Anac O. Synthesis and investigation of tuberculosis inhibition activities of some 1,2,3-triazole derivatives. Eur J Med Chem 2003;38:215-218.
32. Chu CH, Sun XW, Sun L, Zhang ZY, Li ZC, Liao RA. Synthesis and biological activity of omega-(5-aryl-1,3,4-oxadiazol-2-thio)- and mega- (5-aryl-l,3,4-oxadiazol-2-thioacetoxyl)-omega-(1-H-1,2,4-triazol-1-yl) acetophenones. J Chin Chem Soc 1999;46:229-232
33. Czollner L, Sxilagli G, Janaky J. Synthesis of new 1,5-diphenyl-3-1H- 1,2,4-triazoles substituted with H-, alkyl, or carboxyl groups at C-3. Arch Pharmazie 1990;323:225-251
34. Izumi K, Yamaguchi I, Wada A, Oshio, Takahashi HN. Effects of a new plant-growth retardant (E)-1-(4-chlorophenyl)-4,4 dimethyl-2-(1,2,4- triazol-1-yl)-1-penten-3-ol (s-3307) on the growth and gibberellin content of rice plants. Plant Cell Physiol 1984;25:611-615
35. Chohan ZH, Supuran CT. In-vitro antibacterial and cytotoxic activity of cobalt (II), copper (II), nickel (II) and zinc (II) complexes of the antibiotic drug cephalothin (keflin). J Enzyme Inhib Med Chem 2005;20:463-468
36. Chohan ZH, Arif M, Shafiq Z, Yaqub M, Supuran CT. In vitro antibacterial, antifungal and cytotoxic activity of some isonicotinoylhydrazide Schiff bases and their cobalt (II), copper (II), nickel (II) and zinc (II) complexes. J Enzyme Inhib Med Chem 2006;21:95-103.
37. McLaughlin JL, Chang C-J, Smith DL. "Bench-top" bioassays for the discovery of bioactive natural products: an update. In: Atta-ur-Rahman, ed. Studies in Natural Products Chemistry. Amsterdam: Elsevier Science, 1991;9:383-409.
38. Atta-ur-Rahman, Choudhary MI, Thomsen WJ. Bioassay Techniques for Drug Development. Amsterdam: Harwood Academic Publishers, 2001:22.
39. Bauer AW, Kirby WM, Sherris JC, Turck M. Antibiotic susceptibility testing by a standardized single disk method. Am J Clin Pathol 1966;45:493.
40. Meyer BN, Ferrigni NR, Putnam JE, Jacobsen LB, Nichols DE, McLaughlin JL. Brine shrimp: a convenient general bioassay for active plant constituents. Planta Med 1982;45:31-34
41. Finney DJ. Probit Analysis, 3rd ed. Cambridge: Cambridge University Press, 1971.
42. Geary WJ. The use of conductivity measurements in organic solvents for the characterization of coordination compounds. Coord Chem Rev 1971;7:81-121.
43. Pandey OP. Oxovanadium(IV) complexes of carbohydrazones and thiocarbohydrazones. Polyhedron 1986;5:1587-1591
44. Yadawe MS, Patil SA. Synthesis, characterization and biological studies of cobalt(II) and nickel(II) complexes with new Schiff bases. Transition Met Chem 1997;22;220-224
45. Bagihalli GB, Badami PS, Patil SA. Synthesis, spectral characterization and in vitro biological studies of Co(II), Ni(II) and Cu(II) complexes with 1,2,4-triazole Schiff bases. J Enzyme Inhib Med Chem 2008;23:1-14.
46. Stoilova D, Georgiev M, Marinova D. Infrared study of the vibrational behavior of SO4 2 guest ions matrix-isolated in metal (II) chromates (Me = Ca, Sr, Ba). Vib Spectrosc 2005;39:46.
47. Simmons WW. The Sadtler Handbook of Proton NMR Spectra. Philadelphia, PA: Sadtler Research Laboratories, 1978.
48. Pasto DJ. Organic Structure Determination. London: Prentice Hall International, 1969.
49. Ballhausen CJ, Gray HB. The electronic structure of the vanadyl ion. Inorg Chem 1962;1:111-122
50. Selbin J. The chemistry of oxovanadium (IV). Chem Rev 1965;65:153-175
51. Selbin J. Oxovanadium (IV) complexes. Coord Chem Rev 1966;1:293-314.
52. Selbin J, Morpurgo L. Spectral studies of low symmetry oxovanadium(IV) complexes. J Inorg Nucl Chem 1965;27:673-678.
53. Chohan ZH. Synthesis and biological properties of Cu(II) complexes with 1,10-disubstituted ferrocenes. Synth React Inorgan Met Organ Chem 2004;34:833-846
54. Chohan ZH, Supuran CT. Structural and biological properties of first row d-transition metal complexes with N-substituted sulfonamides. J Enzyme Inhib Med Chem 2008;23:240-251
55. Chohan ZH, Shad HA. Structural elucidation and biological significance of 2-hydroxy-1-naphthaldehyde derived sulfonamides and their first row d-transition metal chelates. J Enzyme Inhib Med Chem 2008;23:369-379
56. Chohan ZH. Metal-based sulfonamides: their preparation, characterization and in vitro antibacterial, antifungal and cytotoxic properties. X-ray structure of 4-[(2-hydroxybenzylidene)amino] benzosulfonamide. J Enzyme Inhib Med Chem 2008;23:120-130
57. Chohan ZH. Metal-based antibacterial and antifungal sulfonamides: synthesis, characterization and biological properties. Transition Met Chem 2009;34:153-161
58. Chohan ZH. Synthesis of organometallic-based biologically active compounds: in vitro antibacterial, antifungal and cytotoxic properties of some sulfonamide incorporated ferrocenes. J Enzyme Inhib Med Chem 2009;24:169-175
59. Chohan ZH, Shad HA, Nasim FH. Synthesis, charcterization and biological properties of sulfonamide-derived compounds and their transition metal complexes. Appl Organomet Chem 2009;23:319-328