Dioxo- and oxovanadium(V) complexes of thiohydrazone ONS donor ligands: Synthesis, characterization, reactivity, and antiamoebic activity

Inorganic Chemistry

Volumn 45, Issue 3, 2006, Pages 1260-1269

  Maurya, Mannar R ^a   Kumar, Amit ^a   Bhat, Abdul R ^b   Azam, Amir ^b   Bader, Cerstin ^c   Rehder, Dieter ^c  

^a INDIAN INSTITUTE OF TECHNOLOGY ROORKEE   (India)

^b JAMIA MILLIA ISLAMIA CENTRAL UNIVERSITY   (India)

^c UNIVERSITY OF HAMBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIPROTOZOAL AGENT; HYDRAZONE DERIVATIVE; LIGAND; ORGANOMETALLIC COMPOUND; THIOL DERIVATIVE; VANADIUM;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; DRUG SENSITIVITY; ENTAMOEBA HISTOLYTICA; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SENSITIVITY AND SPECIFICITY; SPECIES DIFFERENCE; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; ANTIPROTOZOAL AGENTS; ENTAMOEBA HISTOLYTICA; HYDRAZONES; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PARASITIC SENSITIVITY TESTS; SENSITIVITY AND SPECIFICITY; SPECIES SPECIFICITY; STRUCTURE-ACTIVITY RELATIONSHIP; SULFHYDRYL COMPOUNDS; VANADIUM;

EID: 32544446772     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic050811+     Document Type: Article

References (87)

1. Schuster, H.; Chiodini, P. L. Curr. Opin. Infect. Dis. 2001, 14, 587-591.
2. Edwards, D. I. J. Antibiot. Chemother. 1993, 31, 9-20.
3. Lopez Nigro, M. M.; Gadano, A. B.; Carballo, M. A. Toxicol. in Vitro 2001, 15, 209-213.
4. Moreno, S. N.; Docampo, R. Environ. Health Perspect. 1985, 64, 199-208.
5. Akgun, Y.; Tacyldz, I.; Celik, Y. World J. Surg. 1999, 123, 102-106.
6. Caylor, K. B.; Cassimatis, M. K. J. Am. Anim. Hosp. Assoc. 2001, 37, 258-262.
7. Conoor, T. H.; Stoeckel, M.; Evrard, J.; Legator, M. S. Cancer Res. 1977, 37, 629-633.
8. Kapoor, K.; Chandra, M.; Nag, D.; Paliwal, J. K.; Gupta, R. C.; Saxena, R. C. Int. J. Clin. Pharmacol. Res. 1999, 19, 83-88.
9. Rosenkranz, H. S.; Speck, W. T. Biochem. Biophys. Res. Commun. 1975, 66, 520-525.
10. Rowley, A.; Knight, C.; Skolimowski, M.; Edwards, D. I. Biochem. Pharmacol. 1980, 29, 2095-2098.
11. IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans; International Agency for Research on Cancer: Lyon, France, 1987; Supplement 7, pp 250 and 251.
12. Klayman, D. L.; Scovill, J. P.; Bartosevitch, J. F.; Bruce, J. J. Med. Chem. 1983, 26, 35-39.
13. Klayman, D. L. U.S. Patent 4,665,173, 1987; Chem. Abstr. 1987, 107, 115488.
14. Pai, S. G.; Shirodkar, P. Y. Indian Drugs 1988, 25, 153-158.
15. William, D. R. Chem. Rev. 1972, 72, 203-213.
16. Hossain, M. E.; Alam, M. N.; Begum, J.; Ali, M. A.; Nazimuddin, M.; Smith, F. E.; Hynes, R. C. Inorg. Chim. Acta 1996, 249, 207-213.
17. Maurya, M. R. Coord. Chem. Rev. 2003, 237, 163-181.
18. (a) Butler, A. In Bioinorganic Catalysis, 2nd ed.; Reedijk, J., Bouwman, E., Eds.; Marcel Dekker: New York, 1999; Chapter 5.
19. (b) Butler, A. Coord. Chem. Rev. 1999, 187, 17-25.
20. (c) Vanadium in biological systems; Chasteen, N. D., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1990.
21. (d) Vanadium and its role in life [Metal ions in biological systems]; Sigel, H., Sigel, A., Eds.; Marcel Dekker: New York, 1995; Vol. 31.
22. (e) Messerschmidt, A.; Prade, L.; Wever, R. Biol. Chem. 1997, 378, 309-315.
23. (f) Martinez, J. S.; Carrol, G. L.; Tschirret-Guth, R. A.; Altenhoff, G.; Little, R. D.; Butler, A. J. Am. Chem. Soc. 2001, 123, 3289-3294.
24. (g) Robson, R. L.; Eady, R. R.; Richardson, T. H.; Miller, R. W.; Hawkins, M.; Postgate, J. R. Nature 1986, 322, 388-390.
25. (h) Rehder, D. J. Inorg. Biochem. 2000, 80, 133-136.
26. (a) Ligtenbarg, A. G. J.; Hage, R.; Feringa, B. L. Coord. Chem. Rev. 2003, 237, 89-101.
27. (b) Conte, V.; Di Furia, F.; Licini, G. Appl. Catal. A 1997, 157, 335-361.
28. (a) Pecoraro, V. L.; Slebodnick, C.; Hamstra, B. In Vanadium Compounds: Chemistry, Biochemistry and Therapeutic Applications; Crans, D. C., Tracy, A. S., Eds.; ACS Symposium Series; American Chemical Society: Washington, DC, 1998; Chapter 12.
29. (b) Rehder, D. Inorg. Chem. Commun. 2003, 6, 604-617.
30. (c) Thompson, K. H.; Orvig, C. Met. Ions Biol. Syst. 2004, 41, 221.
31. (d) Sakurai, H.; Kojima, Y.; Yoshikawa, Y.; Kawabe, K.; Yasui, H. Coord. Chem. Rev. 2002, 226, 187-198.
32. (e) Rehder, D.; Pessoa, J. C.; Geraldes, C. F. G. C.; Castro, M. M. C. A.; Kabanos, T.; Kiss, T.; Meier, B.; Micera, G.; Pettersson, L.; Rangel, M.; Salifoglou, A.; Turel, I.; Wang, D. J. Biol. Inorg. Chem. 2002, 7, 384-396.
33. (f) Melchier, M.; Thompson, K. H.; Jong, J. M.; Rettig, S. J.; Shuter, E.; Yuen, V. G.; Zhou, Y.; McNeill, J. H.; Orvig, C. Inorg. Chem. 1999, 38, 2288-2293.
34. (g) Clarke, M. J.; Zhu, F.; Frasca, D. R. Chem. Rev. 1999, 99, 2511-2533.
35. (h) Thompson, K. H.; McNeill, J. H.; Orvig, C. Chem. Rev. 1999, 99, 2561-2571.
36. Trends in the use of vanadium. A report of the National Materials Advisory Board, National Academy of Science; Publication NMAB-267; Clearinghouse for Federal Scientific and Technical Information: Springfield, VA, 1970; p 46.
37. Baran, E. J. J. Inorg. Biochem. 2000, 80, 1-2.
38. (a) Kiss, T.; Jakusch, T.; Pessoa, J. C.; Tomaz, I. Coord. Chem. Rev. 2003, 237, 123-133.
39. (b) Kiss, T.; Jakusch, T.; Kilyen, M.; Kiss, E.; Lakatos, A. Polyhedron 2000, 19, 2389-2401.
40. (a) Rehder, D. Coord. Chem. Rev. 1999, 182, 297-322.
41. (b) Rahder, D. In Transition Metals in Biology and Their Coordination Chemistry; Trautwein, A. X., Ed.; Wiley-VCH: Weinheim, Germany, 1997; pp 491-504.
42. (c) Samanta, S.; Ghosh, D.; Mukhopadhyay, S.; Endo, A.; Weakley, T. J. R.; Chaudhury, M. Inorg. Chem. 2003, 42, 1508-1517.
43. (d) Dutta, S. K.; Samanta, S.; Kumar, S. B.; Han, O. H.; Burckel, P.; Pinkerton, A. A.; Chaudhury, M. Inorg. Chem. 1999, 38, 1982-1988.
44. (e) Dutta, S. K.; Kumar, S. B.; Bhattacharyya, S.; Tiekink, E. R. T.; Chaudhury, M. Inorg. Chem. 1997, 36, 4954-4960.
45. (f) Dutta, S. K.; Tiekink, E. R. T.; Chaudhury, M. Polyhedron 1997, 16, 1863-1871.
46. (g) Maurya, M. R.; Khurana, S.; Zhang, W.; Rehder, D. Eur. J. Inorg. Chem. 2002, 1749-1760.
47. (h) Maurya, M. R.; Khurana, S.; Shailendra Azam, A.; Zhang, W.; Rehder, D. Eur. J. Inorg. Chem. 2003, 1966-1973.
48. (i) Wang, V.; Ebel, M.; Schulzke, C.; Grüning, C.; Hazari, S. K. S.; Rehder, D. Eur. J. Inorg. Chem. 2001, 935-942.
49. (j) Dutta, S. K.; Samanta, S.; Ghosh, D.; Butcher, R. J.; Chaudhury, M. Inorg. Chem. 2002, 41, 5555-5560.
50. (k) Bhattacharyya, S.; Mukhopadhyay, S.; Samanta, S.; Weakley, T. J. R.; Chaudhury, M. Inorg. Chem. 2002, 41, 2433-2440.
51. (l) Samanta, S.; Mukhopadhyay, S.; Mandal, D.; Butcher, R. J.; Chaudhury, M. Inorg. Chem. 2003, 42, 6284-6293.
52. (m) Tarafder, M. T. H.; Ali, M. A.; Saravanan, N.; Weng, W. Y.; Kumar, S.; Umar-Tsafe, N.; Crouse, K. A.; Serdang, M. Trans. Met. Chem. 2000, 25, 295-298.
53. (n) Monga, V.; Thompson, K. H.; Yuen, V. G.; Sharma, V.; Patrick, B. O.; McNeill, J. H.; Orvig, C. Inorg. Chem. 2005, 44, 2678-2688.
54. (a) Watanabe, H.; Nakai, M.; Komazawa, K.; Sakurai, H. J. Med. Chem. 1994, 37, 876-877.
55. (b) Sakurai, H.; Watanabe, H.; Tamura, H.; Yasui, H.; Matsushita, R.; Takada, J. Inorg. Chim. Acta 1998, 283, 175-183.
56. (c) Sakurai, H.; Sano, H.; Takino, T.; Yasui, H. Chem. Lett. 1999, 913-914.
57. (d) Sakurai, H.; Sano, H.; Takiro, T.; Yasui, H. J. Inorg. Biochem. 2000, 80, 99-105.
58. (e) Takeshita, S.; Kawamura, I.; Yashuno, T.; Kimura, C.; Yamamoto, T.; Seki, J.; Tamura, A.; Sakirai, H. J. Inorg. Biochem. 2001, 85, 179-186.
59. (f) Kiss, E.; Kawabe, K.; Tamura, A.; Jakusch, T.; Sakurai, H.; Kiss, T. J. Inorg. Biochem. 2003, 95, 69-76.
60. (g) Katoh, A.; Yamaguchi, M.; Saito, R.; Adachi, Y.; Sakurai, H. Chem. Lett. 2004, 30, 1274-1275.
61. (a) Biology and Biochemistry of Nitrogen Fixation; Dilworth, J. M., Glenn, A. R., Eds.; Elsevier: Amsterdam, 1991.
62. (b) Eady, R. R.; Legh, G. J. J. Chem. Soc., Dalton Trans. 1994, 2739-2747.
63. Ali, M. A.; Tarafder, M. T. H. J. Inorg. Nucl. Chem. 1977, 39, 1785-1791.
64. Das, M.; Livingstone, S. E. Inorg. Chim. Acta 1976, 19, 5-10.
65. Row, R. A.; Jones, M. M. Inorg. Synth. 1957, 5, 113-116.
66. Wright, C. W.; O'Neill, M. J.; Phillipson, J. D.; Warhurst, D. C. Antimicrob. Agents Chemother. 1988, 32, 1725-1709.
67. Diamond, L. S.; Harlow, D. R.; Cunnick, C. C. Trans. R. Soc. Trop. Med. Hyg. 1978, 72, 431-432.
68. Gillin, F. D.; Reiner, D. S.; Suffness, M. Antimicrob. Agents Chemother. 1982, 22, 342-345.
69. Keene, A. T.; Harris, A.; Phillipson, J. D.; Warhurst, D. C. Planta Med. 1986, 278-285.
70. Dutta, S.; Basu, P.; Chakravorty, A. Inorg. Chem. 1993, 32, 5343-5348.
71. Sangeetha, N. R.; Pal, S. Bull. Chem. Soc. Jpn. 2000, 73, 357-363.
72. (a) Pessoa, J. C.; Silva, J. A. L.; Vieira, A. L.; Vilas-Boas, L.; O'Brien, P.; Thornton, V. J. Chem. Soc., Dalton Trans. 1992, 1745-1749.
73. (b) Grüning, C.; Schmidt, H.; Rehder, D. Inorg. Chem. Commun. 1999, 2, 57-59.
74. (c) Mondal, S.; Ghosh, P.; Chakravorty, A. Inorg. Chem. 1997, 36, 59-63.
75. Keramidas, A. D.; Papaioannou, A. B.; Vlahos, A.; Kabanos, T. A.; Bonas, G.; Makriyannis, A.; Rapropoulou, C. P.; Terzis, A. Inorg. Chem. 1996, 35, 357-367.
76. Rehder, D.; Weidemann, C.; Duch, A.; Priebsch, W. Inorg. Chem. 1988, 27, 584-587.
77. Rehder, D. In Transition Metal Nuclear Magnetic Resonance; Pregosin, P. S., Ed.; Elsevier: New York, 1991; pp 1-58.
78. (a) Cavaco, I.; Pessoa, J. C.; Costa, D.; Duarte, M. T.; Gillard, R. D.; Matias, P. J. Chem. Soc., Dalton Trans. 1994, 149-157.
79. (b) Asgedom, G.; Sreedhara, A.; Kivikoski, J.; Valkonen, J.; Rao, C. P. J. Chem. Soc., Dalton Trans. 1995, 2459-2466.
80. Maurya, M. R.; Khurana, S.; Schulzke, C.; Rehder, D. Eur. J. Inorg. Chem. 2001, 779-788.
81. Maurya, M. R.; Agarwal, S.; Bader, C.; Rehder, D. Eur. J. Inorg. Chem. 2005, 147-157.
82. Plass, W.; Pohlmann, A.; Yozgatli, H. K. J. Inorg. Biochem. 2000, 80, 181-183.
83. Macedo-Ribeiro, S.; Hemrika, W.; Renirie, R.; Wever, R.; Messerschmidt, A. J. Biol. Inorg. Chem. 1999, 4, 209-219.
84. Colpas, G. J.; Hamstra, B. J.; Kampf, J. W.; Pecoraro, V. L. Inorg. Chem. 1994, 33, 4669-4675.
85. Giacomelli, A.; Floriani, C.; De Souza Duarte, A. O.; Chiesi-Villa, A.; Guastino, C. Inorg. Chem. 1982, 21, 3310-3316.
86. Kosugi, M.; Hikichi, S.; Akita, V.; Moro-oka, Y. Inorg. Chem. 1999, 38, 2567-2578.
87. Ramadan, A. M. J. Inorg. Biochem. 1997, 65, 183-189.