Citation: REN Jin-Qi, JIAO Qing-Zhu, WANG Yi-Nuo, XU Fang-Yuan, CHENG Xiao-Shao, YOU Zhong-Lu. Synthesis, Structures and Helicobacter Pylori Urease Inhibition of Schiff Base Vanadium Complexes Containing Acetohydroxamate Ligands[J]. Chinese Journal of Inorganic Chemistry, ;2014, 30(3): 640-648. doi: 10.11862/CJIC.2014.106 shu

Synthesis, Structures and Helicobacter Pylori Urease Inhibition of Schiff Base Vanadium Complexes Containing Acetohydroxamate Ligands

1.
1 Department of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, Liaoning 116029, China;

Received Date: 21 September 2013
Available Online: 14 November 2013
Fund Project: 辽宁省高校优秀青年人才支持计划(No.LJQ2011114) (No.LJQ2011114)南京大学配位化学国家重点实验室开放课题基金,国家自然科学基金(No.20901036) 资助项目。 (No.20901036)

Two new Schiff base vanadium complexes containing acetohydroxamate ligands, [V^ⅢL¹(HAHA)] (1) and [V^ⅤOL²(AHA)] (2), where L¹ is the dianionic form of N,N'-bis(5-methylsalicylidene)ethane-1, 2-diamine, L² is the monoanionic form of 2-{[2-(2-hydroxyethylamino)ethylimino]methyl}-6-methylphenol, HAHA and AHA are the mono-anionic and di-anionic forms of acetohydroxamic acid, have been synthesized and characterized by physico-chemical methods and single-crystal X-ray diffraction. The V atoms in the complexes adopt octahedral coordination. Thermal stability and urease inhibitory activities of the complexes were studied. The percent inhibition of complexes 1 and 2 at the concentration of 100 μmol·L^-1 on Helicobacter pylori urease are 37.2% and 81.5%, respectively. Complex 2 has IC50 value of 21.5 μmol·L^-1. Molecular docking study indicates that there form effective interactions between complex 2 and the active site of the urease. CCDC: 961635, 1; 961636, 2.
- schiff base;acetohydroxamate;vanadium complex;crystal structure;urease inhibitor
1. [1]
  [1] Francisco S S, Urrutia O, Martin V, et al. J. Sci. Food Agr., 2011,91:1569-1575
2. [2]
  [2] Xiao Z P, Ma T W, Fu W C, et al. Eur. J. Med. Chem., 2010,45:5064-5070
3. [3]
  [3] Barros T G, Williamson J S, Antunes O A C, et al. Lett. Drug Des. Discov., 2009,6:186-192
4. [4]
  [4] Louie A Y, Meade T J. Chem. Rev., 1999,99:2711-2734
5. [5]
  [5] Sumangala V, Poojary B, Chidananda N, et al. Med. Chem. Res., 2013,22:2921-2928
6. [6]
  [6] Tehrani K H M E, Sardari S, Mashayekhi V, et al. Chem. Pharm. Bull., 2013,61:160-166
7. [7]
  [7] Azizian J, Mohammadi M K, Firuzi O, et al. Med. Chem. Res., 2012,21:3730-3740
8. [8]
  [8] Willsky G R, Goldfine A B, Kostyniak P J, et al. J. Inorg. Biochem., 2001,85:33-42
9. [9]
  [9] Orvig C, Caravan P, Gelmini L, et al. J. Am. Chem. Soc., 1995,117:12759-12770
10. [10]
  [10] Messerschmidt A, Prade L, Wever R. Biol. Chem., 1997, 378:309-315
11. [11]
  [11] Ara R, Ashiq U, Mahroof-Tahir M, et al. Chem. Biodivers., 2007,4:58-71
12. [12]
  [12] Aslam M A S, Mahmood S, Shahid M, et al. Eur. J. Med. Chem., 2011,46:5473-5479
13. [13]
  [13] ZHANG Ji-Cai(张吉才), LI Hai-Hua(李海华), XIAN Dong-Mei(献冬梅), et al. Chinese J. Inorg. Chem. (无机化学学报), 2012,28(9):1959-1966
14. [14]
  [14] You Z L, Shi D H, Zhang J C, et al. Inorg. Chim. Acta, 2012,384:54-61
15. [15]
  [15] Kumar S, Kayastha A M. Med. Chem. Res., 2010,19:S113-S114
16. [16]
  [16] Ohta T, Shibata H, Kawamori T, et al. Biochem. Biophys. Res. Commun., 2001,285:728-733
17. [17]
  [17] Krajewska B, Zaborska W, Leszko M, et al. J. Mol. Catal. B -Enzymatic, 2001,14:101-109
18. [18]
  [18] Bruker, SMART and SAINT. Bruker AXS Inc, Madison, 2002.
19. [19]
  [19] Sheldrick G M. SADABS. University of Göttingen, Germany, 1996.
20. [20]
  [20] Sheldrick G M. SHELXTL V5.1, Software Reference Manual, Bruker AXS Inc, Madison, 1997.
21. [21]
  [21] Mao W J, Lü P C, Shi L, et al. Bioorg. Med. Chem., 2009, 17:7531-7536
22. [22]
  [22] Weatherburn M W. Anal. Chem., 1967,39:971-974
23. [23]
  [23] Krajewska B, Zaborska W. Bioorg. Chem., 2007,35:355-365
24. [24]
  [24] Geary W J. Coord. Chem. Rev., 1971,7:81-122
25. [25]
  [25] Schmidt H, Bashirpoor M, Rehder D. J. Chem. Soc., Dalton Trans., 1996,19:3865-3870
26. [26]
  [26] Vergopoulos V, Jantzen S, Rodewald D, et al. Chem. Commun., 1995,3:377-378
27. [27]
  [27] Cornman C R, Colpas G J, Hoeschele J D, et al. J. Am. Chem. Soc., 1992,114:9925-9933
28. [28]
  [28] Xie M J, Niu Y F, Yang X D, et al. Eur. J. Med. Chem., 2010,45:6077-6084
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沈阳化工大学材料科学与工程学院沈阳 110142