Citation: SUN Sang-Dun, MI Si-Qi, YOU Jing, YU Ji-Liang, HU Song-Qing, LIU Xin-Yong. HQSAR Study and Molecular Design of Benzimidazole Derivatives as Corrosion Inhibitors[J]. Acta Physico-Chimica Sinica, ;2013, 29(06): 1192-1200. doi: 10.3866/PKU.WHXB201303154 shu

HQSAR Study and Molecular Design of Benzimidazole Derivatives as Corrosion Inhibitors

1.
1 Oil Production Technology Research Institute of Shengli Oilfield, Dongying 257061, Shandong Province, P. R. China;
2 College of Science, China University of Petroleum (East China), Qingdao 266580, Shandong Province, P. R. China;
3 Oil Production Engineering Research Institute of Huabei Oilfield, Renqiu 062500, Hebei Province, P. R. China;
4 College of Pharmacy, Shandong University, Jinan 250012, P. R. China

Received Date: 15 January 2013
Available Online: 15 March 2013
Fund Project: 山东省自然科学基金(ZR2012BM010) (ZR2012BM010)中国石油科技创新基金项目(2011D-5006-0202)资助 (2011D-5006-0202)

Hologram quantitative structure-activity relationship (HQSAR) analysis was conducted on a series of benzimidazole compounds to build the HQSAR model between corrosion inhibition properties and molecular structures in acid environment. The optimal HQSAR model was determined by investigating the influence of different fragment distinction and fragment size on the models, and the models’ stability and predictive ability were evaluated. The results show that the optimal HQSAR model was generated using atoms(A), bonds(B), connectivity(C), hydrogen(H), chirality(Ch), donor and acceptor(D&A) as fragment distinction and fragment size of 1-3. The model had a non-cross validated coefficient (r²) value of 0.996, a cross-validated (q²) value of 0.960, and a cross-validated standard error (SE_cv) value of 3.709, which indicates od statistics stability and predictive power. On the basis of the maps derived from the optimal HQSAR model, 38 new benzimidazole derivatives were designed and screened using the optimal HQSAR model, giving potential candidates with high predictive inhibition efficiency. This work provides valuable information for further research and design of more promising corrosion inhibitors in the oil and gas field.
- Benzimidazole,
- Corrosion inhibitor,
- Hologram quantitative structure-activity relationship,
- Molecular design
1. [1]
  
  (1) Migahed, M. A. Mater. Chem. Phys. 2005, 93 (1), 48. doi: 10.1016/j.matchemphys.2005.02.003
2. [2]
  (2) Abd El-Maksoud, S. A.; Fouda, A. S. Mater. Chem. Phys. 2005,93 (1), 84. doi: 10.1016/j.matchemphys.2005.02.020
3. [3]
  (3) Mernari, B.; Elattari, H.; Traisnel, M.; Bentiss, F.; Lagrenee, M.Corrosion Sci. 1998, 40 (2-3), 391. doi: 10.1016/S0010-938X(97)00142-X
4. [4]
  (4) Khaled, K. F. Electrochim. Acta 2003, 48 (17), 2493. doi: 10.1016/S0013-4686(03)00291-3
5. [5]
  (5) Mu, G. N.; Li, X. H.; Qu, Q.; Zhou, J. Corrosion Sci. 2006, 48 (2), 445. doi: 10.1016/j.corsci.2005.01.013
6. [6]
  (6) Trabanelli, G. Corrosion 1991, 47 (6), 410. doi: 10.5006/1.3585271
7. [7]
  (7) Gómez, B.; Likhanova, N. V.; Domínguez Aguilar, M. N.;Olivares, O.; Hallen, J. M.; Martínez-Magadán, J. M. J. Phys.Chem. A 2005, 109 (39), 8950. doi: 10.1021/jp052188k
8. [8]
  (8) Wang, X. M.; Yang, H. Y.; Wang, F. H. Corrosion Sci. 2011, 53 (1), 113. doi: 10.1016/j.corsci.2010.09.029
9. [9]
  (9) Wang, P. Quantitative Structure-Activity Relationship andResearch Methods; Harbin Institute of Technology Press:Harbin, 2004; pp 1-3. [王鹏.定量构效关系及研究方法.哈尔滨: 哈尔滨工业大学出版社, 2004: 1-3.]
10. [10]
  (10) Hansch, C.; Fujita, T. J. Am. Chem. Soc. 1964, 86 (8), 1616. doi: 10.1021/ja01062a035
11. [11]
  (11) Bentiss, F.; Traisnel, M.; Vezin, H.; Lagrenée, M. Corrosion Sci.2003, 45 (2), 371. doi: 10.1016/S0010-938X(02)00102-6
12. [12]
  (12) Khaled, K. F.; Babi?-Samard?ija, K.; Hackerman, N.Electrochim. Acta 2005, 50 (12), 2515. doi: 10.1016/j.electacta.2004.10.079
13. [13]
  (13) Zhang, S. G.; Lei, W.; Xia, M. Z.; Wang, F. Y. J. Mol.Struct.-Theochem 2005, 732 (1-3), 173. doi: 10.1016/j.theochem.2005.02.091
14. [14]
  (14) Lebrini, M.; Traisnel, M.; Lagrenée, M.; Mernari, B.; Bentiss, F.Corrosion. Sci. 2008, 50 (2), 473. doi: 10.1016/j.corsci.2007.05.031
15. [15]
  (15) Hu, S. Q.; Hu, J. C.; Shi, X.; Zhang, J.; Guo, W. Y. ActaPhys. -Chim. Sin. 2009, 25 (12), 2524. [胡松青, 胡建春, 石鑫,张军,郭文跃.物理化学学报, 2009, 25 (12), 2524.]doi: 10.3866/PKU.WHXB20091126
16. [16]
  (16) Ashry, E. S. H. E.; Senior, S. A. Corrosion Sci. 2011, 53 (3),1025. doi: 10.1016/j.corsci.2010.11.037
17. [17]
  (17) Marshall, G. R.; Cramer, R. D. Trends. Pharmacol. Sci. 1988, 9 (8), 285. doi: 10.1016/0165-6147(88)90012-0
18. [18]
  (18) Hu, S. Q.; Mi, S. Q.; Jia, X. L.; Guo, A. L.; Chen, S. H.; Zhang,J.; Liu, X. Y. Chem. J. Chin. Univ. 2011, 32 (10), 2402. [胡松青,米思奇, 贾晓林,郭爱玲, 陈生辉,张军,刘新泳.高等学校化学学报, 2011, 32 (10), 2402.]
19. [19]
  (19) Winkler, D. A.; Burden, F. R. Quant. Struct. -Act. Relat. 1998, 17 (3), 224.
20. [20]
  (20) Chen, D.; Yin, C. S.; Wang, X. D.; Wang, L. S. Chemosphere2004, 57 (11), 1739. doi: 10.1016/j.chemosphere.2004.08.075
21. [21]
  (21) Honorio, K. M.; Garratt, R. C.; Andricopulo, A. D. Bioorg. Med.Chem. Lett. 2005, 15 (12), 3119. doi: 10.1016/j.bmcl.2005.04.017
22. [22]
  (22) Nair, P. C.; Srikanth, K.; Sobhia, M. E. Bioorg. Med. Chem.Lett. 2008, 18 (4), 1323. doi: 10.1016/j.bmcl.2008.01.023
23. [23]
  (23) Ye, M.; Dawson, M. I. Bioorg. Med. Chem. Lett. 2009, 19 (12),3310. doi: 10.1016/j.bmcl.2009.04.072
24. [24]
  (24) Cheng, Y. H.; Zhou, M.; Tung, C. H.; Ji, M. J.; Zhang, F. S.Med. Chem. Lett. 2010, 20 (11), 3329. doi: 10.1016/j.bmcl.2010.04.033
25. [25]
  (25) Popova, A.; Sokolova, E.; Raicheva, S.; Christov, M. CorrosionSci. 2003, 45 (1), 33. doi: 10.1016/S0010-938X(02)00072-0
26. [26]
  (26) Abboud, Y.; Abourriche, A.; Saffaj, T.; Berrada, M.; Charrouf,M.; Bennamara, A.; Cherqaoui, A.; Takky, D. Appl. Surf. Sci.2006, 252 (23), 8178. doi: 10.1016/j.apsusc.2005.10.060
27. [27]
  (27) Aljourani, J.; Raeissi, K.; lozar, M. A. Corrosion Sci. 2009, 51 (8), 1836. doi: 10.1016/j.corsci.2009.05.011
28. [28]
  (28) Benabdellah, M.; Tounsi, A.; Khaled, K. F.; Hammouti, B. Arab.J. Chem. 2011, 4 (1), 17. doi: 10.1016/j.arabjc.2010.06.010
29. [29]
  (29) Sybyl Software, Version 8.1; Tripos Associates Inc.: St. Louis,MO, USA, 2008.
30. [30]
  (30) Doddareddy, M. R.; Lee, Y. J.; Cho, Y. S.; Choi, K.; Koh, H. Y.;Pae, A. N. Bioorg. Med. Chem. Lett. 2004, 12 (14), 3815. doi: 10.1016/j.bmc.2004.05.005
31. [31]
  (31) Flower, R. D. J. Chem. Inf. Comput. Sci. 1998, 38 (3), 379. doi: 10.1021/ci970437z
32. [32]
  (32) Bush, B. L.; Nachbar, R. B. J. Comput. -Aided. Mol. Des. 1993,7(5), 587. doi: 10.1007/BF00124364
33. [33]
  (33) Wold, S.; Sjöström, M.; Eriksson, L. Chemom. Intell. Lab. Syst.2001, 58 (2), 109. doi: 10.1016/S0169-7439(01)00155-1
34. [34]
  (34) Cawley, G. C.; Talbot, N. L. C. Neural Netw. 2004, 17 (10),1467. doi: 10.1016/j.neunet.2004.07.002
35. [35]
  (35) Clark, M.; Cramer, R. D.; Jones, D. M.; Patterson, D. E.;Simeroth, P. E. Tetrahedron Comput. Method 1990, 3 (1), 47.doi: 10.1016/0898-5529(90)90120-W
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