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Journal of Chemistry
Volume 2013 (2013), Article ID 427181, 14 pages
http://dx.doi.org/10.1155/2013/427181
Research Article

Molecular Modeling Studies of Substituted 2,4,5-Trisubstituted Triazolinones Aryl and Nonaryl Derivatives as Angiotensin II AT1 Receptor Antagonists

1Drug Research Laboratory, Department of Pharmaceutical Sciences, Dr. H. S. Gour University, Sagar 470 003, India
2Department of Chemistry, Chaudher Dilip Singh Kanya Mahavidyalaya, Bhind 477001, India

Received 26 June 2012; Revised 21 October 2012; Accepted 21 October 2012

Academic Editor: Tomokazu Yoshimura

Copyright © 2013 Mukesh C. Sharma et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. I. H. Page and O. M. Helmer, “A crystalline pressor substance (angiotonin) resulting from the reaction between renin and renin activator,” The Journal of Experimental Medicine, vol. 71, pp. 29–42, 1940. View at Google Scholar
  2. E. Braun-Menendez, E. Fasciolo, J. C. Leloir, and J. M. Munoz, “The substance causing renal hypertension,” The Journal of Physiology, vol. 98, pp. 283–298, 1940. View at Google Scholar
  3. C. M. Ferrario, “The renin-angiotensin system: importance in physiology and pathology,” Journal of Cardiovascular Pharmacology, vol. 15, supplement 3, no. 3, pp. S1–S5, 1990. View at Google Scholar · View at Scopus
  4. M. B. Vallotton, “The renin-angiotensin system,” Trends in Pharmacological Sciences, vol. 8, no. 2, pp. 69–74, 1987. View at Google Scholar · View at Scopus
  5. M. De Gasparo, K. J. Catt, T. Inagami, J. W. Wright, and T. Unger, “International union of pharmacology. XXIII. The angiotensin II receptors,” Pharmacological Reviews, vol. 52, no. 3, pp. 415–472, 2000. View at Google Scholar · View at Scopus
  6. M. De Gasparo, “AT1 and AT2 angiotensin II receptors: key features,” Drugs, vol. 62, no. 1, pp. 1–10, 2002 (French). View at Google Scholar · View at Scopus
  7. D. F. Guo, Y. L. Sun, P. Hamet, and T. Inagami, “The angiotensin II type 1 receptor and receptor-associated proteins,” Cell Research, vol. 11, no. 3, pp. 165–180, 2001. View at Google Scholar · View at Scopus
  8. M. M. Ibrahim, “RAS inhibition in hypertension,” Journal of Human Hypertension, vol. 20, no. 2, pp. 101–108, 2006. View at Publisher · View at Google Scholar · View at Scopus
  9. U. Gether, “Uncovering molecular mechanisms involved in activation of G protein-coupled receptors,” Endocrine Reviews, vol. 21, no. 1, pp. 90–113, 2000. View at Publisher · View at Google Scholar · View at Scopus
  10. D. T. Dinh, A. G. Frauman, C. I. Johnston, and M. E. Fabiani, “Angiotensin receptors: distribution, signalling and function,” Clinical Science, vol. 100, no. 5, pp. 481–492, 2001. View at Publisher · View at Google Scholar · View at Scopus
  11. A. Parate and S. C. Chaturvedi, “Predicting 3H-1,2,4-triazolinones as angiotensin II receptor antagonists: 2D and 3D QSAR by kNN-molecular field analysis approach,” Medicinal Chemistry Research, vol. 21, no. 7, pp. 1166–1178, 2011. View at Publisher · View at Google Scholar · View at Scopus
  12. C. Hansch, “A quantitative approach to biochemical structure-activity relationships,” Accounts of Chemical Research, vol. 2, no. 8, pp. 232–239, 1969. View at Google Scholar · View at Scopus
  13. A. M. Doweyko, “QSAR: dead or alive?” Journal of Computer-Aided Molecular Design, vol. 22, no. 2, pp. 81–89, 2008. View at Publisher · View at Google Scholar · View at Scopus
  14. M. C. Sharma, D. V. Kohli, S. C. Chaturvedi, and S. Sharma, “Molecular modelling studies of some substitued 2-butylbenzimidazoles angiotensin II receptor antagonists as antihypertensive agents,” Digest Journal of Nanomaterials and Biostructures, vol. 4, no. 4, pp. 843–856, 2009. View at Google Scholar · View at Scopus
  15. M. C. Sharma and D. V. Kohli, “3D QSAR studies on series of 2, 3-dihydro-4(1H)-quinazolinone derivatives angiotensin II receptor antagonists: kNNMFA approach,” American-Eurasian Journal of Agricultural & Environmental Sciences, vol. 6, no. 2, pp. 85–94, 2011. View at Google Scholar
  16. M. C. Sharma and D. V. Kohli, “3D QSAR kNNMFA approach studies on series of substituted piperidin-2-one biphenyl tetrazoles as angiotensin II receptor antagonists,” American-Eurasian Journal of Toxicological Sciences, vol. 3, no. 2, pp. 75–84, 2011. View at Google Scholar
  17. M. C. Sharma and D. V. Kohli, “QSAR study on sulfonylcarbamate derivatives: an insight into the structural requirement for the angiotensin II receptor antagonist,” European Journal of Applied Sciences, vol. 3, no. 1, pp. 9–14, 2011. View at Google Scholar
  18. M. C. Sharma and D. V. Kohli, “3D-QSAR studies of some substituted imidazolinones angiotensin II receptor antagonists,” World Applied Sciences Journal, vol. 12, no. 11, pp. 2129–2134, 2011. View at Google Scholar
  19. M. C. Sharma and D. V. Kohli, “3D QSAR studies on a series of-[(1- Benzyl-1H-Imidazol-5-yl)-alkyl]-amino derivatives as angiotensin II AT1 antagonists,” American-Eurasian Journal of Agricultural & Environmental Sciences, vol. 6, no. 2, pp. 79–84, 2011. View at Google Scholar
  20. M. C. Sharma and D. V. Kohli, “3D QSAR approach on substituted isoxazolidines derivatives as angiotensin II receptor antagonist,” American-Eurasian Journal of Toxicological Sciences, vol. 3, no. 2, pp. 85–91, 2011. View at Google Scholar
  21. M. C. Sharma and D. V. Kohli, “3D QSAR studies of substituted- 4(3H) quinazolinones derivatives as angiotensin II receptor antagonists,” European Journal of Applied Sciences, vol. 3, no. 1, pp. 15–23, 2011. View at Google Scholar
  22. M. C. Sharma and D. V. Kohli, “Predicting alkylbenzimidazole derivatives as angiotensin II receptor antagonists: 3D QSAR by kNN-MFA approach,” Advanced Biology Research, vol. 5, no. 3, pp. 161–169, 2011. View at Google Scholar
  23. M. C. Sharma and D. V. Kohli, “3D QSAR studies on a series of sulfonylcarbamate isostere derivatives as non-peptide angiotensin II receptor antagonists: kNNMFA method,” American-Eurasian Journal of Agricultural & Environmental Sciences, vol. 6, no. 2, pp. 64–70, 2011. View at Google Scholar
  24. M. C. Sharma and D. V. Kohli, “Exploration of quantitative structure activity relationship studies on a series of substituted quinazolinones as angiotensin II AT1 receptor antagonists,” World Applied Sciences Journal, vol. 12, no. 11, pp. 2111–2119, 2011. View at Google Scholar
  25. M. C. Sharma and D. V. Kohli, “2D- and 3D- QSAR studies of substituted 4H-pyrido [1, 2-a] pyrimidin-4-ones angiotensin II receptor antagonists,” American-Eurasian Journal of Agricultural & Environmental Sciences, vol. 3, no. 2, pp. 92–100, 2011. View at Google Scholar
  26. M. C. Sharma and D. V. Kohli, “An insight into the structural requirement QSAR approach on substituted isoxazolidines derivatives as angiotensin II receptor antagonist,” American-Eurasian Journal of Agricultural & Environmental Sciences, vol. 6, no. 2, pp. 71–78, 2011. View at Google Scholar
  27. M. C. Sharma and D. V. Kohli, “QSAR studies on substituted benzimidazoles as angiotensin II receptor antagonists: kNNMFA approach,” Arabian Journal of Chemistry. In press. View at Publisher · View at Google Scholar
  28. M. C. Sharma and D. V. Kohli, “An approach to design antihypertensive agents by 2D QSAR studies on series of substituted benzimidazoles derivatives as angiotensin II receptor antagonists,” Arabian Journal of Chemistry. In press. View at Publisher · View at Google Scholar
  29. M. C. Sharma and and D. V. Kohli, “QSAR analysis and 3D QSAR kNN-MFA approach on a series of substituted quinolines derivatives as angiotensin II receptor antagonists,” Arabian Journal of Chemistry. In press. View at Publisher · View at Google Scholar
  30. M. C. Sharma and D. V. Kohli, “Quantitative structure-activity analysis studies on triazolinone aryl and nonaryl substituents as angiotensin II receptor antagonists,” Journal of Saudi Chemical Society. In press. View at Publisher · View at Google Scholar
  31. M. C. Sharma and D. V. Kohli, “Two dimensional and k-Nearest neighbor molecular field analysis approach on substituted triazolone derivatives: an insight into the structural requirement for the angiotensin II receptor antagonist,” Journal of Saudi Chemical Society. In press. View at Publisher · View at Google Scholar
  32. M. C. Sharma and D. V. Kohli, “Insight into the structural requirement of substituted quinazolinone biphenyl acylsulfonamides derivatives as angiotensin II receptor antagonists: 2D and 3D QSAR approach,” Journal of Saudi Chemical Society. In press. View at Publisher · View at Google Scholar
  33. M. C. Sharma and D. V. Kohli, “QSAR analysis of imidazo[4, 5-b] pyridine substituted á-phenoxyphenylacetic acids as angiotensin II AT1 receptor antagonists,” Journal of Saudi Chemical Society. In press. View at Publisher · View at Google Scholar
  34. M. C. Sharma and D. V. Kohli, “Predicting substituted 2-butylbenzimidazoles derivatives as angiotensin II receptor antagonists: three-dimensional QSAR and pharmacophore mapping,” Journal of Saudi Chemical Society. In press. View at Publisher · View at Google Scholar
  35. M. C. Sharma and D. V. Kohli, “QSAR studies of a series of angiotensin II receptor substituted benzimidazole bearing acidic heterocycles derivatives,” Journal of Saudi Chemical Society. In press.
  36. M. C. Sharma, S. Sharma, N. K. Sahu, and D. V. Kohli, “3D QSAR kNNMFA studies on 6-substituted benzimidazoles derivatives as nonpeptide angiotensin II receptor antagonists: a rational approach to antihypertensive agents,” Journal of Saudi Chemical Society. In press. View at Publisher · View at Google Scholar
  37. M. C. Sharma, S. Sharma, N. K. Sahu, and D. V. Kohli, “QSAR Studies of some substituted imidazolinones angiotensin II receptor antagonist using partial least squares regression (PLSR) based feature selection,” Journal of Saudi Chemical Society. In press. View at Publisher · View at Google Scholar
  38. M. C. Sharma and D. V. Kohli, “Insight into the structural requirement of aryltriazolinone derivatives as angiotensin II AT1 receptor: 2D and 3D-QSAR k-nearest neighbor molecular field analysis approach,” Medicinal Chemistry Research, vol. 21, pp. 2837–2853, 2012. View at Google Scholar
  39. M. C. Sharma and D. V. Kohli, “A comprehensive structure-activity analysis 2, 3,5-trisubstituted 4,5-dihydro-4-oxo-3H-imidazo [4,5-c] pyridine derivatives as angiotensin II receptor antagonists: using 2D- and 3D-QSAR approach,” Medicinal Chemistry Research. In press. View at Publisher · View at Google Scholar
  40. M. C. Sharma and D. V. Kohli, “Comprehensive two and three-dimensional QSAR studies of 3-substituted 6-butyl-1, 2dihydropyridin-2-ones derivatives as angiotensin II receptor antagonists,” Medicinal Chemistry Research. In press. View at Publisher · View at Google Scholar
  41. M. C. Sharma and D. V. Kohli, “Comprehensive structure-activity relationship analysis of isoxazolinyl and isoxazolidinyl substituted quinazolinone derivatives as angiotensin II receptor antagonists,” Journal of Saudi Chemical Society. In press.
  42. M. C. Sharma, S. Sharma, and D. V. Kohli, “Structural insights for 5-â ketosulfoxide imidazolyl biphenyl sulfonylureas derivatives as angiotensin II AT1 receptor antagonists using kNN-MFA with genetic algorithm,” Journal of Saudi Chemical Society. In press.
  43. M. C. Sharma and D. V. Kohli, “A comprehensive structure-activity analysis of 5-carboxyl imidazolyl biphenyl sulfonylureas derivatives angiotensin AT1 receptor antagonists: 2D- and 3D-QSAR approach,” Arabian Journal of Chemistry. In press. View at Publisher · View at Google Scholar
  44. M. C. Sharma, “Structural insight for (6-oxo-3-pyridazinyl)-benzimidazoles derivatives as angiotensin II receptor antagonists: QSAR, pharmacophore identification and kNNMFA approach,” Journal of Saudi Chemical Society. In press. View at Publisher · View at Google Scholar
  45. M. C. Sharma and D. V. Kohli, “Comprehensive structure-activity relationship analysis of substituted 5-(biphenyl-4-ylmethyl) pyrazoles derivatives as AT1 selective angiotensin II receptor antagonists: 2D and kNNMFA QSAR approach,” Medicinal Chemistry Research. In press. View at Publisher · View at Google Scholar
  46. M. C. Sharma, S. Sharma, and D. V. Kohli, “QSAR approach insight the structural requirement of substituted quinazolinones derivatives as angiotensin II receptor antagonists,” Oxidation Communication, vol. 3, pp. 694–707, 2012. View at Google Scholar
  47. M. C. Sharma, S. Sharma, and D. V. Kohli, “QSAR studies of 2-alkylbenzimidazole derivatives as angiotensin II receptor antagonists,” Oxidation Communication, vol. 3, pp. 708–721, 2012. View at Google Scholar
  48. M. C. Sharma and D. V. Kohli, “Predicting 2, 3-dihydroquinazolinones derivatives as angiotensin II receptor antagonists: 2D QSAR approach,” Oxidation Communication, vol. 3, pp. 721–734, 2012. View at Google Scholar
  49. P. A. Datar, P. V. Desai, and E. C. Coutinho, “A 3D-QSAR of angiotensin II (AT1) receptor antagonists based on receptor surface analysis,” Journal of Chemical Information and Computer Sciences, vol. 44, no. 1, pp. 210–220, 2004. View at Publisher · View at Google Scholar · View at Scopus
  50. T. Tuccinardi, V. Calderone, S. Rapposelli, and A. Martinelli, “Proposal of a new binding orientation for non-peptide AT1 antagonists: homology modeling, docking and three-dimensional quantitative structure—activity relationship analysis,” Journal of Medicinal Chemistry, vol. 49, no. 14, pp. 4305–4316, 2006. View at Publisher · View at Google Scholar · View at Scopus
  51. L. L. Chang, W. T. Ashton, K. L. Flanagan et al., “Triazolinones as nonpeptide angiotensin II antagonists. 1. Synthesis and evaluation of potent 2,4,5-trisubstituted triazolinones,” Journal of Medicinal Chemistry, vol. 36, no. 17, pp. 2558–2568, 1993. View at Google Scholar · View at Scopus
  52. VLife MDS 3.5, “Molecular design suite. Vlife Sciences Technologies Pvt. Ltd.,” Pune, India, 2008, http://www.vlifesciences.com/.
  53. T. A. Halgren, “Merck molecular force field. III. Molecular geometries and vibrational frequencies for MMFF94,” Journal of Computational Chemistry, vol. 17, no. 5-6, pp. 553–586, 1996. View at Google Scholar · View at Scopus
  54. T. Scior, J. L. Medina-Franco, Q. T. Do, K. Martínez-Mayorga, J. A. Y. Rojas, and P. Bernard, “How to recognize and workaround pitfalls in QSAR studies: a critical review,” Current Medicinal Chemistry, vol. 16, no. 32, pp. 4297–4313, 2009. View at Publisher · View at Google Scholar · View at Scopus
  55. A. Golbraikh and A. Tropsha, “Predictive QSAR modeling based on diversity sampling of experimental datasets for the training and test set selection,” Journal of Computer-Aided Molecular Design, vol. 16, no. 5-6, pp. 357–369, 2002. View at Publisher · View at Google Scholar · View at Scopus
  56. S. Ajmani, K. Jadhav, and S. A. Kulkarni, “Group-based QSAR (G-QSAR): mitigating interpretation challenges in QSAR,” QSAR and Combinatorial Science, vol. 28, no. 1, pp. 36–51, 2009. View at Publisher · View at Google Scholar · View at Scopus
  57. S. Ajmani, A. Agrawal, and S. A. Kulkarni, “A comprehensive structure-activity analysis of protein kinase B-alpha (Akt1) inhibitors,” Journal of Molecular Graphics and Modelling, vol. 28, no. 7, pp. 683–694, 2010. View at Publisher · View at Google Scholar · View at Scopus
  58. S. Ajmani, K. Jadhav, and S. A. Kulkarni, “Three-dimensional QSAR using the k-nearest neighbor method and its interpretation,” Journal of Chemical Information and Modeling, vol. 46, no. 1, pp. 24–31, 2006. View at Publisher · View at Google Scholar · View at Scopus
  59. P. Ghosh and M. C. Bagchi, “QSAR modeling for quinoxaline derivatives using genetic algorithm and simulated annealing based feature selection,” Current Medicinal Chemistry, vol. 16, no. 30, pp. 4032–4048, 2009. View at Publisher · View at Google Scholar · View at Scopus
  60. M. Clark, R. D. Cramer III, and O. N. Van, “Validation of the general purpose tripos 5.2 force field,” Journal of Computational Chemistry, vol. 10, pp. 982–1012, 1989. View at Google Scholar
  61. J. Gasteiger and M. Marsili, “Iterative partial equalization of orbital electronegativity-a rapid access to atomic charges,” Tetrahedron, vol. 36, no. 22, pp. 3219–3228, 1980. View at Google Scholar · View at Scopus
  62. M. A. Sharaf, D. L. Illman, and B. R. Kowalski, Chemometrics, Chemical Analysis Series, Wiley, New York, NY, USA, 1986.
  63. K. S. Bhadoriya, M. C. Sharma, S. V. Jain, G. S. Raut, and J. R. Rananaware, “Three-dimensional quantitative structure-activity relationship (3D-QSAR) analysis and molecular docking-based combined in silico rational approach to design potent and novel TRPV1 antagonists,” Medicinal Chemistry Research. In press. View at Publisher · View at Google Scholar
  64. W. Zheng and A. Tropsha, “Novel variable selection quantitative structure–property relationship approach based on the k-nearest neighbor principle,” Journal of Chemical Information and Computer Sciences, vol. 40, no. 1, pp. 185–194, 2000. View at Google Scholar · View at Scopus
  65. S. Kirkpatrick, C. D. Gelatt, and M. P. Vecchi, “Optimization by simulated annealing,” Science, vol. 220, no. 4598, pp. 671–680, 1983. View at Google Scholar · View at Scopus
  66. N. Metropolis, A. W. Rosenbluth, M. N. Rosenbluth, A. H. Teller, and E. Teller, “Equation of state calculations by fast computing machines,” The Journal of Chemical Physics, vol. 21, no. 6, pp. 1087–1092, 1953. View at Google Scholar · View at Scopus
  67. L. X. Sun, Y. L. Xie, X. H. Song, J. H. Wang, and R. Q. Yu, “Cluster analysis by simulated annealing,” Computers and Chemistry, vol. 18, no. 2, pp. 103–108, 1994. View at Google Scholar · View at Scopus
  68. M. C. Sharma, S. Sharma, and K. S. Bhadoriya, “QSAR analyses and pharmacophore studies of tetrazole and sulfonamide analogs of imidazo[4, 5-b]pyridine using simulated annealing based feature selection,” Journal of Saudi Chemical Society. In press.
  69. R. D. Cramer, D. E. Patterson, and J. D. Bunce, “Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins,” Journal of the American Chemical Society, vol. 110, no. 18, pp. 5959–5967, 1988. View at Google Scholar · View at Scopus
  70. M. N. Noolvi and H. M. Patel, “A comparative QSAR analysis and molecular docking studies of quinazoline derivatives as tyrosine kinase (EGFR) inhibitors: a rational approach to anticancer drug design,” Journal of Saudi Chemical Society. In press. View at Publisher · View at Google Scholar
  71. K. S. Bhadoriya, S. V. Jain, S. B. Bari, M. L. Chavhan, and K. R. Vispute, “3D-QSAR study of indol-2-yl ethanones derivatives as novel indoleamine 2, 3-dioxygenase (IDO) inhibitors,” E-Journal of Chemistry, vol. 9, pp. 1753–1759, 2012. View at Publisher · View at Google Scholar