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

Volumn 21, Issue 10, 2012, Pages 2837-2853

  Sharma, Mukesh C ^a   Kohli, D V ^a  

^a DR H S GOUR UNIVERSITY   (India)

Author keywords

2D QSAR; Angiotensin II receptor; Aryltriazolinone; AT1; kNN MFA; MDS 3.5 ; Partial least square (PLS)

Indexed keywords

ANGIOTENSIN 1A RECEPTOR; ANTIHYPERTENSIVE AGENT; ARYLTRIAZOLINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; GENETIC ALGORITHM; HYDROPHOBICITY; KERNEL METHOD; NONHUMAN; PARTIAL LEAST SQUARES REGRESSION; PREDICTIVE VALUE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SIMULATION;

EID: 84866360070     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9815-x     Document Type: Article

References (50)

1. Afantitis A, Melagraki G, Sarimveis H, Igglessi-Markopoulou O, Kolliasnovel GA (2009) QSAR model for predicting the inhibition of CXCR3 receptor by 4-N-aryl-[1,4] diazepane ureas. Eur J Med Chem 44:877-884
2. Ajmani S, Jhadav K, Kulkarni SA (2006) Three-dimensional QSAR using the k-nearest neighbor method and its interpretation. J Chem Inf Model 46:24-31
3. Belvisi L, Bravi G, Catalano G, Mabiliab M, Salimbeni A, Scolastico C (1996) A 3D QSAR CoMFA study of non-peptide angiotensin II receptor antagonists. J Comput Aided Mol Des 10(6):567-582
4. Conlin PR (2000) Angiotensin II antagonists in the treatment of hypertension: more similarities than differences. J Clin Hypertens (Greenwich) 2(4):253-257
5. Coulter MD, Edwards IR (1987) Cough associated with captopril and enalapril. Br Med J 294:1521-1523
6. Cramer RD, Patterson DE, Bunce JD (1988) Comparative molecular field analysis (CoMFA) 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 110:5959-5967
7. Darlington RB (1990) Regression and linear models. McGraw-Hill, New York
8. Datar PA, Desai PV, Coutinho EC (2004) A 3D-QSAR of angiotensin II (AT1) receptor antagonists based on receptor surface analysis. J Chem Inf Model 44(1):210-220
9. Erdos EG, Skidgel RA (1986) The unusual substrate specificity and the distribution of human angiotensin I converting enzyme. Hypertension 8(Suppl I):34-37
10. Fogarty DJ, Sanchez-Gomez MV, Matute C (2002) Multiple angiotensin receptor subtypes in normal and tumor astrocytes in vitro. Glia 39:304-313
11. Ghosh P, Bagchi MC (2009a) Comparative QSAR studies of nitrofuranyl amide derivatives using theoretical structural properties. Mol Simul 35(14):1185-1200
12. Ghosh P, Bagchi MC (2009b) QSAR modeling for quinoxaline derivatives using genetic algorithm and simulated annealing based feature selection. Curr Med Chem 16:4032-4048
13. Golbraikh A, Tropsha A (2002a) Predictive QSAR modeling based on diversity sampling of experimental datasets for the training and test set selection. J Comput Aided Mol Des 16:357-369
14. Golbraikh A, Tropsha A (2002b) Beware of q2! J Mol Graph Model 20:269-276
15. Golbraikh A, Tropsha A (2003) QSAR modeling using chirality descriptors derived from molecular topology. J Chem Inf Comput Sci 43:144-154
16. Guyon I, Elisseeff A (2003) An introduction to variable and feature selection. J Mach Learn Res 3:1157-1182
17. Halgren TA (1996) Merck molecular force field. III. Molecular geometries and vibrational frequencies for MMFF94. J Comput Chem 17:553-586
18. Hansch C, Fujita T (1964) p-r-p Analysis. A method for the correlation of biological activity and chemical structure. J Am Chem Soc 86:1616-1630
19. Hasegawa K, Kimura T, Funatsu K (1999) GA strategy for variable selection in QSAR studies: enhancement of comparative molecular binding energy analysis by GA-based PLS method. Quant Struct Activ Relatsh 18:262-272
20. Holland JH (1992) Genetic algorithms. Sci Am 267:66-72
21. Ito M (2005) ACE: gene, biosynthesis and functions. Nippon Rinsho 63(3):22-27
22. Juillerat-Jeanneret L, Celerier J, ChapuisBernasconi C, Nguyen G, Wostl W, Maerki HP, Janzer RC, Corvol P, Gasc JM (2004) Renin and angiotensinogen expression and functions in growth and apoptosis of human glioblastoma. Br J Cancer 90: 1059-1068
23. Klebe G, Abraham U, Mietzner T (1994) Molecular similarity indexes in a comparative-analysis (CoMSIA) of drug molecules to correlate and predict their biological-activity. J Med Chem 37: 4130-4146
24. Kurup A, Garg R, Carini DJ, Hansch C (2001) Comparative QSAR: angiotensin II antagonists. Chem Rev 101:2727
25. Linda LC, Wallace TA, Kelly LF, Tsing BC, Stacey SOM, Gloria JZ, Salah DK, Peter KSS, Victor JL, Raymond SLC, William JG (1995) Potent and orally active angiotensin II receptor antagonists with equal affinity for human AT1 and AT2 subtypes. J Med Chem 38:3741-3758
26. Peach MJ (1977) Renin-angiotensin system: biochemistry and mechanism of action. Physiol Rev 57:313-370
27. Reid JL, Rubin PC (1987) Peptides and central neural regulation of the circulation. Physiol Rev 67:725-749
28. Sharaf MA, Illman DL, Kowalski BR (1986) Chemometrics. Wiley, New York
29. Sharma MC, Kohli DV (2011a) 3D QSAR studies on series of 2,3-dihydro-4(1H)-quinazolinone derivatives angiotensin II receptor antagonists: kNNMFA approach. Am Euras J Sci Res 6(2): 85-94
30. Sharma MC, Kohli DV (2011b) 3D QSAR kNNMFA approach studies on series of substituted piperidin-2-one biphenyl tetrazoles as angiotensin II receptor antagonists. Am Euras Toxicol Sci 3(2):75-84
31. Sharma MC, Kohli DV (2011c) QSAR study on sulfonylcarbamate derivatives: an insight into the structural requirement for the angiotensin II receptor antagonist. Eur J Appl Sci 3(1):9-14
32. Sharma MC, Kohli DV (2011d) 3D-QSAR studies of some substituted imidazolinones angiotensin II receptor antagonists. World Appl Sci J 12(11):2129-2134
33. Sharma MC, Kohli DV (2011e) 3D QSAR studies on a series of-[(1-benzyl-1H-imidazol-5-yl)-alkyl]-amino derivatives as angiotensin II AT1 antagonists. Am Euras J Sci Res 6(2):79-84
34. Sharma MC, Kohli DV (2011f) 3D QSAR approach on substituted isoxazolidines derivatives as angiotensin II receptor antagonist. Am Euras Toxicol Sci 3(2):85-91
35. Sharma MC, Kohli DV (2011g) 3D QSAR studies of substituted- 4(3H) quinazolinones derivatives as angiotensin II receptor antagonists. Eur J Appl Sci 3(1):15-23
36. Sharma MC, Kohli DV (2011h) Predicting alkylbenzimidazole derivatives as angiotensin II receptor antagonists: 3D QSAR by kNN-MFA approach. Adv Biol Res 5(3):161-169
37. Sharma MC, Kohli DV (2011i) 3D QSAR studies on a series of sulfonylcarbamate isostere derivatives as non-peptide angiotensin II receptor antagonists: kNNMFA method. Am Euras J Sci Res 6(2):64-70
38. Sharma MC, Kohli DV (2011j) Exploration of quantitative structure activity relationship studies on a series of substituted quinazolinones as angiotensin II AT1 receptor antagonists. World Appl Sci J 12(11):2111-2119
39. Sharma MC, Kohli DV (2011k) 2D- and 3D-QSAR studies of substituted 4H-pyrido [1,2-a] pyrimidin-4-ones angiotensin II receptor antagonists. Am Euras Toxicol Sci 3(2):92-100
40. Sharma MC, Kohli DV (2011l) An insight into the structural requirement QSAR approach on substituted isoxazolidines derivatives as angiotensin II receptor antagonist. Am Euras J Sci Res 6(2):71-78
41. Sharma MC, Kohli DV, Chaturvedi SC, Sharma S (2009) Molecular modeling studies of some substituted 2-butylbenzimidazoles angiotensin II receptor antagonists as antihypertensive agents. Dig J Nanomater Biostruct 4(4):843-856
42. Shen M, LeTiran A, Xiao Y, Golbraikh A, Kohn H, Tropsha A (2002) Quantitative structure-activity relationship analysis of functionalized amino acid anticonvulsant agents using k nearest neighbor and simulated annealing PLS methods. J Med Chem 45: 2811-2823
43. Shen M, Xiao Y, Golbraikh A, Gombar VK, Tropsha A (2003) Development and validation of k-nearest-neighbor QSPR models of metabolic stability of drug candidates. J Med Chem 46: 3013-3020
44. Smith RD, Chiu AT, Wong PC, Herblin WF, Timmermans PBMWM (1992) Pharmacology of nonpeptide angiotensin-II receptor antagonists. Ann Rev Pharmacol Toxicol 32:135-165
45. Timmermans PB, Chiu AT, Herblin WF, Wong PC, Smith RD (1992) Angiotensin II receptor subtypes. Am J Hypertens 5:406-410
46. Tiwari P, Mishra JP (2010) QSAR studies on a series of N2-aryltriazolinone biphenylsulfonamide derivatives in order to evolve potent and orally active angiotensin II receptor antagonists. Orient J Chem 26(3):1113-1117 (40422)
47. Tuccinardi T, Calderone V, Rapposelli S, Martinelli A (2006) Proposal of a new binding orientation for non-peptide AT1 antagonists. J Med Chem 49:4305-4316
48. Vlife MDS software package (2008) version 3.5, supplied by Vlifescience technologies Pvt. Ltd, Pune
49. Wold S (1995) In: van de Waterbeemd H (ed) PLS for multivariate linear modeling. VCH, Weinheim, pp 195-218
50. Zheng W, Tropsha A (2000) Novel variable selection quantitative structure-property relationship approach based on the k-nearest neighbor principle. J Chem Inf Comput Sci 40:185-194