3D-QSAR and docking studies on adenosine A_2A receptor antagonists by the CoMFA method

References

• P. Hickey and M. Stacy, Adenosine A2A antagonists in Parkinson's disease: What's next?, Curr. Neur. Neurosci. Report. 12 (2012), pp. 376–385.
   PubMed Web of Science ®Google Scholar
• T.C. Pomfret, J. Gagnon, and J. Pietarinen, An adenosine receptor antagonist for the treatment of Parkinson disease, Formulary 43 (2008), pp. 157–165.
   Web of Science ®Google Scholar
• A. Pinna, R. Volpini, G. Cristalli, and M. Morelli, New adenosine A2A receptor antagonists: Actions on Parkinson's disease models, Eur. J. Pharm. 512 (2005), pp. 157–164.
   PubMed Web of Science ®Google Scholar
• M. Cieślak, M. Komoszyński, and A. Wojtczak, Adenosine A2A receptors in Parkinson's disease treatment, Puriner. Signal. 4 (2008), pp. 305–312.
   PubMed Web of Science ®Google Scholar
• A.B. Davidson and E. Weidley, Differential effects of neuroleptic and other psychotropic agents on acquisition of avoidance in rats, Life Sci. 18 (1976), pp. 1279–1284.
   PubMed Web of Science ®Google Scholar
• M.P. DeNinno, Chapter 11. Adenosine, Annu. Rep. Med. Chem. 33 (1998), pp. 111–120.
   Google Scholar
• C.E. Muller and T. Scior, Adenosine receptors and their modulators, Pharm. Acta Helv. 68 (1993), pp. 77–111.
   PubMedGoogle Scholar
• V.A. Pires, F.A. Pamplona, P. Pandolfo, D. Fernandes, R.D.S. Prediger, and R.N. Takahashi, Adenosine receptor antagonists improve short-term object-recognition ability of spontaneously hypertensive rats: A rodent model of attention-deficit hyperactivity disorder, Behav. Pharm. 20 (2009), pp. 134–145.
   PubMed Web of Science ®Google Scholar
• B.B. Fredholm, A.P. Ijzerman, K.A. Jacobson, J. Linden, and C.E. Mueller, International Union of Basic and Clinical Pharmacology. LXXXI. Nomenclature and classification of adenosine receptors-an update, Pharm. Rev. 63 (2011), pp. 1–34.
   PubMed Web of Science ®Google Scholar
• M.T. Armentero, A. Pinna, S. Ferré, J.L. Lanciego, C.E. Müller, and R. Franco, Present and future of A2A adenosine receptor antagonists in the therapy of Parkinson's disease, Pharm. Therap. 132 (2011), pp. 280–299.
   PubMed Web of Science ®Google Scholar
• U. Shah and R. Hodgson, Recent progress in the discovery of adenosine A2A receptor antagonists for the treatment of Parkinson's disease, Curr. Opin. Drug. Disc. Develop. 13 (2010), pp. 466–480.
   PubMed Web of Science ®Google Scholar
• B.C. Shook and P.F. Jackson, Adenosine A2A receptor antagonists and Parkinson's disease, ACS Chem. Neurosci. 2 (2011), pp. 555–567.
   PubMed Web of Science ®Google Scholar
• N. Szabó, Z.T. Kincses, and L. Vécsei, Novel therapy in Parkinson's disease: Adenosine A2A receptor antagonists, Exp. Opin. Drug Metab. Toxicol. 7 (2011), pp. 441–455.
   PubMed Web of Science ®Google Scholar
• K. Ikeda, M. Kurokawa, S. Aoyama, and Y. Kuwana, Neuroprotection by adenosine A2A receptor blockade in experimental models of Parkinson's disease, J. Neurochem. 80 (2002), pp. 262–270.
   PubMed Web of Science ®Google Scholar
• B.C. Shook, D. Chakravarty, J.K. Barbay, A. Wang, K. Leonard, V. Alford, M.T. Powell, S. Rassnick, R.H. Scannevin, K. Carroll, Wallace, J. Crooke, M. Ault, L. Lampron, L. Westover, K. Rhodes, and P.F. Jackson, Substituted thieno[2,3-d]pyrimidines as adenosine A2A receptor antagonists, Bioorg. Med. Chem. Lett. 23 (2013), pp. 2688–2691.
   PubMed Web of Science ®Google Scholar
• V. Ravichandran, B.R. Prashanthakumar, S. Sankar, and R.K. Agrawal, Predicting anti-HIV activity of 1,1,3-trioxo[1,2,4]-thiadiazine (TTD) derivatives: 3D QSAR approach, Med. Chem. Res. 18 (2009), pp. 511–522.
   Web of Science ®Google Scholar
• O. Nicolotti, I. Giangreco, T.F. Miscioscia, and A. Carotti, Improving quantitative structure−activity relationships through multiobjective optimization, J. Chem. Inf. Model. 49 (2009), pp. 2290–2302.
   PubMed Web of Science ®Google Scholar
• E. Pourbasheer, R. Aalizadeh, M.R. Ganjali, and P. Norouzi, QSAR study of IKKβ inhibitors by the genetic algorithm: Multiple linear regressions, Med. Chem. Res. 23 (2014), pp. 57–66.
   Web of Science ®Google Scholar
• E. Pourbasheer, R. Aalizadeh, M.R. Ganjali, P. Norouzi, and A. Banaei, QSAR study of mGlu5 inhibitors by genetic algorithm-multiple linear regressions, Med. Chem. Res. 23 (2014), pp. 3082–3091.
   Web of Science ®Google Scholar
• G.L. Wilson and M.A. Lill, Integrating structure-based and ligand-based approaches for computational drug design, Future Med. Chem. 3 (2011), pp. 735–750.
   PubMed Web of Science ®Google Scholar
• E. Pourbasheer, A. Beheshti, H. Khajehsharifi, M.R. Ganjali, and P. Norouzi, QSAR study on hERG inhibitory effect of kappa opioid receptor antagonists by linear and non-linear methods, Med. Chem. Res. 22 (2013), pp. 4047–4058.
   Web of Science ®Google Scholar
• V.P. Zambre, P.R. Murumkar, R. Giridhar, and M.R. Yadav, Structural investigations of acridine derivatives by CoMFA and CoMSIA reveal novel insight into their structures toward DNA G-quadruplex mediated telomerase inhibition and offer a highly predictive 3D-model for substituted acridines, J. Chem. Inf. Mod. 49 (2009), pp. 1298–1311.
   PubMed Web of Science ®Google Scholar
• R.D. Cramer I, D.E. Patterson, and J.D. Bunce, Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins, J. Am. Chem. Soc. 110 (1988), pp. 5959–5967.
   PubMed Web of Science ®Google Scholar
• A. Pandey, J. Mungalpara, and C.G. Mohan, Comparative molecular field analysis and comparative molecular similarity indices analysis of hydroxyethylamine derivatives as selective human BACE-1 inhibitor, Mol. Divers. 14 (2010), pp. 39–49.
   PubMed Web of Science ®Google Scholar
• N.J. Zhu, A. Harrison, M.L. Trudell, and C.L. Klein-Stevens, QSAR and CoMFA study of cocaine analogs: Crystal and molecular structure of (-)-cocaine hydrochloride and N-methyl-3 beta-(p-fluorophenyl)tropane-2 beta-carboxylic acid methyl ester, Struct. Chem. 10 (1999), pp. 91–103.
   Web of Science ®Google Scholar
• N.J. Zhu, L. Liang, and C.L.K. Stevens, A CoMFA study of dopamine D2 receptor agonists and X-ray crystal structure of quinelorane dihydrochloride dihydrate, R(-)-apomorphine hydrochloride and R(-)-N-n-propylnorapomorphine hydrochloride, Struct. Chem. 15 (2004), pp. 553–565.
   Web of Science ®Google Scholar
• V.N. Telvekar, H.S. Kundaikar, K.N. Patel, and H.K. Chaudhari, QSAR and molecular docking studies on aryl benzofuran-2-yl ketoxime derivatives as candida albicans N-myristoyl transferase inhibitors, QSAR Comb. Sci. 27 (2008), pp. 1193–1203.
   Google Scholar
• E. Pourbasheer, R. Bazl, and M. Amanlou, Molecular docking and 3D-QSAR studies on the MAPKAP-K2 inhibitors, Med. Chem. Res. 23 (2014), pp. 2252–2263.
   Web of Science ®Google Scholar
• E. Pourbasheer, R. Aalizadeh, S. Shokouhi Tabar, M.R. Ganjali, P. Norouzi, and J. Shadmanesh, 2D and 3D Quantitative Structure–Activity Relationship Study Of Hepatitis C virus NS5B polymerase inhibitors by comparative molecular field analysis and comparative molecular similarity indices analysis methods, J. Chem. Inf. mod. 54 (2014), pp. 2902–2914.
   PubMed Web of Science ®Google Scholar
• E. Pourbasheer and M. Amanlou, 3D-QSAR analysis of anti-cancer agents by CoMFA and CoMSIA, Med. Chem. Res. 23 (2014), pp. 800–809.
   Web of Science ®Google Scholar
• N. Vanopdenbosch, R. Cramer, and F.F. Giarrusso, SYBYL, the integrated molecular modeling system, J. Mol. Graphic. 3 (1985), pp. 110–111.
   Google Scholar
• K. Kaur and T.T. Talele, Structure-based CoMFA and CoMSIA study of indolinone inhibitors of PDK1, J. Comp. Aided. Mol. Design. 23 (2009), pp. 25–36.
   PubMed Web of Science ®Google Scholar
• M. Clark, R.D. Cramer, and N. Vanopdenbosch, Validation of the general purpose tripos 5.2 force field, J. Comp. Chem. 10 (1989), pp. 982–1012.
   Web of Science ®Google Scholar
• J. Zheng, G. Xiao, J. Guo, Y. Zheng, H. Gao, S. Zhao, K. Zhang, and P. Sun, Exploring QSARs for 5-lipoxygenase (5-LO) inhibitory activity of 2-substituted 5-hydroxyindole-3-carboxylates by CoMFA and CoMSIA, Chem. Biology Drug Design. 78 (2011), pp. 314–321.
   PubMed Web of Science ®Google Scholar
• H. Chen, Q. Li, X. Yao, B. Fan, S. Yuan, A. Panaye, and J.P. Doucet, 3D-QSAR and docking study of the binding mode of steroids to progesterone receptor in active site, QSAR Comb. Sci. 22 (2003), pp. 604–613.
   Google Scholar
• H. Chen, Q. Li, X. Yao, B. Fan, S. Yuan, A. Panaye, and J.P. Doucet, Structure-based CoMFA and CoMSIA study of indolinone inhibitors of PDK1, QSAR Comb. Sci. 23 (2004), pp. 36–55.
   Google Scholar
• P. Datar, P. Desai, E. Coutinho, and K. Iyer, CoMFA and CoMSIA studies of angiotensin (AT1) receptor antagonists, J. Mol. Model. 8 (2002), pp. 290–301.
   PubMed Web of Science ®Google Scholar
• R. Wehrens, H. Putter, and L.M.C. Buydens, The bootstrap: A tutorial, Chemomet. Intell. Lab. Systems 54 (2000), pp. 35–52.
   Web of Science ®Google Scholar
• G.M. Morris, R. Huey, W. Lindstrom, M.F. Sanner, R.K. Belew, D.S. Goodsell, and A.J. Olson, AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility, J. Comp. Chem. 30 (2009), pp. 2785–2791.
   PubMed Web of Science ®Google Scholar
• W. Liu, E. Chun, A.A. Thompson, P. Chubukov, F. Xu, V. Katritch, G.W. Han, C.B. Roth, L.H. Heitman, A.P. Ijzerman, V. Cherezov, and R.C. Stevens, Structural basis for allosteric regulation of GPCRs by sodium ions, Science 337 (2012), pp. 232–236.
   PubMed Web of Science ®Google Scholar
• U.C. Singh and P.A. Kollman, An approach to computing electrostatic charges for molecules, J. Comp. Chem. 5 (1984), pp. 129–145.
   Web of Science ®Google Scholar
• G. Wolber and T. Langer, LigandScout: 3-d pharmacophores derived from protein-bound ligands and their use as virtual screening filters, J. Chem. Inf. Mod. 45 (2005), pp. 160–169.
   PubMed Web of Science ®Google Scholar
• S. Wold, Cross-validatory estimation of the number of components in factor and principal components models, Technometrics 20 (1978), pp. 397–405.
   Web of Science ®Google Scholar
• D.S. Cao, Y.Z. Liang, Q.S. Xu, H.D. Li, and X. Chen, A new strategy of outlier detection for QSAR/QSPR, J. Comp. Chem. 31 (2010), pp. 592–602.
   PubMed Web of Science ®Google Scholar
• H.Y. Liu, S.S. Liu, L.T. Qin, and L.Y. Mo, CoMFA and CoMSIA analysis of 2,4-thiazolidinediones derivatives as aldose reductase inhibitors, J. Mol. Mod. 15 (2009), pp. 837–845.
   PubMed Web of Science ®Google Scholar