2,577
Views
15
CrossRef citations to date
0
Altmetric
Original Article

3D QSAR studies, pharmacophore modeling, and virtual screening of diarylpyrazole–benzenesulfonamide derivatives as a template to obtain new inhibitors, using human carbonic anhydrase II as a model protein

, , , , &
Pages 688-700 | Received 06 Aug 2016, Accepted 22 Sep 2016, Published online: 19 Mar 2017

References

  • Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81.
  • Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov 2011;10:767–77.
  • Capasso C, Supuran CT. An overview of the alpha-, beta-and gamma-carbonic anhydrases from Bacteria: can bacterial carbonic anhydrases shed new light on evolution of bacteria? J Enzyme Inhib Med Chem 2015;30:325–32.
  • Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003;23:146–89.
  • Ghasemi JB, Meftahi N. Docking, CoMFA and CoMSIA studies of a series of sulfonamides derivatives as carbonic anhydrase I inhibitors. J Enzyme Inhib Med Chem 2013;28:320–7.
  • Supuran CT. Structure-based drug discovery of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2012;27:759–72.
  • Supuran CT. Carbonic anhydrases: from biomedical applications of the inhibitors and activators to biotechnological use for CO(2) capture. J Enzyme Inhib Med Chem 2013;28:229–30.
  • Supuran CT. How many carbonic anhydrase inhibition mechanisms exist? J Enzyme Inhib Med Chem 2016;31:345–60.
  • Supuran CT. Structure and function of carbonic anhydrases. Biochem J 2016;473:2023–32.
  • Kose LP, Gülçin İ, Özdemir H, et al. The effects of some avermectins on bovine carbonic anhydrase enzyme. J Enzyme Inhib Med Chem 2016;31:773–8.
  • Khloya P, Celik G, Vullo D, et al. 4-Functionalized 1,3-diarylpyrazoles bearing benzenesulfonamide moiety as selective potent inhibitors of the tumor associated carbonic anhydrase isoforms IX and XII. Eur J Med Chem 2014;76:284–90.
  • Rogez-Florent T, Meignan S, Foulon C, et al. New selective carbonic anhydrase IX inhibitors: synthesis and pharmacological evaluation of diarylpyrazole-benzenesulfonamides. Bioorg Med Chem 2013;21:1451–64.
  • Scozzafava A, Menabuoni L, Mincione F, Supuran CT. Carbonic anhydrase inhibitors. A general approach for the preparation of water solublesulfonamides incorporating polyamino-polycarboxylate tails and of their metal complexes possessing long lasting, topical intraocular pressure lowering properties. J Med Chem 2002;45:1466–76.
  • Garaj V, Puccetti L, Fasolis G, et al. Carbonic anhydrase inhibitors. Novel sulfonamides incorporating 1,3,5-triazine moieties as inhibitors of the cytosolic and tumor-associated carbonic anhydrase isozymes I, II and IX. Bioorg Med Chem Lett 2005;15:3102–8.
  • Carta F, Supuran CT. Diuretics with carbonic anhydrase inhibitory action: a patent and literature review (2005–2013). Expert Opin Ther Pat 2013;23:681–91.
  • Clare BW, Supuran CT. Carbonic anhydrase activators. 3: structure–activity correlations for a series of isozyme II activators. J Pharm Sci 1994;83:768–73.
  • Makhuri FR, Ghasemi JB. Computer-aided scaffold hopping to identify a novel series of casein kinase 1 delta (CK1d) inhibitors for amyotrophic lateral sclerosis. Eur J Pharm Sci 2015;78:151–62.
  • Yang W, Shu M, Wang Y, et al. 3D-QSAR and docking studies of 3-pyridine heterocyclic derivatives as potent PI3K/mTOR inhibitors. J Mol Struct 2013;1055:107–16.
  • Hong YD, Baek HS, Cho H, et al. 3D-QSAR study of adamantyl N-benzylbenzamides as melanogenesis inhibitors. Bioorg Med Chem Lett 2014;24:667–73.
  • Desiraju GR, Gopalakrishnan B, Jetti RKR, et al. Three-Dimensional Quantitative Structural Activity Relationship (3D-QSAR) Studies of some 1,5-diarylpyrazoles: analog based design of selective cyclooxygenase-2 inhibitors. Molecules 2000;5:945–55.
  • QikProp 3.2 UserManual, Schrçdinger, USA, 2009. Three-dimensional quantitative similarity-activity relationships (3D QSiAR) from SEAL similarity matrices. J Med Chem 1998;41:2553–64.
  • Dove S, Buschauer A. Improved alignment by weighted field fit in CoMFA of histamine H2 receptor agonistic imidazolylpropylguanidines. Quant Struct-Act Relat 1999;18:329–41.
  • Wang R, Gao Y, Liu L, Lai L. All-orientation search and all-placement search in comparative molecular field analysis. J Mol Model 1998;4:276–83.
  • Patel MR, Dimmock JR, Talele TT. CoMFA and CoMSIA studies on 1,3-bis(benzylidene)-3,4-dihydro-1H-naphthalen-2-one, 2,6-bis(benzylidene)cyclohexanone, and 3,5-bis(benzylidene)-4-piperidone series of cytotoxic compounds. J Chem Inf Model 2007;47:2110–23.
  • Kamath S, Buolamwini JK. Receptor-guided alignment-based comparative 3D-QSAR studies of benzylidene malonitrile tyrphostins as EGFR and HER-2 kinase inhibitors. J Med Chem 2003;46:4657–68.
  • Tobias RD. An introduction to partial least squares regression. Proceedings: ANN SAS Users Group International Conference, 20th, Orlando, FL: Citeseer; 1995:2–5.
  • Güner OF, Bowen JP. Setting the record straight: the origin of the pharmacophore concept. J Chem Inf Model 2014;54:1269–83.
  • Verdonk ML, Cole JC, Hartshorn MJ, et al. Improved protein-ligand docking using GOLD. Proteins: Struct Funct Bioinform 2003;52:609–23.
  • Discovery Studio version 2.5 (DS 2.5) User Manual., 2009. Accelrys Inc., San Diego, CA.
  • Brooks BR, Brooks CL, MacKerell AD, et al. CHARMM: the biomolecular simulation program. J Comput Chem 2009;30:1545–614.
  • Koes DR, Camacho CJ. ZINCPharmer: pharmacophore search of the ZINC database. Nucleic Acids Res 2012;40:W409–14.
  • Lipinski CA. Drug-like properties and the causes of poor solubility and poor permeability. J Pharmacol Toxicol Methods 2000;44:235–49.
  • Pirhadi S, Ghasemi JB. Pharmacophore identification, molecular docking, virtual screening, and in silico ADME studies of non-nucleoside reverse transcriptase inhibitors. Mol Inform 2012;31:856–66.
  • Gibbs JE, Gaffen Z, Thomas SA. Nevirapine uptake into the central nervous system of the Guinea pig: an in situ brain perfusion study. J Pharmacol Exp Ther 2006;317:746–51.
  • Hitchcock SA, Pennington LD. Structure-brain exposure relationships. J Med Chem 2006;49:7559–83.
  • QikProp 3.2 User Manual, Schrçdinger, USA; 2009.
  • Tropsha A, Gramatica P, Gombar VK. The importance of being earnest: validation is the absolute essential for successful application and interpretation of QSPR models. QSAR Comb Sci 2003;22:69–77.