Exploring QSARs of some benzenesulfonamides incorporating cyanoacrylamide moieties as a carbonic anhydrase inhibitors (specifically against tumor-associated isoforms IX and XII)

References

• Cope DG. Breast cancer: reviewing the past to give direction for the future. Oncol Nurs Forum 2013;40:425–8
   PubMed Web of Science ®Google Scholar
• Jemal A, Bray F, Center MM, et al. Global cancer statistics. CA Cancer J Clin 2011;61:69–90
   PubMed Web of Science ®Google Scholar
• DeSantis C, Virgo K, Stein K, et al. Cancer treatment and survivorship statistics 2012. CA Cancer J Clin 2012;62:220–41
   PubMed Web of Science ®Google Scholar
• Foye OW, Lemke LT, Williams AD. Principles of medicinal chemistry, 6th ed. Lippincott (PA): Williams and Wilkins; 2008
   Google Scholar
• Moeker J, Peat ST, Bornaghi LF, et al. Cyclic secondary sulfonamides: unusually good inhibitors of cancer-related carbonic anhydrase enzymes. J Med Chem 2014;57:3522–31
   PubMed Web of Science ®Google Scholar
• Lehneck R, Neumann P, Vullo D, et al. Crystal structures of two tetrameric β-carbonic anhydrases from the filamentous Ascomycete sordariamacrospora. FEBS J 2014;281:1759–72
   PubMed Web of Science ®Google Scholar
• Carroux JC, Rankin MG, Moeker J, et al. A prodrug approach toward cancer-related carbonic anhydrase inhibition. J Med Chem 2013;56:9623–34
   PubMed Web of Science ®Google Scholar
• Rami M, Dubois L, Parvathaneni NK, et al. Hypoxia-targeting carbonic anhydrase IX inhibitors by a new series of nitroimidazole-sulfonamides/sulfamides/sulfamates. J Med Chem 2013;56:8512–20
   PubMed Web of Science ®Google Scholar
• Monti MS, Supuran CT, De Simone G. Anticancer carbonic anhydrase inhibitors: a patent review (2008–2013). Expert Opin Ther Pat 2013;23:737–49
   PubMed Web of Science ®Google Scholar
• Capasso C, Supuran CT. Anti-infective carbonic anhydrase inhibitors: a patent and literature review. Expert Opin Ther Pat 2013;23:693–704
   PubMed Web of Science ®Google Scholar
• Ward C, Langdon PS, Mullen P, et al. New strategies for targeting the hypoxic tumour microenvironment in breast cancer. Cancer Treat Rev 2013;39:171–9
   PubMed Web of Science ®Google Scholar
• Supuran CT. Inhibition of carbonic anhydrase IX as a novel anticancer mechanism. World J Clin Oncol 2012;3:98–103
   PubMedGoogle Scholar
• Lee SH, Bae T, Lee HJ, et al. Rational drug repositioning guided by an integrated pharmacological network of protein, disease and drug. BMC Syst Biol 2012;2:6–80
   Google Scholar
• Garro Martinez JC, Vega-Hissi EG, Andrada MF, et al. Lacosamide derivatives with anticonvulsant activity as carbonic anhydrase inhibitors. molecular modeling, docking and QSAR analysis. Curr Comput Aided Drug Des 2014;10:160–7
   Google Scholar
• Malikowski MT, Bosch BJ, Min S, et al. Carbonic anhydrase inhibitors in corneal endothelial transport. Invest Ophthalmol Vis Sci 2014;55:2652–8
   PubMed Web of Science ®Google Scholar
• Swenson ER. Safety of carbonic anhydrase inhibitors. Expert Opin Drug Saf 2014;13:459–72
   PubMed Web of Science ®Google Scholar
• Gilmour MK. Perspectives on carbonic anhydrase. Comp Biochem Physiol A Mol Integr Physiol 2010;157:193–7
   PubMed Web of Science ®Google Scholar
• Alafeefy MA, Alqasoumi IS, Ashour EA, et al. Quinazoline-tyrphostin as a new class of antitumor agents, molecular properties prediction, synthesis and biological testing. Eur J Med Chem 2012;53:133–40
   PubMed Web of Science ®Google Scholar
• Alafeefy MA, Isik S, Abdel-Aziz HA, et al. Carbonic anhydrase inhibitors: benzenesulfonamides incorporating cyanoacrylamide moieties are low nanomolar/subnanomolar inhibitors of the tumor-associated isoforms IX and XII. Bioorg Med Chem 2013;21:1396–403
   Google Scholar
• Wermuth GC. The practice of medicinal chemistry, 3rd ed. London: Academic Press; 2008:491–510
   Google Scholar
• Frisch A, Hratchian PH, Dennington DRII, et al. Gauss ViewVersion 5.0.8. Wallingford (CT): Gaussian, Inc.; 2009
   Google Scholar
• Beck DA. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 1993;98:5648–52
   Web of Science ®Google Scholar
• Lee C, Yang W, Parr GR. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 1988;37:785–9
   PubMed Web of Science ®Google Scholar
• Miehlich B, Savin A, Stoll H, Preuss H. Results obtained with the correlation-energy density functionals of Becke and Lee, Yang and Parr. Chem Phys Lett 1989;157:200–6
   Web of Science ®Google Scholar
• Kohn W, Sham J. Self L-consistent equations including exchange and correlation effects. Phys Rev A 1965;140:1133–8
   Web of Science ®Google Scholar
• Frisch JM, Trucks WG, Schlegel BH, et al. Gaussian 09W, Revision A.1. Wallingford (CT): Gaussian, Inc.; 2009
   Google Scholar
• HyperChem (Molecular Modeling System) Hypercube, Inc, 1115 NW, 4th Street, Gainesville, FL 32601; USA, 2007. Available from: http://www.hyperchem.com/
   Google Scholar
• Tetko IV, Gasteiger J, Todeschini R, et al. Virtual computational chemistry laboratory design and description. J Comput Aid Mol Des 2005;19:453–63
   Google Scholar
• IBM Corp. Released 2012. IBM SPSS Statistics for Windows, Version 21.0. Armonk (NY): IBM Corp
   Google Scholar
• Hawkins MD, Basak CS, Mills D. Assessing model fit by cross-validation. J Chem Inf Model 2003;43:579–86
   Web of Science ®Google Scholar