Pharmacophore modeling, 3D-QSAR, and in silico ADME prediction of N-pyridyl and pyrimidine benzamides as potent antiepileptic agents

References

• Barrese V, Miceli F, Soldovieri MV, et al. Neuronal potassium channel openers in the management of epilepsy: role and potential of retigabine. Clin Pharmacol 2010;2:225–36.
   PubMedGoogle Scholar
• Catterall WA. Sodium channels, inherited epilepsy, and antiepileptic drugs. Annu Rev Pharmacol Toxicol 2014;54:317–38.
   PubMed Web of Science ®Google Scholar
• Lason W, Dudra-Jastrzebska M, Rejdak K, Czuczwar SJ. Basic mechanisms of antiepileptic drugs and their pharmacokinetic/pharmacodynamic interactions: an update. Pharmacol Rep 2011;63:271–92.
   PubMed Web of Science ®Google Scholar
• Rogawski MA, Loscher W. The neurobiology of antiepileptic drugs. Nature Rev Neurosci 2004;5:553–64.
   PubMed Web of Science ®Google Scholar
• Rogawski MA, Loscher W. The neurobiology of antiepileptic drugs for the treatment of nonepileptic conditions. Nat Med 2004;10:685–92.
   PubMed Web of Science ®Google Scholar
• Schmidt D, Rogawski MA. New strategies for the identification of drugs to prevent the development or progression of epilepsy. Epilepsy Res 2002;50:71–8.
   PubMed Web of Science ®Google Scholar
• Kwan P, Sills GJ, Brodie MJ. The mechanisms of action of commonly used antiepileptic drugs. Pharmacol Ther 2001;90:21–34.
   PubMed Web of Science ®Google Scholar
• Remy S, Beck H. Molecular and cellular mechanisms of pharmacoresistance in epilepsy. Brain 2006;129:18–35.
   PubMed Web of Science ®Google Scholar
• Noebels J. Pathway-driven discovery of epilepsy genes. Nat Neurosci 2015;18:344–50.
   PubMed Web of Science ®Google Scholar
• Maljevic S, Lerche H. Potassium channel genes and benign familial neonatal epilepsy. In: Steinlein OK, ed. Genetics of epilepsy, progress in brain research. Vol. 213. Munich: Elsevier Amsterdam; 2014:17–53.
   Google Scholar
• Wickenden AD, Roeloffs R, McNaughton-Smith G, Rigdon GC. KCNQ potassium channels: drug targets for the treatment of epilepsy and pain. Expert Opin Ther Patents 2004;14:457–69.
   Web of Science ®Google Scholar
• Giudice EMD, Coppola G, Scuccimarra G, et al. Benign familial neonatal convulsions (BFNC) resulting from mutation of the KCNQ2 voltage sensor. Eur J Hum Genet 2000;8:994–7.
   PubMed Web of Science ®Google Scholar
• Stafstrom CE, Carmant L. Seizures and epilepsy: an overview for neuroscientists. Cold Spring Harb Perspect Med 2015;5:a022426.
   PubMed Web of Science ®Google Scholar
• Peretz A, Degani-Katzav N, Talmon M, et al. A tale of switched functions: from cyclooxygenase inhibition to M-channel modulation in new diphenylamine derivatives. PLoS One 2007;2:e1332.
   Google Scholar
• Sliwoski G, Kothiwale SK, Meiler J, Lowe EW Jr. Computational methods in drug discovery. Pharmacol Rev 2014;66:334–95.
   PubMed Web of Science ®Google Scholar
• Cramer RD. Template CoMFA generates single 3D-QSAR models that, for twelve of twelve biological targets, predict all ChEMBL-tabulated affinities. PLoS One 2015;10:e0129307.
   Google Scholar
• Wilson GL, Lill MA. Integrating structure-based and ligand-based approaches for computational drug design. Future Med Chem 2011;3:735–50.
   PubMed Web of Science ®Google Scholar
• Li P, Chen Z, Xu H, et al. The gating charge pathway of an epilepsy-associated potassium channel accommodates chemical ligands. Cell Res 2013;23:1106–18.
   PubMed Web of Science ®Google Scholar
• Rostock A, Tober C, Rundfeldt C, et al. D-23129: a new anticonvulsant with a broad spectrum of activity in animal models of epileptic seizures. Epilepsy Res 1996;23:211–23.
   PubMed Web of Science ®Google Scholar
• Rundfeldt C. The new anticonvulsant retigabine (D-23129) acts as an opener of K+ channels in neuronal cells. Eur J Pharmacol 1997;336:243–9.
   PubMed Web of Science ®Google Scholar
• Hu HN, Zhou PZ, Chen F, et al. Discovery of a retigabine derivative that inhibits KCNQ2 potassium channels. Acta Pharmacol Sin 2013;34:1359–66.
   PubMed Web of Science ®Google Scholar
• Craig D, Rice S, Paton F, et al. Retigabine for the adjunctive treatment of adults with partial-onset seizures in epilepsy with and without secondary generalization. PharmacoEcon 2013;31:101–10.
   PubMed Web of Science ®Google Scholar
• Szelenyi I. Flupirtine, a re-discovered drug, revisited. Inflamm Res 2013;62:251–8.
   PubMed Web of Science ®Google Scholar
• Wu YJ, He H, Sun LQ, et al. Synthesis and structure-activity relationship of acrylamides as KCNQ2 potassium channel openers. J Med Chem 2004;47:2887–96.
   PubMed Web of Science ®Google Scholar
• Yu H, Wu M, Townsend SD, et al. Discovery, synthesis, and structure.gov/pubmed/15139767 des as KCNQ2 potassium bicyclo[2.2.1]heptane-2-carboxamides: characterization of ML213 as a novel KCNQ2 and KCNQ4 potassium channel opener. ACS Chem Neurosci 2011;2:572–7.
   PubMed Web of Science ®Google Scholar
• McNaughton-Smith GA, Gross MF Wickenden AD. Icagen Inc. Benzanilides as potassium channel openers. United States Patent 6737422; 2004 May 18.
   Google Scholar
• Attali B, Peretz A. Ramot At Tel Aviv University. Derivatives of N-phenyl anthranilic acid and 2-benzimidazolone as potassium channel and/or neuron activity modulators. United States Patent 7632866; 2009 December 15.
   Google Scholar
• Peretz A, Pell L, Gofman Y, et al. Targeting the voltage sensor of Kv7.2 voltage-gated K+ channels with a new gating-modifier. Proc Natl Acad Sci USA 2010;107:15637–42.
   PubMed Web of Science ®Google Scholar
• Amato G, Roeloffs R, Rigdon GC, et al. N-pyridyl and pyrimidine benzamides as KCNQ2/Q3 potassium channel openers for the treatment of epilepsy. ACS Med Chem Lett 2011;2:481–4.
   PubMed Web of Science ®Google Scholar
• Dixon SL, Smondyrev AM, Knoll EH, et al. PHASE: a new engine for pharmacophore perception, 3D QSAR model development, and 3D database screening. 1. Methodology and preliminary results. J Comput Aided Mol Des 2006;20:647–71.
   PubMed Web of Science ®Google Scholar
• Dixon SL, Smondyrev AM, Rao SN. PHASE: a novel approach to pharmacophore modeling and 3D database searching. Chem Biol Drug Des 2006;67:370–2.
   PubMed Web of Science ®Google Scholar
• Schrodinger Release 2013-2: Maestro Version 9.5. New York (NY): Schrodinger, LLC; 2013.
   Google Scholar
• Schrodinger, Schrodinger Release 2013-2: LigPrep Version 2.7. New York (NY): Schrodinger, LLC; 2013.
   Google Scholar
• Jorgensen WL, Maxwell DS, Tirado-Rives J. Development and testing of the OPLS all-atom force field on conformational energetics and properties of organic liquids. J Am Chem Soc 1996;118:11225–36.
   Web of Science ®Google Scholar
• Watts KS, Dalal P, Murphy RB, et al. ConfGen: a conformational search method for efficient generation of bioactive conformers. J Chem Inf Model 2010;50:534–46.
   PubMed Web of Science ®Google Scholar
• Friesner RA, Banks JL, Murphy RB, et al. Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J Med Chem 2004;47:1739–49.
   PubMed Web of Science ®Google Scholar
• Halgren TA, Murphy RB, Friesner RA, et al. Glide: a new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening. J Med Chem 2004;47:1750–9.
   PubMed Web of Science ®Google Scholar
• Schrodinger Release 2015-4: Prime, Version 4.2. New York (NY): Schrödinger, LLC; 2015.
   Google Scholar
• Small-Molecule Drug Discovery Suite 2015-4: QikProp, Version 4.6. New York (NY): Schrödinger, LLC; 2015.
   Google Scholar