A QSAR study on 2-(4-methylpiperazin-1-yl)quinoxalines as human histamine H₄ receptor ligands

References

• Hill SJ. Distribution, properties, and functional characteristics of three classes of histamine receptor. Pharmacol Rev 1990;42:45–83.
   PubMed Web of Science ®Google Scholar
• Black JW, Duncan WA, Durant CJ, Ganellin CR, Parsons EM. Definition and antagonism of histamine H2-receptors. Nature 1972;236:385–390.
   PubMed Web of Science ®Google Scholar
• Celanire S, Wijtmans M, Talaga P, Leurs R, de Esch IJP. Histamine H3 receptor antagonists reach out for the clinic. Drug Discov Today 2005;23/24:1613–1627.
   Google Scholar
• Liu C, Ma X-J Jiang, X, Wilson SJ, Hofstra CL, Blevitt K, Li X, Chai W, Carruthers N, Lovenberg TW. Cloning and pharmacological characterization of a fourth histamine receptor (H4) expressed in bone marrow. Mol Pharmacol 2001;59:420–426.
   PubMed Web of Science ®Google Scholar
• Morse KL, Behan J, Laz TM, West RE Jr, Greenfender SA, Anthes JC, Umland S, Wan Y, Hipkin RW, Gonsiorek W, Shin N, Gustafson EL, Qiao X, Wang S, Hedrick JA, Green J, Bayne M, Monsma FJ Jr. Cloning and characterization of a novel human histamine receptor. J Pharmacol Exp Ther 2001;296:1058–1066.
   PubMed Web of Science ®Google Scholar
• Nguyen T, Shapiro DA, George SR, Setola V, Lee DK, Cheng R, Rauser L, Lee SP, Lynch KR, Roth BL, O’Dowd BF. Discovery of a novel member of the histamine receptor family. Mol Pharmacol 2001;59:427–433.
   PubMed Web of Science ®Google Scholar
• Oda T, Morikawa N, Saito Y, Masuho Y, Matsumoto S. Molecular cloning and characterization of a novel type of histamine receptor preferentially expressed in leukocytes. J Biol Chem 2000;275:36781–36786.
   PubMed Web of Science ®Google Scholar
• Zhu Y, Michalovich D, Wu H-L Tan, KB, Dytko GM, Mannan IJ, Boyce R, Alston J, Tierney LA, Li X, Herrity NC, Vawter L, Sarau HM, Ames RS, Davenport CM, Hieble JP, Wilson S, Bergsma DJ, Fitzgerald LR. Cloning, expression, and pharmacological characterization of a novel human histamine receptor. Mol Pharmacol 2001;59:434–444.
   PubMed Web of Science ®Google Scholar
• de Esch IJP, Thurmond RLJA, Jongejan A, Leurs R. The histamine H4 receptor as a new therapeutic target for inflammation. Trends Pharmacol Sci 2005;26:462–469.
   PubMed Web of Science ®Google Scholar
• Gantner F, Sakai K, Tusche MW, Cruikshank WW, Center DM, Bacon KB. Histamine H4 and H2 receptors control histamine induced interleukin-16 release from human CD8+ T cells. J Pharmacol Exp Ther 2002;303:300–307.
   PubMed Web of Science ®Google Scholar
• Varga C, Horvath K, Berko A, Thurmond RL, Dunford PJ, Whittle BJ. Inhibitory effects of histamine H4 receptor antagonists on experimental colitis in the rat. Eur J Pharmacol 2005;522:130–138.
   PubMed Web of Science ®Google Scholar
• Thurmond RL, Desai PJ, Dunford PJ, Fung-Leung WP, Hofstra CL, Jiang W, Nguyen S, Riley JP, Sun S, Williams KN, Edwards JP, Karlsson L. A potent and selective histamine H4 receptor antagonist with anti-inflammatory properties. J Pharmacol Exp Ther 2004;309:404–413.
   PubMed Web of Science ®Google Scholar
• Ikawa Y, Suzuki M, Shiono S, Ohki E, Moriya H, Negishi E, Ueno K. Histamine H4 receptor expression in human synovial cells obtained from patients suffering from rheumatoid arthritis. Biol Pharm Bull 2005;10:2016–2018.
   Google Scholar
• Bell JK, McQueen DS, Rees JL. Involvement of histamine H4 and H1 receptors in scratching induced by histamine receptor agonists in BalbC mice. Br J Pharmacol 2004;142:374–380.
   PubMed Web of Science ®Google Scholar
• Cianchi F, Cortesini C, Schiavone N, Perna F, Magnelli L, Fanti E, Bani D, Messerini L, Fabbroni V, Perigli G, Capaccioli S, Masini E. The role of cyclooxygenase-2 in mediating the effects of histamine on cell proliferation and vascular endothelial growth factor production in colorectal cancer. Clin Cancer Res 2005;19(Pt 1):6807–6815.
   Google Scholar
• Smits RA, Lim HD, Hanzer A, Zuiderveld OP, Guaita E, Adami M, Coruzzi G, Leurs R, de Esch IJP. Fragment based design of new H4 receptor-ligands with anti-inflammatory properties in vivo. J Med Chem 2008;51:2457–2467.
   PubMed Web of Science ®Google Scholar
• Kiss R, Kiss B, Könczöl Á, Szalai F, Jelinek I, László V, Noszál B, Falus A, Keserű GM. Discovery of novel human histamine H4 receptor ligands by large-scale structure-based virtual screening. J Med Chem 2008;51:3145–3153.
   PubMed Web of Science ®Google Scholar
• Todeschini R, Consonni V. Dragon software (version 1.11-2001). Milano, Italy.
   Google Scholar
• Chemdraw Ultra 6.0 and Chem3D Ultra. Cambridge Soft Corporation, Cambridge, USA.
   Google Scholar
• Smits RA, Lim HD, Stegink B, Bakker RA, de Esch IJP, Leurs R. Characterization of the histamine H4 receptor binding site: Part I. Synthesis and pharmacological evaluation of dibenzodiazepine derivatives. J Med Chem 2006;49:4512–4516.
   PubMed Web of Science ®Google Scholar
• Prabhakar YS. A combinatorial approach to the variable selection in multiple linear regression: analysis of Selwood et al. data set—a case study. QSAR Comb Sci 2003;22:583–595.
   Google Scholar
• Sharma BK, Pilania P, Singh P. Modeling of cyclooxygnase-2 and 5-lipooxygenase inhibitory activity of apoptosis inducing agents potentially useful in prostate cancer chemotherapy: the derivatives of diarylpyrazole. J Enz Inhib Med Chem 2009;24:607–615.
   PubMed Web of Science ®Google Scholar
• Sharma S, Sharma BK, Pilania P, Singh P, Prabhakar YS. Modeling of the growth hormone secretagogue receptor antagonistic activity using chemometric tools. J Enz Inhib Med Chem 2009;24:1024–1033.
   PubMed Web of Science ®Google Scholar
• Sharma BK, Pilania P, Singh P, Prabhakar YS. Combinatorial protocol in multiple linear regression/partial least-squares directed rationale for the caspase-3 inhibition activity of isoquinoline-1,3,4-trione derivatives. SAR QSAR Environ Res 2010;21:169–185.
   PubMed Web of Science ®Google Scholar
• Sharma BK, Pilania P, Sarbhai K, Singh P, Prabhakar YS. Chemometric descriptors in modeling the carbonic anhydrase inhibition activity of sulfonamide and sulfamate derivatives. Mol Divers 2010;14:371–384.
   PubMedGoogle Scholar
• Wold S. Cross-validatory estimation of the number of components in factor and principal components models. Technometrics 1978;20:397–405.
   Web of Science ®Google Scholar
• Kettaneh N, Berglund A, Wold S. PCA and PLS with very large data sets. Comput Stat Data Anal 2005;48:69–85.
   Web of Science ®Google Scholar
• Stahle L, Wold S. Multivariate data analysis and experimental design. In: Ellis GP, West WB. Eds., Biomedical research. Progress in medicinal chemistry. Elsevier Science Publishers, BV, Amsterdam. 1988;25:291–338.
   Google Scholar
• Topliss JG, Edwards RP. Chance factors in studies of quantitative structure–activity relationships. J Med Chem 1979;22:1238–1244.
   PubMed Web of Science ®Google Scholar
• Katritzky AR, Dobchev DA, Slavov S, Karelson M. Legitimate utilization of large descriptor pools for QSAR/QSPR models. J Chem Inf Model 2008;48:2207–2213.
   PubMed Web of Science ®Google Scholar
• So S-S, Karplus M. Three-dimensional quantitative structure–activity relationship from molecular similarity matrices and genetic neural networks. 1. Method and validation. J Med Chem 1997;40:4347–4359.
   PubMed Web of Science ®Google Scholar
• Prabhakar YS, Solomon VR, Rawal RK, Gupta MK, Katti SB. CP-MLR/PLS directed structure–activity modeling of the HIV-1 RT inhibitory activity of 2,3-diaryl-1,3-thiazolidin-4-ones. QSAR Comb Sci 2004;23:234–244.
   Google Scholar
• Gramatica P. Principles of QSAR models validation: internal and external. QSAR Comb Sci 2007;26:694–701.
   Google Scholar