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Probing the cannabinoid CB1/CB2 receptor subtype selectivity limits of 1,2-diarylimidazole-4-carboxamides by fine-tuning their 5-substitution pattern.
Lange JH, van der Neut MA, Borst AJ, Yildirim M, van Stuivenberg HH, van Vliet BJ, Kruse CG. Lange JH, et al. Among authors: van Stuivenberg HH. Bioorg Med Chem Lett. 2010 May 1;20(9):2770-5. doi: 10.1016/j.bmcl.2010.03.068. Epub 2010 Mar 19. Bioorg Med Chem Lett. 2010. PMID: 20363132
Synthesis, SAR and intramolecular hydrogen bonding pattern of 1,3,5-trisubstituted 4,5-dihydropyrazoles as potent cannabinoid CB(1) receptor antagonists.
Lange JH, van der Neut MA, den Hartog AP, Wals HC, Hoogendoorn J, van Stuivenberg HH, van Vliet BJ, Kruse CG. Lange JH, et al. Among authors: van Stuivenberg HH. Bioorg Med Chem Lett. 2010 Mar 1;20(5):1752-7. doi: 10.1016/j.bmcl.2010.01.049. Epub 2010 Jan 20. Bioorg Med Chem Lett. 2010. PMID: 20137935
Synthesis and SAR of novel imidazoles as potent and selective cannabinoid CB2 receptor antagonists with high binding efficiencies.
Lange JH, van der Neut MA, Wals HC, Kuil GD, Borst AJ, Mulder A, den Hartog AP, Zilaout H, Goutier W, van Stuivenberg HH, van Vliet BJ. Lange JH, et al. Among authors: van Stuivenberg HH. Bioorg Med Chem Lett. 2010 Feb 1;20(3):1084-9. doi: 10.1016/j.bmcl.2009.12.032. Epub 2009 Dec 11. Bioorg Med Chem Lett. 2010. PMID: 20031412
SAR study of 1-aryl-4-(phenylarylmethyl)piperazines as ligands for both dopamine D2 and serotonin 5-HT1A receptors showing varying degrees of (Ant)agonism. Selection of a potential atypical antipsychotic.
Feenstra RW, van den Hoogenband A, Stroomer CN, van Stuivenberg HH, Tulp MT, Long SK, van der Heyden JA, Kruse CG. Feenstra RW, et al. Among authors: van Stuivenberg HH. Chem Pharm Bull (Tokyo). 2006 Sep;54(9):1326-30. doi: 10.1248/cpb.54.1326. Chem Pharm Bull (Tokyo). 2006. PMID: 16946546 Free article.
Piperazinyl oxime ethers as NK-1 receptor antagonists.
van den Hoogenband A, van Maarseveen JH, McCreary AC, Mulder AT, van Scharrenburg GJ, van Stuivenberg HH, Zethof TJ, Zijta B, Iwema Bakker WI. van den Hoogenband A, et al. Among authors: van Stuivenberg HH. Bioorg Med Chem Lett. 2006 Feb 15;16(4):1045-8. doi: 10.1016/j.bmcl.2005.10.077. Epub 2005 Nov 11. Bioorg Med Chem Lett. 2006. PMID: 16289817
Synthesis, structure-activity relationships, and biological properties of 1-heteroaryl-4-[omega-(1H-indol-3-yl)alkyl]piperazines, novel potential antipsychotics combining potent dopamine D2 receptor antagonism with potent serotonin reuptake inhibition.
Smid P, Coolen HK, Keizer HG, van Hes R, de Moes JP, den Hartog AP, Stork B, Plekkenpol RH, Niemann LC, Stroomer CN, Tulp MT, van Stuivenberg HH, McCreary AC, Hesselink MB, Herremans AH, Kruse CG. Smid P, et al. Among authors: van Stuivenberg HH. J Med Chem. 2005 Nov 3;48(22):6855-69. doi: 10.1021/jm050148z. J Med Chem. 2005. PMID: 16250644
Bioisosteric replacements of the pyrazole moiety of rimonabant: synthesis, biological properties, and molecular modeling investigations of thiazoles, triazoles, and imidazoles as potent and selective CB1 cannabinoid receptor antagonists.
Lange JH, van Stuivenberg HH, Coolen HK, Adolfs TJ, McCreary AC, Keizer HG, Wals HC, Veerman W, Borst AJ, de Looff W, Verveer PC, Kruse CG. Lange JH, et al. Among authors: van Stuivenberg HH. J Med Chem. 2005 Mar 24;48(6):1823-38. doi: 10.1021/jm040843r. J Med Chem. 2005. PMID: 15771428
Synthesis, biological properties, and molecular modeling investigations of novel 3,4-diarylpyrazolines as potent and selective CB(1) cannabinoid receptor antagonists.
Lange JH, Coolen HK, van Stuivenberg HH, Dijksman JA, Herremans AH, Ronken E, Keizer HG, Tipker K, McCreary AC, Veerman W, Wals HC, Stork B, Verveer PC, den Hartog AP, de Jong NM, Adolfs TJ, Hoogendoorn J, Kruse CG. Lange JH, et al. Among authors: van Stuivenberg HH. J Med Chem. 2004 Jan 29;47(3):627-43. doi: 10.1021/jm031019q. J Med Chem. 2004. PMID: 14736243
Design, synthesis and biological activity of rigid cannabinoid CB1 receptor antagonists.
Stoit AR, Lange JH, Hartog AP, Ronken E, Tipker K, Stuivenberg HH, Dijksman JA, Wals HC, Kruse CG. Stoit AR, et al. Among authors: Stuivenberg HH. Chem Pharm Bull (Tokyo). 2002 Aug;50(8):1109-13. doi: 10.1248/cpb.50.1109. Chem Pharm Bull (Tokyo). 2002. PMID: 12192147 Free article.
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