Yous Saíd, Durieux-Poissonnier Sophie, Lipka-Belloli Emmanuelle, Guelzim Halim, Bochu Christophe, Audinot Valérie, Boutin Jean A, Delagrange Philippe, Bennejean Caroline, Renard Pierre, Lesieur Daniel
Laboratoire de Chimie Thérapeutique, Faculté des Sciences Pharmaceutiques et Biologiques, Université de Lille 2, BP 83, 59006 Lille Cedex, France.
Bioorg Med Chem. 2003 Mar 6;11(5):753-9. doi: 10.1016/s0968-0896(02)00473-x.
Tetrahydronaphthalenic analogues of melatonin have been synthesized and evaluated as melatonin receptor ligands. Introduction of a phenyl substituent in the 3-position of the tetraline ring allows to obtain MT(2) selective ligands. Activity and MT(2) selectivity can be modulated with suitable modifications of the N-acyl substituent. The (+)-(RR)-cis enantiomer of the N-[2-(7-methoxy-3-phenyl-1,2,3,4-tetrahydro-naphthalen-1-yl)ethyl]cyclobutyl carboxamide (14) is one of the most MT(2) selective ligands described until now and behaves as an antagonist.
褪黑素的四氢萘类似物已被合成并作为褪黑素受体配体进行评估。在四氢萘环的3位引入苯基取代基可得到MT(2)选择性配体。通过对N-酰基取代基进行适当修饰，可以调节活性和MT(2)选择性。N-[2-(7-甲氧基-3-苯基-1,2,3,4-四氢萘-1-基)乙基]环丁基甲酰胺(14)的(+)-(RR)-顺式对映体是迄今为止所描述的最具MT(2)选择性的配体之一，并且表现为拮抗剂。
