Substituted oxygenated heterocycles and thio-analogues:: Synthesis and biological evaluation as melatonin ligands

被引：15
作者：
Charton, I
Mamai, A
Bennejean, C
Renard, P
Howell, EH
Guardiola-Lemaître, B
Delagrange, P
Morgan, PJ
Viaud, MC
Guillaumet, G
机构：
[1] Univ Orleans, CNRS, Inst Chim Organ & Analyt, F-45067 Orleans 2, France
[2] ADIR, F-92415 Courbevoie, France
[3] Rowett Res Inst, Aberdeen, Scotland
[4] Inst Rech Int Servier, F-92415 Courbevoie, France
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2000年 / 8卷 / 01期
关键词：
1,4-benzodioxins; 2,3-dihydro-1,4-benzoxathiins; chromans; thiochromans; melatonin ligands;
D O I：
10.1016/S0968-0896(99)00265-5
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A new series of substituted oxygenated heterocycles and thio-analogues were synthesized and evaluated as melatonin receptor ligands. The replacement of the indolic moiety of melatonin by heterocyclic skeleton such as 1,4-benzodioxin, 2,3-dihydro-1,4-benzodioxin, chroman, 2,3-dihydro-1,4-benzoxathiin, thiochroman, carrying the amidic chain on the aromatic ring, leads to compounds showing a weak affinity for melatonin receptors, except for the compounds 1cb and 1hb. (C) 2000 Elsevier Science Ltd, All rights reserved.
引用
收藏
页码：105 / 114
页数：10
相关论文
共 41 条
[1]   MELATONIN AND CIRCADIAN CONTROL IN MAMMALS [J].
ARMSTRONG, SM .
EXPERIENTIA, 1989, 45 (10) :932-938
[2]   CIRCADIAN RHYTHMICITY IN VERTEBRATE RETINAS - REGULATION BY A PHOTORECEPTOR OSCILLATOR [J].
CAHILL, GM ;
BESHARSE, JC .
PROGRESS IN RETINAL AND EYE RESEARCH, 1995, 14 (01) :267-291
[3]  
CHARTON I, UNPUB PHARM PHARM CO
[4]   The roles sf valine 208 and histidine 211 in ligand binding and receptor function of the ovine Mel(1a beta) melatonin receptor [J].
Conway, S ;
Canning, SJ ;
Barrett, P ;
GuardiolaLemaitre, B ;
Delagrange, P ;
Morgan, PJ .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1997, 239 (02) :418-423
[5]   2-AMIDO-8-METHOXYTETRALINS - A SERIES OF NONINDOLIC MELATONIN-LIKE AGENTS [J].
COPINGA, S ;
TEPPER, PG ;
GROL, CJ ;
HORN, AS ;
DUBOCOVICH, ML .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (20) :2891-2898
[6]  
DAVIES D, 1992, J MED CHEM, V35, P1484
[7]  
DEPREUX P, 1994, J MED CHEM, V37, P2331
[8]   EFFECT OF INDUCING NOCTURNAL SERUM MELATONIN CONCENTRATIONS IN DAYTIME ON SLEEP, MOOD, BODY-TEMPERATURE, AND PERFORMANCE [J].
DOLLINS, AB ;
ZHDANOVA, IV ;
WURTMAN, RJ ;
LYNCH, HJ ;
DENG, MH .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (05) :1824-1828
[9]   MELATONIN RECEPTORS - ARE THERE MULTIPLE SUBTYPES [J].
DUBOCOVICH, ML .
TRENDS IN PHARMACOLOGICAL SCIENCES, 1995, 16 (02) :50-56
[10]  
DUBOCOVICH ML, 1998, IUPHAR COMPENDIUM RE, P186
12345