1-甲氧基、1-脱氧-11-羟基和11-羟基-1-甲氧基-Δ(8)-四氢大麻酚：CB2受体的新型选择性配体。
1-Methoxy-, 1-deoxy-11-hydroxy- and 11-hydroxy-1-methoxy-Delta(8)-tetrahydrocannabinols: new selective ligands for the CB2 receptor.
作者信息
Huffman John W, Bushell Simon M, Miller John R A, Wiley Jenny L, Martin Billy R
机构信息
Howard L. Hunter Laboratory, Clemson University, Clemson, SC 29634-1905, USA.
出版信息
Bioorg Med Chem. 2002 Dec;10(12):4119-29. doi: 10.1016/s0968-0896(02)00331-0.
Three series of new cannabinoids were prepared and their affinities for the CB(1) and CB(2) cannabinoid recptors were determined. These are the 1-methoxy-3-(1',1'-dimethylalkyl)-, 1-deoxy-11-hydroxy-3-(1',1'-dimethylalkyl)- and 11-hydroxy-1-methoxy-3-(1',1'-dimethylalkyl)-Delta(8)-tetrahydrocannabinols, which contain alkyl chains from dimethylethyl to dimethylheptyl appended to C-3 of the cannabinoid. All of these compounds have greater affinity for the CB(2) receptor than for the CB(1) receptor, however only 1-methoxy-3-(1',1'-dimethylhexyl)-Delta(8)-THC (JWH-229, 6e) has effectively no affinity for the CB(1) receptor (K(i)=3134+/-110nM) and high affinity for CB(2) (K(i)=18+/-2nM).
制备了三类新型大麻素，并测定了它们对CB(1)和CB(2)大麻素受体的亲和力。这些是1-甲氧基-3-(1',1'-二甲基烷基)-、1-脱氧-11-羟基-3-(1',1'-二甲基烷基)-和11-羟基-1-甲氧基-3-(1',1'-二甲基烷基)-Δ(8)-四氢大麻酚，它们在大麻素的C-3位连接有从二甲基乙基到二甲基庚基的烷基链。所有这些化合物对CB(2)受体的亲和力都高于对CB(1)受体的亲和力，然而只有1-甲氧基-3-(1',1'-二甲基己基)-Δ(8)-THC (JWH-229, 6e)对CB(1)受体实际上没有亲和力(K(i)=3134±110 nM)，而对CB(2)受体具有高亲和力(K(i)=18±2 nM)。
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