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8-表-萨尔文诺灵B：晶体结构及对κ阿片受体的亲和力

8-epi-Salvinorin B: crystal structure and affinity at the kappa opioid receptor.

作者信息

Munro Thomas A, Duncan Katharine K, Staples Richard J, Xu Wei, Liu-Chen Lee-Yuan, Béguin Cécile, Carlezon William A, Cohen Bruce M

机构信息

Mailman Research Center, McLean Hospital, 115 Mill St, Belmont, MA 02478-9106, USA.

出版信息

Beilstein J Org Chem. 2007 Jan 9;3:1. doi: 10.1186/1860-5397-3-1.

DOI:10.1186/1860-5397-3-1
PMID:17212822
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1805503/
Abstract

There have been many reports of epimerization of salvinorins at C-8 under basic conditions, but little evidence has been presented to establish the structure of these compounds. We report here the first crystal structure of an 8-epi-salvinorin or derivative: the title compound, 2b. The lactone adopts a boat conformation with the furan equatorial. Several lines of evidence suggest that epimerization proceeds via enolization of the lactone rather than a previously proposed indirect mechanism. Consistent with the general trend in related compounds, the title compound showed lower affinity at the kappa opioid receptor than the natural epimer salvinorin B (2a). The related 8-epi-acid 4b showed no affinity.

摘要

已有许多关于在碱性条件下萨尔维诺醇在C-8位发生差向异构化的报道，但几乎没有证据能确定这些化合物的结构。我们在此报告首个8-表-萨尔维诺醇或其衍生物的晶体结构：标题化合物2b。内酯采取船式构象，呋喃处于平伏键。多条证据表明差向异构化是通过内酯的烯醇化进行的，而非先前提出的间接机制。与相关化合物的一般趋势一致，标题化合物在κ阿片受体上的亲和力低于天然差向异构体萨尔维诺醇B（2a）。相关的8-表-酸4b没有亲和力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1e61/1805503/24b10f7c6148/Beilstein_J_Org_Chem-03-01-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1e61/1805503/be84c85b9826/Beilstein_J_Org_Chem-03-01-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1e61/1805503/75b4e4602e43/Beilstein_J_Org_Chem-03-01-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1e61/1805503/24b10f7c6148/Beilstein_J_Org_Chem-03-01-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1e61/1805503/be84c85b9826/Beilstein_J_Org_Chem-03-01-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1e61/1805503/75b4e4602e43/Beilstein_J_Org_Chem-03-01-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1e61/1805503/24b10f7c6148/Beilstein_J_Org_Chem-03-01-g004.jpg

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