（13S）-甲基取代花生四烯酸类似物的设计与合成：新型内源性大麻素的模板。
Design and synthesis of (13S)-methyl-substituted arachidonic acid analogues: templates for novel endocannabinoids.
机构信息
Institute of Organic and Pharmaceutical Chemistry, National Hellenic Research Foundation, 48 Vass. Constantinou, Athens 116-35, Greece.
出版信息
Chemistry. 2010 Apr 6;16(13):4091-9. doi: 10.1002/chem.200902880.
Abstract
Two novel methyl-substituted arachidonic acid derivatives were prepared in an enantioselective manner from commercially available chiral building blocks, and were found to be excellent templates for the development of (13S)-methyl-substituted anandamide analogues. One of the compounds synthesized, namely, (13S,5Z,8Z,11Z,14Z)-13-methyl-eicosa-5,8,11,14-tetraenoic acid N-(2-hydroxyethyl)amide, is an endocannabinoid analogue with remarkably high affinity for the CB1 cannabinoid receptor.
摘要
两种新型的甲基取代花生四烯酸衍生物从商业可得的手性砌块中以对映选择性方式制备，并被发现是开发（13S）-甲基取代的安那芬尼类似物的极好模板。所合成的化合物之一，即（13S，5Z，8Z，11Z，14Z）-13-甲基二十碳-5，8，11，14-四烯酸 N-（2-羟乙基）酰胺，是一种内源性大麻素类似物，对 CB1 大麻素受体具有显著高的亲和力。
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The endocannabinoid system: its general strategy of action, tools for its pharmacological manipulation and potential therapeutic exploitation.
Pharmacol Res. 2009 Aug;60(2):77-84. doi: 10.1016/j.phrs.2009.02.010. Epub 2009 Mar 4.
2
Development of novel tail-modified anandamide analogs.
Bioorg Med Chem Lett. 2008 Nov 15;18(22):5912-5. doi: 10.1016/j.bmcl.2008.07.110. Epub 2008 Jul 31.
3
The endocannabinoid anandamide is a substrate for the human polymorphic cytochrome P450 2D6.
J Pharmacol Exp Ther. 2008 Nov;327(2):538-45. doi: 10.1124/jpet.108.141796. Epub 2008 Aug 12.
4
Novel, potent THC/anandamide (hybrid) analogs.
Bioorg Med Chem. 2007 Dec 15;15(24):7850-64. doi: 10.1016/j.bmc.2007.08.039. Epub 2007 Aug 25.
5
Endocannabinoid metabolism and uptake: novel targets for neuropathic and inflammatory pain.
Br J Pharmacol. 2007 Nov;152(5):624-32. doi: 10.1038/sj.bjp.0707433. Epub 2007 Aug 20.
6
C1'-cycloalkyl side chain pharmacophore in tetrahydrocannabinols.
J Med Chem. 2007 Aug 23;50(17):4048-60. doi: 10.1021/jm070121a. Epub 2007 Aug 2.
7
The contribution of cyclooxygenase-2 to endocannabinoid metabolism and action.
Br J Pharmacol. 2007 Nov;152(5):594-601. doi: 10.1038/sj.bjp.0707379. Epub 2007 Jul 9.
8
Synthesis of C13-C25 fragment of 24-demethylbafilomycin C(1) via diastereoselective aldol reactions of a ketone boron enolate as the key step.
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9
Cannabinoid receptors as therapeutic targets.
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10
Structural requirements for cannabinoid receptor probes.
Handb Exp Pharmacol. 2005(168):209-46. doi: 10.1007/3-540-26573-2_7.
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