The synthesis of N-vanillyl-arachidonoyl-amide (arvanil) and its analogs:: An improved procedure for the synthesis of the key synthon methyl 14-hydroxy-(all-cis)-5,8,11-tetradecatrienoate

被引：26

作者：

Dasse, O

Mahadevan, A

Han, LN

Martin, BR

Di Marzo, V

Razdan, RK

机构：

[1] Organix Inc, Woburn, MA 01801 USA

[2] Virginia Commonwealth Univ, Med Coll Virginia, Dept Pharmacol & Toxicol, Richmond, VA 23298 USA

[3] CNR, Ist Chim Mol Interesse Biol, I-80072 Arco Felice, Napoli, Italy

来源：

TETRAHEDRON | 2000年 / 56卷 / 47期

关键词：

cannabinoid receptor; vanilloid receptors; anandamide; arvanil analogs;

D O I：

10.1016/S0040-4020(00)00877-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several arvanil analogs were synthesized where the end n-pentyl chain was branched and carried substituents at the terminal end of the chain. A high yielding total synthesis of these analogs was developed from methyl hex-5-ynoate, which was converted to the synthon 6 in a facile five strip sequence (overall yield, 33%). The pharmacological profile of these novel analogs suggests that they may be acting through a novel site of action for anandamide (arachidonylethanolamide, AEA). (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：9195 / 9202

页数：8

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