Potent anandamide analogs: the effect of changing the length and branching of the end pentyl chain

WJ Ryan, WK Banner, JL Wiley, BR Martin…

Index: Ryan, William J.; Kenneth Banner; Wiley, Jenny L.; Martin, Billy R.; Razdan, Raj K. Journal of Medicinal Chemistry, 1997 , vol. 40, # 22 p. 3617 - 3625

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Citation Number: 72

Abstract

To examine the effect of changing the length and branching of the end pentyl chain (C5H11) of anandamide (AN), various analogs 1a-h and 2a-f were synthesized from either the known aldehyde ester 6a or from the alcohol 6b and tested for their pharmacological activity. A reproducible procedure was developed for the conversion of arachidonic acid to 6a or 6b in gram quantities (overall yield 15%). The appropriate tetraene esters 7 were prepared by ...