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Synthesis and biological evaluation of 2-alkyl-2-methoxymethyl-salvinorin ethers as selective ?-opioid receptor agonists.

ABSTRACT: The synthesis of a new series of C-2-alkyl-2-methoxymethyl-salvinorin ethers and their binding affinities at ?-, ?-, and ?-opioid receptors are presented. We have developed a synthesis that enables installation of alkyl-substituents at C-2 while maintaining the integrity of the C-2 methoxymethyl ether and retaining ?-opioid receptor binding activity. Among these new compounds, 2-methyl-2-methoxymethyl-salvinorin ether (9a) is a potent full agonist at the ? receptor and shows comparable potency in Ki and EC50 with salvinorin A and U50488H. These C2-alkylated analogs have been identified as full ? agonists.

SUBMITTER: Lee DY 

PROVIDER: S-EPMC4620681 | biostudies-literature | 2015 Oct

REPOSITORIES: biostudies-literature

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Synthesis and biological evaluation of 2-alkyl-2-methoxymethyl-salvinorin ethers as selective κ-opioid receptor agonists.

Lee David Y W DY   Deng Gang G   Ma Zhongze Z   Xu Wei W   Yang Lu L   Liu Jing J   Dai Ronghua R   Liu-Chen Lee-Yuan LY  

Bioorganic & medicinal chemistry letters 20150703 20

The synthesis of a new series of C-2-alkyl-2-methoxymethyl-salvinorin ethers and their binding affinities at κ-, μ-, and δ-opioid receptors are presented. We have developed a synthesis that enables installation of alkyl-substituents at C-2 while maintaining the integrity of the C-2 methoxymethyl ether and retaining κ-opioid receptor binding activity. Among these new compounds, 2-methyl-2-methoxymethyl-salvinorin ether (9a) is a potent full agonist at the κ receptor and shows comparable potency i  ...[more]

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