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Synthetic studies of neoclerodane diterpenes from Salvia divinorum: exploration of the 1-position.


ABSTRACT: Modification of the C-1 ketone of salvinorin A (2a) produces analogues with opioid antagonist properties. Of particular significance is the finding that 1-deoxo-1,10-dehydrosalvinorin A (11a) is a moderately potent antagonist at all three opioid receptor subtypes, and that herkinorin (2b), a mu agonist, is converted to a weak antagonist by removal of the C-1 ketone (3b and 11b). These observations suggest that the ketone of 2b is a key structural feature responsible for mu agonist activity.

SUBMITTER: Holden KG 

PROVIDER: S-EPMC2111044 | biostudies-literature | 2007 Nov

REPOSITORIES: biostudies-literature

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Synthetic studies of neoclerodane diterpenes from Salvia divinorum: exploration of the 1-position.

Holden Kenneth G KG   Tidgewell Kevin K   Marquam Alfred A   Rothman Richard B RB   Navarro Hernán H   Prisinzano Thomas E TE  

Bioorganic & medicinal chemistry letters 20070915 22


Modification of the C-1 ketone of salvinorin A (2a) produces analogues with opioid antagonist properties. Of particular significance is the finding that 1-deoxo-1,10-dehydrosalvinorin A (11a) is a moderately potent antagonist at all three opioid receptor subtypes, and that herkinorin (2b), a mu agonist, is converted to a weak antagonist by removal of the C-1 ketone (3b and 11b). These observations suggest that the ketone of 2b is a key structural feature responsible for mu agonist activity. ...[more]

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