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Synthesis of 8-Oxa analogues of norcocaine endowed with interesting cocaine-like activity.

Abstract：

:In order to further explore the importance of cocaine's bridge nitrogen atom in binding to the dopamine transporter (DAT), we have synthesized the previously known racemic 8-oxa-norcocaines 3-6 in which the nitrogen atom has been replaced by oxygen. Additionally, to avoid incorrect interpretations of biological data that may stem from the use of racemic materials, several of these analogues were synthesized and tested in non-racemic form. (-)-8-Oxa-norcocaine (3) was found to bind to the cocaine recognition site and to inhibit the dopamine transporter with potencies only about 8-fold and 4-fold, respectively, less than those of norcocaine (2). (-)-8-Oxa-pseudonorcocaine (4) as well as (+)-8-oxa-norcocaine (3) were found to be comparable in activity to (-)-oxa-norcocaine. These pharmacological findings support our earlier suggestion that cocaine is likely to bind in its neutral form to the DAT.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Kozikowski AP,Simoni D,Roberti M,Rondanin R,Wang S,Du P,Johnson KM

doi

10.1016/s0960-894x(99)00273-5

subject

Has Abstract

pub_date

1999-07-05 00:00:00

pages

1831-6

issue

13

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(99)00273-5

journal_volume

9

pub_type

杂志文章

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