Medical College of Wisconsin
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Synthesis of aza and carbocyclic β-carbolines for the treatment of alcohol abuse. Regiospecific solution to the problem of 3,6-disubstituted β- and aza-β-carboline specificity. Org Biomol Chem 2015 Nov 21;13(43):10705-15

Date

09/10/2015

Pubmed ID

26349488

Pubmed Central ID

PMC4704088

DOI

10.1039/c5ob01572c

Scopus ID

2-s2.0-84946601118   10 Citations

Abstract

A novel two step protocol was developed to gain regiospecific access to 3-substituted β- and aza-β-carbolines, 3-PBC (1), 3-ISOPBC (2), βCCt (3), 6-aza-3-PBC (4) and 6-aza-3-ISOPBC (5). These β-carbolines (1-3) are potential clinical agents to reduce alcohol self-administration, especially 3-ISOPBC·HCl (2·HCl) which appears to be a potent anti-alcohol agent active against binge drinking in a rat model of maternally deprived (MD) rats. The method consists of two consecutive palladium-catalyzed reactions: a Buchwald-Hartwig amination followed by an intramolecular Heck-type cyclization in high yield.

Author List

Phani Babu Tiruveedhula VV, Methuku KR, Deschamps JR, Cook JM

Author

James M. Cook PhD University Distinguished Professor in the Chemistry and Biochemistry department at University of Wisconsin - Milwaukee




MESH terms used to index this publication - Major topics in bold

Alcoholism
Animals
Aza Compounds
Binge Drinking
Carbolines
Catalysis
Models, Molecular
Palladium
Rats
Stereoisomerism