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
09/10/2015Pubmed ID
26349488Pubmed Central ID
PMC4704088DOI
10.1039/c5ob01572cScopus ID
2-s2.0-84946601118 (requires institutional sign-in at Scopus site) 13 CitationsAbstract
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 JMAuthor
James M. Cook PhD University Distinguished Professor in the Chemistry and Biochemistry department at University of Wisconsin - MilwaukeeMESH terms used to index this publication - Major topics in bold
AlcoholismAnimals
Aza Compounds
Binge Drinking
Carbolines
Catalysis
Models, Molecular
Palladium
Rats
Stereoisomerism
