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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.

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.
AuthorsV V N Phani Babu Tiruveedhula, Kashi Reddy Methuku, Jeffrey R Deschamps, James M Cook
JournalOrganic & biomolecular chemistry (Org Biomol Chem) Vol. 13 Issue 43 Pg. 10705-15 (Nov 21 2015) ISSN: 1477-0539 [Electronic] England
PMID26349488 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S.)
Chemical References
  • Aza Compounds
  • Carbolines
  • Palladium
Topics
  • Alcoholism (drug therapy)
  • Animals
  • Aza Compounds (chemical synthesis, chemistry, therapeutic use)
  • Binge Drinking (drug therapy)
  • Carbolines (chemical synthesis, chemistry, therapeutic use)
  • Catalysis
  • Models, Molecular
  • Palladium (chemistry)
  • Rats
  • Stereoisomerism

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