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.
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Authors | V V N Phani Babu Tiruveedhula, Kashi Reddy Methuku, Jeffrey R Deschamps, James M Cook |
Journal | Organic & biomolecular chemistry
(Org Biomol Chem)
Vol. 13
Issue 43
Pg. 10705-15
(Nov 21 2015)
ISSN: 1477-0539 [Electronic] England |
PMID | 26349488
(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.)
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Chemical References |
- Aza Compounds
- Carbolines
- Palladium
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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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