Amberlyst-15 catalyzed Povarov reaction of N-arylidene-1H-indazol-6-amines and indoles: a greener approach to the synthesis of exo-1,6,7,7a,12,12a-hexahydroindolo[3,2-c]pyrazolo[3,4-f]quinolines as potential sirtuin inhibitors

[Display omitted] Amberlyst® 15(H) has been shown for the first time to be effective as a greener catalyst in promoting the Povarov reaction between an imine, derived from the aryl/heteroaryl aldehydes and 1H-indazol-6-amine, and indole/5-bromo-1H-indole. Representative candidates from the library o...

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Bibliographic Details
Published in:Tetrahedron letters 2015-04, Vol.56 (18), p.2289-2292
Main Authors: Pasha, Jakeer, Kandagatla, Bhaskar, Sen, Saikat, Seerapu, Guru Pavan Kumar, Bujji, Sushmitha, Haldar, Devyani, Nanduri, Srinivas, Oruganti, Srinivas
Format: Article
Language:English
Subjects:
Amberlyst-15
Hexahydroindolo[3,2-c]pyrazolo[3,4-f]quinolines
Povarov reaction
Sirtuin inhibitors
Yeast assay
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Summary:[Display omitted] Amberlyst® 15(H) has been shown for the first time to be effective as a greener catalyst in promoting the Povarov reaction between an imine, derived from the aryl/heteroaryl aldehydes and 1H-indazol-6-amine, and indole/5-bromo-1H-indole. Representative candidates from the library of exo-1,6,7,7a,12,12a-hexahydroindolo[3,2-c]pyrazolo[3,4-f]quinolines, thus synthesized, were tested for their sirtuin (Sir-2) inhibitory activity using a yeast based assay. Among the ten compounds investigated in the assay, those derived from 5-bromoindole exhibited a higher degree of Sir-2 inhibition as compared to their analogs, derived from indole.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.03.078