Issue 35, 2015

Palladium-catalyzed arylation of 2H-chromene: a new entry to pyrano[2,3-c]carbazoles

Abstract

Pyrano[2,3-c]carbazoles which are biologically valuable and synthetically challenging frameworks are synthesized in high yields over five steps from commercially available resorcinol. Palladium-catalyzed arylation remains a key step in this novel strategy. The versatility of this protocol has been demonstrated by the synthesis of naturally occurring alkaloid clauraila C and 7-methoxyglycomaurin. The anti-proliferative activity of these designed compounds (5a, 5f, and 5l) has been evaluated in a cancer cell line (MOLT-4). The molecular docking study revealed that this pyrano[2,3-c]carbazole class of molecules selectively occupies the colchicine binding site of the tubulin-polymer.

Graphical abstract: Palladium-catalyzed arylation of 2H-chromene: a new entry to pyrano[2,3-c]carbazoles

Supplementary files

Article information

Article type
Paper
Submitted
25 Jun 2015
Accepted
21 Jul 2015
First published
21 Jul 2015

Org. Biomol. Chem., 2015,13, 9285-9293

Author version available

Palladium-catalyzed arylation of 2H-chromene: a new entry to pyrano[2,3-c]carbazoles

K. Ranjith Reddy, A. Siva Reddy, D. K. Dhaked, S. K. Rasheed, A. S. Pathania, R. Shankar, F. Malik and P. Das, Org. Biomol. Chem., 2015, 13, 9285 DOI: 10.1039/C5OB01295C

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