Bioorganic & Medicinal Chemistry Letters 2011-07-15

Gold(III) chloride catalyzed regioselective synthesis of pyrano[3,4-b]indol-1(9H)-ones and evaluation of anticancer potential towards human cervix adenocarcinoma.

Chandrasekaran Praveen, Asairajan Ayyanar, Paramasivan Thirumalai Perumal

Index: Bioorg. Med. Chem. Lett. 21 , 4170, (2011)

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Abstract

A highly regioselective synthesis of pyrano[3,4-b]indol-1(9H)-ones via gold(III) chloride catalyzed cycloisomerization of 3-ethynyl-indole-2-carboxylic acid was achieved in good to excellent yields. These compounds were screened for their in vitro cytotoxicity against human cervical (HeLa) cell lines. Out of ten compounds, three compounds (7d, 7e and 7j) showed comparable proliferation inhibitory activity against the standard drug cisplatin. Compound 7d was found to be the most efficacious with IC(50) value of 0.22μM.Copyright © 2011 Elsevier Ltd. All rights reserved.


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