One-pot synthesis and in-vitro anticancer evaluation of 5-(2′-indolyl)thiazoles
Open Access
- 29 March 2016
- journal article
- research article
- Published by Springer Nature in Scientific Reports
- Vol. 6 (1) , 23401
Abstract
A series of 5-(2′-indolyl)thiazoles were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of thioamides 3 with 3-tosyloxypentane-2,4-dione 4 led to in situ formation of 5-acetylthiazole 5 which upon treatment with arylhydrazines 6 in polyphosphoric acid resulted in the formation of 5-(2′-indolyl)thiazoles 2. Among the synthesized 5-(2′-indolyl)thiazoles, compounds 2d–f and 2h exhibited encouraging anticancer activity and also selectivity towards particular cell lines (IC50 = 10–30 μM). Further studies on the SAR of compound 2e may result in good anticancer activity.Keywords
This publication has 24 references indexed in Scilit:
- Benign by design: catalyst-free in-water, on-water green chemical methodologies in organic synthesisChemical Society Reviews, 2013
- Synthesis of Novel Indolyl-1,2,4-triazoles as Potent and Selective Anticancer AgentsChemical Biology & Drug Design, 2011
- Synthesis and anticancer activity of 5-(3-indolyl)-1,3,4-thiadiazolesEuropean Journal of Medicinal Chemistry, 2010
- An expeditious synthesis and anticancer activity of novel 4-(3′-indolyl)oxazolesEuropean Journal of Medicinal Chemistry, 2010
- Microwave-Assisted Organic Synthesis and Transformations using Benign Reaction MediaAccounts of Chemical Research, 2008
- Synthesis and antitumor properties of 2,5-bis(3′-indolyl)thiophenes: Analogues of marine alkaloid nortopsentinBioorganic & Medicinal Chemistry Letters, 2007
- Application of 2-Substituted Ethyl Isothiocyanates and 2-Aminothiols in the Synthesis of the Analogs of Indole Phytoalexin CamalexinCollection of Czechoslovak Chemical Communications, 1999
- Solid state synthesis of 2-aroylbenzo[b]furans, 1,3-thiazoles and 3-aryl-5,6-dihydroimidazo[2,1-b][1,3]thiazoles from α-tosyloxyketones using microwave irradiation †Journal of the Chemical Society, Perkin Transactions 1, 1998
- Synthesis and Biological Activity of Thiazolylindolequinones, Analogs of the Natural Product BE 10988Journal of Medicinal Chemistry, 1995
- Synthesis of the naturally occurring indolequinone BE 10988, an inhibitor of topoisomerase IIJournal of the Chemical Society, Perkin Transactions 1, 1993