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Molecules 2017, 22(9), 1540; doi:10.3390/molecules22091540

A Facile Oxidative Opening of the C-Ring in Luotonin A and Derivatives

1
Department of Pharmaceutical Chemistry, University of Vienna, Althanstraße 14, A-1090 Vienna, Austria
2
Institute of Cancer Research, Medical University of Vienna, Borschkegasse 8a, A-1090 Vienna, Austria
*
Author to whom correspondence should be addressed.
Received: 7 August 2017 / Revised: 11 September 2017 / Accepted: 11 September 2017 / Published: 12 September 2017
(This article belongs to the Collection Heterocyclic Compounds)
View Full-Text   |   Download PDF [1039 KB, uploaded 14 September 2017]   |  

Abstract

An oxidative ring opening reaction of the central ring C in the alkaloid Luotonin A and two of its derivatives was found to occur upon heating with an excess amine and potassium carbonate in dimethylsulfoxide (DMSO) solution in the presence of air oxygen. The structure of the novel amide-type products was elucidated and a possible mechanism for this reaction is proposed. Four of the new compounds show moderate in vitro anticancer activity towards human colon adenocarcinoma cells. View Full-Text
Keywords: Luotonin A; quinazoline; quinoline; ring opening; oxidation; anticancer activity Luotonin A; quinazoline; quinoline; ring opening; oxidation; anticancer activity
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Ibric, A.; Dutter, K.; Marian, B.; Haider, N. A Facile Oxidative Opening of the C-Ring in Luotonin A and Derivatives. Molecules 2017, 22, 1540.

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