1. Hetero-Diels-Alder approach to Bis(indolyl)methanes
- Author
-
Maria João Rodrigues, Cátia Marques, Carla Grosso, Teresa M.D.V. Pinho e Melo, Luísa Barreira, Ana L. Cardoso, and Américo Lemos
- Subjects
Indoles ,Cell Survival ,Clinical Biochemistry ,Terminal alkynes ,Pharmaceutical Science ,Activation ,Antineoplastic Agents ,Conjugated system ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Medicinal chemistry ,Cell Line ,Enantioselective synthesis ,Structure-Activity Relationship ,Drug Discovery ,Diels alder ,Friedel-crafts reactions ,Humans ,Organic chemistry ,Bis-indolylmethanes ,Carbonyl-compounds ,Molecular Biology ,Cell Proliferation ,Biological evaluation ,Recyclable catalyst ,Cycloaddition Reaction ,Dose-Response Relationship, Drug ,Molecular Structure ,Nitrosoalkenes ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Stereoisomerism ,Cycloaddition ,0104 chemical sciences ,Electrophile ,Molecular Medicine ,Drug Screening Assays, Antitumor ,Methane ,Derivatives - Abstract
A novel synthetic approach to bis(indolyl)methanes has been established. Our one-pot synthetic strategy based on two consecutive hetero-Diels-Alder cycloaddition reactions of electrophilic conjugated nitrosoalkenes with indoles was extended to a range of new 1-hydroxyiminomethyl-bis(indolyl) methanes. Furthermore, a similar and broad range approach was applied to the synthesis of previously unknown 1-hydrazonomethyl-bis(indolyl)methanes. The biological evaluation of the new bis(indolyl) methanes as anti-cancer agents was investigated. (C) 2016 Elsevier Ltd. All rights reserved. Portuguese Agency for Scientific Research Fundacao para a Ciencia e a Tecnologia (FCT) [007630 UID/QUI/00313/2013] COMPETE-UE FCT Coimbra Chemistry Centre [CQC-QO-BPD-2015]
- Published
- 2017