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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Design, synthesis and biological evaluation of new naphtalene diimides bearing isothiocyanate functionality
Anna Minarini1, Andrea Milelli, Vincenzo Tumiatti
1Dipartimento di Scienze Farmaceutiche, Alma Mater Studiorum, Università di Bologna, Via Belmeloro 6, 40126 Bologna, Italy. anna.minarini@unibo.it
Abstract:
The synthesis and the biological activities of new derivatives 1-3, characterized by the isothiocyanate (ITC) functionalities coming from sulforaphane (SFN), a well-known anticancer natural product, were reported. The most interesting compound of the series was 2. It was chemically characterized by two ITC functionalities mounted on the 1,4,5,8-naphthalentetracarboxylic diimide (NDI) scaffold through two polymethylene chains, each constituted by three carbon units. It demonstrated an IC(50) value in the submicromolar range, more potent than SFN, displaying also the ability to trigger apoptotic induction in the same range by eliciting both extrinsic and intrinsic apoptotic pathways. Finally, it was observed that 2 inhibited the cell growth by blocking the cell cycle in G1 phase.
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