Novel phenyl(thio)ureas bearing (thio)oxothiazoline group as potential BACE-1 inhibitors: synthesis and biological evaluation

Andreoli, Federico; Doukara, Abdallah Larbi; Mehdid, Mohammed Amine; Vanthuyne, Nicolas; Roussel, Christian; Dessolin, Jean; Kraus, Jean‐Louis

doi:10.3109/14756366.2011.642375

Cited by 2 publications

(1 citation statement)

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“…7 For instance, they display many biological activities such as antimicrobial, 8 antimalarial, 9 anti-inflammatory, 10 anticancer, 11 antiviral, 12 pesticidal, 13 and inhibition of HIV-1, 14 gp41, 15 JSP-1, 16 IKKβ, 17 PRL-3, 18 cholesterol esterase, 19 and potential BACE-1. 20 Furthermore, 3-phenylthiazole-2(3H)-thiones act as COX-2 inhibitors, 21 tyrosinase inhibitors 22 and combretastatin analogs. 23 In this manuscript, we present a new class of atropisomeric compounds belonging to the 3-arylthiazolidine-2-thione family (Scheme 1) that can be easily prepared by reacting an aryl isothiocyanate and 1,4-dithiane-2,5-diol under microwave irradiation.…”

Section: Introductionmentioning

confidence: 99%

Atropisomerism in 3-arylthiazolidine-2-thiones. A combined dynamic NMR and dynamic HPLC study

et al. 2016

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Sterically hindered 3-arylthiazolidine-2-thiones were prepared by a solvent-free reaction with arylisothiocyanates and 1,4-dithiane-2,5-diol. Atropisomerism was observed in two compounds (3 and 4, aryl = 1-naphthyl and 2-methylnaphth-1-yl), whose rotational energy barriers were measured using dynamic NMR and dynamic HPLC. The experimental analyses were supported by DFT calculations. Thermally stable atropisomers were obtained by dehydration of compounds 3 and 4 and the absolute configuration of the atropisomers of compound 6 was determined by theoretical simulation of the ECD and VCD spectra.

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