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Issue 85, 2018
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Exploring physicochemical space via a bioisostere of the trifluoromethyl and ethyl groups (BITE): attenuating lipophilicity in fluorinated analogues of Gilenya® for multiple sclerosis

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Abstract

The direct, catalytic vicinal difluorination of terminal alkenes via an I(I)/I(III) manifold was exploited to install a chiral, hybrid bioisostere of the CF3 and Et groups (BITE) in Gilenya®; the first orally available drug for the clinical management of Multiple Sclerosis (MS). This subtle fluorination pattern allows lipophilicity (log D) to be tempered compared to the corresponding CF3 and Et derivatives (CH2CH3 > CH2CF3 > CHFCH2F).

Graphical abstract: Exploring physicochemical space via a bioisostere of the trifluoromethyl and ethyl groups (BITE): attenuating lipophilicity in fluorinated analogues of Gilenya® for multiple sclerosis

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Publication details

The article was received on 12 Jul 2018, accepted on 07 Sep 2018 and first published on 07 Sep 2018


Article type: Communication
DOI: 10.1039/C8CC05643A
Citation: Chem. Commun., 2018,54, 12002-12005
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    Exploring physicochemical space via a bioisostere of the trifluoromethyl and ethyl groups (BITE): attenuating lipophilicity in fluorinated analogues of Gilenya® for multiple sclerosis

    N. Erdeljac, G. Kehr, M. Ahlqvist, L. Knerr and R. Gilmour, Chem. Commun., 2018, 54, 12002
    DOI: 10.1039/C8CC05643A

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