Issue 85, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
12 iyl 2018
Accepted
07 sen 2018
First published
07 sen 2018

Chem. Commun., 2018,54, 12002-12005

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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