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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. Issue 85 (17th September 2018)
Record Type:
Journal Article
Title:
Exploring physicochemical space via a bioisostere of the trifluoromethyl and ethyl groups (BITE): attenuating lipophilicity in fluorinated analogues of Gilenya® for multiple sclerosis. Issue 85 (17th September 2018)
Main Title:
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 BITE bioisostere of Et and CF3 allows lipophilicity to be tempered in analogues of the multiple sclerosis drug Gilenya®. 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 (CH2 CH3 > CH2 CF3 > CHFCH2 F).