Preparation and biological evaluation of β-Trifluoromethyl-α,β-unsaturated carbonyl compounds

Bioorganic & Medicinal Chemistry Letters
1995.0

Abstract

β-Trifluoromethyl-α,β-unsaturated carbonyl compounds derived from (E)-3-(trifluoromethyl)acrylic acid 1 and D-(-)-pantoic acid lactone 3 and/or D-mannitol 5 were found to possess in vitro interleukin-2 antiproducing effect. Research on the incorporation of fluorine into organic molecules which can lead to profound and unexpected results on biological activity has been extensive in recent years. 1-4 Recently, we have reported that ethyl (E)-3-(trifluoromethyl)acrylate (1) is revealed to have significantly lower LUMO energy level than the corresponding nonfluorinated material and the similar value for the corresponding p_z orbital coefficients at the reaction sites, which demonstrated the higher reactivity of (E)-1 as a Michael acceptor. 5 From our reported calculation results, β-trifluoromethyl-α,β-unsaturated carbonyl compounds are preferred due to their ability to act as an inhibitor. 6 Accordingly, we have been studying a new type of inhibitors possessing a β-trifluoromethyl-α,β-unsaturated carbonyl group. Herein, we report the synthesis of β-trifluoromethyl-α,β-unsaturated carbonyl compounds 4 and 7 and their interleukin-2 antiproducing effect.7-11

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