Asymmetric synthesis and biological evaluation of natural or bioinspired cytotoxic C-2-symmetrical lipids with two terminal chiral alkynylcarbinol pharmacophores - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2015

Asymmetric synthesis and biological evaluation of natural or bioinspired cytotoxic C-2-symmetrical lipids with two terminal chiral alkynylcarbinol pharmacophores

Résumé

Bidirectional syntheses of C-2-symmetrical lipids embedding two terminal alkynylcarbinol pharmacophores are reported. Naturally occurring chiral alkenylalkynylcarbinol units were generated using Pus procedure for enantioselective addition of terminal alkynes to aldehydes, allowing the first asymmetric synthesis of (3R,4E,16E,18R)-icosa-4,16-diene-1,19-diyne-3,18-diol, isolated from Callyspongia pseudoreticulata. Two synthetic analogues embedding the recently uncovered (S)-dialkynylcarbinol pharmacophore were secured using Carreiras procedure adapted to ynal substrates. The dramatic effect of the carbinol configuration on cytotoxicity was confirmed with submicromolar IC50 values against HCT116 cells.
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hal-01916643 , version 1 (08-11-2018)

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Dymytrii Listunov, Isabelle Fabing, N. Saffon-Merceron, Hafida Gaspard, Yulian Volovenko, et al.. Asymmetric synthesis and biological evaluation of natural or bioinspired cytotoxic C-2-symmetrical lipids with two terminal chiral alkynylcarbinol pharmacophores. Journal of Organic Chemistry, 2015, 80 (11), pp.5386-5394. ⟨10.1021/acs.joc.5b00494⟩. ⟨hal-01916643⟩
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