Identification of chiral alkenyl- and alkynylcarbinols as pharmacophores for potent cytotoxicity

Dounia El Arfaoui; Dymytrii Listunov; Isabelle Fabing; Mohamed Oukessou; Céline Frongia; Valérie Lobjois; Arnaud Samson; Frédéric Ausseil; Abdeslem Ben-Tama; El Mestafa El Hadrami; Remi Chauvin; Yves Génisson

doi:10.1002/cmdc.201300230

Identification of chiral alkenyl- and alkynylcarbinols as pharmacophores for potent cytotoxicity

ChemMedChem. 2013 Nov;8(11):1779-86. doi: 10.1002/cmdc.201300230. Epub 2013 Sep 6.

Authors

Dounia El Arfaoui¹, Dymytrii Listunov, Isabelle Fabing, Mohamed Oukessou, Céline Frongia, Valérie Lobjois, Arnaud Samson, Frédéric Ausseil, Abdeslem Ben-Tama, El Mestafa El Hadrami, Remi Chauvin, Yves Génisson

Affiliation

¹ SPCMIB, UMR-CNRS 5068, Université Paul Sabatier-Toulouse III, 118 route de Narbonne, 31062 Toulouse Cedex 9 (France); LCOA, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fès (Marocco).

PMID: 24014463
DOI: 10.1002/cmdc.201300230

Abstract

Illumination by acetylene: Systematic structural variations in a series of archetypal acetylenic lipids derived from the naturally occurring (S,E)-icos-4-en-1-yn-3-ol allowed the discovery of a series of 3R-like 1,4-di-unsaturated carbinol units with a significant and systematic enantiomeric effect on cytotoxicity.

Keywords: asymmetric synthesis; carbinols; cytotoxicity; lipids; polyacetylene.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkanes* / chemistry
Alkanes* / pharmacology
Alkenes* / chemistry
Alkenes* / pharmacology
Animals
Antineoplastic Agents* / chemistry
Antineoplastic Agents* / pharmacology
Cell Line
Cell Line, Tumor
Cell Survival / drug effects
Drug Discovery*
Inhibitory Concentration 50
Methanol* / chemistry
Methanol* / pharmacology
Molecular Structure
Petrosia / chemistry
Stereoisomerism

Substances

Alkanes
Alkenes
Antineoplastic Agents
Methanol