title: Isocombretastatins a versus combretastatins a: the forgotten isoCA-4 isomer as a highly promising cytotoxic and antitubulin agent.
abstract: Herein is reported a convergent synthesis of isocombretastatins A, a novel class of potent antitubulin agents. These compounds having a 1,1-diarylethylene scaffold constitute the simplest isomers of natural Z-combretastatins A that are easy to synthesize without need to control the Z-olefin geometry. The discovery of isoCA-4 with biological activities comparable to that of CA-4 represents a major progress in this field.
authors.affiliation: Laboratoire de Chimie Therapeutique, Faculte de Pharmacie, Univ Paris-Sud, CNRS, BioCIS-UMR 8076, Clement, Chatenay-Malabry F-92296, France.
authors.forename: Samir
authors.initials: S
authors.lastname: Messaoudi
authors.forename: Bret
authors.initials: B
authors.lastname: Tréguier
authors.forename: Abdallah
authors.initials: A
authors.lastname: Hamze
authors.forename: Olivier
authors.initials: O
authors.lastname: Provot
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Peyrat
authors.forename: Jordi Rodrigo
authors.initials: JR
authors.lastname: De Losada
authors.forename: Jian-Miao
authors.initials: JM
authors.lastname: Liu
authors.forename: Jérôme
authors.initials: J
authors.lastname: Bignon
authors.forename: Joanna
authors.initials: J
authors.lastname: Wdzieczak-Bakala
authors.forename: Sylviane
authors.initials: S
authors.lastname: Thoret
authors.forename: Joëlle
authors.initials: J
authors.lastname: Dubois
authors.forename: Jean-Daniel
authors.initials: JD
authors.lastname: Brion
authors.forename: Mouâd
authors.initials: M
authors.lastname: Alami
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology; D001632:Bibenzyls / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002733:Chlorophenols / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D008958:Models, Molecular; D008968:Molecular Conformation; D010456:Peptides, Cyclic / Q000737:chemistry* / Q000494:pharmacology*; D013237:Stereoisomerism; D050257:Tubulin Modulators / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D001632:Bibenzyls; D002733:Chlorophenols; D010456:Peptides, Cyclic; D050257:Tubulin Modulators; C023490:complestatin; C040105:combretastatin