Isocombretastatins A versus Combretastatins A: The Forgotten isoCA-4 Isomer as a Highly Promising Cytotoxic and Antitubulin Agent

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...

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Published inJournal of medicinal chemistry Vol. 52; no. 14; pp. 4538 - 4542
Main Authors Messaoudi, Samir, Tréguier, Bret, Hamze, Abdallah, Provot, Olivier, Peyrat, Jean-François, De Losada, Jordi Rodrigo, Liu, Jian-Miao, Bignon, Jérôme, Wdzieczak-Bakala, Joanna, Thoret, Sylviane, Dubois, Joëlle, Brion, Jean-Daniel, Alami, Mouâd
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 23.07.2009
Amer Chemical Soc
Subjects
Antineoplastic Agents
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Bibenzyls
Bibenzyls - chemistry
Bibenzyls - pharmacology
Biological and medical sciences
Cell Line, Tumor
Cell Proliferation
Cell Proliferation - drug effects
Cellular Biology
Chemistry, Medicinal
Chlorophenols
Chlorophenols - chemistry
Chlorophenols - pharmacology
General aspects
Humans
Life Sciences
Life Sciences & Biomedicine
Medical sciences
Models, Molecular
Molecular Conformation
Peptides, Cyclic
Peptides, Cyclic - chemistry
Peptides, Cyclic - pharmacology
Pharmacology & Pharmacy
Pharmacology. Drug treatments
Science & Technology
Stereoisomerism
Tubulin Modulators
Tubulin Modulators - chemistry
Tubulin Modulators - pharmacology
ANTINEOPLASTIC AGENTS
A-4
COLCHICINE
ANALOGS
Antineoplastic agent
Human
Solid tumor
Leukemia
Lung
Antitubulin
Cytotoxicity
In vitro
Biological activity
Isomer
Cell line
Binding mode
Phenols
Colon
Mammary gland
Chemical synthesis
Antimitotic
Tumor cell
Combretastatin derivative
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-2623
1520-4804
DOI:10.1021/jm900321u