Developments of isoCombretastatin A-4 derivatives as highly cytotoxic agents.
Cancer
Combretastatin A-4
Cytotoxicity
Heterocycles
Tubulin
isoCombretastatin A-4
Journal
European journal of medicinal chemistry
ISSN: 1768-3254
Titre abrégé: Eur J Med Chem
Pays: France
ID NLM: 0420510
Informations de publication
Date de publication:
15 Mar 2020
15 Mar 2020
Historique:
received:
02
12
2019
revised:
29
01
2020
accepted:
29
01
2020
pubmed:
18
2
2020
medline:
15
12
2020
entrez:
17
2
2020
Statut:
ppublish
Résumé
Combretastatin A-4 (CA-4) is a natural anti-cancer agent isolated in 1989 from the African willow tree, Combretum caffrum. Due to its chemical simplicity, this (Z)-stilbene has been the subject of many structural modifications mainly to improve its chemical and metabolic stability. Beside a large number of synthetic analogues, isoCombretastatin A-4 (isoCA-4), has proved to be a solution of choice since this non-natural isomer of CA-4 is stable, easier to synthesize and has equivalent antitumor properties as CA-4. In this review, we will present the structure-activity relationships (SARs) around isoCA-4 since its discovery in 2007. In a first part, we will describe some alternatives to replace the phenol B-ring of isoCA-4, then we will focus on the variations made on the 1,1-ethylene double bond and then, we will evocate very recent exiting results concerning the possible replacements of the 3,4,5-trimethoxyphenyl A-ring of isoCA-4 by suitable heterocycles.
Identifiants
pubmed: 32061961
pii: S0223-5234(20)30077-5
doi: 10.1016/j.ejmech.2020.112110
pii:
doi:
Substances chimiques
Antineoplastic Agents
0
Stilbenes
0
Tubulin Modulators
0
fosbretabulin
I5590ES2QZ
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
112110Informations de copyright
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