Developments of isoCombretastatin A-4 derivatives as highly cytotoxic agents
| Autor: | Mouad Alami, Abdallah Hamze, Olivier Provot |
|---|---|
| Přispěvatelé: | Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Biomolécules : Conception, Isolement, Synthèse (BioCIS), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Paris-Sud - Paris 11 (UP11)-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine |
| Rok vydání: | 2019 |
| Předmět: |
Combretum caffrum
Cytotoxicity Antineoplastic Agents Heterocycles [CHIM.THER]Chemical Sciences/Medicinal Chemistry 01 natural sciences 03 medical and health sciences chemistry.chemical_compound Structure-Activity Relationship [CHIM.GENI]Chemical Sciences/Chemical engineering Tubulin Cell Line Tumor Drug Discovery Stilbenes [CHIM]Chemical Sciences Animals Humans 030304 developmental biology Cancer Pharmacology Combretastatin Combretastatin A-4 0303 health sciences biology Molecular Structure 010405 organic chemistry Organic Chemistry General Medicine Metabolic stability biology.organism_classification Combinatorial chemistry Tubulin Modulators 0104 chemical sciences isoCombretastatin A-4 chemistry |
| Zdroj: | European Journal of Medicinal Chemistry European Journal of Medicinal Chemistry, Elsevier, 2020, 190, pp.112110. ⟨10.1016/j.ejmech.2020.112110⟩ |
| ISSN: | 1768-3254 0223-5234 |
| DOI: | 10.1016/j.ejmech.2020.112110⟩ |
| Popis: | International audience; 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 Bring 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. |
| Databáze: | OpenAIRE |
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