N-Phenyl-N′-(2-chloroethyl)urea analogues of combretastatin A-4: Is the N-phenyl-N′-(2-chloroethyl)urea pharmacophore mimicking the trimethoxy phenyl moiety? - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Bioorganic and Medicinal Chemistry Letters Année : 2007

N-Phenyl-N′-(2-chloroethyl)urea analogues of combretastatin A-4: Is the N-phenyl-N′-(2-chloroethyl)urea pharmacophore mimicking the trimethoxy phenyl moiety?

Résumé

A series of novel N-phenyl-N'-(2-chloroethyl)urea derivatives potentially mimicking the structure of combretastatin A-4 were synthesized and tested for their cell growth inhibition and their binding to the colchicine-binding site of beta-tubulin. Compounds 2a, 3a, and 3b were found to inhibit cell growth at the micromolar level on four human tumor cell lines. Flow cytometric analysis indicates that the new compounds act as antimitotics and arrest the cell cycle in G(2)/M phase. Covalent binding of 2a, 3a, and 3b to the colchicine-binding site of beta-tubulin was confirmed also using SDS-PAGE and competition assays.

Dates et versions

hal-01677582 , version 1 (08-01-2018)

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Citer

Emmanuel Moreau, Sébastien Fortin, Jacques Lacroix, Jean-Claude Teulade, Alexandre Patenaude, et al.. N-Phenyl-N′-(2-chloroethyl)urea analogues of combretastatin A-4: Is the N-phenyl-N′-(2-chloroethyl)urea pharmacophore mimicking the trimethoxy phenyl moiety?. Bioorganic and Medicinal Chemistry Letters, 2007, 17 (7), pp.2000 - 2004. ⟨10.1016/j.bmcl.2007.01.023⟩. ⟨hal-01677582⟩
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