Synthesis, antiproliferative activity evaluation and structure-activity relationships of novel aromatic urea and amide analogues of N-phenyl-N’-(2-chloroethyl)ureas
Fiche du document
- 20.500.11794/34853
- 0223-5234
- doi: 10.1016/j.ejmech.2010.03.018
- 20400211
http://purl.org/coar/access_right/c_abf2
Mots-clés
Aromatic ureas Aromatic amides N-phenyl-N0 -(2-chloroethyl)ureas CEU Anticancer drugs Antimitotic agents Anticancéreux Amides Urée Composés aromatiquesSujets proches
Carbamide Carcinoma Cancers Malignancy (Cancer) Malignant tumorsCiter ce document
Sébastien Fortin et al., « Synthesis, antiproliferative activity evaluation and structure-activity relationships of novel aromatic urea and amide analogues of N-phenyl-N’-(2-chloroethyl)ureas », CorpusUL, l'archive ouverte de l'université Laval, ID : 10.1016/j.ejmech.2010.03.018
Métriques
Partage / Export
Résumé
Seven subsets of aromatic urea and amide analogues of N-phenyl-N0-(2-chloroethyl)ureas (CEU) have been synthesized by nucleophilic addition of 3-chloropropylisocyanate, 2-chloroacetylisocyanate, ethylisocyanate, 2-chloroacetyl chloride, 3-chloropropanoyl chloride, 4-chlorobutanoyl chloride, and acryloyl chloride, espectively, to selected anilines or benzylamines to afford 3-chloropropylureas (1, CPU), 2-chloroacetylureas (2, CAU), ethylureas (3, EU), 2-hloroacetamides (4, CA), 3-chloropropionamides (5, CPA), 4-chlorobutyramides (6, CBA) and acrylamides (7, cr). The molecular structure of these compounds has been confirmed by IR, 1H and 13C NMR, and MS spectra and their purity also confirmed by HPLC. The CEU analogues were evaluated for their antiproliferative activity against three human tumor cell lines, namely human colon carcinoma HT-29, human skin melanoma M21, and human breast carcinoma MCF-7. CAU (2c to 2g), CA (4a to 4d, 4f and 4g), CPA (5a) and Acr (7a and 7b) had IC50 ranging from 1.4 to 25 mM. CAU, CA, CPA and Acr exhibited interesting antiproliferative activity through mechanism(s) of action unrelated to the acylation of glutamic acid at position 198 on b-tubulin that is characterizing CEU.
