title: Optically active 1,3,4,4-tetrasubstituted β-lactams: synthesis and evaluation as tumor cell growth inhibitors.
abstract: The in vitro cytotoxicity assays of several enantiopure (3S,4S)- and (3R,4R)-1,3,4,4-tetrasubstituted β-lactams derived from amino acids have shown that the (3S,4S)-4-benzyl-1-p-methoxybenzyl-3-methyl-4-methoxycarbonyl derivative 2a, obtained from Phe, displays significant activity, which is comparable to that of the anticancer drug Doxorubicin against HT29 cell lines. Modifications at positions 1 and 4 of the β-lactam ring led to identify the Tyr(2,6-ClBz) analogu 26d with similar activity data to those of 2a. The synthesis and SAR of all these tetrasubstituted β-lactams are reported here.
authors: Instituto de Química Médica (IQM-CSIC), Juan de la Cierva 3, 28006 Madrid, Spain.
authors: Paula
authors: P
authors: Pérez-Faginas
authors: M Teresa
authors: MT
authors: Aranda
authors: M Teresa
authors: MT
authors: García-López
authors: Andrés
authors: A
authors: Francesch
authors: Carmen
authors: C
authors: Cuevas
authors: Rosario
authors: R
authors: González-Muñiz
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D003110:Colonic Neoplasms / Q000188:drug therapy; D006801:Humans; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D047090:beta-Lactams / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D047090:beta-Lactams