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Paper | Regular issue | Vol 55, No. 2, 2001, pp.303-312
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9093
Glycosyl-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones. Synthesis, Tensioactivity and Anitbacterial Activity

Driss Bouhlal, Paul Godé, Gérard Goethals, Mohamed Massoui, Pierre Villa, and Patrick Martin*

*Laboratoire de Chimie Organique et Cinétique, Faculté des Sciences, Université de Picardie Jules Verne, 33 rue Saint Leu, 80039 Amiens Cedex, France

Abstract

Glycosyl-pyrrolo[2,1-c][1,4]benzodiazepin-5,11-diones have been obtained by condensing, at the N-10, different polyhydroxylated groups Su (Su = 6-deoxy-D-glucopyranos-6-yl, 6-deoxy-3-O-R-D-glucopyranos-6-yl (R = n-CnH2n+1; n = 8, 12 and 16), 1-deoxy-D,L-xylit-1-yl and 1-deoxy-D,L-glycer-1-yl). The structural variations of Su allowed us to compare amphiphilic data like water solubility (Sw), critical micelle concentration (CMC) and corresponding surface tension (γ) values. Results of a preliminary antibacterial study are also reported.