1045730-28-6

Basic information

• Product Name: (+)-benzyl {(1S,1'R)-1-(1'-chloroethyl)-3-[(5-(2-(N,N-dimethylamino)ethoxy)indol-2-yl)carbonyl]-1,2-dihydro-3H-benz[e]indol-5-yl}-2,3,4-tri-O-acetyl-β-D-glucopyranuronate
• CAS NO: 1045730-28-6
• Molecular Weight: 870.353
• Mol File: 1045730-28-6.mol

Chemical Properties

• CAS DataBase Reference: (+)-benzyl {(1S,1'R)-1-(1'-chloroethyl)-3-[(5-(2-(N,N-dimethylamino)ethoxy)indol-2-yl)carbonyl]-1,2-dihydro-3H-benz[e]indol-5-yl}-2,3,4-tri-O-acetyl-β-D-glucopyranuronate(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-benzyl {(1S,1'R)-1-(1'-chloroethyl)-3-[(5-(2-(N,N-dimethylamino)ethoxy)indol-2-yl)carbonyl]-1,2-dihydro-3H-benz[e]indol-5-yl}-2,3,4-tri-O-acetyl-β-D-glucopyranuronate(1045730-28-6)
• EPA Substance Registry System: (+)-benzyl {(1S,1'R)-1-(1'-chloroethyl)-3-[(5-(2-(N,N-dimethylamino)ethoxy)indol-2-yl)carbonyl]-1,2-dihydro-3H-benz[e]indol-5-yl}-2,3,4-tri-O-acetyl-β-D-glucopyranuronate(1045730-28-6)

Safety Data

• Hazardous Substances Data: 1045730-28-6(Hazardous Substances Data)

Relevant articles and documents

Duocarmycin-based prodrugs for cancer prodrug monotherapy

The synthesis and biological evaluation of novel prodrugs based on the cytotoxic antibiotic duocarmycin SA (1) for a selective treatment of cancer using a prodrug monotherapy (PMT) are described. Transformation of the phenol 8 with the glucuronic acid benzyl ester trichloroacetimidate 9b followed by reaction with DMAI·HCl (10) gives the glucuronide 11b, which is deprotected to afford the desired prodrug 4a containing a glucuronic acid moiety. In addition, the prodrug 4b with a glucuronic methyl ester unit is prepared. The cytotoxicity of the glucuronides is determined using a HTCFA-assay with IC50 values of 610 nM for 4a and 3300 nM for 4b. In the presence of β-glucuronidase, 4a expresses an IC50 value of 0.9 nM and 4b of 2.1 nM resulting in QIC50 values of about 700 for 4a and 1600 for 4b.