845863-38-9

Basic information

• Product Name: 11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]-N-methyl]carbamate
• Synonyms: 11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]-N-methyl]carbamate
• CAS NO: 845863-38-9
• Molecular Weight: 676.72
• Mol File: 845863-38-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]-N-methyl]carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: 11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]-N-methyl]carbamate(845863-38-9)
• EPA Substance Registry System: 11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-[N-[3-(N',N'-dimethylaminopropyl)]-N-methyl]carbamate(845863-38-9)

Safety Data

• Hazardous Substances Data: 845863-38-9(Hazardous Substances Data)

Upstream product

• 845863-32-3 4-O-(tert-butyldimethylsilyl)-11-oxo-13-deoxo-4'-demethylepipodophyllotoxin 
• 642409-85-6 11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 
• 642409-76-5 11-oxo-13-deoxo-4'-demethylepipodophyllotoxin 
• 153230-77-4 4,4'-bis(tert-butyldimethylsilyl)-4'-O-demethylepipodophyllol 
• 501-53-1 benzyl chloroformate 
• 4543-96-8 N,N,N'-trimethylpropane-1,3-diamine 
• 845863-33-4 11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin 4-(p-nitrophenyl)carbonate 

Relevant articles and documents

Synthesis and biological study of a new series of 4′- demethylepipodophyllotoxin derivatives

Etoposide (VP-16) is a potent human DNA topoisomerase II poison, derived from 4′-demethylepipodophyllotoxin, widely used in cancer chemotherapy. Continuous efforts have driven to synthesize new related compounds, presenting decreased toxic side effects, metabolic inactivation, drug resistance, and increased water solubility. Identified structure-activity relationships have pointed out the importance of the 4β-substitution and of the configuration of the D ring. Here we report the synthesis of two novel series of derivatives of 4′-demethylepipodophyllotoxin. The first bears a carbamate chain in the 4 position (13a-f), whereas, in the second series, in addition to this chain, the lactone ring has been modified by shifting the carbonyl from position 13 to position 11 (27a-f). Moreover, an analogue of TOP-53 having this lactone modification has also been prepared (32). From this study, structure-activity relationships were established. Compounds 13a and 27a displayed potent cytotoxic activity against the L1210 cell line (10 to 20-fold higher than VP-16) and proved to be strong topoisomerase II poisons more potent than VP-16. From preliminary in vivo investigation of both compounds against P388 leukemia and orthotopically grafted human A549 lung carcinoma, it appeared that 13a and 27a constitute promising leads for a new class of antitumor agents.