189454-47-5

Basic information

• Product Name: 4-O-(3-aminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin
• Synonyms: 4-O-(3-aminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin
• CAS NO: 189454-47-5
• Molecular Weight: 839.85
• Mol File: 189454-47-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-O-(3-aminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin(CAS DataBase Reference)
• NIST Chemistry Reference: 4-O-(3-aminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin(189454-47-5)
• EPA Substance Registry System: 4-O-(3-aminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin(189454-47-5)

Safety Data

• Hazardous Substances Data: 189454-47-5(Hazardous Substances Data)

Upstream product

• 189454-41-9 tert-butyldimethylsilyl 3-azido-4,6-di-O-acetyl-2,3-dideoxy-β-D-arabino-hexopyranoside 
• 189454-43-1 3-azido-1-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-arabinohexopyranoside 
• 189454-45-3 tert-butyldimethylsilyl 3-amino-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranoside 
• 6559-91-7 4'-demethylepipodophyllotoxin 
• 23363-33-9 4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin 
• 189454-46-4 tert-butyldimethylsilyl 3-aminobenzyloxycarbonyl-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranoside 

Downstream Products

• 189454-48-6 4-O-(3-amino-2,3-dideoxy-4,6-O-ethylidene-β-D-arabino-hexopyranosyl)-epipodophyllotoxin 

Relevant articles and documents

Synthesis and antitumor activity of new glycosides of epipodophyllotoxin, analogues of etoposide, and NK 611

A series of 3-amino- and 3-alkylamino-2-deoxy-β-D-ribo- and β-D- arabino-glycosides of 4'-demethylepipodophyllotoxin have been synthesized by means of an improved trimethylsilyl-iodide procedure for the podophyllotoxin- 4'-demethylepipodophyllotoxin conversion, an efficient and high yielding synthesis of silyl glycoside donors of 3-azido-2,3-dideoxy-β-D-ribo-and β- D-arabino-hexopyranosides and stereoselective glycosylations. In vitro evaluation of cytotoxic effects against murine L1210 leukemia critically demonstrates the essential role played by a 4,6-acetal for biological activity. Among the most cytotoxic compounds, 3-amino-2,3-dideoxy-and 3-N,N- (dimethylamino)-2,3-dideoxy etoposide analogues, 17 and 27-29 are at least as potent as etoposide on the in vivo P388 (iv/ip) murine leukemia models. However, surprisingly enough, none of these compounds inhibits the human DNA topoisomerases I or II or binds to tubulin to prevent its polymerization and microtubule assembly. Therefore, their mechanism of action remains to be cleared up.