118356-07-3

Upstream product

• 6559-91-7 4'-demethylepipodophyllotoxin 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 518-28-5 podofilox 

Downstream Products

• 683805-43-8 8-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-6,7-bis-hydroxymethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-5-ol 
• 33419-42-0 α-peltatin 5-<4,6-O-(R)-ethylidene-β-D-glucopyranoside> 
• 118356-10-8 4'-demethylepipodophyllotoxin 4-phthalate 
• 118356-09-5 hemisuccinic acid 4'-demethylepipodophyllotoxin-4-O-ester 
• 118356-12-0 4'-demethylepipodophyllotoxin 4-phenylacetate 
• 118356-11-9 4'-demethylepipodophyllotoxin 4-crotonate 
• 118356-13-1 4'-demethylepipodophyllotoxin 4(R,S)-tetrahydropyranyl ether 
• 118356-08-4 4'-demethylepipodophyllotoxin 4-propionate 
• 111712-27-7 4'-demethylepipodophyllotoxin 4-acetate 
• 491580-72-4 4'-O-benzyloxycarbonyl-4'-O-demethyl-4-deoxy-4-hydroxymethyl-epipodophyllotoxin 
• 491580-73-5 4'-O-benzyloxycarbonyl-4'-O-demethyl-4-deoxy-4-hydroxymethyl-podophyllotoxin 
• 491580-74-6 4'-O-benzyloxycarbonyl-4'-O-demethyl-4-deoxy-4-formyl-epipodophyllotoxin 
• 491580-75-7 4'-O-benzyloxycarbonyl-4'-O-demethyl-4-deoxy-4-formyl-podophyllotoxin 
• 491580-65-5 4'-O-tert-butyldimethylsilanyl-4'-O-demethyl-4-deoxy-4-methylene-podophyllotoxin 

Relevant academic research and scientific papers

Synthesis of podophyllotoxin analogues: δ-lactone-containing picropodophyllin, podophyllotoxin and 4′-demethyl-epipodophyllotoxin derivatives

Non-epimerizable cis and trans δ-lactone analogues of podophyllotoxin have been prepared. Thus the synthesis of the cis isomer 4 has been achieved in 8 steps and 4% overall yield from podophyllotoxin 1 via the reduction of the γ lactone ring into the tran

Hemi-synthesis and biological activity of new analogues of podophyllotoxin

Various 4-analogues of podophyllotoxin and epipodophyllotoxin were obtained via the formation of the corresponding 4-keto derivatives. Methyloximation of podophyllotoxone, followed by subsequent catalytic hydrogenation, gave stereoselective access to 4-α-amino-4-deoxypodophyllotoxin and from there, to the corresponding acetamido and formamido derivatives. Base-catalyzed isomerisation of 4-α-amino-4-deoxypodophyllotoxin led to the corresponding picropodophyllin isomer while the 4-β-amino afforded a neopodophyllotoxin-like derivative. On the other hand, oxirane and hydroxymethyl-containing analogues were prepared from podophyllotoxin and 4-epi-4′-demethyl-podophyllotoxin, using a Takai olefination strategy. In the latter series, carboxaldehyde- and carboxylic acid-containing derivatives were also synthesized.

Antitumor agents. 100. Inhibition of human DNA topoisomerase II by cytotoxic ether and ester derivatives of podophyllotoxin and α-peltatin

A principal mechanism of action of the clinical antitumor drugs etoposide (1) and teniposide (2) is the inhibition of catalytic activity of type II DNA topoisomerase and concurrent enzyme-mediated production of lethal DNA strand breaks. Substitution of the glycosidic moiety of 1 or 2 by ester and ethers, as well as the esterification and etherification of α-peltatin (4) including its glucosidic ethylidene and thenylidene cyclic acetals (25 and 26), has afforded compounds of much less activity than that of 1. The in vitro cytotoxicity (KB) appears to have no correlation with the inhibitory activity of the human DNA topoisomerase II.