199996-63-9

Upstream product

• 540-63-6 ethane-1,2-dithiol 
• 171483-26-4 (-)-(1R,2S)-1-(3,4,5-trimethoxyphenyl)-2-(methoxycarbonyl)-1,2-dihydro-3-naphthalenecarbaldehyde 
• 78216-03-2 (5R,6S,7R,8R)-8-Hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester 
• 477-67-8 picropodophyllic acid 
• 518-28-5 podofilox 

Downstream Products

• 1207261-09-3 C₂₄H₂₄O₇S₂ 
• 171296-56-3 (-)-(1R,2S)-1,2-dihydro-1-(3,4,5-trimethoxyphenyl)-2-(hydroxymethyl)-3-formylnaphthalene 
• 199996-64-0 [(5R,6S)-7-[1,3]Dithiolan-2-yl-5-(3,4,5-trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxol-6-yl]-methanol 

Relevant academic research and scientific papers

Synthesis and biological evaluation of new podophyllic aldehyde derivatives with cytotoxic and apoptosis-inducing activities

Several series of nonlactonic podophyllic aldehyde analogues were prepared and evaluated against several human tumor cell lines. They had different combinations of aldehyde, imine, amine, ester, and amide functions at C-9 and C-9′ of the cyclolignan skeleton. All the compounds synthesized showed cytotoxicity levels in the μM range and below. Within the new series tested, compounds having an aldehyde or imine at C-9 and an ester at C-9′ were the most potent, with GI50 values in the nM range, some of them being several times more potent against HT-29 and A-549 carcinoma than against MB-231 melanoma cells. Cell cycle studies and analysis of the microtubule-disrupting capacity have demonstrated the existence of two different mechanisms of cell death induction for compounds with closely related structures.

Synthesis and antineoplastic activity of cyclolignan aldehydes

Several aldehydes related to methyl 9-deoxy-9-oxo-α- apopicropodophyllate, a selective antitumour agent against the HT-29 colon carcinoma, have been prepared and evaluated for their cytotoxic activities on four neoplastic cell lines (P-388, A-549, HT-29 and MEL-28). All of them lacked the lactone ring but maintained their cytotoxicity at, or under, the μM level. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

Preparation and cytotoxicity of podophyllotoxin derivatives lacking the lactone ring

Several cyclolignans lacking of the Iactone moiety can easily be prepared from naturally occurring lignans such as podophyllotoxin and deoxypodophyllotoxin by simple chemical transformations. Their cytotoxicity has been studied in four tumoral cell lines. Most of the compounds show similar effects in all the neoplastic systems tested, except the 3 aldehyde 9 (methyl 9-deoxy-9-oxo-α-apopicropodophyllate) and the hydrazones 16 and 17 which show a highly selective cytotoxicity towards HT-29 human colon carcinoma. Additionally, several molecular modeling studies have been done with aldehyde 9 and the correspnding saturated aldehyde 13 in comparison with podophyllotoxin.