3590-93-0

Basic information

• Product Name: 4’－Demethyldeoxypodophyllotoxin
• Synonyms: 4’－Demethyldeoxypodophyllotoxin;(5R)-5,5aα,6,8,8aβ,9-Hexahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6-one;(5R,5aα)-5,8,8aβ,9-Tetrahydro-5β-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one;(5R,5aα,8aβ)-5,8,8a,9-Tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one;4'-Demethyl-4-deoxypodophyllotoxin;7-Dehydroxy-4-demethylpodophyllotoxin;4'-DeMethyldesoxypodophyllotoxin
• CAS NO: 3590-93-0
• Molecular Formula: C₂₁H₂₀O₇
• Molecular Weight: 398.40588
• Product Categories: Non-nucleoside Reverse Transcriptase, Pharmaceuticals, Intermediates & Fine Chemicals, Inhibitors
• Mol File: 3590-93-0.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4’－Demethyldeoxypodophyllotoxin(CAS DataBase Reference)
• NIST Chemistry Reference: 4’－Demethyldeoxypodophyllotoxin(3590-93-0)
• EPA Substance Registry System: 4’－Demethyldeoxypodophyllotoxin(3590-93-0)

Safety Data

• Hazardous Substances Data: 3590-93-0(Hazardous Substances Data)

Usage

Uses

4'-Demethyldesoxypodophyllotoxin is a flavonoid that exhibit inhibitory activity against human immunodeficiency virus reverse transcriptase and glycohydrolase.

Definition

ChEBI: A member of the class of furonaphthodioxoles that is (5R,5aR,8aR)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one substituted a position 5 by a 4-hydroxy-3,5-dimethoxyphenyl group.

Upstream product

• 477-51-0 deoxypodophyllotoxin 
• 96548-65-1 3-(benzo[d][1,3]dioxol-5-ylmethyl)-4-methoxy-4-oxobutanoic acid 
• 104485-87-2 (R)-(+)-α-(methylenedioxy-3,4 benzyl)hemisuccinate de methyle 
• 17187-77-8 (R)-(+)-3-piperonyl-4-butanolide 
• 123287-52-5 <(dimethoxy-3,5 hydroxy-4 phenyl)hydroxymethyl>-2 (methylenedioxy-3,4 benzyl)-3 butanolide-4 
• 70381-90-7 (S)-(-)-α-(methylenedioxy-3,4 benzyl)hemisuccinate de methyle 
• 70148-37-7 (S)-(-)-4-(3,4-methylenedioxybenzyl)dihydrofuran-2(3H)-one 
• 123287-52-5 <(dimethoxy-3,5 hydroxy-4 phenyl)hydroxymethyl>-2 (methylenedioxy-3,4 benzyl)-3 butanolide-4 
• 199464-34-1 C₂₂H₂₀O₇ 
• 518-28-5 podofilox 
• 6559-91-7 4'-demethylepipodophyllotoxin 
• 40505-27-9 4-demethylpodophyllotoxin 

Downstream Products

• 13091-61-7 Ethyl-carbamic acid 2,6-dimethoxy-4-((5R,5aR,8aR)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-phenyl ester 
• 581799-49-7 4'-demethyl-9-deoxypodophyllol 
• 1308813-91-3 C₃₇H₄₀N₄O₁₁S 
• 1308813-92-4 C₃₇H₄₀N₄O₁₁S 
• 1308813-80-0 4'-demethyl-4-deoxypodophyllotoxin 4'-(4-methylpiperazine) carbamate 
• 1308813-81-1 4'-demethyl-4-deoxypodophyllotoxin 4'-(4-p-nitrophenylpiperazine) carbamate 
• 1308813-82-2 4'-demethyl-4-deoxypodophyllotoxin 4'-(4-p-fluorophenylpiperazine) carbamate 

Relevant articles and documents

Isolation, Semisynthesis, and Molecular Modeling of Deoxypodophyllotoxin Analogs for an Anti-oral Cancer Agent

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Design, synthesis and biological evaluation of 4′-demethyl-4-deoxypodophyllotoxin derivatives as novel tubulin and histone deacetylase dual inhibitors

A new class of 4′-demethyl-4-deoxypodophyllotoxin derivatives has been designed and synthesized as tubulin-HDAC dual inhibitors. Biological evaluation of these hybrids included the inhibitory activity of HDAC, in vitro cell cycle analysis in HCT-116 cells as well as cytotoxicity against two cancer cell lines (A549 and HCT116). The distance and angle between the HDAC capping group and the zinc binding group were systematically varied. Compounds 14a and 14c showed most potent dual inhibitory activity and powerful antiproliferative activity on HCT116 and A549 cell lines. This journal is

Carbamates of 4′-demethyl-4-deoxypodophyllotoxin: Synthesis, cytotoxicity and cell cycle effects

In an attempt to generate compounds with superior bioactivity and reduced toxicity, 12 carbamates of 4′-demethyl-4-deoxypodophyllotoxin, N-(1-oxyl-4′-demethyl- 4-deoxypodophyllic)-α-amino acids amides, were synthesized and evaluated for antiproliferative activity and cell cycle effects. These synthesized compounds proved to be more hydrophilic, as well as improved or comparable in vitro cytotoxicities against four cell lines (A-549, HeLa, SiHa, and HL-60) compared with either parent DPT or anti-cancer drug VP-16. Furthermore, flow cytometric analysis exhibited that N-(1-oxyl-4′- demethyl-4-deoxypodophyllic)-d-α-methine amide (15f) induced cell cycle arrest in the G2/M phase in A-549 cells.