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

Description

4'-Demethyldeoxypodophyllotoxin is a member of the furonaphthodioxoles class, specifically identified as (5R,5aR,8aR)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one, which is substituted at the 5 position by a 4-hydroxy-3,5-dimethoxyphenyl group. It is a flavonoid known for its inhibitory activity against human immunodeficiency virus reverse transcriptase and glycohydrolase.

Uses

Used in Pharmaceutical Industry:
4'-Demethyldeoxypodophyllotoxin is used as an active pharmaceutical ingredient for its inhibitory activity against human immunodeficiency virus reverse transcriptase and glycohydrolase, making it a potential candidate for the development of antiviral drugs, particularly for the treatment of HIV.
Used in Research and Development:
In the field of research and development, 4'-Demethyldeoxypodophyllotoxin is utilized as a key compound for studying its potential applications in medicine, including the development of new drugs targeting viral infections and other related diseases.
Used in Drug Synthesis:
4'-Demethyldeoxypodophyllotoxin serves as a starting material or intermediate in the synthesis of various pharmaceutical compounds, particularly those with antiviral properties, contributing to the advancement of drug discovery and innovation in the medical field.

Upstream product

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

Downstream Products

• 111142-77-9 Acetylderivat des 4-Desmethyl-7'-dehydroxy-podophyllotoxins 
• 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 

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.