130322-38-2

Basic information

• Product Name: (+/-)-isopodophyllotoxone
• CAS NO: 130322-38-2
• Molecular Weight: 412.396
• Mol File: 130322-38-2.mol
• Article Data: 36

Chemical Properties

• CAS DataBase Reference: (+/-)-isopodophyllotoxone(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-isopodophyllotoxone(130322-38-2)
• EPA Substance Registry System: (+/-)-isopodophyllotoxone(130322-38-2)

Safety Data

• Hazardous Substances Data: 130322-38-2(Hazardous Substances Data)

Upstream product

• 477-48-5 podophyllotoxone 
• 67-56-1 methanol 
• 620116-42-9 (+)-isopicropodophyllone 
• 64-19-7 acetic acid 
• 518-28-5 podofilox 
• 4375-07-9 epipodophyllotoxin 
• 477-51-0 deoxypodophyllotoxin 
• 1180-34-3 podophyllotoxinyl acetate 
• 101707-95-3 Benzo[1,3]dioxol-5-yl-(tert-butyl-dimethyl-silanyloxy)-acetonitrile 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 56579-86-3 2-(3,4-methylenedioxyphenyl)-1,3-dithiane 
• 90359-54-9 3,4-methylenedioxycinnamyl 3-(3,4,5-trimethoxyphenyl)acrylate 
• 107377-38-8 trans-2-(3,4,5-trimethoxyphenyl)benzocyclobutyl acetate 
• 131897-56-8 2,2-Dimethyl-propionic acid (5S,5aR,6R,8aR,9S)-9-hydroxy-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-ylmethyl ester 

Downstream Products

• 121976-16-7 (3aR)-2-phenyl-5c-(3,4,5-trimethoxy-phenyl)-(3ar)-3,3a,4,5-tetrahydro-2H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]indazole-4c-carboxylic acid 
• 55515-07-6 (1α,2α,3α)-podophyllotoxin 
• 157904-78-4 <5R-(5α,6α)>-5,6,7,8-tetrahydro-7-methylidene-8-oxo-5-(3,4,5-trimethoxyphenyl)naphtho<2,3-d><1,3>dioxole-6-carboxylic acid 
• 477-48-5 (5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione 
• 4375-07-9 epipodophyllotoxin 
• 518-28-5 podofilox 
• 138935-77-0 4-Hydroxy-3-methyl-6,7-(methylenedioxy)-1-(3,4,5-trimethoxyphenyl)-2-naphthoic acid 
• 1014671-34-1 (-)-podophyllotoxin 
• 211043-48-0 (5R,6R,7R)-7-Hydroxymethyl-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid butyl ester 
• 124131-03-9 (5R,6R,7R)-7-Hydroxymethyl-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester 
• 211043-47-9 (5R,6R,7R)-7-Hydroxymethyl-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid propyl ester 
• 211043-39-9 (5R,6R,7R)-methyl 7-(hydroxymethyl)-8-oxo-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate 
• 172096-08-1 [(3aR,4R,5R)-2-Phenyl-5-(3,4,5-trimethoxy-phenyl)-3,3a,4,5-tetrahydro-2H-7,9-dioxa-1,2-diaza-dicyclopenta[a,g]naphthalen-4-yl]-methanol 

Relevant articles and documents

Synthesis and biological evaluation of podophyllotoxin congeners as tubulin polymerization inhibitors

A series of new podophyllotoxin derivatives containing structural modifications at C-7, C-8, and C-9 were synthesized and evaluated for their cytotoxic activity against three human cancer cell lines. All the synthesized compounds showed significant growth inhibition with GI50values in micromolar levels while some of the compounds were several times more potent against MCF-7 and HeLa cell lines than MIAPACA cell line. Three compounds (12a, 12d and 12e) emerged as potent compounds with broad spectrum of cytotoxic activity against all the tested cell lines with GI50values in the range of 0.01-2.1 μM. These compounds induce microtubule depolymerization and arrests cells at the G2/M phase of the cell cycle. Moreover, compounds 12d and 12e disrupted microtubule network and accumulated tubulin in the soluble fraction in a similar manner to their parent podophyllotoxin scaffold. In addition, structure activity relationship studies within the series were also discussed. Molecular docking studies of these compounds into the colchicine-binding site of tubulin, revealed possible mode of inhibition by these compounds.

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A new approach to the synthesis of podophyllotoxin based on epimerization reactions

A formal synthesis of podophyllotoxin has been achieved by means of the well known conjugate addition-alkylation of 5H-furan-2-one, followed by cyclization and controlled epimerizations. This approach represents a useful new route to the 8,7'-trans-stereo

Scalable Aerobic Oxidation of Alcohols Using Catalytic DDQ/HNO3

A selective, practical, and scalable aerobic oxidation of alcohols is described that uses catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and HNO3, with molecular oxygen serving as the terminal oxidant. The method was successfully applied to the oxidation of a wide range of benzylic, propargylic, and allylic alcohols, including two natural products, namely, carveol and podophyllotoxin. The conditions are also applicable to the selective oxidative deprotection of p-methoxybenzyl ethers.

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

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