1256-91-3

Basic information

• Product Name: (5R,6R,7R,8R)-methyl 8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate
• Synonyms: (5R,6R,7R,8R)-methyl 8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate
• CAS NO: 1256-91-3
• Molecular Weight: 446.454
• Mol File: 1256-91-3.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (5R,6R,7R,8R)-methyl 8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (5R,6R,7R,8R)-methyl 8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate(1256-91-3)
• EPA Substance Registry System: (5R,6R,7R,8R)-methyl 8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate(1256-91-3)

Safety Data

• Hazardous Substances Data: 1256-91-3(Hazardous Substances Data)

Upstream product

• 86301-75-9 (5S,6S,7R,8S)-5-Hydroxy-8-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6,7-dicarboxylic acid dimethyl ester 
• 75101-87-0 C₂₄H₂₄O₁₀ 
• 75101-87-0 C₂₄H₂₄O₁₀ 
• 75101-87-0 dimethyl 1,4-epoxy-1,2,3,4-tetrahydro-6,7-(methylenedioxy)-1-(1,2-cis)-(3',4',5'-trimethoxyphenyl)-2,3-trans-naphthalenedicarboxylate 
• 75101-87-0 dimethyl 1,4-epoxy-1,2,3,4-tetrahydro-6,7-(methylenedioxy)-1-(1,2-cis)-(3',4',5'-trimethoxyphenyl)-2,3-cis-naphthalenedicarboxylate 
• 76886-74-3 C₂₄H₂₂O₁₀ 
• 74879-25-7 -3,4-methylenedioxybenzaldehyde dimethyl acetal 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 74879-22-4 6-bromobenzo-1,3-dioxole-5-carboxaldehyde dimethyl acetal 
• 120-57-0 piperonal 
• 86301-74-8 5-Dimethoxymethyl-6-(3,4,5-trimethoxy-benzyl)-benzo[1,3]dioxole 
• 42123-15-9 6-<(3,4,5-trimethoxyphenyl)methyl>benzo-1,3-dioxole-5-carboxaldehyde 
• 21852-50-6 3,4,5-trimethoxybenzyl bromide 
• 624-49-7 dimethylfumarate 

Downstream Products

• 518-28-5 podofilox 
• 477-47-4 (+/-)-epi-picropodophyllin 
• 477-47-4 (+/-)-epipodophyllotoxin 
• 1643-12-5 (5S,6S,7S)-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 epipicropodophyllic acid 
• 122763-50-2 methyl 3-(hydroxymethyl)-6,7-(methylenedioxy)-1-(1,2-cis)-(3',4',5'-trimethoxyphenyl)-1,2-dihydronaphthalene-2-carboxylate 
• 477-47-4 (+/-)-isopicropodophyllin 
• 1178-07-0 4-O-methylisopicropodophyllin 
• 1178-07-0 4-O-methylepiisopicropodophyllin 
• 79305-58-1 methyl epipodophyllate 4,11-acetonide 
• 79305-58-1 (4aR,5R,6S,11bS)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene-5-carboxylic acid methyl ester 
• 77519-37-0 9-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 
• 477-47-4 (+/-)-epiisopodophyllotoxin 
• 79289-93-3 (4aR,5R,6S,11bS)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene-5-carboxylic acid 

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.

Asymmetric total synthesis of (-)-podophyllotoxin

(-)-Podophyllotoxin of 98% optical purity has been synthesized in eight steps and in 15% overall yield. The key step, Diels-Alder addition of the o-quinonoid pyrone 2 [6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-2-benzopyran-3-one] to the chiral dienophile 5 [5-(-)-menthyloxyfuran-2(5H)-one], proceeds with very high regio-, endo- and facial selectivity.

Asymmetric total synthesis of (-)-podophyllotoxin

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