4'-Demethylepipodophyllotoxin

CAS

6559-91-7

Catalog Number

ACM6559917

Category

Inhibitors

Molecular Weight

400.38

Molecular Formula

C21H20O8

MSDS COA Spec Sheet

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Specification

Description

4'-Demethylepipodophyllotoxin(4'-DMEP) is a key intermediate compound for the preparation of podophyllotoxin-type anti-cancer drugs; a potent inhibitor of microtubule assembly.IC50 Value: 0.31uM(EC5 0in HL60 cell, MTT assay, 48h); 0.37uM(EC50 in HepG2 cell, MTT assay, 48h) Target: microtubulein vitro: 4-TMP-DMEP showed strong cytotoxicity activity against the above-mentioned five tumor cell lines. The EC50s of 4-TMP-DMEP against these tumor cell lines ranged from 0.24 to 0.11 μM, which were 0.29 to 3618 times lower than that of DMEP .in vivo: Treatment of animals with DMEP (until the end of the experiment), 30 min before TPA treatment, significantly reduced the tumor incidence, tumor volume and the conversion efficiency of papillomas to squamous cell carcinomas. The tumor formation and growth was also delayed by DMEP pre-treatment .

Synonyms

4-Domethylpodophyllotoxin, 4'-demethyl-epi-podophyllotoxin

IUPAC Name

(5S,5aR,8aR,9R)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one

Canonical SMILES

COC1=CC(=CC(=C1O)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@@H](C4=CC5=C(C=C24)OCO5)O

InChI

InChI=1S/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3/t12-,17+,18-,19+/m0/s1

InChI Key

YVCVYCSAAZQOJI-JHQYFNNDSA-N

Boiling Point

626.5±55.0 °C

Melting Point

246-248 °C

Density

1.446±0.06 g/ml

Appearance

Powder

Storage

Powder-20°C, 3 years; 4°C, 2 years; In solvent-80°C, 6 months; -20°C, 1 month.