(-)-4′-Demethylepipodophyllotoxin

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) [1]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, whic

4'-demethylepipodophyllotoxin is an organic heterotetracyclic compound that is the 9- epimer of 4'-demethylpodophyllotoxin. It has a role as an antineoplastic agent. It is a furonaphthodioxole, an organic heterotetracyclic compound and a member of phenols.

The podophyllotoxin 2.1g (5.0mmol) was dissolved in dry methylenechloride, sodium iodide (2.3g, 15.0mmol) Was added to the above solution andstirred for 5 minutes. The reaction solution was cooled to ice-water bath 0 °C, 1.48 Methanesulfonic acid (15.0 mmol) is slowly added dropwise to thereaction mixture and stirring was continued, and then raised to The reactionwas continued at room temperature for 5 hours. Nitrogen, removed HI gasesproduced during the reaction. Then, Reduced pressure in the above reactionsolvent was removed under no processing to the next step. The above crudeproduct Was dissolved in acetone - water (25mL-25mL) mixed solvent was addedbarium carbonate (2.0g, 10.0mmol), For 30 minutes at 40 ° C the reactionconditions, after 100mL of dichloromethane was added to the mixed solution, Thenpour in 500ml of 10percent aqueous sodium thiosulfate, and extracted withdichloromethane, the organic phase, dry Dried over sodium sulfate, andconcentrated to give the crude product was purified by silica gelchromatography (eluent: chloroform: methanol = 92: 8), The product was VII1.8g, yield: 90percent, white solid.

A potent inhibitor of microtubule assembly

Molecular Weight:400.4
XLogP3:1.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:3
Exact Mass:400.11581759
Monoisotopic Mass:400.11581759
Topological Polar Surface Area:104
Heavy Atom Count:29
Complexity:614
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes