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CAS 6559-91-7

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(-)-4′-Demethylepipodophyllotoxin

Description:
(-)-4′-Demethylepipodophyllotoxin, with the CAS number 6559-91-7, is a naturally occurring lignan derived from the plant Podophyllum peltatum, commonly known as the mayapple. This compound is characterized by its complex polycyclic structure, which includes a phenolic moiety and an ether linkage. It exhibits significant biological activity, particularly as an inhibitor of topoisomerase II, making it of interest in cancer research for its potential therapeutic applications. The compound is known for its cytotoxic properties, which can lead to the inhibition of cell division and induction of apoptosis in cancer cells. Additionally, (-)-4′-Demethylepipodophyllotoxin has been studied for its effects on various cellular pathways and its potential use in developing chemotherapeutic agents. Its stereochemistry plays a crucial role in its biological activity, with the specific configuration contributing to its interaction with biological targets. As a natural product, it is also of interest in the field of medicinal chemistry for the synthesis of analogs with improved efficacy and reduced toxicity.
Formula:C21H20O8
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:InChIKey=YVCVYCSAAZQOJI-JHQYFNNDSA-N
SMILES:O=C1[C@@]2([C@@H](C=3C([C@@H](O)[C@]2(CO1)[H])=CC4=C(C3)OCO4)C5=CC(OC)=C(O)C(OC)=C5)[H]
Synonyms:
  • (5R,5aR,8aR)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
  • (5R,5aR,8aR,9S)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
  • (5R,5aR,8aR,9S)-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
  • 4'-Demethylepipodo phyllotoxin
  • 4′-O-demethylepipodophyllotoxin
  • Epipodophyllotoxin, 4′-demethyl-
  • Furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR,9S)-
  • Furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-, [5R-(5α,5aβ,8aα,9β)]-
  • (-)-4′-Demethylepipodophyllotoxin
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