Syntheses of Taxuspine C Derivatives as Functional Inhibitors of P-Glycoprotein, an ATP-Associated Cell-Membrane Transporter

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概要

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• UV-Irradiation of taxinine and related compounds in acetonitrile induced a smooth transannulation between the C-3 and C-11 positions without any influence from the C-2,C-9 and C-10 substituents to give tetracyclic taxuspine C derivatives in almost quantitative yields. Photochemical transannular reaction of taxoids possessing a cinnamoyl group in the side-chain was accompanied by an E, Z-isomerization of the cinnamoyl moiety. Cellular accumulation of vincristine, a useful drug for cancer chemotherapy, in multidrug-resistant ovarian cancer cells was found to increase most effectively in the case of 5-O-benzoylated 5-O-decinnamoyltaxuspine C. This indicates that the 5-O-benzoylated taxuspine C derivative may be a promising functional inhibitor of P-glycoprotein, which acts as an ATP-associated efflux pump for cancer chemotherapeutic agents.

• 公益社団法人日本薬学会の論文
• 1998-07-15

著者

• Hirota K

  Gifu Pharmaceutical Univ. Gifu Jpn

• Hirota Kosaku

  Gifu College Of Pharmacy

• SAKO Magoichi

  Gifu Pharmaceutical University

• SUZUKI Hikokazu

  Gifu Pharmaceutical University

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