Water soluble derivatives of taxol

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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549511, C07D30514

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active

053528050

ABSTRACT:
Sulfonated 2'-acryloyltaxol and sulfonated 2'-O-acyl acid taxol derivatives are synthesized which have improved water solubility and stability while maintaining bio-activity. In particular, 2'-[(3-sulfo-1-oxopropyl)oxy]taxol sodium salt is synthesized by reacting taxol with acrylic acid, and subsequently reacting the 2'-acryloyltaxol with bisulfite in a Michael reaction. 2'-{[4-((2-sulfoethyl)amino)-l,4-dioxobutyl]oxy} taxol sodium salt and 2'-{[4-((3-sulfopropyl)amino)-1,4-dioxobutyl]oxy} taxol sodium salt are synthesized by reacting 2'-succinyltaxol with the tetrabutylammonium salts of taurine and 3-aminopropyl sulfonic acid, respectively, and subsequently exchanging the ammonium with sodium. Glycol derivatives of 2'-O-acyl acid taxols with improved water solubility are synthesized by reaction of a glycol with 2'-O-acyl acid taxol.

REFERENCES:
patent: 4942184 (1990-07-01), Haugwitz et al.

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