Synthesis and anti-tubulin activity of a 3′-(4-Azidophenyl)-3′- dephenylpaclitaxel photoaffinity probe

Jared T. Spletstoser; Patrick T. Flaherty; Richard H. Himes; Gunda I. Georg

doi:10.1021/jm030581d

Synthesis and anti-tubulin activity of a 3′-(4-Azidophenyl)-3′- dephenylpaclitaxel photoaffinity probe

Jared T. Spletstoser, Patrick T. Flaherty, Richard H. Himes, Gunda I. Georg

Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

Abstract

The synthesis and biological evaluation of a novel paclitaxel photoaffinity probe is described. The synthesis involved the preparation of an azide-containing C13 side chain through a Staudinger cycloaddition followed by a lipase-mediated kinetic resolution to obtain the azetidinone in 99% ee. Coupling of the enantiopure side chain precursor to 7-TES-baccatin III and subsequent silyl ether deprotection afforded 3′-(4-azidophenyl)-3′- dephenylpaclitaxel, which was shown to be as active as paclitaxel in tubulin assembly and cytotoxicity assays.

Original language	English (US)
Pages (from-to)	6459-6465
Number of pages	7
Journal	Journal of medicinal chemistry
Volume	47
Issue number	26
DOIs	https://doi.org/10.1021/jm030581d
State	Published - Dec 16 2004

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title = "Synthesis and anti-tubulin activity of a 3′-(4-Azidophenyl)-3′- dephenylpaclitaxel photoaffinity probe",

abstract = "The synthesis and biological evaluation of a novel paclitaxel photoaffinity probe is described. The synthesis involved the preparation of an azide-containing C13 side chain through a Staudinger cycloaddition followed by a lipase-mediated kinetic resolution to obtain the azetidinone in 99% ee. Coupling of the enantiopure side chain precursor to 7-TES-baccatin III and subsequent silyl ether deprotection afforded 3′-(4-azidophenyl)-3′- dephenylpaclitaxel, which was shown to be as active as paclitaxel in tubulin assembly and cytotoxicity assays.",

author = "Spletstoser, {Jared T.} and Flaherty, {Patrick T.} and Himes, {Richard H.} and Georg, {Gunda I.}",

year = "2004",

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AU - Spletstoser, Jared T.

AU - Flaherty, Patrick T.

AU - Himes, Richard H.

AU - Georg, Gunda I.

PY - 2004/12/16

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N2 - The synthesis and biological evaluation of a novel paclitaxel photoaffinity probe is described. The synthesis involved the preparation of an azide-containing C13 side chain through a Staudinger cycloaddition followed by a lipase-mediated kinetic resolution to obtain the azetidinone in 99% ee. Coupling of the enantiopure side chain precursor to 7-TES-baccatin III and subsequent silyl ether deprotection afforded 3′-(4-azidophenyl)-3′- dephenylpaclitaxel, which was shown to be as active as paclitaxel in tubulin assembly and cytotoxicity assays.

AB - The synthesis and biological evaluation of a novel paclitaxel photoaffinity probe is described. The synthesis involved the preparation of an azide-containing C13 side chain through a Staudinger cycloaddition followed by a lipase-mediated kinetic resolution to obtain the azetidinone in 99% ee. Coupling of the enantiopure side chain precursor to 7-TES-baccatin III and subsequent silyl ether deprotection afforded 3′-(4-azidophenyl)-3′- dephenylpaclitaxel, which was shown to be as active as paclitaxel in tubulin assembly and cytotoxicity assays.

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JF - Journal of Medicinal Chemistry

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Synthesis and anti-tubulin activity of a 3′-(4-Azidophenyl)-3′- dephenylpaclitaxel photoaffinity probe

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