Synthesis and Structure-Activity Relationships of Novel Nor-Seco Analogs of Taxol and Taxotere

Iwao Ojima; Ivana Fenoglio; Young Hoon Park; Chung-Ming Sun; Giovanni Appendino; Paula Pera; Ralph J. Bernacki

doi:10.1021/jo00082a003

Synthesis and Structure-Activity Relationships of Novel Nor-Seco Analogs of Taxol and Taxotere

Iwao Ojima^*, Ivana Fenoglio, Young Hoon Park, Chung-Ming Sun, Giovanni Appendino, Paula Pera, Ralph J. Bernacki

^*Corresponding author for this work

Department of Applied Chemistry

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

29 Scopus citations

Abstract

Novel nor-seco analogs of taxol and taxotere are synthesized from 14-hydroxy-10-deacetylbaccatin III through periodic acid oxidation and NaBH₃CN reduction, followed by coupling with the C-13 side chain precursors using a highly efficient β-lactam synthon method. The new reduced structure analogs show muted cytotoxicity aganist human cancer cell lines compared with taxol but still retain a certain level of activity despite the destruction of the A ring.

Original language	English
Pages (from-to)	515-517
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	59
Issue number	3
DOIs	https://doi.org/10.1021/jo00082a003
State	Published - 1 Feb 1994

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title = "Synthesis and Structure-Activity Relationships of Novel Nor-Seco Analogs of Taxol and Taxotere",

abstract = "Novel nor-seco analogs of taxol and taxotere are synthesized from 14-hydroxy-10-deacetylbaccatin III through periodic acid oxidation and NaBH3CN reduction, followed by coupling with the C-13 side chain precursors using a highly efficient β-lactam synthon method. The new reduced structure analogs show muted cytotoxicity aganist human cancer cell lines compared with taxol but still retain a certain level of activity despite the destruction of the A ring.",

author = "Iwao Ojima and Ivana Fenoglio and Park, {Young Hoon} and Chung-Ming Sun and Giovanni Appendino and Paula Pera and Bernacki, {Ralph J.}",

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T1 - Synthesis and Structure-Activity Relationships of Novel Nor-Seco Analogs of Taxol and Taxotere

AU - Ojima, Iwao

AU - Fenoglio, Ivana

AU - Park, Young Hoon

AU - Sun, Chung-Ming

AU - Appendino, Giovanni

AU - Pera, Paula

AU - Bernacki, Ralph J.

PY - 1994/2/1

Y1 - 1994/2/1

N2 - Novel nor-seco analogs of taxol and taxotere are synthesized from 14-hydroxy-10-deacetylbaccatin III through periodic acid oxidation and NaBH3CN reduction, followed by coupling with the C-13 side chain precursors using a highly efficient β-lactam synthon method. The new reduced structure analogs show muted cytotoxicity aganist human cancer cell lines compared with taxol but still retain a certain level of activity despite the destruction of the A ring.

AB - Novel nor-seco analogs of taxol and taxotere are synthesized from 14-hydroxy-10-deacetylbaccatin III through periodic acid oxidation and NaBH3CN reduction, followed by coupling with the C-13 side chain precursors using a highly efficient β-lactam synthon method. The new reduced structure analogs show muted cytotoxicity aganist human cancer cell lines compared with taxol but still retain a certain level of activity despite the destruction of the A ring.

UR - http://www.scopus.com/inward/record.url?scp=0028346210&partnerID=8YFLogxK

U2 - 10.1021/jo00082a003

DO - 10.1021/jo00082a003

M3 - Letter

AN - SCOPUS:0028346210

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SP - 515

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 3

ER -

Synthesis and Structure-Activity Relationships of Novel Nor-Seco Analogs of Taxol and Taxotere

Abstract

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