Synthesis and evaluation of 14-nor-a-secotaxoids

Giovanni Appendino; Emanuela Belloro; Erika Del Grosso; Alberto Minassi; Ezio Bombardelli

doi:10.1002/1099-0690(20021)2002:2<277::AID-EJOC277>3.0.CO;2-F

Synthesis and evaluation of 14-nor-a-secotaxoids

Giovanni Appendino
, Emanuela Belloro
, Erika Del Grosso
, Alberto Minassi
, Ezio Bombardelli

Department of Pharmaceutical Sciences

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

Abstract

A series of 14-nor-A-secotaxoids has been prepared from 10-deacetyl-14β-hydroxybaccatin III (3a) and some unexpected and new reactivity of the taxane system has been revealed. The observation that the final compounds were considerably less active than taxol and their 1,10-oxygen-bridged ana-logues shows that the 1,10-oxygen tether can partially compensate for the opening of ring A, and suggests that 14-norA-secotaxoids warrant further investigation as simplified taxol mimics.

Original language	English
Pages (from-to)	277-283
Number of pages	7
Journal	European Journal of Organic Chemistry
Issue number	2
DOIs	https://doi.org/10.1002/1099-0690(20021)2002:2<277::AID-EJOC277>3.0.CO;2-F
Publication status	Published - 2002

Keywords

Antitumor agents
Natural products
Structure-activity relationships
Terpenoids

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10.1002/1099-0690(20021)2002:2<277::AID-EJOC277>3.0.CO;2-F

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title = "Synthesis and evaluation of 14-nor-a-secotaxoids",

abstract = "A series of 14-nor-A-secotaxoids has been prepared from 10-deacetyl-14β-hydroxybaccatin III (3a) and some unexpected and new reactivity of the taxane system has been revealed. The observation that the final compounds were considerably less active than taxol and their 1,10-oxygen-bridged ana-logues shows that the 1,10-oxygen tether can partially compensate for the opening of ring A, and suggests that 14-norA-secotaxoids warrant further investigation as simplified taxol mimics.",

keywords = "Antitumor agents, Natural products, Structure-activity relationships, Terpenoids",

author = "Giovanni Appendino and Emanuela Belloro and \{Del Grosso\}, Erika and Alberto Minassi and Ezio Bombardelli",

year = "2002",

doi = "10.1002/1099-0690(20021)2002:2<277::AID-EJOC277>3.0.CO;2-F",

language = "English",

pages = "277--283",

journal = "European Journal of Organic Chemistry",

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T1 - Synthesis and evaluation of 14-nor-a-secotaxoids

AU - Appendino, Giovanni

AU - Belloro, Emanuela

AU - Del Grosso, Erika

AU - Minassi, Alberto

AU - Bombardelli, Ezio

PY - 2002

Y1 - 2002

N2 - A series of 14-nor-A-secotaxoids has been prepared from 10-deacetyl-14β-hydroxybaccatin III (3a) and some unexpected and new reactivity of the taxane system has been revealed. The observation that the final compounds were considerably less active than taxol and their 1,10-oxygen-bridged ana-logues shows that the 1,10-oxygen tether can partially compensate for the opening of ring A, and suggests that 14-norA-secotaxoids warrant further investigation as simplified taxol mimics.

AB - A series of 14-nor-A-secotaxoids has been prepared from 10-deacetyl-14β-hydroxybaccatin III (3a) and some unexpected and new reactivity of the taxane system has been revealed. The observation that the final compounds were considerably less active than taxol and their 1,10-oxygen-bridged ana-logues shows that the 1,10-oxygen tether can partially compensate for the opening of ring A, and suggests that 14-norA-secotaxoids warrant further investigation as simplified taxol mimics.

KW - Antitumor agents

KW - Natural products

KW - Structure-activity relationships

KW - Terpenoids

UR - https://www.scopus.com/pages/publications/0036158065

U2 - 10.1002/1099-0690(20021)2002:2<277::AID-EJOC277>3.0.CO;2-F

DO - 10.1002/1099-0690(20021)2002:2<277::AID-EJOC277>3.0.CO;2-F

M3 - Article

SN - 1434-193X

SP - 277

EP - 283

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 2

ER -

Synthesis and evaluation of 14-nor-a-secotaxoids

Abstract

Keywords

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