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

Dipartimento di Scienze del Farmaco

Risultato della ricerca: Contributo su rivista › Articolo in rivista › 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.

Lingua originale	Inglese
pagine (da-a)	277-283
Numero di pagine	7
Rivista	European Journal of Organic Chemistry
Numero di pubblicazione	2
DOI	https://doi.org/10.1002/1099-0690(20021)2002:2<277::AID-EJOC277>3.0.CO;2-F
Stato di pubblicazione	Pubblicato - 2002

Accesso al documento

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

Altri file e collegamenti

Link to publication in Scopus

Cita questo

@article{06f5c27e3d414770ada9fd34fcccc32f,

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",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "2",

}

TY - JOUR

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 - http://www.scopus.com/inward/record.url?scp=0036158065&partnerID=8YFLogxK

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

Accesso al documento

Altri file e collegamenti

Fingerprint

Cita questo