New 7-aryl analogues of anthracyclines: Synthesis and cytotoxic activity of (+/-)-7-(3,4,5-trimethoxyphenyl)-7-deoxyidarubicinone

JC Acosta; E Caballero; DG Gravalos; M Medarde; H Sahagun; RJ Stoodley; F Tome

New 7-aryl analogues of anthracyclines: Synthesis and cytotoxic activity of (+/-)-7-(3,4,5-trimethoxyphenyl)-7-deoxyidarubicinone

JC Acosta, E Caballero, DG Gravalos, M Medarde^*, H Sahagun, RJ Stoodley, F Tome

^*Corresponding author for this work

Deanery of Molecular, Genetic and Population Health Sciences

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

Abstract / Description of output

The synthetic methodology for the preparation of 7-aryl-7-deoxyanthracyclinones, a new class of anthracycline analogues, is described. Readily available materials are easily transformed into the key intermediate ketone, that is converted into bent and planar tetracyclic compounds. Cytotoxic studies of the final and intermediate products reveal a moderate activity of bent products and a lack of activity of planar products, thus supporting a non-intercalating mechanism for their cytotoxic activity. (C) 1997 Elsevier Science Ltd.

Original language	English
Pages (from-to)	2955-2958
Number of pages	4
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	7
Issue number	23
Publication status	Published - 2 Dec 1997

Keywords / Materials (for Non-textual outputs)

TUBULIN
RESOLUTION
COMBRETASTATIN
TRIMETREXATE
DNA
ANTITUMOR AGENT
NATURAL-PRODUCTS
PODOPHYLLOTOXIN
COLCHICINE
INHIBITION

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@article{118dbb2144b74e73aa2743b23620a804,

title = "New 7-aryl analogues of anthracyclines: Synthesis and cytotoxic activity of (+/-)-7-(3,4,5-trimethoxyphenyl)-7-deoxyidarubicinone",

abstract = "The synthetic methodology for the preparation of 7-aryl-7-deoxyanthracyclinones, a new class of anthracycline analogues, is described. Readily available materials are easily transformed into the key intermediate ketone, that is converted into bent and planar tetracyclic compounds. Cytotoxic studies of the final and intermediate products reveal a moderate activity of bent products and a lack of activity of planar products, thus supporting a non-intercalating mechanism for their cytotoxic activity. (C) 1997 Elsevier Science Ltd.",

keywords = "TUBULIN, RESOLUTION, COMBRETASTATIN, TRIMETREXATE, DNA, ANTITUMOR AGENT, NATURAL-PRODUCTS, PODOPHYLLOTOXIN, COLCHICINE, INHIBITION",

author = "JC Acosta and E Caballero and DG Gravalos and M Medarde and H Sahagun and RJ Stoodley and F Tome",

year = "1997",

month = dec,

day = "2",

language = "English",

volume = "7",

pages = "2955--2958",

journal = "Bioorganic & Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier",

number = "23",

}

TY - JOUR

T1 - New 7-aryl analogues of anthracyclines: Synthesis and cytotoxic activity of (+/-)-7-(3,4,5-trimethoxyphenyl)-7-deoxyidarubicinone

AU - Acosta, JC

AU - Caballero, E

AU - Gravalos, DG

AU - Medarde, M

AU - Sahagun, H

AU - Stoodley, RJ

AU - Tome, F

PY - 1997/12/2

Y1 - 1997/12/2

N2 - The synthetic methodology for the preparation of 7-aryl-7-deoxyanthracyclinones, a new class of anthracycline analogues, is described. Readily available materials are easily transformed into the key intermediate ketone, that is converted into bent and planar tetracyclic compounds. Cytotoxic studies of the final and intermediate products reveal a moderate activity of bent products and a lack of activity of planar products, thus supporting a non-intercalating mechanism for their cytotoxic activity. (C) 1997 Elsevier Science Ltd.

AB - The synthetic methodology for the preparation of 7-aryl-7-deoxyanthracyclinones, a new class of anthracycline analogues, is described. Readily available materials are easily transformed into the key intermediate ketone, that is converted into bent and planar tetracyclic compounds. Cytotoxic studies of the final and intermediate products reveal a moderate activity of bent products and a lack of activity of planar products, thus supporting a non-intercalating mechanism for their cytotoxic activity. (C) 1997 Elsevier Science Ltd.

KW - TUBULIN

KW - RESOLUTION

KW - COMBRETASTATIN

KW - TRIMETREXATE

KW - DNA

KW - ANTITUMOR AGENT

KW - NATURAL-PRODUCTS

KW - PODOPHYLLOTOXIN

KW - COLCHICINE

KW - INHIBITION

M3 - Article

SN - 0960-894X

VL - 7

SP - 2955

EP - 2958

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 23

ER -

New 7-aryl analogues of anthracyclines: Synthesis and cytotoxic activity of (+/-)-7-(3,4,5-trimethoxyphenyl)-7-deoxyidarubicinone

Abstract / Description of output

Keywords / Materials (for Non-textual outputs)

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