An unhydrolyzable analogue of N-(4-hydroxyphenyl)retinamide: Synthesis and preliminary biological studies

Kevin L. Weiss; Galal Alshafie; Jason S. Chapman; Serena M. Mershon; Hussein Abou-Issa; Margaret Clagett-Dame; Robert W. Curley

doi:10.1016/S0960-894X(01)00230-X

An unhydrolyzable analogue of N-(4-hydroxyphenyl)retinamide: Synthesis and preliminary biological studies

Kevin L. Weiss, Galal Alshafie, Jason S. Chapman, Serena M. Mershon, Hussein Abou-Issa, Margaret Clagett-Dame, Robert W. Curley

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

18 Scopus citations

Abstract

The synthesis of a nonhydrolyzable, carbon-linked analogue (4-HBR) of the retinoid N-(4-hydroxyphenyl)retinamide (4-HPR) using Umpolung methods is described. Preliminary studies of biological activity show 4-HBR is similar to 4-HPR in its actions although a potentially relevant and desirable difference is its reduced suppression of plasma vitamin A levels. These results show that 4-HPR does not have to be hydrolyzed to retinoic acid to produce its chemotherapeutic effects.

Original language	English
Pages (from-to)	1583-1586
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	11
Issue number	12
DOIs	https://doi.org/10.1016/S0960-894X(01)00230-X
State	Published - Jun 18 2001
Externally published	Yes

Funding

Financial support in the form of a grant (CA49837) from the National Cancer Institute is gratefully acknowledged.

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10.1016/S0960-894X(01)00230-X

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title = "An unhydrolyzable analogue of N-(4-hydroxyphenyl)retinamide: Synthesis and preliminary biological studies",

abstract = "The synthesis of a nonhydrolyzable, carbon-linked analogue (4-HBR) of the retinoid N-(4-hydroxyphenyl)retinamide (4-HPR) using Umpolung methods is described. Preliminary studies of biological activity show 4-HBR is similar to 4-HPR in its actions although a potentially relevant and desirable difference is its reduced suppression of plasma vitamin A levels. These results show that 4-HPR does not have to be hydrolyzed to retinoic acid to produce its chemotherapeutic effects.",

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doi = "10.1016/S0960-894X(01)00230-X",

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T1 - An unhydrolyzable analogue of N-(4-hydroxyphenyl)retinamide

T2 - Synthesis and preliminary biological studies

AU - Weiss, Kevin L.

AU - Alshafie, Galal

AU - Chapman, Jason S.

AU - Mershon, Serena M.

AU - Abou-Issa, Hussein

AU - Clagett-Dame, Margaret

AU - Curley, Robert W.

PY - 2001/6/18

Y1 - 2001/6/18

N2 - The synthesis of a nonhydrolyzable, carbon-linked analogue (4-HBR) of the retinoid N-(4-hydroxyphenyl)retinamide (4-HPR) using Umpolung methods is described. Preliminary studies of biological activity show 4-HBR is similar to 4-HPR in its actions although a potentially relevant and desirable difference is its reduced suppression of plasma vitamin A levels. These results show that 4-HPR does not have to be hydrolyzed to retinoic acid to produce its chemotherapeutic effects.

AB - The synthesis of a nonhydrolyzable, carbon-linked analogue (4-HBR) of the retinoid N-(4-hydroxyphenyl)retinamide (4-HPR) using Umpolung methods is described. Preliminary studies of biological activity show 4-HBR is similar to 4-HPR in its actions although a potentially relevant and desirable difference is its reduced suppression of plasma vitamin A levels. These results show that 4-HPR does not have to be hydrolyzed to retinoic acid to produce its chemotherapeutic effects.

UR - https://www.scopus.com/pages/publications/0035907473

U2 - 10.1016/S0960-894X(01)00230-X

DO - 10.1016/S0960-894X(01)00230-X

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AN - SCOPUS:0035907473

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VL - 11

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 12

ER -

An unhydrolyzable analogue of N-(4-hydroxyphenyl)retinamide: Synthesis and preliminary biological studies

Abstract

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