An unhydrolyzable analogue of N-(4-hydroxyphenyl)retinamide. synthesis and preliminary biological studies.

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Weiss KL, Alshafie G, Chapman JS, Mershon SM, Abou-Issa H, Clagett-Dame M, Curley RW Jr

An unhydrolyzable analogue of N-(4-hydroxyphenyl)retinamide. synthesis and preliminary biological studies.

Bioorg Med Chem Lett. 2001 Jun 18;11(12):1583-6.

PubMed ID

11412986 [ View in PubMed

]

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.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Tretinoin	Retinoic acid receptor gamma	Ki (nM)	0.7	N/A	N/A	Details