e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthesis and properties of some 13??cis and all??trans??retinamides

…, JL Frye, CA O'Dell, MC Thorpe, MC Kirk…

Index: Shealy; Frye; O'Dell; Thorpe; Kirk; Coburn Jr.; Sporn Journal of Pharmaceutical Sciences, 1984 , vol. 73, # 6 p. 745 - 751

Full Text: HTML

Citation Number: 23

Abstract

Abstract Several 13-cis-retinamides were synthesized from 13-cis-retinoic acid via either 13- cis-retinoyl chloride or 13-cis-1-retinoylimidazole. All-trans-retinoylglycine was prepared from all-trans-retinoyl chloride and ethyl glycinate. Detailed procedures were developed for the preparation of other all-trans-retinamides on a large scale for studies of the chemoprevention of cancer.

Retinoic acid Structure

~%

vitamin A acid ethylamide Structure

vitamin A acid ...

Retinoyl chloride Structure

Retinoyl chloride

Ethylamine Structure

~%

vitamin A acid ethylamide Structure

vitamin A acid ...

Retinoic acid Structure

~%

[4-[[(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl]amino]phenyl] 2,2-dimethylpropanoate Structure

[4-[[(2Z,4E,6E,...

Retinoyl chloride Structure

Retinoyl chloride

~%

[4-[[(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl]amino]phenyl] 2,2-dimethylpropanoate Structure

[4-[[(2Z,4E,6E,...

Pivaloyl chloride Structure

Pivaloyl chloride

Fenretinide Structure

~%

[4-[[(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl]amino]phenyl] 2,2-dimethylpropanoate Structure

[4-[[(2Z,4E,6E,...

Retinoic acid Structure

~%

N-(2-hydroxyethyl)retinamide Structure

N-(2-hydroxyeth...

Retinoyl chloride Structure

Retinoyl chloride

2-Aminoethanol Structure

~%

N-(2-hydroxyethyl)retinamide Structure

N-(2-hydroxyeth...

Retinoic acid Structure

~%

(2Z,4E,6Z,8Z)-N-butyl-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenamide Structure

(2Z,4E,6Z,8Z)-N...

Retinoyl chloride Structure

Retinoyl chloride

n-butylamine Structure

~%

(2Z,4E,6Z,8Z)-N-butyl-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenamide Structure

(2Z,4E,6Z,8Z)-N...

4-Amino-1-butanol Structure

4-Amino-1-butanol

Isotretinoin Structure

~61%

(2Z,4E,6E,8E)-N-(4-hydroxybutyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide Structure

(2Z,4E,6E,8E)-N...

Ethylamine Structure

13-cis-retinoyl chloride Structure

13-cis-retinoyl...

~75%

(2Z,4E,6E,8E)-N-ethyl-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide Structure

(2Z,4E,6E,8E)-N...

Isotretinoin Structure

~%

(2Z,4E,6E,8E)-N-ethyl-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide Structure

(2Z,4E,6E,8E)-N...

4-Amino-1-butanol Structure

4-Amino-1-butanol

Retinoic acid Structure

~73%

(2E,4E,6E,8E)-N-(4-hydroxybutyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide Structure

(2E,4E,6E,8E)-N...

4-Aminophenol Structure

13-cis-retinoyl chloride Structure

13-cis-retinoyl...

~82%

13-cis-Fenretinide Structure

13-cis-Fenretinide

Isotretinoin Structure

~%

13-cis-Fenretinide Structure

13-cis-Fenretinide

Retinoic acid Structure

3-Aminopropan-1-ol Structure

3-Aminopropan-1-ol

~64%

(7cis,9cis,13cis)-15-[(3-Hydroxypropyl)amino]retinal Structure

(7cis,9cis,13ci...