4-Aryl-4-aminocyclohexanones and their derivatives, a novel class of analgesics. 3. m-Hydroxyphenyl derivatives

Autor:	Emmert De, Von Voigtlander Pf, Lednicer D
Rok vydání:	1981
Předmět:	Analgesics Cyclohexanones Narcotic antagonist Aryl Cyanide Substituent Antagonist Ether Medicinal chemistry Mice Structure-Activity Relationship chemistry.chemical_compound chemistry Cyclohexanes Bromide Reagent Drug Discovery Animals Molecular Medicine Female
Zdroj:	Journal of Medicinal Chemistry. 24:341-346
ISSN:	1520-4804 0022-2623
Popis:	Derivatives of 4-aryl-4-(dimethylamino)cyclohexan-1-ones substituted by m-hydroxy groups were obtained by using as a key reaction the displacement of cyanide from the alpha-aminonitrile of 1,4-cyclohexanedione ketal, with the THP ether of m-hydroxyphenylmagnesium bromide. A number of the products show narcotic antagonist activity. Amino alcohols obtained on reaction of the free ketones with phenethyl Grignard reagents are potent analgetics, though devoid of antagonist activity. Systematic variation of the substituent on nitrogen revealed nonclassical structure-activity relationships; the dimethylamino group gives the most potent antagonist.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::bd9dd4a4bf7207821da38b739c6b7664 https://doi.org/10.1021/jm00135a019 Zobrazit plný text záznamu