2-(Aminomethyl)phenols, a new class of saluretic agents. 6. Effects of N,O-spiroannulation and subsequent quarternization

Autor:	Cragoe Edward J, Gerald E. Stokker, Charles S. Sweet, H. F. Russo, L. S. Watson, Smith Robert L, Ludden Ct, Everett M. Schultz
Rok vydání:	1983
Předmět:	Benzylamines Blood Pressure Sodium Chloride Rats chemistry.chemical_compound Hydrolysis Dogs chemistry In vivo Drug Discovery Animals Molecular Medicine Organic chemistry Phenols Amines
Zdroj:	Journal of Medicinal Chemistry. 26:585-590
ISSN:	1520-4804 0022-2623
DOI:	10.1021/jm00358a024
Popis:	The synthesis of a number of 3,4-dihydrospiro-2H-1,3-benzoxazines and their corresponding benzoxazinium salts are reported. The saluretic effects displayed by these N,O-spiroannulated 2-(aminomethyl)phenols appear to be, in part, inversely related to their respective in vivo rates of hydrolysis. Good antihypertensive effects are found only in spirobenzoxazinium 22. Thus, a combination of spiroannulation and quaternization on 2 to produce 22 leads to a loss of saluretic effects with maintenance of antihypertensive effects and, thereby, serves to separate these pharmacological properties.
Databáze:	OpenAIRE
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