ABSTRACT
Fluoxetine, imipramine, doxepine and opipramol after liquid-liquid extraction were separated by TLC on silica gel 60 GF254 by ascending and horizontal technique using suitable mobile phases. The substances were identified by UV irradiation at 254 nm and by spraying of Amelinka's reagnet (up to the amount 0.25 microgram fluoxetine and 0.05 microgram imipramine, doxepine and opipramol).
Subject(s)
Antidepressive Agents/blood , Chromatography, Thin Layer/methods , Doxepin/blood , Fluoxetine/blood , Humans , Imipramine/blood , Opipramol/blood , Spectrophotometry, UltravioletABSTRACT
In the reactions of 3-hydroxy-1,2-benzisoxazole (BIO) and its 5-Cl and 6-Cl derivatives with ethyl bromoacetate were obtained the mixtures of O- and N- substituted esters but 7-NO2-BIO formed only O-ester. The products of N-aminomethylation of 5-NO2-BIO were active against Trichomonas vaginalis. The structures of pure compounds have been confirmed by elementary analysis and IR spectrometry. Determinations of dissociation constants (pKa) of BIO, 5-Cl-BIO, 6-Cl-BIO, 7-Cl-BIO, 5-F-BIO, 5-NO2-BIO, 7-NO2-BIO by potentiometric titration method were described. Investigated compounds have two values of ionisation constants except the nitro derivatives, this is the confirmation of equilibrium 3-hydroxy-1,2-benzisoxazole <==> 1,2-benzisoxazolinone-3.
Subject(s)
Antiprotozoal Agents/chemistry , Isoxazoles/chemistry , Alkylation , Animals , Spectrometry, Fluorescence , Trichomonas vaginalis/drug effectsABSTRACT
In the search for pharmacological active new derivatives of 1,2-benzisothiazolin-3-on amides of (3-oxo-1,2-benzisothiazolin-2-yl)acetic acid and 3-(3-oxo-1,2-benzisothiazolin-2-yl)propionic acid were obtained. In the reaction of these amides with formaldehyde and various second aryl amines the title compounds are formed. Morpholinmethylamide of (3-oxo-1,2-benzisothiazolin-2-yl)acetic acid showed activity against Trichomonas vaginalis. In the reaction of ethyl esters of (3-oxo-1,2-benzisothiazolin-2-yl) acetic- and -propionic acids with hydrazine hydrate products of ring-opening of isothiazole-2,2'-dithio-bis [N- (ethoxycarbonylmethyl)benzamide] and 2,2'-dithio-bis[N-(ethoxycarbonylethyl)benzamide are formed.
Subject(s)
Acetamides/chemical synthesis , Amides/chemical synthesis , Antitrichomonal Agents/chemical synthesis , Propionates/chemical synthesis , Thiazoles/chemical synthesis , Trichomonas vaginalis/drug effects , Acetamides/pharmacology , Amides/pharmacology , Animals , Microbial Sensitivity Tests , Propionates/pharmacology , Thiazoles/pharmacologyABSTRACT
The acylation courses of 5-bromo and 5,7-dibromo derivatives of benzoxazolin-2--one (BO) and isomeric 3-hydroxy-1,2-benzisoxazoles (BIO) with acetic anhydride, benzoyl chlorides and alkyl chloroformates were investigated. In view of principal course of N-acylation in BO-and O-acylation in BIO-group some of the newly obtained compounds, namely 5,7-Br2-2-(o-chlorobenzoyloxy)-BO (5a) and N-alkoxycarbonyl BIO (22a--27a) make the exceptions. Compounds 25a and 26a were found to possess relatively the most intensive depressant action on the CNS.
