ABSTRACT
New ester, acetamide and aminomethylacetamide derivatives of 3-benzoxazolin-2-one and its 5- and 6-chloro derivatives, 2-methyl-l-benzimidazole, and of 1- and 2-benzotriazole were obtained. Pharmacological screening has shown that amides VII, VIII, XI and XII exert slight deppressory effects on the central nervous system.
Subject(s)
Acetates/pharmacology , Benzimidazoles/pharmacology , Benzoxazoles/pharmacology , Motor Activity/drug effects , Triazoles/pharmacology , Acetates/chemical synthesis , Animals , Benzimidazoles/chemical synthesis , Benzoxazoles/chemical synthesis , Chemical Phenomena , Chemistry , Depression, Chemical , Drug Evaluation, Preclinical , Mice , Motor Activity/physiology , Triazoles/chemical synthesisABSTRACT
Either the alkylation of 5(6)-nitro-benzimidazoles (R = H, CH3) or the nitration of 1-alkyl-benzimidazoles afforded corresponding mixtures of 1-alkyl-5-nitro- and 1-alkyl-6-nitro-benzimidazoles (III, IV, VII, VIII, XI). Fractional crystallization from water was employed for isolation of 6-nitro isomers V, VI and IX from mixtures III, IV and VII. On the other hand, application of this isolation method to mixtures VIII and XI proved unsuccessful. 6-Nitro-compound X and 5-nitro derivatives XIII and XV were obtained by direct syntheses. From calibration curves depicting dependence of absorbance of the mixtures upon their composition, percentage ratios of 5-nitro to 6-nitro isomers in the mixtures were estimated. Usefulness of thin-layer chromatography, and UV and IR spectrometry for identification of 5-nitro and 6-nitro isomers was stated; e. g. 5-nitro isomers have higher epsilon values, while 6-nitro isomers exhibit two vmax values of the benzene ring. Compounds IV, IX and X proved to exert antihelminthic, antibacterial and antiphlogistic activities.
Subject(s)
Bacterial Infections/drug therapy , Benzimidazoles/therapeutic use , Nematode Infections/drug therapy , Nitro Compounds/therapeutic use , Animals , Anti-Infective Agents , Anti-Inflammatory Agents, Non-Steroidal , Antinematodal Agents , Benzimidazoles/chemical synthesis , Chemical Phenomena , Chemistry , Drug Evaluation, Preclinical , Inflammation/drug therapy , Mice , Nitro Compounds/chemical synthesisSubject(s)
Isoxazoles/chemical synthesis , Oxazoles/chemical synthesis , Animals , Antinematodal Agents , Antitrichomonal Agents , Chemical Phenomena , Chemistry , Depression/chemically induced , Drug Evaluation, Preclinical , Humans , Isoxazoles/pharmacology , Mice , Morpholines/chemical synthesis , Morpholines/pharmacology , Nematoda/drug effects , Piperazines/chemical synthesis , Piperazines/pharmacology , Piperidines/chemical synthesis , Piperidines/pharmacology , Trichomonas vaginalis/drug effectsABSTRACT
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.
