鎮痙作用を有するキサンテン誘導体の合成研究(第7報) : クロルチオキサンテン-9-酢酸誘導体について
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概要
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2-Chlorothioxanthen-9-one (IVa) was prepared from 2-aminothioxanthen-9-one (IIIa). IVa was also obtained from o-mercaptobenzoic acid, chlorobenzene and concentrated sulfuric acid. 2-Chlorothioxanthen-9-ol (Va) was prepared by the reduction of IVa with sodium amalgam and ethano1. Va was condensed with malonic acid to 2-chlorothioxan-thene-9-malonic acid (VIa), and the acid was decarboxylated to 2-chlorothioxanthene-9-acetic acid (VIIa). Similarly 3-chlorothioxanthene-9-acetic acid (VIIb) was obtained from 3-aminothioxanthen-9-one (IIIb). 4-Aminothioxanthen-9-one (IIIc) was prepared by the reduction of 4-nitrothioxanthen-9-one (IIc) with stannous chloride and hydrochloric acid, which result is contrary to that presented in the literature. 4-Chloro-thioxanthene-9-acetic acid (VIIc) was obtained from IIIc. 2-Diethylaminoethyl ester hydrochlorides (VIIIa-c) of VIIa-c were obtained. Oxidation of VIIa-c with hydrogen peroxide gave 2-, 3- and 4-chlorothioxanthene-9-acetic acid 10,10-dioxide (IXa-c) from which were derived their 2-diethylaminoethyl ester hydrochlorides (Xa-c). The anti-acetylcholine, anti-barium chloride and anti-histamine activities of VIIIa-c and Xa-c were examined and it was found that the introduction of chlorine on the 2- or 3-position of thioxanthene rings of the 2-diethylaminoethyl ester hydrochlorides of thioxanthene-9-acetic acid and its 10,10-dioxide resulted in the weakening of the antiacetylcholine activity.
- 公益社団法人日本薬学会の論文
- 1969-01-25
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関連論文
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- 鎮痙作用を有するキサンテン誘導体の合成研究(第8報)1-クロルチオキサンテン誘導体について
- 鎮痙作用を有するキサンテン誘導体の合成研究(第7報) : クロルチオキサンテン-9-酢酸誘導体について
- 鎮痙作用を有するキサンテン誘導体の合成研究(第6報) : キサンテン-およびチオキサンテン-9-マロン酸誘導体について
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