药学学报, 1986, 21(6): 434-440
引用本文:
陆见明;徐懋丽;雷兴翰. 3(4)溴代和3,4-二烷氧基-5-硝基呋喃衍生物的合成及其抗菌活性[J]. 药学学报, 1986, 21(6): 434-440.
Lu Jian-Ming; XU Mao-li and LEI Xing-Han . SYNTHESIS OF SOME 3(4)-BROMO AND 3, 4-DIALKOXY-5-NITROFURAN AZOMETHINE DERIVATIVES AND THEIR ANTIBACTERIAL ACTIVITIES[J]. Acta Pharmaceutica Sinica, 1986, 21(6): 434-440.

3(4)溴代和3,4-二烷氧基-5-硝基呋喃衍生物的合成及其抗菌活性
陆见明;徐懋丽;雷兴翰
上海医药工业研究院
摘要:
为了探索呋吨类药物的构效关系,本文在已知硝基呋哺类有效药物的3-位或4-位分别引入溴原子和3,4-位引入二烷氧基,进行结构修饰,合成了32个化合物,其中28个为新化合物。经药理试验,发现Ⅰ2~3,Ⅰ6~7,Ⅱ2~8和Ⅲ1~8有抑菌作用,4-溴代化合物的抑菌活性明显高于3-溴代异构体。
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SYNTHESIS OF SOME 3(4)-BROMO AND 3, 4-DIALKOXY-5-NITROFURAN AZOMETHINE DERIVATIVES AND THEIR ANTIBACTERIAL ACTIVITIES
Lu Jian-Ming; XU Mao-li and LEI Xing-Han
Abstract:
Thirty two new compounds of 3(4)-bromo-5-nitrofuran azomethine derivatives were synthesized and their antimicrobial activities investigated.3(4)-Bromo-2-furaldehyde was prepared from 2-furoic acid or furfural respectively by known method, followed by nitration and condensation to afford compounds Ⅰ2~Ⅰ8, Ⅱ2~Ⅱ8.Condensation of diethyl diglycolate with diethyl oxalate in the presence of sodium methoxide afforded dimethyl 3,4-dihydroxy-2,5-furandicarboxyiate, from which 3,4-dialkoxy-2-furaldehydes were prepared via subsequent O-alkylation, hydrolysis, decarboxylation and Vilsmeier reaction. Nitration of the above aldehydes led to tile corresponding 5-nitrated aldehyde diacetates which were converted to the lille compounds Ⅲ2~Ⅲ8, Ⅳ2~Ⅳ8.Compouds Ⅰ2~Ⅰ3, Ⅰ6~Ⅰ7, Ⅱ2~Ⅱ8 and Ⅲ1~Ⅲ8 showed bacterial activities in preliminary pharmacological tests and the 4-bromo compounds are more active than the corresponding 3-bromo-isomers and their parent compounds. Most of 3-brominated, 3,4-dimethoxylated compounds showed less activities than their respective parent drugs. All of 3,4-diethoxylated compounds did not possess antibacterial activities.
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