Synthesis and Antimicrobial Activity of Flavone Derivatives Containing 1,3,4-Oxadiazoline Structure

doi:10.6023/cjoc201502028

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (9): 2004-2012.DOI: 10.6023/cjoc201502028 Previous Articles Next Articles

Notes

含1,3,4-噁二唑啉苯氧乙氧基黄酮衍生物的合成及抗菌活性

段志芳^a,b, 邵玲^a

a 肇庆学院生命科学学院肇庆 526061;
b 肇庆学院生物医药工程中心肇庆 526061

收稿日期:2015-02-23 修回日期:2015-04-24 发布日期:2015-05-08
通讯作者: 段志芳 E-mail:zhaoqing606@126.com
基金资助:
国家自然科学基金(No. 31201142)和肇庆市科技基金(No. 2012G25)资助项目.

Synthesis and Antimicrobial Activity of Flavone Derivatives Containing 1,3,4-Oxadiazoline Structure

Duan Zhifang^a,b, Shao Ling^a

a College of Life Science, Zhaoqing University, Zhaoqing 526061;
b Biopharmaceutical Research and Development Center, Zhaoqing University, Zhaoqing 526061

Received:2015-02-23 Revised:2015-04-24 Published:2015-05-08
Supported by:
Project supported by the National Natural Science Foundation of China (No. 31201142) and the Research Fund of Science and Technology of Zhaoqing City (No. 2012G25).

1. Synthesis and Antimicrobial Activity of Flavone Derivatives Containing 1,3,4-Oxadiazoline Structure.PDF(2678KB)

Abstract

The 7-salicylidene ethoxy flavone was synthesized from salicylaldehyde and 7-bromoethoxy flavones which was obtained by the reaction of 7-hydroxy flavone and 1,2-dibromoethane. Then fourteen flavone derivatives containing acylhydrazone Schiff bases were synthesized by the condensation reaction of this compound with three types of hydrazide compounds, such as benzoylhydrazine, phenoxy acetyl hydrazine and phenylacetyl hydrazine compounds. Finally eight flavone derivatives containing 1,3,4-oxadiazoline structure had been obtained by the cyclodehydration of these hydrazones in acetic anhydride. These new compounds were characterized by IR, ¹H NMR, ESI-MS and HRMS. Their antimicrobial activity in vitro was tested. The results showed that at the concentration 0.5 mg/mL most of the compounds had relatively antibacterial activity, in which 7-(2-p-nitrobenzoyl hydrazone)-phenoxyethoxy flavone (4i) had stronger effects on S. aureu and B. subtilis than the others and the activity was similar with that of the control drug chloramphenicol.

Key words: acylhydrazone, 1,3,4-oxadiazoline, flavone, synthesis, antimicrobial activity

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Duan Zhifang, Shao Ling. Synthesis and Antimicrobial Activity of Flavone Derivatives Containing 1,3,4-Oxadiazoline Structure[J]. Chin. J. Org. Chem., 2015, 35(9): 2004-2012.

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含1,3,4-噁二唑啉苯氧乙氧基黄酮衍生物的合成及抗菌活性

Synthesis and Antimicrobial Activity of Flavone Derivatives Containing 1,3,4-Oxadiazoline Structure

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