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
收稿日期: 2015-02-23
修回日期: 2015-04-24
网络出版日期: 2015-05-08
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
Received date: 2015-02-23
Revised date: 2015-04-24
Online 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).
7-羟基黄酮与过量1,2-二溴乙烷反应得到7-溴乙氧基黄酮, 将其与水杨醛反应得到7-水杨醛乙氧基黄酮, 然后与酰肼类化合物反应得到14个相应的含酰腙结构的苯氧乙氧基黄酮衍生物, 该类化合物与乙酸酐作用分别得到三种类型的产物, 其中有8个为含1,3,4-噁二唑啉杂环结构的苯氧乙氧基黄酮环合衍生物. 用红外(IR)、核磁共振氢谱(1H NMR)、质谱(ESI-MS)和高分辨质谱(HR-MS)对化合物的结构进行了确证. 对所合成的化合物进行了初步抗菌活性测定, 结果表明, 在0.5 mg/mL浓度时, 多数化合物对大肠杆菌、金黄色葡萄球菌、枯草芽孢杆菌具有抑制作用, 而对黑曲霉抑制作用较弱, 其中7-(2-对硝基苯甲酰腙基)-苯氧乙氧基黄酮(4i)对金黄色葡萄球菌和枯草芽孢杆菌作用与对照氯霉素相近.
关键词： 酰腙; 1,3,4-噁二唑啉; 黄酮; 合成; 抗菌
段志芳 , 邵玲 . 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[J]. 有机化学, 2015 , 35(9) : 2004 -2012 . DOI: 10.6023/cjoc201502028
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
[1] Vicente-Sanchez, C.; Egido, J.; Sanchez-Gonzalez, P. D. Food Chem. Toxicol. 2008, 46, 2279.
[2] Yan, X.; Liu, H.-Q.; Zou, Y.-Q.; Ren, Z.-H. Chin. J. Org. Chem. 2008, 28, 1534 (in Chinese).(延玺, 刘会青, 邹永青, 任占华, 有机化学, 2008, 28, 1534.)
[3] Newell, D.-R.; Searle, K.-M.; Westwood, N.-B.; Burtles, S.-S. Br. J. Cancer 2003, 89, 437.
[4] Yan, X.; Xia, L.-L.; Yu, J.; Ding, W.-J. Acta Chim. Sinica 2008, 66, 39 (in Chinese). (延玺, 夏玲玲, 于静, 丁万见, 化学学报, 2008, 66, 39.)
[5] Chen, Z.-G; Wang, C.-N.; Zhao, P.-F., Wang, Y.; Zhou, L.-Y. Acta Chim. Sinica 2010, 68, 2347 (in Chinese). (陈战国, 王传宁, 赵朋飞, 王芸, 周利燕, 化学学报, 2010, 68, 2347.)
[6] Cui, Z.-N.; Li, Y.; Ling, Y.; Huang, J.; Gui, J.-R.; Wang, R.-Q.; Yang, X.-L. Eur. J. Med. Chem. 2010, 45, 5576.
[7] Jin, Y. X.; Tan, Z. W.; He, M. Z.; Tian, B. H.; Tang, S. X.; Hewlett, I.; Yang, M. Bioorg. Med. Chem. 2010, 18, 2135.
[8] Sevim, R.; Nehir, G.; Habib, E. Farmaco 2002, 57, 171.
[9] Abdel, K. M.; Mohga, M. E.; Nasser, S. A. Molecules 2003, 8, 744.
[10] Wyrzykiewicz, E.; Prukaia, D. J. Heterocycl. Chem. 1998, 35, 381.
[11] Cui, Z.-N.; Zhang, L.; Huang, J.; Ling, Y.; Yang, X.-L. Chin. J. Org. Chem. 2010, 30, 1482 (in Chinese). (崔紫宁, 张莉, 黄娟, 凌云, 杨新玲, 有机化学, 2010, 30, 1482.)
[12] Tang, L.-J. J. Bohai Univ. (Nat. Sci. Ed.) 2007, 28, 310 (in Chinese). (汤立军, 渤海大学学报(自然科学版), 2007, 28, 310.)
[13] Duan, Z.-F; Fu, L.; Li, C.-B. Chem. J. Chin. Univ. 2015, 36, 109 (in Chinese). (段志芳, 付莉, 李充璧, 高等学校化学学报, 2015, 36, 109.)
[14] Qu, L.-B.; Tian, M.-C.; Cheng, S.-X.; Chen, R.-F. Acta Pharm. Sinica 2003, 38, 264 (in Chinese). (屈凌波, 田孟超, 程森祥, 陈荣峰, 药学学报, 2003, 38, 264.)
/
| 〈 |
|
〉 |
