Chinese Journal of Organic Chemistry >
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).
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
Duan Zhifang , Shao Ling . Synthesis and Antimicrobial Activity of Flavone Derivatives Containing 1,3,4-Oxadiazoline Structure[J]. Chinese Journal of Organic Chemistry, 2015 , 35(9) : 2004 -2012 . DOI: 10.6023/cjoc201502028
[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.)
/
| 〈 |
|
〉 |
