含亚磺酸酯或亚磺酰胺基团的香豆素衍生物的合成及生物活性研究
收稿日期: 2016-01-11
修回日期: 2016-02-22
网络出版日期: 2016-03-11
基金资助
高等学校学科创新引智计划(No.B06005)、元素有机化学国家重点实验室和天津化学化工协同创新中心资助项目.
Synthesis and Bioactivities of Novel Coumarin Derivatives Containing Sulfinic Esters or Sulfinamide Moiety
Received date: 2016-01-11
Revised date: 2016-02-22
Online published: 2016-03-11
Supported by
Project supported by the “111” Project of Ministry of Education of China (No. B06005), and the State Key Laboratory of Elemento-organic Chemistry and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin).
刘明 , 刘阳 , 刘艾林 , 张冬凯 , 陈明桂 , 吴长春 , 华学文 , 周莎 , 李正名 . 含亚磺酸酯或亚磺酰胺基团的香豆素衍生物的合成及生物活性研究[J]. 有机化学, 2016 , 36(7) : 1653 -1661 . DOI: 10.6023/cjoc201601011
A series of novel coumarin derivatives containing sulfinic esters or sulfonamide were designed and synthesized. Their structures were characterized by 1H NMR, 13C NMR and elemental analysis. The preliminary bioassays indicated that several target compounds exhibited good in vitro antitumor activities on A549 (up to 67.82%), Bel7402 (up to 58.47%) and HCT-8 (up to 74.80%) at 5.0 mg/L and moderate antifungal activities on Physalospora piricola (up to 82.0 %) at 50 mg/L. The structure-activity relationship of these target compounds was discussed accordingly.
Key words: coumarin; sulfinic esters; sulfinamide; anticancer activity; antifungal activity
[1] Liu, M.; Liu, Y.; Hua, X.; Wu, C.; Zhou, S.; Wang, B.; Li, Z. Chin. J. Chem. 2015, 33, 1353.
[2] Qin, Y.; Qu, Y.; Zhang, J.; Tan, X.; Song, L.; Li, W.; Song, D.; Yang, X. Chin. J. Org. Chem. 2015, 35, 455 (in Chinese). (秦耀果, 曲焱焱, 张景朋, 谭晓庆, 宋丽芳, 李文浩, 宋敦伦, 杨新玲, 有机化学, 2015, 35, 455.)
[3] Xu, Y.-M.; Liu, M. X.; Grunow, N.; Wijeratne, E. M. K.; Paine-Murrieta, G.; Felder, S.; Kris, R. M.; Gunatilaka, A. A. L. J. Med. Chem. 2015, 58, 6984.
[4] Ma, Q.; Liu, Y.; Zhang, P.; Li, Y.; Xiong, L.; Wang, Q. J. Agric. Food Chem. 2014, 62, 6072.
[5] Han, Y.; Ding, Y.; Xie, D.; Hu, D.; Li, P.; Li, X.; Xue, W.; Jin, L.; Song, B. Eur. J. Med. Chem. 2015, 92, 732.
[6] Yang, J.; Gu, Q.; Shu, B.; Song, B.; Liu, J. Chin. J. Org. Chem. 2013, 33, 1113 (in Chinese). (杨家强, 谷晴, 束波, 宋宝安, 刘静姿, 有机化学, 2013, 33, 1113.)
[7] Wang, D.; Wei, Y.; Hao, S. Chin. J. Org. Chem. 2015, 35, 1691 (in Chinese). (王栋, 魏艳, 郝双红, 有机化学, 2015, 35, 1691.)
[8] Liu, M.-M.; Chen, X.-Y.; Huang, Y.-Q.; Feng, P.; Guo, Y.-L.; Yang, G.; Chen, Y. J. Med. Chem. 2014, 57, 9343.
[9] Thakur, A.; Singla, R.; Jaitak, V. Eur. J. Med. Chem. 2015, 101, 476.
[10] Nasr, T.; Bondock, S.; Youns, M. Eur. J. Med. Chem. 2014, 76, 539.
[11] Städler, E.; Buser, H.-R. Experientia 1984, 40, 1157.
[12] Wang, C.-M.; Guan, W.; Fang, S.; Chen, H.; Li, Y.-Q.; Cai, C.; Fan, Y.-J.; Shi, Z.-Q. J. Asian Nat. Prod. Res. 2010, 12, 672.
[13] Kwon, Y.-S.; Kobayashi, A.; Kajiyama, S.-I.; Kawazu, K.; Kanzaki, H.; Kim, C.-M. Phytochemistry 1997, 44, 887.
[14] Venugopala, K. N.; Rashmi, V.; Odhav, B. BioMed Res. Int. 2013, 2013, 963248.
[15] Kenchappa, R.; Bodke, Y.; Peethambar, S. K.; Telkar, S.; Bhovi, V. Med. Chem. Res. 2013, 22, 4787.
[16] Singh, S.; Gupta, S.; Singh, B.; Sharma, S. K.; Gupta, V. K.; Sharma, G. L. J. Proteome Res. 2012, 11, 3259.
[17] Guan, A.-Y.; Liu, C.-L.; LI, Z.-N.; Zhang, M.-X.; Si, N.-G. Agrochemicals 2011, 50, 90 (in Chinese). (关爱莹, 刘长令, 李志念, 张明星, 司乃国, 农药, 2011, 50, 90.)
[18] Guan, A.; Liu, C.; Yang, X.; Dekeyser, M. Chem. Rev. 2014, 114, 7079.
[19] Wei, J.; Sun, Z. Org. Lett. 2015, 17, 5396.
[20] Li, Q.; Yu, H.; Guan, A.; Liang, S.; Song, Y.; Li, B. Chin. J. Org. Chem. 2012, 32, 1736 (in Chinese). (李琴, 于海波, 关爱莹, 梁松军, 宋玉泉, 李斌, 有机化学, 2012, 32, 1736.)
[21] Jiang, X.-R. M. S. Thesis, Central China Normal University, Hubei, 2002 (in Chinese). (蒋翔锐, 硕士论文, 华中师范大学, 湖北, 2002.)
[22] Lee, J.; Gupta, S.; Huang, J.-S.; Jayathilaka, L. P.; Lee, B.-S. Anal. Biochem. 2013, 436, 187.
[23] Wang, J.; Cao, Y.; Wang, C.; Sun, B. J. Sci. Food Agric. 2011, 91, 1766.
[24] Kumar, J. A.; Saidachary, G.; Mallesham, G.; Sridhar, B.; Jain, N.; Kalivendi, S. V.; Rao, V. J.; Raju, B. C. Eur. J. Med. Chem. 2013, 65, 389.
[25] Peng, S.; Wang, L.; Huang, J.; Sun, S.; Guo, H.; Wang, J. Adv. Synth. Catal. 2013, 355, 2550.
[26] Siddiqui, N.; Ahsan, W. Eur. J. Med. Chem. 2010, 45, 1536.
[27] Chen, Y.; Wan, Y.; Liu, Q.; Liu, J.; Xiong, L.; Yu, S.; Li, Z. Chin. J. Org. Chem. 2015, 35, 882 (in Chinese). (陈有为, 万莹莹, 刘巧霞, 刘敬波, 熊丽霞, 于淑晶, 李正名, 有机化学, 2015, 35, 882.)
[28] Jiang, W.; Hu, F.; Gu, H.; Liu, C.; Wei, N.; Wan, L.; Ren, S.; Wang, J.; Xu, F. Chin. J. Org. Chem. 2014, 34, 774 (in Chinese). (姜文涛, 胡方中, 顾翰, 刘传, 魏乃翔, 万蕾, 任士钊, 王俊婷, 徐凤波, 有机化学 2014, 34, 774.)
/
| 〈 |
|
〉 |