3,4-二苯基香豆素衍生物的合成及其促自然杀伤细胞活性研究
收稿日期: 2012-08-21
修回日期: 2012-09-27
网络出版日期: 2012-10-09
基金资助
国家自然科学基金(Nos. 20902016, 20972039);河北省自然科学基金石药集团医药联合基金(No. B2011201169)和河北省教育厅自然科学基金(No. ZH2011110)资助项目.
Synthesis of 3,4-Biphenyl Coumarin Derivatives and Their Promoting Effects on the Killing Activity of Natural Killing Cell
Received date: 2012-08-21
Revised date: 2012-09-27
Online published: 2012-10-09
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 20902016, 20972039), the Medicinal Joint Funds of the Natural Science Foundation of Hebei Province and Shijiazhuang Pharmaceutical Group Foundation (No. B2011201169) and the Natural Science Foundations of Education Department of Hebei Province (No. ZH2011110).
陈华 , 周利凯 , 李帅 , 姚玉超 , 谷云景 , 李春晓 , 李娜 , 孟明 , 李小六 . 3,4-二苯基香豆素衍生物的合成及其促自然杀伤细胞活性研究[J]. 有机化学, 2013 , 33(01) : 164 -168 . DOI: 10.6023/cjoc201208022
A series of novel 3,4-biphenyl coumarin derivatives containing an amino side chain 1a～1e were synthesized using salicylic acid as starting material via Fridel-Crafts acylation, then the microwave-assisted Perkin reaction and double SN2 substitution reactions. The preliminary biological evaluation showed that compounds 1a～1e had significant promoting effects on the killing activity of natural killer cell, and hold potential as immunomodulating agents.
Key words： coumarin; Perkin reaction; natural killer cell; immunomodulating activity
[1] Stockinger, B. Nature 2009, 458, 44.
[2] Sun, J. C.; Lanier, L. L. Nat. Rev. Immunol. 2011, 11, 645.
[3] Thielens, A.; Vivier, E.; Romagné, F. Curr. Opin. Immunol. 2012, 24, 239.
[4] Suck, G. Semin. Cancer Biol. 2006, 16, 412.
[5] Failli, A.; Caggiano, T. J. Curr. Opin. Ther. Pat. 1992, 2, 882.
[6] Zhang, C.; Zhang, J.; Niu, J.; Zhou, Z.; Zhang, J.; Tian, Z. Cytokine 2008, 42, 128.
[7] Werner, G. H.; Jollès, P. Eur. J. Biochem. 1996, 242, 1.
[8] Zhao, H. P.; Donnelly, A. C.; Kusuma, B. R.; Brandt, G. E. L.; Brown, D.; Rajewski, R. A.; Vielhauer, G.; Holzbeierlein, J.; Cohen, M. S.; Blagg, S. J. J. Med. Chem. 2011, 54, 3839.
[9] Stefanachi, A.; Favia, A. D.; Nicolotti, O.; Leonetti, F.; Pisani, L.; Catto, M.; Zimmer, C.; Hartmann, R. W.; Carotti, A. J. Med. Chem. 2011, 54, 1613.
[10] Katzenellenbogen, B. S.; Katzenellebogen, J. K. Science 2002, 295, 2380.
[11] Jordan, V. C. J. Med. Chem. 2003, 46, 883.
[12] Jordan, V. C. J. Med. Chem. 2003, 46, 1081.
[13] Brady, H.; Desai, I.; Gayo-Fung, L. M.; Khammungkhune, S.; McKie, J. A.; O'Leary, E.; Pascasio, L.; Sutherland, M. K.; Anderson, D. W.; Bhagwat, S. S.; Stein, B. Cancer Res. 2002, 62, 1439.
[14] McKie, J. A.; Bhagwat, S. S.; Brady, H.; Doubleday, M.; Gayo, L.; Hickman, M.; Jalluri, R. K.; Khammungkhune, S.; Kois, A.; Mortensen, D.; Richard, N.; Sapienza, J.; Shevlin, G.; Stein, B.; Sutherland, M. Bioorg. Med. Chem. Lett. 2004, 14, 3407.
[15] Wang, C. N.; Wu, C. Y.; Zhu, J. Q.; Miller, R.; Wang, Y. M. J. Med. Chem. 2011, 54, 2331.
[16] Roussaki, M.; Kontogiorgis, C. A.; Hadjipavlou-Litina, D.; Hamilakis, S.; Detsi, A. Bioorg. Med. Chem. Lett. 2010, 20, 3889.
[17] Du, X. F.; Jiang, C. Z.; Wu, C. F.; Won, E. K.; Choung, S. Y. Arch. Pharm. Res. 2008, 31, 1153.
[18] Weng, F.; Wang, C. M.; Xu, B. Tetrahedron Lett. 2010, 51, 2593.
[19] Chen, H.; Gao, F.; Yin, Q. M.; Li, C. X.; Li, N.; Meng, M.; Li, X. L. Chin. J. Org. Chem. 2012, 32, 943 (in Chinese). (陈华, 高芳, 殷庆梅, 李春晓, 李娜, 孟明, 李小六, 有机化学, 2012, 32, 943.)
/
| 〈 |
|
〉 |
