Chinese Journal of Organic Chemistry >
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).
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
Chen Hua , Zhou Likai , Li Shuai , Yao Yuchao , Gu Yunjing , Li Chunxiao , Li Na , Meng Ming , Li Xiaoliu . Synthesis of 3,4-Biphenyl Coumarin Derivatives and Their Promoting Effects on the Killing Activity of Natural Killing Cell[J]. Chinese Journal of Organic Chemistry, 2013 , 33(01) : 164 -168 . DOI: 10.6023/cjoc201208022
[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.)
/
〈 |
|
〉 |