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Chinese Journal of Organic Chemistry >

2014 , Vol. 34 >Issue 4: 749 - 755

DOI: https://doi.org/10.6023/cjoc201311025

Articles

Synthesis and AChE Inhibitory Activity of Chalcones Mannich Base Derivatives

  • Xu Shouhui ,
  • Liu Haoran ,
  • Lou Dinghui ,
  • Wang Qiuan
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  • College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Received date: 2013-11-14

  Revised date: 2013-12-18

  Online published: 2013-12-23

Supported by

Project supported by the Hunan Provincial Natural Science Foundation of China (No. 14JJ2048) and the National Natural Science Foundation of China (No. 21342015).

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Abstract

Chalcone flavokawain A (1) and chalcone prenyl ether derivative 2 were synthesized from naringin, through glycoside hydrolysis, O-methylation or O-prenylation, and base-catalyzed ring-opening reaction. Based on Mannich reaction of chalcone 1 and chalcone prenyl ether derivative 2, fourteen new chalcone Mannich base derivatives 3～16 were synthesized. The aminomethylation occurred preferentially at 3'-C position of chalcones. The structures of all synthesized compounds were determined by MS, NMR and IR spectra. All the synthetic compounds were evaluated for acetylcholinesterase (AChE) inhibitory activity. The results show that chalcone mannich base derivatives 3～5, 9 exhibit good AChE inhibitory activity.

Key words： chalcone; flavokawain A; Mannich base; synthesis; acetylcholinesterases inhibitory activity

Cite this article

Xu Shouhui , Liu Haoran , Lou Dinghui , Wang Qiuan . Synthesis and AChE Inhibitory Activity of Chalcones Mannich Base Derivatives[J]. Chinese Journal of Organic Chemistry, 2014 , 34(4) : 749 -755 . DOI: 10.6023/cjoc201311025

References

[1] Dharmaratnea, H. R. W.; Nanayakkara, N. P. D.; Khan, I. A. Phytochemistry 2002, 59, 429.
[2] Tang, Y. X.; Simoneau, A. R.; Xie, J. J. Cancer Prev. Res. 2008, 1, 439.
[3] Zi, X. L.; Simoneau, A. R. J. Cancer Res. 2005, 65, 3479.
[4] Wu, D.; Yu, L.; Nair, M. G.; Ramsewak, R. S. Pytomed. 2002, 9, 41.
[5] Wu, J.-Z.; Li, W.-L.; Yang, S.-L. Chin. J. Org. Chem. 2012, 32, 2141 (in Chinese).(吴建章, 李物兰, 杨树林, 有机化学, 2012, 32, 2141.)
[6] Luo, W.; Su, Y.-B.; Wang, C.-J. Bioorg. Med. Chem. 2013, 21, 7275.
[7] Fernández-Bachiller, M. I.; Pérez, C.; Monjas, L.; Rademann, J.; Rodríguez-Franco, M. I. J. Med. Chem. 2012, 55, 1303.
[8] Joshi, D.; Field, J.; Murphy, J.; Zask, A. J. Nat. Prod. 2013, 76, 450.
[9] Wu, Z.; Cai, S.-L.; Fan, W.-J.; Wang, Q.-A. Chin. J. Org. Chem. 2012, 32, 1296 (in Chinese).(吴峥, 蔡双莲, 范文金, 汪秋安, 有机化学, 2012, 32, 1296.)
[10] Aponte, J. C.; Verastegui, M.; Malaga, E. J. Med. Chem. 2008, 51, 6230.
[11] Chu, H. W.; Wu, H. T.; Lee, Y. J. Tetrahedron Lett. 2004, 60, 2647.
[12] Liu, A.-L.; Guang, H.-M.; Du, G.-H.; Li, M.-Y. Sci. China, Sci. Life 2007, 37, 503 (in Chinese).(刘艾林, 光红梅, 杜冠华, 李铭源, 中国科学C辑: 生命科学, 2007, 37, 503.)Zhou, J. F.; Xu, G. B.; Fang, W. J. Biomed. Environ. Sci. 2002, 15, 177.
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