Synthesis of Aminoalkyl-substituted Polymethoxychalcone Derivatives and Their Antiproliferative Activities Against Three Human Cancer Cell Lines

doi:10.1007/s40242-016-6190-7

Chemical Research in Chinese Universities ›› 2016, Vol. 32 ›› Issue (5): 754-759.doi: 10.1007/s40242-016-6190-7

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Synthesis of Aminoalkyl-substituted Polymethoxychalcone Derivatives and Their Antiproliferative Activities Against Three Human Cancer Cell Lines

CHEN Mingxia, SHI Ling, TANG Jiaqing, WANG Qiuan

College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China

Received:2016-05-09 Revised:2016-06-17 Online:2016-10-01 Published:2016-06-30
Contact: WANG Qiuan E-mail:WangQA@hnu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.J1210040) and the Research Funds for Younger Investigators of Hunan University, China(No.531107040562).

Abstract

Abstract:

Two novel series of sixteen aminoalkyl-substituted polymethoxychalcone derivatives 2a-2h and 3a-3h were synthesized from 2'-hydroxy-3,4,5,4',6'-pentamethoxy chalcone(1) through extending alkoxy side chain at the 2'-position, and introducing amine hydrogen bond receptor at the end of the side chain. The structures of all the synthesized compounds were confirmed by ¹H NMR, ¹³C NMR and MS techniques. Furthermore, all the compounds were tested for antiproliferative activities in vitro against a panel of three human cell lines(HeLa, HCC1954 and SK-OV-3) via CCK-8 assay. The results show that all the target compounds exhibit antiproliferative activities against the three human cancer cells with IC₅₀ values of 4.62-48.21 μmol/L, except compound 2h against SK-OV-3 cells. Most of these compounds were more active when compared to the positive control cis-Platin.

Key words: Polymethoxychalcone, Aminoalkyl-substituted derivative, Antiprolifertive activity

CHEN Mingxia, SHI Ling, TANG Jiaqing, WANG Qiuan. Synthesis of Aminoalkyl-substituted Polymethoxychalcone Derivatives and Their Antiproliferative Activities Against Three Human Cancer Cell Lines[J]. Chemical Research in Chinese Universities, 2016, 32(5): 754-759.

References

[1] Neves M. P., Lima R. T., Choosang K., Pakkong P., Nascimento M., Vasconcelos M. H., Pinto M., Silva A. M. S., Cidade H., Chem. Biodivers., 2012, 9(6), 1133
[2] Liu H. R., Huang X. Q., Lou D. H., Liu X. J., Liu W. K., Wang Q. A., Bioorg. Med. Chem. Lett., 2014, 24(19), 4749
[3] Wang W., Hua M. Q., Huang Y., Zhang Q., Zhang X. Y., Wu J. B., Chem. Res. Chinese Universities, 2015, 31(3), 362
[4] Duan K. K., Liu H. R., Fan H. Q., Zhang J., Wang Q. A., J. Chem. Res., 2014, 38(7), 443
[5] Zhang J. Y., Zhang Q., Zhang H. X., Ma Q., Lu J. Q., Qiao Y. J., J. Agric. Food. Chem., 2012, 60(36), 9023
[6] Raghavan S., Manogaran P., Kalpattu B. K., Venkatraman G., Gadepalli K. K. N., Med. Chem. Res., 2015, 24(12), 4157
[7] Valdameri G., Charlotte G., Raphael T., Kachadourian R., Day B. J., Winnischofer S. M. B., Rocha M. E. M., Frachet V., Ronot X., Pietro A., Ahcene B., J. Med. Chem., 2012, 55(7), 3193
[8] Srinivasan B., Johnson T. E., Lad R., Xing C., J. Med. Chem., 2009, 52(22), 7228
[9] Quintin J., Desrivot J., Thoret S., Menez P. L., Cresteil T., Lewin G., Bioorg. Med. Chem. Lett., 2009, 19(1), 167
[10] Zhang S. X., Ma J. G., Bao Y. M., Yang P. W., Zou L., Li K. J., Sun X. D., Bioorg. Med. Chem., 2008, 16(15), 7128
[11] Ali R., Siddiqui N., Arch. Pharm. Chem. Life Sci., 2015, 348, 254
[12] Bonesi M., Tundis R., Deguin B., Loizzo M. R., Menichini F., Tillequin F., Menichini F., Bioorg. Med. Chem. Lett., 2008, 18(20), 5431
[13] Cholody W. M., Martelli S., Konopa J., J. Med. Chem., 1990, 33(10), 2852
[14] Yang K., Zhang K. J., Hu S. Y., Gu Q. L., Dong J. B., Wang J. X., Chem. J. Chinese Universities, 2015, 36(2), 279
[15] Detsi A., Majdalani M., Kontogiorgis C. A., Dimitra H. L., Kefalas P., Bioorg. Med. Chem., 2009, 17(23), 8073
[16] Wu G., Guo H. F., Gao K., Liu Y. N., Bastow K. F., Susan L. M. N., Lee K. H., Xie L., Bioorg. Med. Chem. Lett., 2008, 18(19), 5272
[17] Mateeva N. N., Kode R. N., Redda K. K., J. Heterocycl. Chem., 2002, 39(6), 1251
[18] Xuan L. N., Wang P., Zhang K., Shi Y. P., Liu Y. M., Zhu T., Chen B. Q., Med. Chem. Res., 2015, 24(2), 543

Synthesis of Aminoalkyl-substituted Polymethoxychalcone Derivatives and Their Antiproliferative Activities Against Three Human Cancer Cell Lines

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