Synthesis, Docking and Biological Evaluation of Isoquinolonic Acid Derivatives

doi:10.1007/s40242-013-3149-9

Chemical Research in Chinese Universities ›› 2013, Vol. 29 ›› Issue (6): 1110-1114.doi: 10.1007/s40242-013-3149-9

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Synthesis, Docking and Biological Evaluation of Isoquinolonic Acid Derivatives

ZHANG Hao, ZHENG Yu-qiong, GUO Jing, WANG Xiao-ming, YANG Yong-hua

State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, P. R. China

Received:2013-04-01 Revised:2013-04-24 Online:2013-12-01 Published:2013-05-15
Contact: WANG Xiao-ming, YANG Yong-hua E-mail:wangxm07@nju.edu.cn;yangyh@nju.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No31171161), the Program for Changjiang Scholars and Innovative Research Team in University, China(NoIRT1020), the Fundamental Research Funds for the Central Universities, China(Nos1106020824, 1082020803) and the Natural Science Foundations of Jiangsu Province, China (NoBK2010053)

Abstract

Abstract:

A series of isoquinolonic acid derivatives(4a-4o) was synthesized via one-pot synthesis for their anti-tumor activity. The structures of all the targeted compounds were confirmed by ¹H nuclear magnetic resonance (¹H NMR) spectrometry and mass spectrometry(MS). The anti-tumor activities of compounds 4a-4o against MG63(human osteosarcoma cells) and B16-F10(mouse melanoma cells) were examined. To evaluate the antitumor effect of the as-synthesized compounds, we compared the half maximal inhibitory concentration(IC₅₀) of compounds 4a-4o to that of camptothecin(CPT) which appeared to be active against a broad range of human cancers. Among all the compounds, compound 4l shows the most potent biological activity against MG63 cells[IC₅₀=(2.16±0.26) μmol/L] and B16-F10 cells[IC₅₀=(6.95±0.24) μmol/L], thus providing useful information for the antitumor activity and potential practical use of isoquinolonic acid compounds. In addition, we screened out an efficient compound(4l) that shows potential inhibit activity against Topoisomerase I(Topo I) by docking simulation.

Key words: Isoquinolonic acid compound, Antitumor activity, Molecular docking

ZHANG Hao, ZHENG Yu-qiong, GUO Jing, WANG Xiao-ming, YANG Yong-hua. Synthesis, Docking and Biological Evaluation of Isoquinolonic Acid Derivatives[J]. Chemical Research in Chinese Universities, 2013, 29(6): 1110-1114.

References

[1] Cushman M., Chen J., J. Org. Chem., 1987, 52, 1517
[2] Fodor L., Szabo J., Bernath G., Sohar P., Maclean D. B., Smith R. W., Ninomiya I., Naito T., J. Heterocyclic Chem., 1989, 26, 333
[3] Cushman M., Cheng L., J. Org. Chem., 1978, 43, 286
[4] Bonnaud B., Carlessi A., Bigg D. C. H., J. Heterocyclic Chem., 1993, 30, 257
[5] Cushman M., Abbaspour A., Gupta Y. P., J. Am. Chem. Soc., 1983, 105, 2873
[6] Povarov L. S., Russ. Chem. Rev., 1967, 36, 656
[7] Yamada N., Kadowaki S., Takahashi S., Biochem. Pharmacol., 1992, 4, 1211
[8] Faber K., Stueckler H., Kappe T., J. Heterocyclic Chem., 1984, 21, 1177
[9] Johnson J. V., Rauckman B. S., Baccanari D. P., Roth B., J. Med. Chem., 1989, 32, 1942
[10] Katherine E. P., Maris A. C., Andrew E. M., J. Med. Chem., 2011, 54, 4937
[11] Cushman M., Gentry J., Dekow F. W., J. Org. Chem., 1977, 42, 1111
[12] Mohammadi M. H., Mohammadi A. A., Synthetic Communications, 2011, 41, 523
[13] Yu N. F., Bourel L., Deprez B., Gesquiere J. C., Tetrahedron Lett., 1998, 39, 829
[14] Yadav J. S., Reddy B. V. S., Reddy K. S., Tetrahedron, 2003, 59, 5333
[15] Azizian J., Mohammadi A. A., Karimi A. R., Mohammadizadeh M. R., J. Org. Chem., 2005, 70, 350
[16] Azizian J., Mohammadi A. A., Soleimani E., Karimi A. R., Mohammadizadeh M. R., J. Heterocyclic Chem., 2006, 43, 187
[17] Yadav J. S., Reddy B. V. S., Reddy A. R., Synthesis-stuttgart, 2007, 20, 3191
[18] Pommier Y., Pourquier P., Yi F., Strumberg D., Biochimica et Biophysica Acta, 1998, 1400, 83
[19] Grummitt O., Egan R., Buck A., Organic Syntheses, 1949, 29, 49
[20] Wang L. M., L J. J., Tian H., Tian C. T., Sun J., Adv. Synth. Catal., 2005, 347, 689
[21] Ma Z. Y., Zhang X. Y., Li C. N., Zheng Y. J., Wang S. K., He Y., Chem. J. Chinese Universities, 2011, 27(5), 787
[22] Liu D., Zhu X. J., Jiang M., Chen H., Lan S. P., Chem. J. Chinese Universities, 2012, 33(10), 2249
[23] Wall M. E., Wani M. C., Cook C. E., Palmer K. H., Mcphail A. T., Sim G. A., J. Am. Chem. Soc., 1966, 88, 3888
[24] Pommier Y., Nat. Rev. Cancer, 2006, 6, 789

Synthesis, Docking and Biological Evaluation of Isoquinolonic Acid Derivatives

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