Application of Enzymatic Promiscuity in Pharmaceutical Synthesis: Papain-catalyzed One-pot Synthesis of 1,4-Dihydropyridine Calcium Channel Antagonists and Derivatives

doi:10.1007/s40242-019-8273-8

Chemical Research in Chinese Universities ›› 2019, Vol. 35 ›› Issue (1): 21-25.doi: 10.1007/s40242-019-8273-8

• Articles • Previous Articles Next Articles

Application of Enzymatic Promiscuity in Pharmaceutical Synthesis: Papain-catalyzed One-pot Synthesis of 1,4-Dihydropyridine Calcium Channel Antagonists and Derivatives

JIANG Ling^1,2, YE Wenting², SU Weike^1,2, YU Chuanming²

1. Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014, P. R. China;
2. Key Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. China

Received:2018-08-30 Revised:2018-10-17 Online:2019-02-01 Published:2018-11-26
Contact: YU Chuanming E-mail:ycm@zjut.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.21706236), the China Postdoctoral Science Foundation (No.2016M592012) and the Foundation for Selected Postdoctoral Project of Zhejiang Province, China(No.BSH1502150).

Abstract

Abstract: A new method for the synthesis of 1, 4-dihydropyridine (1, 4-DHP) calcium channel antagonists felodipine, nitrendipine and their derivatives via papain-catalyzed three-component reactions of aldehyde, methyl acetoacetate and ethyl 3-aminocrotonate was developed. Operational simplicity, mild reaction conditions and eco-friendliness are the key features of this protocol.

Key words: Papain, Catalytic promiscuity, Multicomponent reaction, 1,4-Dihydropyridine calcium channel antagonist

JIANG Ling, YE Wenting, SU Weike, YU Chuanming. Application of Enzymatic Promiscuity in Pharmaceutical Synthesis: Papain-catalyzed One-pot Synthesis of 1,4-Dihydropyridine Calcium Channel Antagonists and Derivatives[J]. Chemical Research in Chinese Universities, 2019, 35(1): 21-25.

References

[1] Mills K. T., Bundy J. D., Kelly T. N., Reed J. E., Kearney P. M., Reynolds K., Chen J., He J., Circulation, 2016, 134(6), 441
[2] Frieden T. R., Jaffe M. G., J. Clin. Hypertens., 2018, 20(2), 208
[3] Pascual I., Moris C., Avanzas P., Cardiovasc. Drugs Ther., 2016, 30(4), 357
[4] Azuaje J., Tubío C. R., Escalante L., Gómez M., Guitián F., Coelho A., Caamaño O., Gil A., Sotelo E., Appl. Catal. A:Gen., 2017, 530, 203
[5] Palermo V., Sathicq Á. G., Constantieux T., Rodríguez J., Vázquez P. G., Romanelli G. P., Catal. Lett., 2016, 146(9), 1634
[6] Ghosh P. P., Paul S., Das A. R., Tetrahedron Lett., 2013, 54(2), 138
[7] Baraldi P. T., Noël T., Wang Q., Hessel V., Tetrahedron Lett., 2014, 55(13), 2090
[8] Sheldon R. A., Woodley J. M., Chem. Rev., 2018, 118(2), 801
[9] Humble M. S., Berglund P., Eur. J. Org. Chem., 2011, (19), 3391
[10] González-Martínez D., Gotor V., Gotor-Fernández V., Eur. J. Org. Chem., 2016, (8), 1513
[11] Zhang M. J., Li R., He Y. H., Guan Z., Catal. Commun., 2017, 98, 85
[12] Koszelewski D., Paprocki D., Madej A., Borys F., Brodzka A., Ostaszewski R., Eur. J. Org. Chem., 2017, (31), 4572
[13] Tian X. M., Zhang S. Q., Zheng L. Y., Enzyme Microb. Technol., 2016, 84, 32
[14] Zhang W. A., Zhao Z. Y., Wang Z., Guo C., Wang C. Y., Zhao R., Wang L., Catalysts, 2017, 7(6), 185
[15] Liang Y. R., Hu Y. J., Zhou X. H., Wu Q., Lin X. F., Tetrahedron Lett., 2017, 58(30), 2923
[16] Bihani M., Bora P. P., Verma A. K., Baruah R., Boruah H. P. D., Bez G., Bioorg. Med. Chem. Lett., 2015, 25(24), 5732
[17] Xie B. H., Guan Z., He Y. H., J. Chem. Technol. Biotechnol., 2012, 87(12), 1709
[18] Li Z. L., Zhou H. Y., Guan Z., Chinese J. Org. Chem., 2017, 37(6), 1494
[19] Jiang L., Wang B., Li R. R., Shen S., Yu H. W., Ye L. D., Process Biochem., 2014, 49(7), 1135
[20] Jiang L., Yu H. W., Biotechnol. Lett., 2014, 36(1), 99
[21] Ma J. B., Wu L., Guo F., Gu J. L., Tang X. L., Jiang L., Liu J., Zhou J. H., Yu H. W., Appl. Microbiol. Biotechnol., 2013, 97(11), 4897

Application of Enzymatic Promiscuity in Pharmaceutical Synthesis: Papain-catalyzed One-pot Synthesis of 1,4-Dihydropyridine Calcium Channel Antagonists and Derivatives

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 6

Recommended Articles

Metrics

Comments

[1]	LÜ Chengwei, LIU Yanhang, ZHOU Xiaoxia, WANG Jiajing. One-pot Three-component Reaction for Efficient and Facile Synthesis of γ-Nitrocarbonyl Compounds Under Solvent-free Conditions [J]. Chemical Research in Chinese Universities, 2015, 31(2): 208-211.
[2]	JIANG Ling, YU Hongwei. Enzymatic Promiscuity：“Amano” Lipase AS-catalysed Synthesis of Naphthopyran Derivatives in Anhydrous Media [J]. Chemical Research in Chinese Universities, 2014, 30(3): 396-399.
[3]	JIANG Ling, YU Hongwei. Enzymatic Promiscuity：Escherichia coli BioH Esterase-catalysed Aldol Reaction and Knoevenagel Reaction [J]. Chemical Research in Chinese Universities, 2014, 30(2): 289-292.
[4]	WANG Ying-lei, LUO Jun, ZHI Hui-zhen. Preparation of 3,4-Dihydropyrimidones via Biginelli Reaction in Efficient and Recyclable PEG₁₀₀₀-DAIL/Toluene Catalyst-mediumCombined Thermoregulated Biphasic System [J]. Chemical Research in Chinese Universities, 2013, 29(5): 879-883.
[5]	CHEN Jiao, MA Zhen and YAN Chao-guo*. Three-component Reaction of Aromatic Aldehyde, Malononitrile and Aliphatic Amine Leading to Different Pyridine Derivatives [J]. Chemical Research in Chinese Universities, 2010, 26(6): 937-941.
[6]	HOU Rui-zhen , LI Hong-mei , LIU Yun-jia , ZHANG Long , XU Li , ZHANG Xue-zhong . Protease-catalyzed Synthesis of Bz-Arg-Gly-Asp-OMein Full Aqueous Medium [J]. Chemical Research in Chinese Universities, 2007, 23(6): 693-696.