Synthesis of Chalcone Derivatives Containing Furan or/and Pyran Ring as Neuraminidase Inhibitors

doi:10.1007/s40242-019-8346-8

高等学校化学研究 ›› 2019, Vol. 35 ›› Issue (3): 395-402.doi: 10.1007/s40242-019-8346-8

Synthesis of Chalcone Derivatives Containing Furan or/and Pyran Ring as Neuraminidase Inhibitors

CHEN Aiyu¹, LIANG Yongdong¹, YE Jiao¹, HU Aixi¹, LIAN Wenwen², LIU Ailin², DU Guanhua²

1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China;
2. Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, P. R. China

收稿日期:2018-10-26 修回日期:2019-01-14 出版日期:2019-06-01 发布日期:2019-02-25
通讯作者: HU Aixi, LIU Ailin E-mail:axhu@hnu.edu.cn;liuailin@imm.ac.cn
基金资助:
Supported by the Hunan Provincial Natural Science Foundation, China(No.2019JJ40030) and the National Natural Science Foundation of China(No.81673480).

Synthesis of Chalcone Derivatives Containing Furan or/and Pyran Ring as Neuraminidase Inhibitors

CHEN Aiyu¹, LIANG Yongdong¹, YE Jiao¹, HU Aixi¹, LIAN Wenwen², LIU Ailin², DU Guanhua²

1. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China;
2. Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, P. R. China

Received:2018-10-26 Revised:2019-01-14 Online:2019-06-01 Published:2019-02-25
Contact: HU Aixi, LIU Ailin E-mail:axhu@hnu.edu.cn;liuailin@imm.ac.cn
Supported by:
Supported by the Hunan Provincial Natural Science Foundation, China(No.2019JJ40030) and the National Natural Science Foundation of China(No.81673480).

摘要/Abstract

摘要： Twenty-seven novel chalcone derivatives were designed and synthesized as neuraminidase(NA) inhibitors. A concise suitable synthetic strategy was employed in the target compounds' synthesis with relatively high yields. The synthesized compounds were evaluated for their inhibitory activities against the NA of influenza A virus in vitro. The results show that compound 9b possesses the most potent NA inhibitory activity. Structure-activity relationship studies indicate that the chalcone system and hydrogen bond donor substituent are significant for the NA inhibitory activity. And the chalcone derivatives containing pyran ring have better NA inhibitory activity than those without the pyran ring. In addition, molecular docking studies reveal that compounds 9b and 9u are in the good binding mode with Zanamivir binding sites. This study indicates that compound 9b could be selected as a potent compound for further structural optimization and development of novel NA inhibitors.

关键词: Chalcone derivative, Neuraminidase inhibitor, Molecular docking

Abstract: Twenty-seven novel chalcone derivatives were designed and synthesized as neuraminidase(NA) inhibitors. A concise suitable synthetic strategy was employed in the target compounds' synthesis with relatively high yields. The synthesized compounds were evaluated for their inhibitory activities against the NA of influenza A virus in vitro. The results show that compound 9b possesses the most potent NA inhibitory activity. Structure-activity relationship studies indicate that the chalcone system and hydrogen bond donor substituent are significant for the NA inhibitory activity. And the chalcone derivatives containing pyran ring have better NA inhibitory activity than those without the pyran ring. In addition, molecular docking studies reveal that compounds 9b and 9u are in the good binding mode with Zanamivir binding sites. This study indicates that compound 9b could be selected as a potent compound for further structural optimization and development of novel NA inhibitors.

Key words: Chalcone derivative, Neuraminidase inhibitor, Molecular docking

CHEN Aiyu, LIANG Yongdong, YE Jiao, HU Aixi, LIAN Wenwen, LIU Ailin, DU Guanhua. Synthesis of Chalcone Derivatives Containing Furan or/and Pyran Ring as Neuraminidase Inhibitors[J]. 高等学校化学研究, 2019, 35(3): 395-402.

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Synthesis of Chalcone Derivatives Containing Furan or/and Pyran Ring as Neuraminidase Inhibitors

Synthesis of Chalcone Derivatives Containing Furan or/and Pyran Ring as Neuraminidase Inhibitors

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