Late-stage functionalization of 5-nitrofurans derivatives and their antibacterial activities

Geshuyi Chen; Zhe Chang; Pei Yuan; Si Wang; Yongxiu Yang; Xiaolei Liang; Depeng Zhao

doi:10.1039/d2ra07676d

Late-stage functionalization of 5-nitrofurans derivatives and their antibacterial activities

RSC Adv. 2023 Jan 20;13(5):3204-3209. doi: 10.1039/d2ra07676d. eCollection 2023 Jan 18.

Authors

Geshuyi Chen¹, Zhe Chang², Pei Yuan¹, Si Wang², Yongxiu Yang^{1

3

4}, Xiaolei Liang^{1

3}, Depeng Zhao²

Affiliations

¹ The First Clinical Medical College, Lanzhou University Lanzhou China chengshy20@lzu.edu.cn.
² Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-Sen University Guangzhou China zhaodp5@mail.sysu.edu.cn.
³ The First Clinical Medical College, Lanzhou University. Department of Obstetrics and Gynecology, The First Hospital of Lanzhou University, Key Laboratory for Gynecologic Oncology Lanzhou 730000 Gansu Province China yxyanglzu@163.com liangxl07@lzu.edu.cn.
⁴ Lead Contact China.

Abstract

Structure modification of drugs is a reliable way to optimize lead compounds, among which the most striking and direct method is late-stage functionalization (LSF). Here, we employed the Cu-catalyzed C-H LSF to modify 5-nitrofuran drugs. A series of modifications have been carried out including hydroxylation, methylation, azidination, cyanation, arylation, etc. Antibacterial activities of all compounds in vitro were measured. The results showed that compound 1 and compound 18 were the most active among all compounds. Meanwhile, the cell cytotoxicity assays of potent compounds 1, 3, 4, 5 & 18 and the parent drug FZD were conducted.