Design, Synthesis and Antitumor Activity of Fluoroquinolone C3 Heterocyclic Bis-oxadiazole Methylsulfide Derivatives Derived from Levofloxacin

高等学校化学研究 ›› 2012, Vol. 28 ›› Issue (6): 980-984.

Design, Synthesis and Antitumor Activity of Fluoroquinolone C3 Heterocyclic Bis-oxadiazole Methylsulfide Derivatives Derived from Levofloxacin

HU Guo-qiang¹, WANG Guo-qiang¹, DUAN Nan-nan¹, WEN Xiao-yi¹, CAO Tie-yao¹, XIE Song-qiang¹, HUANG Wen-long²

1. Institute of Pharmacy, Henan University, Kaifeng 475001, P. R. China;
2. Centre of Drug Discovery, China Pharmaceutical University, Nanjing 210009, P. R. China

收稿日期:2012-02-20 修回日期:2012-04-17 出版日期:2012-11-25 发布日期:2012-11-09
通讯作者: HU Guo-qiang E-mail:hgqxy@sina.com.cn
基金资助:
Supported by the National Natural Science Foundation of China(Nos.20872028, 21072045).

Design, Synthesis and Antitumor Activity of Fluoroquinolone C3 Heterocyclic Bis-oxadiazole Methylsulfide Derivatives Derived from Levofloxacin

HU Guo-qiang¹, WANG Guo-qiang¹, DUAN Nan-nan¹, WEN Xiao-yi¹, CAO Tie-yao¹, XIE Song-qiang¹, HUANG Wen-long²

1. Institute of Pharmacy, Henan University, Kaifeng 475001, P. R. China;
2. Centre of Drug Discovery, China Pharmaceutical University, Nanjing 210009, P. R. China

Received:2012-02-20 Revised:2012-04-17 Online:2012-11-25 Published:2012-11-09
Contact: HU Guo-qiang E-mail:hgqxy@sina.com.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.20872028, 21072045).

摘要/Abstract

摘要：

To discover an efficient route for the shift from an antibacterial fluoroquinolone to an antitumor one based on the mechanistic similarities between targeting topoisomerases and the eukaryotic ones, two series of the title compounds, C3 bis-oxadiazole methylsulfides 6a-6h and corresponding dimethylpiperazinium iodides 7a-7h derived from levofloxacin 1 were designed and synthesized. Their in vitro antiproliferative activities against Chinese hamster ovary cell line(CHO), murine leukemia cell line(L1210) and human leukocytoma cell line(HL60) were evaluated by MTT assay, and inhibitory effect on DNA topoisomerase IIα was also measured by means of densitometric assay.

关键词: Fluoroquinolone, Oxadiazole, Isostere, Sulfide, Piperazinium, Antitumor activity

Abstract:

Key words: Fluoroquinolone, Oxadiazole, Isostere, Sulfide, Piperazinium, Antitumor activity

HU Guo-qiang, WANG Guo-qiang, DUAN Nan-nan, WEN Xiao-yi, CAO Tie-yao, XIE Song-qiang, HUANG Wen-long. Design, Synthesis and Antitumor Activity of Fluoroquinolone C3 Heterocyclic Bis-oxadiazole Methylsulfide Derivatives Derived from Levofloxacin[J]. 高等学校化学研究, 2012, 28(6): 980-984.

[1]	WANG Chaozhi, CUI Jingqin, FANG Xiaoliang, ZHENG Nanfeng. Regulating the Deposition of Insoluble Sulfur Species for Room Temperature Sodium-Sulfur Batteries[J]. 高等学校化学研究, 2022, 38(1): 128-135.
[2]	ZHANG Chen, LIU Donghai, GENG Chuannan, HUA Wuxing, TANG Quanjun, LING Guowei, YANG Quan-Hong. Solution-based Preparation of High Sulfur Content Sulfur/Graphene Cathode Material for Li-S Battery[J]. 高等学校化学研究, 2021, 37(2): 323-327.
[3]	ZHANG Xiulan, ZHANG Huan, MA Jinlong, YU Shujing, LI Zhengming. Design, Synthesis and Biological Activities of Novel N-Aryl-1H-pyrazole-5-carboxylate Derivatives[J]. 高等学校化学研究, 2020, 36(5): 853-858.
[4]	ZHANG Xiulan, ZHANG Huan, LIU Jingbo, XIONG Lixia, LI Zhengming. Synthesis and Biological Evaluation of Novel Anthranilic Diamides Containing N-H/CH₃-1H-Pyrazole[J]. 高等学校化学研究, 2020, 36(5): 829-834.
[5]	YUAN Hong, LIU Jia, LU Yang, ZHAO Chenzi, CHENG Xinbing, NAN Haoxiong, LIU Quanbing, HUANG Jiaqi, ZHANG Qiang. Toward Practical All-solid-state Batteries with Sulfide Electrolyte: A Review[J]. 高等学校化学研究, 2020, 36(3): 377-385.
[6]	ZANG Rui, LI Peng, WANG Guoxiu. Bimetallic Sulfide/Sulfur Doped T₃C₂T_x MXene Nanocomposites as High-performance Anode Materials for Sodium-ion Batteries[J]. 高等学校化学研究, 2020, 36(3): 431-438.
[7]	TIAN Ye, YU Simiao, CAI Lude, GONG Guowei, WU Guodong, QI Hongxia, ZHAO Yanfang, QIN Mingze. Synthesis and Antitumor Activity of Sorafenib Analogs Containing a Tetrazole Moiety[J]. 高等学校化学研究, 2019, 35(1): 41-46.
[8]	SU Jing, YU Mingyue, LIN Zhen, ZHAO Hang, LIU Haiyan. Effects of ZnO Nanoparticles on Rat Glioma C6 Cells[J]. 高等学校化学研究, 2017, 33(6): 908-911.
[9]	CUI Shu, LI Xuesong, LI Yanjuan, ZHAO Haixin, WANG Yuanyuan, LI Nan, LI Xiaotian, LI Guodong. Synthesis of CdS/m-TiO₂ Mesoporous Spheres and Their Application in Photocatalytic Degradation of Rhodamine B Under Visible Light[J]. 高等学校化学研究, 2017, 33(3): 436-441.
[10]	CAI Wenqing, LIU Wei, XIE Yafei, WU Jingwei, LIU Yuqiang, LIU Changying, XU Weiren, TANG Lida, WANG Jianwu, ZHAO Guilong. Design, Synthesis and Biological Activity of Tetrazole-bearing Uric Acid Transporter 1 Inhibitors[J]. 高等学校化学研究, 2017, 33(1): 49-60.
[11]	LI Hongshuang, WANG Xinran, DUAN Guiyun, XIA Chengcai, XIAO Yuliang, LI Furong, GE Yanqing, YOU Guirong, HAN Junfen, FU Xiaopan, TAN Shanhui, WANG Rongwei. Synthesis, Antitumor Activity and Preliminary Structure-activity Relationship of 2-Aminothiazole Derivatives[J]. 高等学校化学研究, 2016, 32(6): 929-937.
[12]	WU Yi, ZHAO Yanping, GUO Jing, LÜ Haoze, ZHENG Nan, WANG Ensi. Synthesis and Biological Evaluation of Amino Alcohol Containing 1,3,4-Oxadiazole[J]. 高等学校化学研究, 2016, 32(5): 760-767.
[13]	ZHANG Dongkai, HUA Xuewen, LIU Ming, WU Changchun, WEI Wei, LIU Yang, CHEN Minggui, ZHOU Sha, LI Yonghong, LI Zhengming. Design, Synthesis and Herbicidal Activity of Novel Sulfonylureas Containing Triazole and Oxadiazole Moieties[J]. 高等学校化学研究, 2016, 32(4): 607-614.
[14]	MA Junjie, HU Gang, XIE Lijun, CHEN Lei, XU Boxuan, GONG Ping. Design, Synthesis and Biological Evaluation of Novel Benzothiazole Derivatives Bearing Semicarbazone Moiety as Antitumor Agents[J]. 高等学校化学研究, 2015, 31(6): 958-963.
[15]	SUN Bing, YIN Xiu'e, ZHANG Jin, HUANG Jian, XU Yue, ZHANG Furong, WANG Jinhui, WANG Guoqing, HU Chun. Synthesis, Characterization and Biological Activity of Tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine Derivatives asEpidermal Growth Factor Receptor Inhibitors[J]. 高等学校化学研究, 2015, 31(6): 936-941.

Design, Synthesis and Antitumor Activity of Fluoroquinolone C3 Heterocyclic Bis-oxadiazole Methylsulfide Derivatives Derived from Levofloxacin

Design, Synthesis and Antitumor Activity of Fluoroquinolone C3 Heterocyclic Bis-oxadiazole Methylsulfide Derivatives Derived from Levofloxacin

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价