Home

Citation: WANG Guoqiang, DUAN Nannan, CAO Tieyao, WEN Xiaoyi, YIN Jun, WANG Wei, XIE Songqiang, HUANG Wenlong, HU Guoqiang. Antitumor Fluoroquinolone C3-Isostere Derivatives(Ⅰ)——Synthesis and Activity of Bis-oxadiazole Methyl-sulfide Derivatives[J]. Chinese Journal of Applied Chemistry, ;2012, 29(7): 769-774. doi: 10.3724/SP.J.1095.2012.00360 shu

Antitumor Fluoroquinolone C3-Isostere Derivatives(Ⅰ)——Synthesis and Activity of Bis-oxadiazole Methyl-sulfide Derivatives

1.
a Institute of Chemistry & Biology, Henan University, Kaifeng 475001, China;
2.
b Center of Drug Discovery, China Pharmaceutical University, Nanjing 210009, China

Corresponding author: HU Guoqiang,
Received Date: 17 August 2011
Available Online: 9 November 2011
Fund Project: 国家自然科学基金(20872028,21072045) (20872028,21072045)河南大学科研基金(06YB2R075)资助项目 (06YB2R075)

To discover an efficient modification for shifting from an antibacterial fluoroquinolone to an antitumor one based on the topological similarities between targeting topoisomerases as the eukaryotic ones and mammals,using oxadiazole heterocycle as an intermediate for the isostere of C-3 carboxylic group of norfloxacin(1),1-ethyl-6-fluoro-7-piperazin-1-yl-3-(5-mercapto-1,3,4-oxadiazol-2-yl)-quinolin-4(1H)-one(3) was subjected to thioetherfication with each of chloromethyl oxadiazole(4a~4e) to give bis-oxadiazole methylsulfides(5a~5e),respectively.The following N-methylations and quaternizations yielded the corresponding N-methyl bis-oxadiazole methylsulfides(6a~6e) and N,N-dimethyl bis-oxadiazole methylsulfide iodides(7a~7e).The structures of fifteen title compounds were characterized by elemental analysis,¹H NMR and MS,and their anticancer activities in vitro against Hep-3B cancer cell lines were also evaluated with a MTT assay.The results reveal that fifteen title compounds show higher cytotoxicity than that of comparison 1,in which quaternary ammonium salts exhibit potential anticancer activity with IC₅₀ values below 25.0 μmol/L.
- fluoroquinolone,
- isostere,
- oxadiazole,
- quaternary ammonium salt,
- antitumor evaluation
1. [1]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
2. [2]
  Shahua Huang , Xiaoming Guo , Lin Lin , Guangping Chang , Sheng Han , Zuxin Zhou . Application of “Integration of Industry and Education” in Engineering Chemistry: Improvement of the Pesticide Fipronil Production. University Chemistry, 2024, 39(3): 199-204. doi: 10.3866/PKU.DXHX202309064
3. [3]
  Jiahao Zeng , Hui Chao . 诱导程序性细胞死亡的金属抗肿瘤药物研究. University Chemistry, 2025, 40(6): 145-159. doi: 10.12461/PKU.DXHX202406019
4. [4]
  Jian Li , Yu Zhang , Rongrong Yan , Kaiyuan Sun , Xiaoqing Liu , Zishang Liang , Yinan Jiao , Hui Bu , Xin Chen , Jinjin Zhao , Jianlin Shi . Highly Efficient, Targeted, and Traceable Perovskite Nanocrystals for Photoelectrocatalytic Oncotherapy. Acta Physico-Chimica Sinica, 2025, 41(5): 100042-0. doi: 10.1016/j.actphy.2024.100042
5. [5]
  Jichao XU , Ming HU , Xichang CHEN , Chunhui WANG , Leichen WANG , Lingyi ZHOU , Xing HE , Xiamin CHENG , Su JING . Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144
6. [6]
  Bingliang Li , Yuying Han , Dianyang Li , Dandan Liu , Wenbin Shang . One-Step Synthesis of Benorilate Guided by Green Chemistry Principles and in vivo Dynamic Evaluation. University Chemistry, 2024, 39(6): 342-349. doi: 10.3866/PKU.DXHX202311070
7. [7]
  Zihao Guo , Shichen Ma , Kin Shing Chan . 烯烃环化反应中6电子试剂的等瓣相似性和等电子关系. University Chemistry, 2025, 40(6): 160-166. doi: 10.12461/PKU.DXHX202408038
8. [8]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
9. [9]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
10. [10]
  Hanxue LIU , Shijie LI , Meng REN , Xuling XUE , Hongke LIU . Design and antitumor properties of dehydroabietic acid functionalized cyclometalated iridium(Ⅲ) complex. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1483-1494. doi: 10.11862/CJIC.20250031
11. [11]
  Xiaotong LU , Pan ZHANG , Zijie ZHAO , Lei HUANG , Hongwei ZUO , Lili LIANG . Antitumor and antibacterial activities of pyridyl Schiff base indium and dysprosium complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1523-1532. doi: 10.11862/CJIC.20250073
12. [12]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
13. [13]
  Xiqing Liang , Tian Zhao , Jiawei Li , Haohui Tan , Hai Chen , Liyan Zeng . Pentaerythritol’s Journey of Making Friends. University Chemistry, 2025, 40(10): 175-185. doi: 10.12461/PKU.DXHX202412009
14. [14]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
15. [15]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
16. [16]
  Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362
17. [17]
  Xiaoning TANG , Shu XIA , Jie LEI , Xingfu YANG , Qiuyang LUO , Junnan LIU , An XUE . Fluorine-doped MnO₂ with oxygen vacancy for stabilizing Zn-ion batteries. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1671-1678. doi: 10.11862/CJIC.20240149
18. [18]
  Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
19. [19]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
20. [20]
  Zhaoyu Wen , Na Han , Yanguang Li . Recent Progress towards the Production of H₂O₂ by Electrochemical Two-Electron Oxygen Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(2): 2304001-0. doi: 10.3866/PKU.WHXB202304001

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(563)
HTML views(49)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return