Citation: Zhang Yaohuan, Wang Ruo, Zhang Tesen, Yan Weitao, Chen Yihong, Zhang Yanping, Zhou Muyang. Benzofuran-isatin-hydroxylimine/thiosemicarbazide hybrids: Design, synthesis and in vitro anti-mycobacterial activity evaluation[J]. Chinese Chemical Letters, ;2019, 30(3): 653-655. doi: 10.1016/j.cclet.2018.11.032 shu

Benzofuran-isatin-hydroxylimine/thiosemicarbazide hybrids: Design, synthesis and in vitro anti-mycobacterial activity evaluation

College of Chemistry, Fuzhou University, Fuzhou 350116, China

wangruo1201@gmail.com

Received Date: 9 November 2018
Revised Date: 29 November 2018
Accepted Date: 30 November 2018
Available Online: 30 March 2018

Figures(3)

A series of novel benzofuran-isatin-hydroxylimine/thiosemicarbazide hybrids were designed, synthesized and evaluated for their in vitro anti-TB activities against drug-sensitive MTB H₃₇Rv and MDR-TB isolates as well as cytotoxicity. All benzofuran-isatin-hydroxylimine/thiosemicarbazide hybrids exhibited considerable in vitro anti-mycobacterial activities against the tested three MTB strains, and all of them also showed acceptable cytotoxicity. The most active hybrid 7f was >4.8 and >51 folds more potent than the first line anti-TB agents RIF and INH against both drug-sensitive MTB H₃₇Rv and MDR-TB isolates, respectively. The results demonstrated the potential utility of benzofuran-isatin-hydroxylimine/-thiosemicarbazide hybrids as anti-TB agents.
- Benzofuran,
- Isatin,
- Hybrid compounds,
- Anti-mycobacterial,
- Anti-tubercular,
- Multi-drug resistant,
- Structure-activity relationship
1. [1]
  World Health Organization, Global Tuberculosis Report, 2018.
2. [2]
  World Health Organization, Global Tuberculosis Report, 2017.
3. [3]
  Y.L. Fan, J.B. Wu, X.W. Cheng, et al., Eur. J. Med. Chem. 146(2018) 554-563. doi: 10.1016/j.ejmech.2018.01.080
4. [4]
  S. Zhang, Z. Xu, C. Gao, et al., Eur. J. Med. Chem. 138(2017) 501-513. doi: 10.1016/j.ejmech.2017.06.051
5. [5]
  The Global Plan to End TB, 2016-2020, Geneva: Stop TB Partnership, 2015.
6. [6]
  World Health Organization, The End TB Strategy-global Strategy and Targets for Tuberculosis Prevention, Care and Control After, 2015.
7. [7]
  A. Baldisserotto, M. Demurtas, I. Lampronti, et al., Eur. J. Med. Chem.156(2018) 118-125. doi: 10.1016/j.ejmech.2018.07.001
8. [8]
  R.J. Nevagi, S.N. Dighe, S.N. Dighe, Eur. J. Med. Chem. 97(2015) 561-581. doi: 10.1016/j.ejmech.2014.10.085
9. [9]
  Z. Xu, S. Zhang, C. Gao, et al., Chin. Chem. Lett. 28(2017) 159-167. doi: 10.1016/j.cclet.2016.07.032
10. [10]
  H.K. Shamsuzzaman, Eur. J. Med. Chem. 97(2015) 483-504. doi: 10.1016/j.ejmech.2014.11.039
11. [11]
  W. Zhang, S.C. Lun, S.H. Wang, et al., J. Med. Chem. 61(2018) 791-803. doi: 10.1021/acs.jmedchem.7b01319
12. [12]
  A. Aggarwal, M.K. Parai, N. Shetty, et al., Cell 170(2017) 249-259. doi: 10.1016/j.cell.2017.06.025
13. [13]
  F. Gao, H. Yang, T.Y. Lu, et al., Eur. J. Med. Chem. 159(2018) 277-281. doi: 10.1016/j.ejmech.2018.09.049
14. [14]
  Z. Xu, X.F. Song, Y.Q. Hu, et al., Eur. J. Med. Chem. 138(2017) 66-71. doi: 10.1016/j.ejmech.2017.05.057
15. [15]
  Z. Xu, S. Zhang, X.F. Song, et al., Bioorg. Med. Chem. Lett. 27(2017) 3643-3646. doi: 10.1016/j.bmcl.2017.07.023
16. [16]
  Z. Xu, X.F. Song, M. Qiang, et al., J. Heterocyclic Chem. 54(2017) 3735-3741. doi: 10.1002/jhet.v54.6
17. [17]
  Z. Xu, X.F. Song, Y.Q. Hu, et al., J. Heterocyclic Chem. 55(2018) 77-82. doi: 10.1002/jhet.3004
18. [18]
  L.S. Feng, M.L. Liu, S. Zhang, et al., Eur. J. Med. Chem. 46(2011) 341-348. doi: 10.1016/j.ejmech.2010.11.023
19. [19]
  L.S. Feng, M.L. Liu, B. Wang, et al., Eur. J. Med. Chem. 45(2010) 3407-3412. doi: 10.1016/j.ejmech.2010.04.027
1. [1]
  Qin Cheng , Ming Huang , Qingqing Ye , Bangwei Deng , Fan Dong . Indium-based electrocatalysts for CO₂ reduction to C1 products. Chinese Chemical Letters, 2024, 35(6): 109112-. doi: 10.1016/j.cclet.2023.109112
2. [2]
  A-Yang Wang , Sheng-Hua Zhou , Mao-Yin Ran , Xin-Tao Wu , Hua Lin , Qi-Long Zhu . Regulating the key performance parameters for Hg-based IR NLO chalcogenides via bandgap engineering strategy. Chinese Chemical Letters, 2024, 35(10): 109377-. doi: 10.1016/j.cclet.2023.109377
3. [3]
  Haiyang Gu , Xiang Xu . Multicolor hybrid metal halides and anti-counterfeiting. Chinese Journal of Structural Chemistry, 2024, 43(9): 100352-100352. doi: 10.1016/j.cjsc.2024.100352
4. [4]
  Liping Zhao , Xixi Guo , Zhimeng Zhang , Xi Lu , Qingxuan Zeng , Tianyun Fan , Xintong Zhang , Fenbei Chen , Mengyi Xu , Min Yuan , Zhenjun Li , Jiandong Jiang , Jing Pang , Xuefu You , Yanxiang Wang , Danqing Song . Novel berberine derivatives as adjuvants in the battle against Acinetobacter baumannii: A promising strategy for combating multi-drug resistance. Chinese Chemical Letters, 2024, 35(10): 109506-. doi: 10.1016/j.cclet.2024.109506
5. [5]
  Wenhao Yan , Shuaiya Xue , Xuerui Zhao , Wei Zhang , Jian Li . Hexagonal boron nitride based slippery liquid infused porous surface with anti-corrosion, anti-contaminant and anti-icing properties for protecting magnesium alloy. Chinese Chemical Letters, 2024, 35(4): 109224-. doi: 10.1016/j.cclet.2023.109224
6. [6]
  Zengchao Guo , Weiwei Liu , Tengfei Liu , Jinpeng Wang , Hui Jiang , Xiaohui Liu , Yossi Weizmann , Xuemei Wang . Engineered exosome hybrid copper nanoscale antibiotics facilitate simultaneous self-assembly imaging and elimination of intracellular multidrug-resistant superbugs. Chinese Chemical Letters, 2024, 35(7): 109060-. doi: 10.1016/j.cclet.2023.109060
7. [7]
  Kun Zhang , Ni Dan , Dan-Dan Ren , Ruo-Yu Zhang , Xiaoyan Lu , Ya-Pan Wu , Li-Lei Zhang , Hong-Ru Fu , Dong-Sheng Li . A small D-A molecule with highly heat-resisting room temperature phosphorescence for white emission and anti-counterfeiting. Chinese Journal of Structural Chemistry, 2024, 43(3): 100244-100244. doi: 10.1016/j.cjsc.2024.100244
8. [8]
  Qiang Li , Jiangbo Fan , Hongkai Mu , Lin Chen , Yongzhen Yang , Shiping Yu . Nucleus-targeting orange-emissive carbon dots delivery adriamycin for enhanced anti-liver cancer therapy. Chinese Chemical Letters, 2024, 35(6): 108947-. doi: 10.1016/j.cclet.2023.108947
9. [9]
  Ji Zhang , Tong Zhang , Qiao An , Peng Zhang , Cai-Yan Tian , Chun-Mao Yuan , Ping Yi , Zhan-Xing Hu , Xiao-Jiang Hao . Five quinolizidine alkaloids with anti-tobacco mosaic virus activities from two species of Sophora. Chinese Chemical Letters, 2024, 35(6): 108927-. doi: 10.1016/j.cclet.2023.108927
10. [10]
  Xiaoning Li , Quanyu Shi , Meng Li , Ningxin Song , Yumeng Xiao , Huining Xiao , Tony D. James , Lei Feng . Functionalization of cellulose carbon dots with different elements (N, B and S) for mercury ion detection and anti-counterfeit applications. Chinese Chemical Letters, 2024, 35(7): 109021-. doi: 10.1016/j.cclet.2023.109021
11. [11]
  Changle Liu , Mingyuzhi Sun , Haoran Zhang , Xiqian Cao , Yuqing Li , Yingtang Zhou . All in one doubly pillared MXene membrane for excellent oil/water separation, pollutant removal, and anti-fouling performance. Chinese Journal of Structural Chemistry, 2024, 43(8): 100355-100355. doi: 10.1016/j.cjsc.2024.100355
12. [12]
  Jiayin Zhou , Depeng Liu , Longqiang Li , Min Qi , Guangqiang Yin , Tao Chen . Responsive organic room-temperature phosphorescence materials for spatial-time-resolved anti-counterfeiting. Chinese Chemical Letters, 2024, 35(11): 109929-. doi: 10.1016/j.cclet.2024.109929
13. [13]
  Kexin Yin , Jingren Yang , Yanwei Li , Qian Li , Xing Xu . Metal-free diatomaceous carbon-based catalyst for ultrafast and anti-interference Fenton-like oxidation. Chinese Chemical Letters, 2024, 35(12): 109847-. doi: 10.1016/j.cclet.2024.109847
14. [14]
  Jianwen Zhao , Shuai Wang , Shanshan Zhao , Liwei Chen , Fangang Meng , Xuelin Tian . A non-fluorinated liquid-like membrane with excellent anti-scaling performance for membrane distillation. Chinese Chemical Letters, 2025, 36(1): 109883-. doi: 10.1016/j.cclet.2024.109883
15. [15]
  Huaran Zhang , Yuting Huang , Yingjie Tang , Dekun Kong , Yi Zou . Genome mining of multi-substituted alkylresorcinols from a hybrid highly reducing- and type Ⅲ- polyketide pathway. Chinese Chemical Letters, 2024, 35(7): 108968-. doi: 10.1016/j.cclet.2023.108968
16. [16]
  Jiajia Wang , XinXin Ge , Yajing Xiang , Xiaoliang Qi , Ying Li , Hangbin Xu , Erya Cai , Chaofan Zhang , Yulong Lan , Xiaojing Chen , Yizuo Shi , Zhangping Li , Jianliang Shen . An ionic liquid functionalized sericin hydrogel for drug-resistant bacteria-infected diabetic wound healing. Chinese Chemical Letters, 2025, 36(2): 109819-. doi: 10.1016/j.cclet.2024.109819
17. [17]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
18. [18]
  Xiaoyao Ma , Jinling Zhang , Ge Fang , He Gao , Jie Gao , Li Fu , Yuanyuan Hou , Gang Bai . Förster resonance energy transfer reveals phillygenin and swertiamarin concurrently target AKT on different binding domains to increase the anti-inflammatory effect. Chinese Chemical Letters, 2024, 35(5): 108823-. doi: 10.1016/j.cclet.2023.108823
19. [19]
  Wenjia Wang , Xingyue He , Xiaojie Wang , Tiantian Zhao , Osamu Muraoka , Genzoh Tanabe , Weijia Xie , Tianjiao Zhou , Lei Xing , Qingri Jin , Hulin Jiang . Glutathione-depleted cyclodextrin pseudo-polyrotaxane nanoparticles for anti-inflammatory oxaliplatin (Ⅳ) prodrug delivery and enhanced colorectal cancer therapy. Chinese Chemical Letters, 2024, 35(4): 108656-. doi: 10.1016/j.cclet.2023.108656
20. [20]
  Xue-Jiao Wang , Jun-Li Xin , Hong Xiang , Ze-Yu Zhao , Yu-Hang He , Haibo Wang , Guangyao Mei , Yi-Cheng Mao , Juan Xiong , Jin-Feng Hu . Holotrichones A and B, potent anti-leukemic lindenane-type sesquiterpene trimers with unprecedented complex carbon skeletons from a rare Chloranthus species. Chinese Chemical Letters, 2024, 35(12): 109682-. doi: 10.1016/j.cclet.2024.109682

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(807)
HTML views(115)

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