Citation: Wang Hongjian, Lv Kai, Li Xiaoning, Wang Bo, Wang Apeng, Tao Zeyu, Geng Yunhe, Wang Bin, Huang Menghao, Liu Mingliang, Guo Huiyuan, Lu Yu. Design, synthesis and antimycobacterial activity of novel nitrobenzamide derivatives[J]. Chinese Chemical Letters, ;2019, 30(2): 413-416. doi: 10.1016/j.cclet.2018.08.005 shu

Design, synthesis and antimycobacterial activity of novel nitrobenzamide derivatives

Wang Hongjian ^a,1 ,
Lv Kai ^a,1 ,
Li Xiaoning ^a ,
Wang Bo ^a ,
Wang Apeng ^a ,
Tao Zeyu ^a ,
Geng Yunhe ^a ,
Wang Bin ^b ,
Huang Menghao ^c ,
Liu Mingliang ^a,*, ,
Guo Huiyuan ^a ,
Lu Yu ^b,*,

a.
Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing 100050, China
b.
Beijing Key Laboratory of Drug Resistance Tuberculosis Research, Department of Pharmacology, Beijing Tuberculosis and Thoracic Tumor Research Institute, Beijing Chest Hospital, Capital Medical University, Beijing 101149, China
c.
Division of Gastroenterology and Hepatology, Department of Medicine, Indiana University School of Medicine, Indianapolis 46202, United States

lmllyx@126.com

luyu4876@hotmail.com

Received Date: 9 July 2018
Revised Date: 9 August 2018
Accepted Date: 10 August 2018
Available Online: 13 February 2018

Figures(1)

We report herein the design and synthesis of a series of novel nitrobenzamide derivatives. Results reveal that many of them display considerable in vitro antitubercular activity. Four N-benzyl or N-(pyridine-2-yl)methyl 3, 5-dinitrobenzamides A6, A11, C1 and C4 have not only the same excellent MIC values of < 0.016 μg/mL against both drug-sensitive MTB strain H37Rv and two drug-resistant clinical isolates as PBTZ169 and the lead 1, but also acceptable safety indices (SI > 1500), opening a new direction for further development.
- Nitrobenzamides,
- Synthesis,
- Antimycobacterial activity,
- Tuberculosis
1. [1]
  Global Tuberculosis Report, World Health Organization, 2017, www.who.Int/tb/publications/lpa-mdr-diagnostics/en/
2. [2]
  N.Nayak, J.Ramprasad, U.Dalimba, et al., Chin.Chem.Lett.27(2016) 365-369. doi: 10.1016/j.cclet.2016.01.015
3. [3]
  A.Wang, Y.Yang, J.Yang, et al., Bioorg.Med.Chem.26(2018) 2073-2084. doi: 10.1016/j.bmc.2018.03.004
4. [4]
  Z.Xu, S.Zhang, C.Gao, et al., Chin.Chem.Lett.28(2017) 159-167. doi: 10.1016/j.cclet.2016.07.032
5. [5]
  K.Lv, L.Li, B.Wang, et al., Eur.J.Med.Chem.137(2017) 117-125. doi: 10.1016/j.ejmech.2017.05.044
6. [6]
  R.S.Wallis, M.Maeurer, P.Mwaba, et al., Lancet Infect.Dis.16(2016) 34-46. doi: 10.1016/S1473-3099(16)00070-0
7. [7]
  A.K.Kakkar, N.Dahiya, Tuberculosis (Edinb.)94(2014) 357-362. doi: 10.1016/j.tube.2014.04.001
8. [8]
  M.T.Gler, V.Skripconoka, E.Sanchez-Garavito, et al., N.Engl.J.Med.366(2012) 2151-2160. doi: 10.1056/NEJMoa1112433
9. [9]
  D.T.Hoagland, J.Liu, R.B.Lee, R.E.Lee, Adv.Drug Deliv.Rev.102(2016) 55-72. doi: 10.1016/j.addr.2016.04.026
10. [10]
  Beena, D.S.Rawat, Med.Res.Rev.33(2013) 693-764. doi: 10.1002/med.2013.33.issue-4
11. [11]
  G.Manina, M.R.Pasca, S.Buroni, E.de Rossi, G.Riccardi, Curr.Med.Chem.17(2010) 3099-3108. doi: 10.2174/092986710791959693
12. [12]
  G.Riccardi, M.R.Pasca, L.R.Chiarelli, et al., Appl.Microbiol.Biotechnol.97(2013) 8841-8848. doi: 10.1007/s00253-013-5218-x
13. [13]
  M.Brecik, I.Centarova, R.Mukherjee, et al., ACS Chem.Biol.10(2015) 1631-1636. doi: 10.1021/acschembio.5b00237
14. [14]
  P.K.Crellin, R.Brammananth, R.L.Coppel, PloS One 6(2011) e16869. doi: 10.1371/journal.pone.0016869
15. [15]
  S.A.Stanley, S.S.Grant, T.Kawate, et al., ACS Chem.Biol.7(2012) 1377-1384. doi: 10.1021/cb300151m
16. [16]
  F.Wang, D.Sambandan, R.Halder, et al., Proc.Natl.Acad.Sci.U.S.A.110(2013) 2510-2517. doi: 10.1073/pnas.1309171110
17. [17]
  M.Naik, V.Humnabadkar, S.J.Tantry, et al., J.Med.Chem.57(2014) 5419-5434. doi: 10.1021/jm5005978
18. [18]
  M.Panda, S.Ramachandran, V.Ramachandran, et al., J.Med.Chem.57(2014) 4761-4771. doi: 10.1021/jm5002937
19. [19]
  P.S.Shirude, R.Shandil, C.Sadler, et al., J.Med.Chem.56(2013) 9701-9708. doi: 10.1021/jm401382v
20. [20]
  T.Christophe, M.Jackson, H.K.Jeon, et al., PLoS Pathog.5(2009) e100645.
21. [21]
  K.J.Schaper, M.Pickert, A.W.Frahm, Archiv der Pharmazie 332(1999) 91-102.
22. [22]
  C.Trefzer, M.Rengifo-Gonzalez, M.J.Hinner, et al., J.Am.Chem.Soc.132(2010) 13663-13665. doi: 10.1021/ja106357w
23. [23]
  V.Makarov, G.Manina, K.Mikusova, et al., Science 324(2009) 801-804. doi: 10.1126/science.1171583
24. [24]
  V.Makarov, B.Lechartier, M.Zhang, et al., EMBO Mol.Med.6(2014) 372-383. doi: 10.1002/emmm.201303575
25. [25]
  A.L.D.L.Ribeiro, G.Degiacomi, F.Ewann, et al., PloS One 6(2011) e26675. doi: 10.1371/journal.pone.0026675
26. [26]
  T.Karoli, B.Becker, J.Zuegg, et al., J.Med.Chem.55(2012) 7940-7944. doi: 10.1021/jm3008882
27. [27]
  R.Zhang, K.Lv, B.Wang, et al., RSC Adv.7(2017) 1480-1483. doi: 10.1039/C6RA25712G
28. [28]
  K.Lv, X.You, B.Wang, et al., ACS Med.Chem.Lett.8(2017) 636-641. doi: 10.1021/acsmedchemlett.7b00106
29. [29]
  K.Lv, Z.Tao, Q.Liu, et al., Eur.J.Med.Chem.151(2018) 1-8. doi: 10.1016/j.ejmech.2018.03.060
30. [30]
  L.Li, K.Lv, Y.Yang, et al., ACS Med.Chem.Lett.9(2018) 741-745. doi: 10.1021/acsmedchemlett.8b00177
31. [31]
  L.Collins, S.G.Franzblau, Antimicrob.Agents Chemother.41(1997) 1004-1009. doi: 10.1128/AAC.41.5.1004
32. [32]
  Y.Lu, M.Zheng, B.Wang, etal., Antimicrob.AgentsChemother.55(2011) 5185-5193. doi: 10.1128/AAC.00699-11
33. [33]
  C.A.Lipinski, F.Lombardo, B.W.Dominy, P.J.Feeney, Adv.Drug Deliv.Rev.46(2001) 3-26. doi: 10.1016/S0169-409X(00)00129-0
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