Citation: Xu Zhi, Zhang Shu, Gao Chuan, Fan Jing, Zhao Feng, Lv Zao-Sheng, Feng Lian-Shun. Isatin hybrids and their anti-tuberculosis activity[J]. Chinese Chemical Letters, ;2017, 28(2): 159-167. doi: 10.1016/j.cclet.2016.07.032 shu

Isatin hybrids and their anti-tuberculosis activity

Xu Zhi ^a,1 ,
Zhang Shu ^b,1 ,
Gao Chuan ^c ,
Fan Jing ^d ,
Zhao Feng ^c ,
Lv Zao-Sheng ^a,, ,
Feng Lian-Shun ^a,c,e,,

a.
Wuhan University of Science and Technology, 430081, China
b.
Pony Testing International Group, Wuhan 430034, China
c.
WuXi AppTec, Wuhan 430075, China
d.
Hengshui University, Hengshui 053000, China
e.
Synthetic and Functional Biomolecules Center, Peking University, Beijing 100871, China

Corresponding author: Lv Zao-Sheng, lzs1961@yahoo.com.cn Feng Lian-Shun, ochemistry@163.com

Received Date: 16 May 2016
Revised Date: 12 July 2016
Accepted Date: 17 July 2016
Available Online: 9 February 2016

Figures(17)

Tuberculosis (TB) is one of the most common and even fatal infectious diseases known to mankind. Millions of new cases are reported every year over the world, and one-third of the world's population is potentially infected with mycobacteria tuberculosis (MTB). Research to develop novel anti-TB drugs led to the identification of several isatin-based antimycobacterial agents, among which a number of potential candidates displayed excellent antimycobacterial activity and were found to be free of cytotoxicity. This review outlines the advances in the application of isatin hybrids as antimycobacterial agents and the critical aspects of design and structure-activity relationship of these derivatives.
- Isatin hybrids,
- Mycobacterium tuberculosis,
- Quinolone,
- Structure-activity relationship,
- Review
1. [1]
  L.S. Feng, M.L. Liu, B. Wang. Synthesis and in vitro antimycobacterial activity of balofloxacin ethylene isatin derivatives[J]. Eur. J. Med. Chem., 2010,45:3407-3412. doi: 10.1016/j.ejmech.2010.04.027
2. [2]
  T. Aboul-Fadl, F.A.S. Bin-Jubair, O. Aboul-Wafa. Schiff bases of indoline-2,3-dione (isatin) derivatives and nalidixic acid carbohydrazide, synthesis, antitubercular activity and pharmacophoric model building[J]. Eur. J. Med. Chem., 2010,45:4578-4586. doi: 10.1016/j.ejmech.2010.07.020
3. [3]
  J. Crofton, P. Chaulet, D. Maher, Guidelines for the Management of Drugresistant Tuberculosis:WHO/TB/96-210(Rev. 1), World Health Organization, Geneva, 1997.
4. [4]
  C. Viegas-Junior, A. Danuello, V. da Silva Bolzani, E.J. Barreiro, C.A.M. Fraga. Molecular hybridization:a useful tool in the design of new drug prototypes[J]. Curr. Med. Chem., 2007,14:1829-1852. doi: 10.2174/092986707781058805
5. [5]
  A. González, J. Quirante, J. Nieto. Isatin derivatives, a novel class of transthyretin fibrillogenesis inhibitors[J]. Bioorg. Med. Chem. Lett., 2009,19:5270-5273. doi: 10.1016/j.bmcl.2009.03.004
6. [6]
  T. Aboul-Fadl, F.A.H. Mohammed, E.A.S. Hassan. Synthesis, antitubercular activity and pharmacokinetic studies of some schiff bases derived from 1-alkylisatin and isonicotinic acid hydrazide (inh)[J]. Arch. Pharm. Res., 2003,26:778-784. doi: 10.1007/BF02980020
7. [7]
  S.K. Sridhar, M. Saravanan, A. Ramesh. Synthesis and antibacterial screening of hydrazones, Schiff and Mannich bases of isatin derivatives[J]. Eur. J. Med. Chem., 2001,36:615-625. doi: 10.1016/S0223-5234(01)01255-7
8. [8]
  E. Piscopo, M.V. Diurno, R. Gogliadi, M. Cucciniello, G. Veneruso. Studies on heterocyclic compounds:indol-2,3-dione derivatives. VII. Variously substituted hydrazones with antimicrobial activity[J]. Boll. Soc. Ital. Biol. Sper., 1987,63:827-832.
9. [9]
  D. Sriram, T.R. Bal, P. Yogeeswari. Newer aminopyrimidinimino isatin analogues as non-nucleoside HIV-1 reverse transcriptase inhibitors for HIV and other opportunistic infections of AIDS:design, synthesis and biological evaluation[J]. Farmaco, 2005,60:377-384. doi: 10.1016/j.farmac.2005.03.005
10. [10]
  N. Karalı, A. Gürsoy, F. Kandemirli. Synthesis and structure-antituberculosis activity relationship of 1H-indole-2,3-dione derivatives[J]. Bioorg. Med. Chem., 2007,15:5888-5904. doi: 10.1016/j.bmc.2007.05.063
11. [11]
  D. Sriram, A. Aubry, P. Yogeeswari, L.M. Fisher. Gatifloxacin derivatives:synthesis, antimycobacterial activities, and inhibition of Mycobacterium tuberculosis DNA gyrase[J]. Bioorg. Med. Chem. Lett., 2006,16:2982-2985. doi: 10.1016/j.bmcl.2006.02.065
12. [12]
  D. Sriram, P. Yogeeswari, J.S. Basha, D.R. Radha, V. Nagaraja. Synthesis and antimycobacterial evaluation of various 7-substituted ciprofloxacin derivatives[J]. Bioorg. Med. Chem., 2005,13:5774-5778. doi: 10.1016/j.bmc.2005.05.063
13. [13]
  S.N. Pandeya, D. Sriram, P. Yogeeswari, S. Ananthan. Antituberculous activity of norfloxacin mannich bases with isatin derivatives[J]. Chemotherapy, 2001,47:266-269. doi: 10.1159/000048533
14. [14]
  S. Talath, B.A. Bhongade. Synthesis, antimicrobial and anticancer studies of isatin derivatives of sparfloxacin[J]. Am. PharmTech Res., 2013,3:570-581.
15. [15]
  B.Y. Zhao, R. Pine, J. Domagala, K. Drlica. Fluoroquinolone action against clinical isolates of Mycobacterium tuberculosis:effects of a C-8 methoxyl group on survival in liquid media and in human macrophages[J]. Antimicrob. Agents Chemother., 1999,43:661-666.
16. [16]
  L.S. Feng, M.L. Liu, S. Zhang. Synthesis and in vitro antimycobacterial activity of 8-OCH₃ ciprofloxacin methylene and ethylene isatin derivatives[J]. Eur. J. Med. Chem., 2011,46:341-348. doi: 10.1016/j.ejmech.2010.11.023
17. [17]
  L.S. Feng, M.L. Liu, S. Wang. Synthesis and in vitro antimycobacterial activity of moxifloxacin methylene and ethylene isatin derivatives[J]. Chem. Res. Chin. Univ., 2012,28:61-66.
18. [18]
  Z.L. Wan, M.L. Liu, L.S. Feng. Synthesis and in vitro antimycobacterial activity of gatifloxacin ethylene isatin derivatives[J]. Chin. J. Antibiot., 2011,36:37-43.
19. [19]
  T.R. Bal, B. Anand, P. Yogeeswari, D. Sriram. Synthesis and evaluation of antiHIV activity of isatin β-thiosemicarbazone derivatives[J]. Bioorg. Med. Chem. Lett., 2005,15:4451-4455. doi: 10.1016/j.bmcl.2005.07.046
20. [20]
  D. Sriram, T.R. Bal, P. Yogeeswari. Aminopyrimidinimino isatin analogues:design of novel non-nucleoside HIV-1 reverse transcriptase inhibitors with broad-spectrum[J]. J. Pharm. Pharm. Sci., 2005,8:565-577.
21. [21]
  D. Banerjee, P. Yogeeswari, P. Bhat. Novel isatinyl thiosemicarbazones derivatives as potential molecule to combat HIV-TB co-infection[J]. Eur. J. Med. Chem., 2011,46:106-121. doi: 10.1016/j.ejmech.2010.10.020
22. [22]
  D. Sriram, P. Yogeeswari, G. Gopal. Synthesis, anti-HIV and antitubercular activities of lamivudine prodrugs[J]. Eur. J. Med. Chem., 2005,40:1373-1376. doi: 10.1016/j.ejmech.2005.07.006
23. [23]
  N. Joy, B. Mathew. Molecular hybridization and preclinical evaluation of imines from para-substituted 4-phenyl 2-amino thiazole incorporated with isatin analogues as antitubercular agents[J]. Anti-Infect. Agents, 2015,13:60-64. doi: 10.2174/2211352512666140905232639
24. [24]
  R.D. Dighe, S.S. Rohom, P.D. Dighe, M.R. Shiradkar. Condensed bridgehead nitrogen heterocyclic systems:synthesis and evaluation of isatinyl thiazole derivatives as anti-Mycobacterium tuberculosis agents and dTDP-rhamnose inhibitors[J]. Der Pharma Chem., 2011,3:418-432.
25. [25]
  V.U. Jeankumar, R. Alokam, J.P. Sridevi. Discovery and structure optimization of a series of isatin derivatives as Mycobacterium tuberculosis chorismate mutase inhibitors[J]. Chem. Biol. Drug Des., 2014,83:498-506. doi: 10.1111/cbdd.2014.83.issue-4
26. [26]
  T.N. Akhaja, J.P. Raval. Design, synthesis, in vitro evaluation of tetrahydropyrimidine-isatin hybrids as potential antibacterial, antifungal and anti-tubercular agents[J]. Chin. Chem. Lett., 2012,23:446-449. doi: 10.1016/j.cclet.2012.01.040
27. [27]
  T.N. Akhaja, J.P. Raval. Design, synthesis and in vitro evaluation of tetrahydropyrimidine-isatin hybrids as potential antitubercular and antimalarial agents[J]. Chin. Chem. Lett., 2012,23:785-788. doi: 10.1016/j.cclet.2012.05.004
28. [28]
  T.N. Akhaja, J.P. Raval, 1,3-Dihydro-2H-indol-2-ones derivatives:design, synthesis, in vitro antibacterial, antifungal and antitubercular study, Eur. J. Med. Chem. 46(2011) 5573-5579.
29. [29]
  A. Kamal, A.A. Shaik, R. Sinha, J.S. Yadav, S.K. Arora. Antitubercular agents. Part 2:new thiolactomycin analogues active against Mycobacterium tuberculosis[J]. Bioorg. Med. Chem. Lett., 2005,15:1927-1929. doi: 10.1016/j.bmcl.2005.01.084
30. [30]
  R.H. Hans, I.J.F. Wiid, P.D. van Helden. Novel thiolactone-isatin hybrids as potential antimalarial and antitubercular agents[J]. Bioorg. Med. Chem. Lett., 2011,21:2055-2058. doi: 10.1016/j.bmcl.2011.02.008
31. [31]
  W.M. Eldehna, M. Fares, M.M. Abdel-Aziz, H.A. Abdel-Aziz. Design, synthesis and antitubercular activity of certain nicotinic acid hydrazides[J]. Molecules, 2015,20:8800-8815. doi: 10.3390/molecules20058800
32. [32]
  J. Sandy, A. Mushtaq, A. Kawamura. The structure of arylamine Nacetyltransferase from Mycobacterium smegmatis-an enzyme which inactivates the anti-tubercular drug, isoniazid[J]. J. Mol. Biol., 2002,318:1071-1083. doi: 10.1016/S0022-2836(02)00141-9
33. [33]
  M.A. Hussein, T. Aboul-Fadl, A. Hussein. Synthesis and antitubercular activity of some mannich bases derived from isatin isonicotinic acid hydrazone[J]. Bull. Pharm. Sci.:Assiut Univ., 2005,28:131-136.
34. [34]
  K. Arul, K.S. Sunisha. In-silico design, synthesis and in vitro anticancer and antitubercular activity of novel azetidinone containing isatin derivatives[J]. Int. J. Pharm. Pharm. Sci., 2014,16:506-513.
35. [35]
  S.K. Gupta, S.S. Pancholi. Synthesis and evaluation of antitubercular activity of some thiobenzimidazolyl derivatives[J]. Der Pharma Chem., 2011,3:274-279.
36. [36]
  A.H. Diacon, A. Pym, M. Grobush. The diarylquinoline TMC207 for multidrug-resistant tuberculosis[J]. N. Engl. J. Med., 2009,360:2397-2405. doi: 10.1056/NEJMoa0808427
37. [37]
  R. Raj, C. Biot, S. Carrère-Kremer, L. Kremer, et al., 7-Chloroquinoline-isatin conjugates:antimalarial, antitubercular, and cytotoxic evaluation, Chem. Biol. Drug Des. 83(2014) 622-629.
38. [38]
  M.T. Cocco, C. Congiu, V. Onnis, M.L. Pellerano, A. De Logu. Synthesis and antimycobacterial activity of new S-alkylisothiosemicarbazone derivatives[J]. Bioorg. Med. Chem., 2002,10:501-506. doi: 10.1016/S0968-0896(01)00310-8
39. [39]
  L.E. Bermudez, R. Reynolds, P. Kolonoski. Thiosemicarbazole (thiacetazone-like) compound with activity against Mycobacterium avium in mice[J]. Antimicrob. Agents Chemother., 2003,47:2685-2687. doi: 10.1128/AAC.47.8.2685-2687.2003
40. [40]
  A. De Logu, M. Saddi, V. Onnis, et al., In vitro antimycobacterial activity of newly synthesised S-alkylisothiosemicarbazone derivatives and synergistic interactions in combination with rifamycins against Mycobacterium avium, Int. J. Antimicrob. Agents 26(2005) 28-32.
41. [41]
  N. Karalı. Synthesis and primary cytotoxicity evaluation of new 5-nitroindole-2,3-dione derivatives[J]. Eur. J. Med. Chem., 2002,37:909-918. doi: 10.1016/S0223-5234(02)01416-2
42. [42]
  N. TerzioÐlu, N. Karalı, A. Gürsoy. Synthesis and primaryantiviral activity evaluation of 3-hydrazono-5-nitro-2-indolinone derivatives[J]. ARKIVOC, 2006,1:109-118.
43. [43]
  Ö. Güzel, N. Karalı, A. Salman. Synthesis and antituberculosis activity of 5-methyl/trifluoromethoxy-1H-indole-2,3-dione-3-thiosemicarbazone derivatives[J]. Bioorg. Med. Chem., 2008,16:8976-8987. doi: 10.1016/j.bmc.2008.08.050
44. [44]
  M. Shahlaei, A. Fassihi, A. Nezami, QSAR study of some 5-methyl/trifluoromethoxy-1H-indole-2,3-dione-3-thiosemicarbazone derivatives as anti-tubercular agents, Res. Pharm. Sci. 4(2009) 123-131.
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