Isoniazid: The magic molecule

Medicinal Chemistry Research

Volumn 21, Issue 12, 2012, Pages 3940-3957

  Judge, Vikramjeet ^a   Narasimhan, Balasubramanian ^b   Ahuja, Munish ^a  

^a GURU JAMBHESHWAR UNIVERSITY OF SCIENCE AND TECHNOLOGY   (India)

^b MAHARSHI DAYANAND UNIVERSITY   (India)

Author keywords

Anti bacterial; Anti fungal; Anti microbial; Anti mycobacterial; Isoniazid

Indexed keywords

ANALGESIC AGENT; ANTIINFECTIVE AGENT; ANTIINFLAMMATORY AGENT; ANTIVIRUS AGENT; HYDRAZIDE DERIVATIVE; HYDRAZONE DERIVATIVE; ISONIAZID; ISONIAZID DERIVATIVE; ISONICOTINICACID HYDRAZIDE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ANALGESIC ACTIVITY; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTIVIRAL ACTIVITY; BIOLOGICAL ACTIVITY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; MOLECULAR DYNAMICS; MULTIDRUG RESISTANCE; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REVIEW; TUBERCULOSIS;

EID: 84881191270     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9948-y     Document Type: Review

References (54)

1. Ali MA, Yar MS, Kumar M, Pandian GS (2007) Synthesis and antitubercular activity of substituted novel pyrazoline derivatives. Nat Prod Res 21(7):575-579
2. Almeida da Silva PE, Ramos DF, Bonacorso HF, Iglesia AIDL, Oliveira MR, Coelho T, Navarini J, Morbidoni HR, Zanatta N, Martins MAP (2008) Synthesis and in vitro antimycobacterial activity of 3-substituted-5-hydroxy-5-trifluoro[chloro] methyl-4,5-dihydro-1H–1-(isonicotinoyl)pyrazoles. Int J Antimicrob Agents 32:139–144
3. Andrade CH, Salum LB, Castilho MS, Pasqualoto KFM, Ferreira EI, Andricopulo AD (2008) Fragment-based and classical quantitative structure–activity relationships for a series of hydrazides as antituberculosis agents. Mol Divers 12:47–59
4. Aparna V, Jeevan J, Ravi M, Desiraju GR, Gopalakrishnan B (2006) 3D-QSAR studies on antitubercular thymidine monophosphate kinase inhibitors based on different alignment methods. Bioorg Med Chem Lett 16:1014–1020
5. Bayrak H, Demirbas A, Demirbas N, Karaoglu SA (2009a) Synthesis of some new 1,2,4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activities. Eur J Med Chem 44:4362–4366
6. Bayrak H, Demirbas A, Karaoglu SA, Demirbas N (2009b) Synthesis of some new 1,2,4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities. Eur J Med Chem 44:1057–1066
7. Bottari B, Maccari R, Monforte F, Ottana R, Rotondo E, Vigorita MG (2001) Antimycobacterial in vitro activity of Cobalt(II) isonicotinoylhydrazone complexes. Part 10. Bioorg Med Chem Lett 11:301–303
8. Carvalho SA, da Silva EF, de Souza MVN, Lourenco MCS, Vicente FR (2008) Synthesis and antimycobacterial evaluation of new trans-cinnamic acid hydrazide derivatives. Bioorg Med Chem Lett 18:538–541
9. Cocco MT, Congiu C, Onnis V, Pusceddu MC, Schivo ML, De Logu A (1999) Synthesis and antimycobacterial activity of some isonicotinoylhydrazones. Eur J Med Chem 34:1071–1076
10. Gilani SJ, Khan SA, Siddiqui N (2010) Synthesis and pharmacological evaluation of condensed heterocyclic 6-substituted 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole and 1,3,4-oxadiazole derivatives of isoniazid. Bioorg Med Chem Lett 20:4762–4765
11. Hearn MJ, Cynamon MH (2003) In vitro and in vivo activities of acylated derivatives of isoniazid against Mycobacterium tuberculosis. Drug Design Discov 18(4):103–108
12. Hearn MJ, Cynamon MH, Chen MF, Coppins R, Davis J, Kang HJ, Noble A, Tu-Sekine B, Terrot MS, Trombino D, Thai M, Webster ER, Wilson R (2009) Preparation and antitubercular activities in vitro and in vivo of novel Schiff bases of isoniazid. Eur J Med Chem 44:4169–4178
13. Imramovsky A, Polanc S, Jarmila Vinsova J, Kocevar M, Jampilek J, Reckovac Z, Kaustova J (2007) A new modification of anti-tubercular active molecules. Bioorgan Med Chem 15:2551–2559
14. Jaju S, Palkar M, Maddi V, Ronad P, Mamledesai S, Satyanarayana D, Ghatole M (2009) Synthesis and antimycobacterial activity of a novel series of isonicotinylhydrazide derivatives. Arch Pharm Chem Life Sci 342:723–731
15. Johnson K, Schultz PG (1994) Mechanistic studies of the oxidation of isoniazid by catalase-peroxidase from Mycobacterium tuberculosis. J Am Chem Soc 116:7425–7426
16. Joshi S, Khosla N, Tiwari P (2004) In vitro study of some medicinally important Mannich bases derived from antitubercular agent. Bioorgan Med Chem 12:571–576
17. Judge V, Narasimhan B, Ahuja M, Sriram D, Yogeeswari P, De Clercq E, Pannecouque C, Balzarini J (2011a) Isonicotinic acid hydrazide derivatives: synthesis, antimicrobial activity and QSAR studies. Med Chem Res. doi: 10.1007/s00044-011-9662-9
18. Judge V, Narasimhan B, Ahuja M, Sriram D, Yogeeswari P, De Clercq E, Pannecouque C, Balzarini J (2011b) Synthesis, antimycobacterial, antiviral, antimicrobial activity and QSAR studies of Isonicotinic acid-1-(substituted phenyl)-ethylidene/cycloheptylidene hydrazides. Med Chem Res. doi: 10.1007/s00044-011-9705-2 (in press)
19. Judge V, Narasimhan B, Ahuja M, Sriram D, Yogeeswari P (2011c) Isonicotinic acid hydrazide derivatives: synthesis, antimycobacterial, antiviral, antimicrobial activity and QSAR studies. Lett Drug Design Discov 8(9): 792-810(19)
20. Judge V, Narasimhan B, Ahuja M (2011d) Topological models for the prediction of antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines. Med Chem Res. doi: 10.1007/s00044-011-9645-x (in press)
21. Khasnobis S, Escuyer VE, Chatterjee D (2002) Emerging therapeutic targets in tuberculosis: post genomic era. Expert Opin Ther Targets 6(1):21–40
22. Kini S, Gandhi AM (2008) Novel 2-pyrazoline derivatives as potential antibacterial and antifungal agents. Indian J Pharm Sci 70(1):105–108
23. Klopman G, Fercu D, Jacob J (1996) Computer-aided study of the relationship between structure and antituberculosis activity of a series of isoniazid derivatives. Chem Phys 204:181–193
24. Kumar A, Patel G, Menon SK (2009) Fullerene isoniazid conjugate—a tuberculostat with increased lipophilicity: synthesis and evaluation of antimycobacterial activity. Chem Biol Drug Des 73:553–557
25. Lourenco MCDS, Ferreira MDL, Nora de Souza MV, Peralta MA, Vasconcelos TRA, Henriques MGMO (2008) Synthesis and anti-mycobacterial activity of (E)-N’-(monosubstituted-benzylidene) isonicotinohydrazide derivatives. Eur J Med Chem 43:1344–1347
26. Maccari R, Ottana R, Monforte F, Vigorita MG (2002) In vitro antimycobacterial activities of 2'-monosubstituted isonicotinohydrazides and their cyanoborane adducts. Antimicrob Agents Chemother 46(2):294–299
27. Maccari R, Ottana R, Bottari B, Rotondo E, Vigorita MG (2004) In vitro advanced antimycobacterial screening of Cobalt(II) and Copper(II) complexes of fluorinated isonicotinoylhydrazones. Bioorg Med Chem Lett 14:5731–5733
28. Maccari R, Ottana R, Vigorita MG (2005) In vitro advanced antimycobacterial screening of isoniazid-related hydrazones, hydrazides and cyanoboranes: part 14. Bioorg Med Chem Lett 15:2509–2513
29. Mamolo MG, Zampieri D, Falagiani V, Vio L, Banfi E (2001) Synthesis and antimycobacterial activity of 5-aryl-1-isonicotinoyl-3-(pyridin-2-yl)-4,5-dihydro-1H-pyrazole derivatives. IL Farmaco 56:593–599
30. Merlani MI, Kemertelidze EP, Papadopoulos K, Men’shova NI (2004) Some derivatives of 5a-ketosteroid hydrazones: synthesis from tigogenin and antituberculosis activity. Russian J Bioorg Chem 30(5):497–501
31. Mohamad S, Ibrahim P, Sadikun A (2004) Susceptibility of Mycobacterium tuberculosis to isoniazid and its derivative, 1-isonicotinyl-2-nonanoyl hydrazine: investigation at cellular level. Tuberculosis 84:56–62
32. Navarrete-Vazquez G, Molina-Salinas GM, Duarte-Fajardo ZV, Vargas-Villarreal J, Estrada-Soto S, Gonzalez-Salazar F, Hernandez-Nunez E, Said-Fernandez S (2007) Synthesis and antimycobacterial activity of 4-(5-substituted-1,3,4-oxadiazol-2-yl)pyridines. Bioorgan Med Chem 15:5502–5508
33. Nayyar A, Monga V, Malde A, Coutinho E, Jain R (2007) Synthesis and anti-tuberculosis activity, and 3D-QSAR study of 4-(admantan-1-yl)-2-substituted quinolines. Bioorgan Med Chem 15:626–640
34. Nunn CM, Djordjevic S, Hillas PJ, Nishida CR, Ortiz de Montellano PR (2002) The crystal structure of Mycobacterium tuberculosis alkylhydroperoxidase AhpD, a potential target for antitubercular drug design. J Biol Chem 277(22):20034–20040
35. Rando DG, Doriguetto AC, Tomich de Paula, da Silva CH, Ellena J, Sato DN, Leite CQF, Varanda EA, Ferreira EI (2006) A duplicated nitrotienyl derivative with antimycobacterial activity: synthesis, X-ray crystallography, biological and mutagenic activity tests. Eur J Med Chem 41:1196–1200
36. Rastogi N, Goh KS (1990) Action of 1-isonicotinyl-2-palmitoyl hydrazine against the Mycobacterium avium complex and enhancement of its activity by m-fluorophenylalanine. Antimicrob Agents Chemother 34(11):2061–2064
37. Rodriguez-Arguelles MC, Mosquera-Vazquez S, Touron-Touceda P, Sanmartin-Matalobos J, Garcia-Deibe AM, Belicchi-Ferrari M, Pelosi G, Pelizzi C, Zani F (2007) Complexes of 2-thiophenecarbonyl and isonicotinoyl hydrazones of 3-(N-methyl)isatin. A study of their antimicrobial activity. J Inorg Biochem 101:138–147
38. Sankar C, Pandiarajan K (2010) Synthesis and anti-tubercular and antimicrobial activities of some 2r,4c-diaryl-3-azabicyclo[3.3.1]nonan-9-one N-isonicotinoylhydrazone derivatives. Eur J Med Chem 45:5480–5485
39. Shaharyar M, Siddiqui AA, Ali MA, Sriram D, Yogeeswari P (2006) Synthesis and in vitro antimycobacterial activity of N 1-nicotinoyl-3-(4'-hydroxy-3'-methyl phenyl)-5-(substituted phenyl)-2-pyrazolines. Bioorg Med Chem Lett 16:3947–3949
40. Shoeb HA, Bowman BU Jr., Ottolenghi AC, Merola AJ (1985) Peroxidase mediated oxidation of isoniazid. Antimicrob Agents Chemother 27:399–403
41. Sinha N, Jain S, Tilekar A, Upadhayaya RS, Kishore N, Jana GH, Arora SK (2005) Synthesis of isonicotinic acid N'-arylidene-N-[2-oxo-2-(4-aryl-piperazin-1-yl)-ethyl]-hydrazides as antituberculosis agents. Bioorg Med Chem Lett 15:1573–1576
42. Sriram D, Yogeeswari P, Madhu K (2005) Synthesis and in vitro and in vivo antimycobacterial activity of isonicotinoyl hydrazones. Bioorg Med Chem Lett 15:4502–4505
43. Sriram D, Yogeeswari P, Madhu K (2006) Synthesis and in vitro antitubercular activity of some 1-[(4-sub)phenyl]-3-(4-{1-[(pyridine-4-carbonyl)hydrazono]ethyl}phenyl)thiourea. Bioorg Med Chem Lett 16:876–878
44. Sriram D, Yogeeswari P, Priya DY (2009) Antimycobacterial activity of novel N-(substituted)-2-isonicotinoylhydrazinocarbothioamide endowed with high activity towards isoniazid resistant tuberculosis. Biomed Pharmcother 63:36–39
45. Stanton MG, Stauffer SR, Gregro AR, Steinbeiser M, Nantermet P, Sankaranarayanan S, Price EA, Wu G, Crouthamel MC, Ellis J, Lai MT, Espeseth AS, Shi XP, Jin L, Colussi D, Pietrak B, Huang Q, Xu M, Simon AJ, Graham SL, Vacca JP, Selnick H (2007) Discovery of isonicotinamide derived ß-Secretase inhibitors: in vivo reduction of ß-Amyloid. J Med Chem 50:3431–3433
46. Swamy BN, Suma TK, Rao GV, Reddy GC (2007) Synthesis of isonicotinoyl hydrazones from anacardic acid and their in vitro activity against Mycobacterium smegmatis. Eur J Med Chem 42:420–424
47. Szymanska E, Kiec-Kononowicz K (2002) Antimycobacterial activity of 5-arylidene aromatic derivatives of hydantoin. IL Farmaco 57:355–362
48. Torres E, Moreno E, Ancizu S, Barea C, Galiano S, Aldana I, Monge A, Perez-Silanes S (2011) New 1,4-di-N-oxide-quinoxaline-2-ylmethylene isonicotinic acid hydrazide derivatives as anti-Mycobacterium tuberculosis agents. Bioorg Med Chem Lett 21:3699–3703
49. Vavrikova E, Polanc S, Kocevar M, Kosmrlj J, Horvati K, Bosze S, Stolarikova J, Imramovsky A, Vinsova J (2011) New series of isoniazid hydrazones linked with electron-withdrawing substituents. Eur J Med Chem 46:5902–5909
50. Ventura C, Martins F (2008) Application of quantitative structure activity relationships to the modeling of antitubercular compounds. 1. The hydrazide family. J Med Chem 51:612–624
51. Wahab HA, Choong YS, Ibrahim P, Sadikun A, Scior T (2009) Elucidating isoniazid resistance using molecular modeling. J Chem Inf Model 49:97–107
52. Yar MS, Siddiqui AA, Ali MA (2007) Synthesis and antimycobacterial activity of novel heterocycles. J Serb Chem Soc 72(1):5–11
53. Zhang Y, Young DB (1993) Molecular mechanisms of isoniazid: a drug at the front line of tuberculosis control. Trends Microbiol 1(3):109–113
54. Zhang P, Heym B, Allen B, Young D, Cole ST (1992) The catalase-peroxidase gene and isoniazid resistance to Mycobacterium tuberculosis. Nature 358:591–593