Pharmacologically potentials of hydrazonone containing compounds: a promising scaffold

  • Authors

    • Mohammad Asif GRD(PG)IMT, RAJPUR, DEHRADUN
    2014-07-04
    https://doi.org/10.14419/ijac.v2i2.2301

  • Abstract

    Hydrazones considered as an important class of compounds for new drug development. Hydrazones are present in many of the bioactive compounds having wide interest because of their diverse biochemical applications. This created interest in researchers to developed variety of hydrazone compounds with effective biological activities. Therefore many compounds have been developed as target structures for their biological activities. This review is focus on the diverse biological activities of hydrazones.

    Keywords: Hydrazones, Biological Activities, Azomethine, Pharmacological Potential.

  • References

    1. Abadi AH, Eissa AAH, Hassan GS. Synthesis of novel 1, 3, 4-trisubstituted pyrazole derivatives and their evaluation as antitumor and antiangiogenic agents. Chem. Pharm. Bull., 2003, 51, 838-844.
    2. Abdel-Aal MT, El-Sayed WA, El-Ashry EH. Synthesis and antriviral evaluation of some sugar arylglycinoylhydrazones and their oxadiazoline derivatives. Arch. Pharm. Chem., Life Sci. 2006, 339, 656-663.
    3. Abdel-Wahab FB, Awad AEG, Badria AF. Synthesis, antimicrobial, antioxidant, anti-hemolytic and cytotoxic evaluation of new imidazole-based heterocycles, Eur. J. Med. Chem, 2011, 46, 1505-1511.
    4. Abdel-Wahab FB, Khidre ER, Awad AEG. Regioselective synthesis and antimicrobial activities of some novel aryloxyacetic acid derivatives, Eur. J. Med. Chem., 2012, 50, 55-62.
    5. Abu-Surrah AS, Safieh KAA, Ahmad IM, Abdalla MY, Ayoub MT, Qaroush AK, Abu-Mahtheieh AM. New palladium (II] complexes bearing pyrazole-based Schiff base ligands: Synthesis, characterization and cytotoxicity, Eur. J. Med. Chem., 2010, 45, 471-475.
    6. Ajani OO, Obafemi, C.A, Nwinyi, O.C, Akinpelu, D.A. Microwave assisted synthesis and antimicrobial activity of 2-quinoxalinone-3-hydrazone derivatives, Bioorg. Med. Chem., 2010, 18, 214-221.
    7. Ali, A, Fisara, P, Freemont, J.A, Kyi, S, Meyer, A.G, Andrew, G, Riches, A.G, Sargent, R.M, Sawutz, D.G, Turner, K.A, Winzenberg, KN, Yang, Q. Discovery of ectoparasiticidal hydrazono-trifluoromethanesulfonanilides, Bioorg. Med. Chem. Lett., 2010, 20, 649-652.
    8. Ali, A, Mohammad, T, Davood, Abbas, S. Synthesis and analgesic activity of N-aryl hydrazone derivatives of mefenmic acid. J Pharm Pharmaceut Sci., 2005, 8(3):419-25.
    9. Ali, M.R, Marella, A, Alam, M.T, Naz, R, Akhter, M, Shaquiquzzaman, M, Saha, R, Tanwar, O, Alam, M.M, Hooda, J. Review of Biological Activities of Hydrazones. Indonesian J. Pharm., 2012, 23(4): 193-202.
    10. Al-Macrosaur, L.Q, Dayam, R, Taheri, L, Witvrouw, M, Debyser, Z, Neamati, N. Discovery of novel non-cytotoxic salicylhydrazine containing HIV-1 integrase Inhibitors. Bioorg. Med. Chem. Lett. 2007, 17: 6472-75.
    11. Al-Said, M.S, Bashandy, M.S, Al-qasoumi, S.I, Ghorab, M.M. Anti-breast cancer activity of some novel 1,2-dihydropyridine, thiophene and thiazole derivatives, Eur. J. Med. Chem., 2011, 46, 137-141.
    12. Angelusiua, M.V, Barbuceanu, S-F, Draghicic, C, Almajan, G.L. New Cu(II), Co(II), Ni(II) complexes with aroyl- hydrazone based ligand. Synthesis, spectroscopic characterization and in vitro antibacterial evaluation. Eur. J. Med. Chem., 2010; 45:2055–62.
    13. Aponte, J.C, Vaisberg, A.J, Castillo, D, Gonzalez, G, Estevez, Y, Arevalo, J, Quiliano, M, Zimic, M, Verastegui, M, Malaga, E, Juan, R.H.G, Bustamante, B, Tarleton, R.L, Wang, Y, Franzblau, S.G, Pauli, G.F, Sauvain, M, Hammond, G.B. Trypanoside, antituberculosis, leishmanicidal, and cytotoxic activities of tetrahydrobenzothienopyrimidines, Bioorg. Med. Chem., 2010, 18, 2880-2886.
    14. Aslam, M.A.S, Mahmood, S, Shahid, M, Saeed, A, Iqbal, J. Synthesis, biological assay in vitro and molecular docking studies of new Schiff base derivatives as potential urease inhibitors, Eur. J. Med. Chem., 2011, 46, 5473-5479.
    15. Belskaya, N.P, Dehaen, W, Bakulev, V.A. Synthesis and properties of hydrazones bearing amide, thioamide and amidine functions. ARKIVOC, 2010, 1, 275-332.
    16. Bernardino, A, Gomes, A., Charret, K, Freitas, A, Machado, G, Canto-Cavalheiro, M, Leon, L, Amaral, V. Synthesis and leishmanicidal activities of 1-(4-X-phenyl)-N′-((4-Yphenyl) methylene)-1H-pyrazole-4-carbohydrazides Eur. J. Med. Chem. 2006, 41, 80-87.
    17. Bijev A. New heterocyclic hydrazones in the search for antitubercular agents: Synthesis and in vitro evaluations. Lett.Drug Des. Discov. 2006, 3, 506-512.
    18. Caffrey, C.R, Schanz, M, Nkemgu-Njinkeng, J, Brush, M, Hausell, E, Cohen, F.E, Flaherty, T.M, Mckerrow, J.H, Steverding, D. Screening of acyl hydrazide proteinase inhibitors for antiparasitic activity against Trypanosomabrucei. Int. J. Antimicrob. Agents. 2002, 19, 227-251.
    19. Çakır, B, Dağ, Ö, Yıldırım, E, Erol, K, Şahin, M.F. Synthesis and anticonvulsant activity of some hydrazones of 2-((3H)-oxobenzoxazolin-3-yl-aceto)hydrazide. J. Fac. Pharm. Gazi. 2001, 18, 99-106.
    20. Caputto, M.E, Fabian, L.E, Benitez, D, Merlinoz, A, Rios, N, Cerecetto, H, Moltrasio, G.Y, Moglioni, A.G, Gonzalez, M, Finkielsztein, L.M. Thiosemicarbazones derived from 1-indanones as new anti-Trypanosoma cruzi agents, Bioorg. Med. Chem., 2011, 19, 6818-6826.
    21. Catto, M, Aliano, R, Carotti, A, Cellamare, S, Palluotto, F, Purgatorio, R, Stradis, A. D, Campagna, F, Design, synthesis and biological evaluation of indane-2-arylhydrazinylmethylene-1,3-diones and indol aryldiazenylmethylene-3-ones as β-amyloid aggregation inhibitors, Eur. J. Med. Chem., 2010, 45, 1359-136.
    22. Cocco, M. T, Congiu, C, Lilliu,V, Onnis, V. Synthesis and in vitro antitumoral activity of new hydrazinopyrimidine-5-carbonitrile derivatives. Bioorg. Med. Chem. 2005, 14, 366-372.
    23. Cui, Z, Li, Y, Ling, Y, Huang, J, Cui, J, Wang, R, Yang, X. New class of potent antitumor acylhydrazone derivatives containing furan, Eur. J. Med. Chem., 2010, 45, 5576-5584.
    24. Darpan, K, Khan, S.A, Gita, C, Kumar, S. N’-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl) methylene) 2/4-substitutedhydrazides: Synthesis and anticonvulsant activity. Eur. J. Med. Chem., 2010, 45, 3943-49.
    25. de Oliveira, K.N, Costa, P, Santin, J. R, Mazzambani, L, Burger, C, Mora, C, Nunes, R. J, de-Souza, M. M. Synthesis and antidepressant-like activity evaluation of sulphonamides and sulphonyl-hydrazones, Bioorg. Med. Chem., 2011, 19, 4295-4306.
    26. Deep, A, Jain, S, Sharma, P. C, Verma, P, Kumar, M, Dora, C.P. Design and biological evaluation of biphenyl-4- carboxylic acid hydrazide-hydrazone for antimicrobial activity. Acta Pol Pharm., 2010, 67(3), 255-9.
    27. Demirbas, N, Karaoglu, S, Demirbas, A, Sancak, K. Synthesis and antimicrobial activities of some new 1-(5-phenylamino-(1,3,4)thiadiazol-2-yl)methyl-5-oxo-(1,2,4)triazole and 1-(4-phenyl-5-thioxo-(1,2,4) triazol-3-yl) methyl-5-oxo-(1,2,4)triazole derivatives. Eur. J. Med. Chem. 2004, 39, 793-804.
    28. Dimmock, J.R, Vashishtha, S.C, Stables, J.P. Anticonvulsant properties of various acetylhydrazones, oxamoylhydrazones and semicarbazones derived from aromatic and unsaturated carbonyl compounds. Eur. J. Med. Chem. 2000, 35, 241-248.
    29. Duarte, C.D, Tributino, J.L.M, Lacerda, D.I, Martins, M.V, Alexandre-Moreira, M.S, Dutra, F, Bechara, E.J.H, De-Paula, F.S, Goulart, M.O.F, Ferreira, J, Calixto, J.B, Nunes, M.P, Bertho, A.L, Miranda, A.L.P, Barreiro, E.J, Fraga, C.A.M. Synthesis, pharmacological evaluation and electrochemical studies of novel 6-nitro-3,4-methylenedioxyphenyl-Nacylhydrazone derivatives : Discovery of LASSBio-881, a new ligand of cannabinoid receptors. Bioorg. Med. Chem., 2007, 15, 2421-2433.
    30. Duarte, C.D, Tributino, J.L.M, Lacerda, D.I, Martins, M.V, Alexandre-Moreira, M.S, Dutra, F, Bechara, E.J.H, De-Paula, F.S, Goulart, M.O.F, Ferreira, J, Calixto, J.B, Nunes, M.P, Bertho, A.L, Miranda, A.L.P, Barreiro, E.J, Fraga, C.A.M. Synthesis, pharmacological evaluation and electrochemical studies of novel 6-nitro-3,4-methylenedioxyphenyl-Nacylhydrazone derivatives : Discovery of LASSBio-881, a new ligand of cannabinoid receptors. Bioorg. Med. Chem., 2007, 15, 2421-2433.
    31. Edrees, M.M, Farghaly, T.A, El-Hag, A.A.F, Abdalla, M.M. Antimicrobial, antitumor and 5 α-reductase inhibitor activities of some hydrazonoyl substituted pyrimidinones, Eur. J. Med. Chem., 2010, 45, 5702-5707.
    32. Effenberger, K, Breyer, S, Schobert R. Modulation of doxorubicin activity in cancer cells by conjugation with fatty acyl and terpenyl hydrazones, Eur. J. Med. Chem., 2010, 45, 1947-1954.
    33. El-Hawash, S.A.M, Abdel Wahab, A.E, El-Dewellawy, M.A. Cyanoacetic acid hydrazones of 3-(and 4-) acetylpyridine and some derived ring systems as potential antitumor and anti-HCV agents. Arch. Pharm. Chem. Life Sci. 2006, 339, 14-23.
    34. El-Nakkady, S.S, Hanna, M.M, Roaiah, H. M, Ghannam, I.A.Y. Synthesis, molecular docking study and antitumor activity of novel 2-phenylindole derivatives, Eur. J. Med. Chem., 2012, 47, 387-398.
    35. El-Sabbagh, O. I, Shabaan, M.A, Kadry, H. H, Al-Din, E.S. New octahydroquinazoline derivatives: Synthesis and hypotensive activity, Eur. J. Med. Chem., 2010, 45, 5390-5396.
    36. El-Sayed, M.A.A, Abdel-Aziz, N.I, Abdel-Aziz, N.A.M, El-Azab, A.S, Asiri, Y.A, Tahir, K.E.H.E. Design, synthesis, and biological evaluation of substituted hydrazone and pyrazole derivatives as selective COX-2 inhibitors, molecular docking study, Bioorg. Med. Chem., 2011, 19, 3416-3424.
    37. Eswaran, S, Adhikari, A.V, Chowdhury, I.H, Pal, N.K, Thomas, K.D. New quinoline derivatives: Synthesis and investigation of antibacterial and antituberculosis properties, Eur. J. Med. Chem., 2010, 45, 3374-3383.
    38. Fan, C.D, Su, H, Zhao, J, Zhao, B.X, Zhang, S.L, Miao, J.Y. A novel copper complex of salicylaldehyde pyrazole hydrazone induces apoptosis through up-regulating integrin β-4 in H322 lung carcinoma cells, Eur. J. Med. Chem., 2010, 45, 1438-1446.
    39. Fraga, A.G.M, Rodrigues, C.R, Miranda, A.L.P, Barreiro, E.J, Fraga, C.A.M. Synthesis and pharmacological evaluation of novel heterocyclic acylhydrazone derivatives, designed as PAF antagonists. Eur. J. Pharm. Sci. 2000, 11, 285-290.
    40. Gage, J.L, Onrust, R, Johnston, D, Osnowski, A, MacDonald, W, Mitchell, L, Urogdi, L, Rohde, A, Harbol, K, Gragerov, S, Dorman, G, Wheeler, T, Florio, V, Cutshall, N.S. N-Acylhydrazones as inhibitors of PDE10A, Bioorg. Med. Chem. Lett., 2011, 21, 4155-4159.
    41. Gemma, S, Kukreja, G, Fattorusso, C, Persico, M, Romano, M, Altarelli, M, Savini, L, Campiani, G, Fattorusso, E, Basilico, N. Synthesis of N1-arylidene-N2-quinolyl- and N2- acrydinylhydrazones as potent antimalarial agents active against CQ-resistant P. falciparum strains. Bioorg. Med. Chem. Lett., 2006, 16, 5384-5388.
    42. Gouda, M.A, Berghot, M.A, Shoeib, A.I, Khalil, M.A. Synthesis and antimicrobial of new anthraquinone derivatives incorporating pyrazole moiety, Eur. J. Med. Chem., 2010, 45, 1843-1848.
    43. Govindasami, T, Pandey, A, Palanivelu, N, Pandey, A. Synthesis, characterization and antibacterial activity of biologically important vanillin related hydrazone derivatives, Int. J. Org. Chem., 2011, 1, 71-77.
    44. Gülerman, N.N, Oruc, E.E, Kartal, F, Rollas, S. In vivo metabolism of 4-fluorobenzoic acid ((5-nitro-2-furanyl) methylene) hydrazide in rats. Eur. J .Drug Metab. Pharmacokinet., 2000, 25, 103-108.
    45. Guniz, K.S, Rollasa, S, Erdeniz, H, Kiraz, M, Cevdet, E.A, Vidinc, A. Some 4-arylhydrazono-2-pyrazoline-5-one derivatives obtained from heterocyclic amines, tested against Mycobacterium avium. Eur. J. Med. Chem., 2007, 35, 761−771.
    46. Gürsoy, A, Karali, N. Synthesis and primary cytotoxicity evaluation of 3-(((3-phenyl-4(3H) - quinazolinone-2-yl)mercaptoacetyl)hydrazono)-1H-2-indolinones. Eur. J. Med. Chem. 2003, 38, 633-643.
    47. Gürsoy, E, Güzeldemirci-Ulusoy, N. Synthesis and primary cytotoxicity evaluation of new imidazo(2,1-b)thiazole derivatives. Eur. J. Med. Chem., 2007, 42, 320-326.
    48. Hassan, G.S, Kadry, H.H, Abou-Seri, S.M, Ali, M.M, Mahmoud, A.E.E. Synthesis and in vitro cytotoxic activity of novel pyrazolo(3,4-d)pyrimidines and related pyrazole hydrazones toward breast adenocarcinoma MCF-7 cell line, Bioorg. Med. Chem., 2011, 19, 6808-6817.
    49. Hayat, F, Salahuddin, A, Zargan, J, Azam, A. Synthesis, characterization, antiamoebic activity and cytotoxicity of novel 2-(quinolin-8-yloxy) acetohydrazones and their cyclized products (1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives), Eur. J. Med. Chem., 2010, 45, 6127- 6134.
    50. Hernandez, P, Cabrera, M, Lavaggi, M.L, Celano, L, Tiscornia, I, da Costa, T.R, Thomson, L, Bollati-Fogolin, M, Miranda, A.L.P, Lima, L.M, Barreirod, E.J, Gonzalezd, M, Cerecettod, H. Discovery of new orally effective analgesic and anti-inflammatory hybrid furoxanyl N-acylhydrazone derivatives, Bioorg. Med. Chem., 2012, 20, 2158-2171.
    51. Imramovsky, A, Polanc, S, Vinsova, J, Kocevar, M, Jampilek, J, Recková, Z, Kaustova, J. A new modification of anti-tubercular active molecules. Bioorg. Med. Chem. 2007, 15, 2551-2559.
    52. Isloor, A.M, Kalluraya, B, Pai, K.S. Synthesis, characterization and biological activities of some new benzo(b) thiophene derivatives, Eur. J. Med. Chem., 2010, 45, 825-830.
    53. Jin, C.A.Y, Tan, Z, He, M, Tian, B, Tang, S, Hewlett, I, Yang, M. SAR and molecular mechanism study of novel acylhydrazone compounds targeting HIV-1, Bioorg. Med. Chem., 2010, 18, 2135-2140.
    54. Jin, L, Chen, J, Song, B, Chen, Z, Yang, S. ; Li, Q, Hu, D, Xu R. Synthesis, structure, and bioactivity of N′-substitutedbenzylidene-3,4,5-trimethoxybenzohydrazide and 3-acetyl-2- substituted phenyl-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole derivatives. Bioorg. Med. Chem. Lett. 2006, 16, 5036-5040.
    55. Jordao, A.K, Sathler, P.C, Ferreira, V.F, Campos, V.R, de Souza, M.C.B.V, Castro, H.C, Lannes, A, Lourenco, A, Rodrigues, C.R, Bello, M.L, Lourenco, M.C.S, Carvalho, G.S.L, Almeida, M.C.B, Cunha, A.C. Synthesis, antitubercular activity, and SAR study of N-substitutedphenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides, Bioorg. Med. Chem., 2011, 19, 5605-5611.
    56. Jubie, S, Meena, S, Ramasheshu, K. V, Jawahar, N, Vijaykumar, S. Synthesis and biological evaluation of some hydrazones and carbazones of indane 1,3-dione. Ind. J. Chem., 2010, 49B, 1261-1263.
    57. Kaushik, D, Khan, S.A, Chawla, G, Kumar, S. N’-((5-chloro-3-methyl-1- phenyl-1H-pyrazol-4-yl] methylene] 2/4-substituted hydrazides: Synthesis and anticonvulsant activity, Eur. J. Med. Chem., 2010, 45, 3943-3949.
    58. Kaymakçıoglu, K. B, Oruc, E.E, Unsalan, S, Kandemirli, F, Shvets, N, Rollas, S, Anatholy, D. Synthesis and characterization of novel hydrazide-hydrazones and the study of their structureantituberculosis activity. Eur. J. Med. Chem., 2006, 41, 1253-1261.
    59. Kaymakçıoglu, K.B, Rollas, S. Synthesis, characterization and evaluation of antituberculosis activity of some hydrazones. Farmaco, 2002, 57, 595-599.
    60. Kendall, J.D, Giddens, A.C, Tsang, K.Y, Frederick, R, Marshall, E.S, Singh, R, Lill, C.L, Lee, W.J, Kolekar, S, Chao, M, Malik, A, Yu, S, Chaussade, C, Buchanan, C, Rewcastle, G.W, Baguley, B.C, Flanagan, J.U, Jamieson, S.M.F, Denny, W.A. Shepherd, P.R., Novel pyrazolo(1,5-a) pyridines as p110α-selective PI3 kinase inhibitors: Exploring the benzenesulfonohydrazide SAR. Bioorg. Med. Chem., 2012, 20, 58-68.
    61. Khan, S.A, Pooja, M, Shabir, P, Darpan, K. Hydrazone derivatives of quinoxalinone as antimicrobial and antiinflammatory agents. Acta Pol Pharm., 2009, 66(2), 169-72.
    62. Kucukguzel, S.G, Kocatepe A, De Clercq, E, Sahin F., Gulluce, M. Synthesis and biological activity of 4-thiazolidinones, thiosemicarbazides derived from diflunisal hydrazide. Eur. J. Med. Chem., 2006, 41, 353-359.
    63. Kuçukguzel, Ş.G, Kuçukguzel, I, Ulgen M. Metabolic and Chemical Studies on N-(4- chlorobenzyl)-N′-benzoylhydrazine, Farmaco, 2000, 55, 624-630.
    64. Kucukguzel, S.G, Mazi, A, Sahin, F, Öztürk S, Stables, J. P. Synthesis and biological activities of diflunisal hydrazide-hydrazones. Eur. J. Med. Chem. 2003, 38, 1005-1009.
    65. Kuçukguzel, S.G, Oruc E.E, Rollas S, Şahin, F, Ozbek, A. Synthesis, Characterization and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds. Eur. J. Med. Chem., 2002, 37, 197-206.
    66. Kuçukguzel, S.G, Rollas, S. Synthesis, Characterization of Novel Coupling Products and 4- Arylhydrazono-2-pyrazoline-5-ones as Potential Antimycobacterial Agents. Farmaco, 2002, 57, 583-587.
    67. Kumar, D, Judge, V, Narang, R, Sangwan, S, Clercq, D.E, Balzarini, J, Narasimhan, B. Benzylidene/2-chlorobenzylidene hydrazides: Synthesis, antimicrobial activity, QSAR studies and antiviral evaluation, Eur. J. Med. Chem., 2010, 45, 2806-2816.
    68. Kumar, D, Kumar, N. M, Ghosh, S, Shah, K. Novel bis(indolyl)hydrazide–hydrazones as potent cytotoxic agents, Bioorg. Med. Chem. Lett., 2012, 22, 212-215.
    69. Kumar, S, Bawai, S, Drabu, S, Kumar, R, Machwal, L. Chloroquinolinylhydrazone derivative as anticonvulsant. Acta Pol Pharm., 2010, 67, 567-3.
    70. Lee, Y.J, Jeong, W.K, Shin, S, Lee, U.J, Kim, Y. Discovery of novel selective inhibitors of Staphylococcus aureus β-ketoacyl acyl carrier protein synthase III. Eur. J. Med. Chem., 2012, 47, 261-269.
    71. Leite, A.C.L, deLima, R.S, Moreira, D.R, Cardoso, M.V, de Brito, A.C.G, dos Santos, L.M.F, Hernandes, M.Z, Kipustok, A.C, de Lima, R.S, Soares, M.B.P. Synthesis, docking, and in vitro activity of thiosemiconbazone, aminoacylthiosemicarbazides and acyl-thiazolidones against Trypanosomacruzi. Bioorg. Med. Chem., 2006, 14, 3749-57.
    72. Lima, P.C, Lima, L. M, Silva, K.C, Leda, P.H, Miranda, A.L.P, Fraga, C.A.M; Barreiro, E.J, Synthesis and analgesic activity of novel N-acylhydrazones and isosters, derived from natural safrole. Eur. J. Med. Chem., 2000, 35, 187-203.
    73. Liu, W-Y, Li, H-Y, Zhao, B-X, Shin, D-S, Lian, S, Miaonovel, J-Y. Ribavirin hydrazone derivatives and anti-proliferative activity against A549 lung cancer cells. Carbohydrate Res., 2009, 344, 1270–5.
    74. Loncle, C, Brunel, J, Vidal, N, Dherbomez, M, Letourneux, Y. Synthesis and antifungal activity of cholesterol-hydrazone derivatives. Eur. J. Med. Chem., 2004, 39, 1067-1071.
    75. Maccari, R, Ottana, R, Vigorita, M.G. In vitro advanced antimycobacterial screening of isoniazid-related hydrazones, hydrazides and cyanoboranes: Part 14. Bioorg. Med. Chem. Lett., 2005, 15, 2509-2513.
    76. Maguene, G.M, Jakhlal, J, Ladyman, M, Vallin, A, Ralambomanana, D.A, Bousquet, T, Maugein, J, Lebibi, J, Pelinski, L. Synthesis and antimycobacterial activity of a series of ferrocenyl derivatives. Eur. J. Med. Chem., 2011, 46, 31-38.
    77. Mahajan, A, Kremer, L, Louw, S, Gueradel, Y, Chibale, K, Biot, C. Synthesis and in vitro antitubercular activity of ferrocene-based hydrazones. Bioorg. Med. Chem. Lett., 2011, 21, 2866-2868.
    78. Mamolo, M.G, Falagiani, V, Zampieri, D, Vio, L, Banfi, E, Scialino, G. Synthesis and antimycobacterial activity of (3,4-diaryl-3H-thiazole-2-ylidene)hydrazide derivatives. Farmaco, 2003, 58, 631-637.
    79. Mamolo, M.G, Falagiani, V, Zampieri, D, Vio, L, Banfi, E. Synthesis and antimycobacterial activity of (5-(pyridin-2-yl)-1, 3, 4-thiadiazole-2-ylthio) acetic acid arylidene-hydrazide derivatives. Farmaco, 2001, 56, 587-592.
    80. Manvar, A, Malde, A, Verma, J, Virsodia, V, Mishra, A, Upadhyay, K, Acharya, H, Countinhe, E, Shah, A. Synthesis, antitubercular activity and 3D-QSAR study of coumarin-4-acetic acid benzylidene hydrazides. Eur. J. Med. Chem, 2008, 3, 342-4.
    81. Masunari, A, Tavares, L.C. A new class of nifuroxazide analogues: Synthesis of 5-nitrophene derivatives with antimicrobial activity against multidrug-resistant Staphylococcus aureus. Bioorg. Med. Chem., 2007, 15, 4229-4236.
    82. Metwally KA, Abdel-Aziz LM, Lashine EM, Husseiny MI, Badawy RH. Hydrazones of 2-aryl-quinoline-4-carboxylic acid hydrazides: synthesis and preliminary evaluation as antimicrobial agents. Bioorg. Med. Chem., 2006, 14, 8675-82.
    83. Mohareb RM, El-Sharkawy KA, Hussein MM, El-Sehrawi HM. Hydrazidehydrazone derivatives as antidepressant, sedative and analgesic agents. J. Pharm. Sci. & Res., 2010, 2, 185-196.
    84. Moldovan CM, Oniga O, Parvu A, Tiperciuc B, Verite P, Pirnau A, Bojit OCM, Pop R. Synthesis and antiinflammatory evaluation of some new acyl-hydrazones bearing 2-aryl-thiazole. Eur. J. Med. Chem., 2011, 46, 526-534.
    85. Musad EA, Mohamed R, Saeed BA, Vishwanath BS, Rai KML. Synthesis and evaluation of antioxidant and antibacterial activities of new substituted bis (1,3,4-oxadiazoles), 3,5-bis(substituted) pyrazoles and isoxazoles, Bioorg. Med. Chem. Lett., 2011, 21, 3536–3540.
    86. Nayyar A, Jain R. Recent advances in new structural classes of anti-tuberculosis agents. Curr. Med. Chem., 2005, 12, 1873-1886.
    87. Nayyar A, Malde A, Coutinho E, Jain R. Synthesis, anti-tuberculosis activity, and 3D-QSAR study of ring-substituted-2/4-quinolinecarbaldehyde derivatives. Bioorg. Med. Chem., 2006, 14, 7302-7310.
    88. Nayyar A, Monga V, Malde A, Coutinho E, Jain R. Synthesis, anti-tuberculosis activity and 3D-QSAR study of 4-(adamantan-1-yl)-2-substituted quinolines. Bioorg. Med. Chem. 2007, 15, 626-40.
    89. Negi VJ, Sharma AK, Negi JS, Ram V. Biological activities of hydrazone derivatives in the new millennium. Int. J. Pharm, Chem., 2012, 2 (4), 100-109.
    90. Olayinka O, Craig A, Obafemi B, Obinna C, Nwinyi C, David A. Akinpelu. Microwave assisted synthesis and antimicrobial activity of 2-quinoxalinone-3-hydrazone derivatives. Bioorg & Med Chem., 2010, 18, 214–21.
    91. Ozdemir A, Turan-Zitouni G, Kaplanciklia AZ, Iscan G, Khan S, Demirci F. Synthesis and the selective antifungal activity of 5,6,7,8-tetrahydroimidazo (1,2-a)pyridine derivatives, Eur. J. Med. Chem., 2010, 45, 2080-2084.
    92. Ozdemir OU, Gulcin O. Sufonylhydrazone derivatives and their nickel complexes as a antibacterial agents. Spectrochimica Acta., 2008, 70, 641-5.
    93. Ozemir A, Kalancikli ZA, Zitouni GT, Revial G. Synthesis of some novel hydrazone derivatives and evalution of their antituberculosis activity. Marmara Pharm J., 2010, 14, 79-83.
    94. Ozkay Y, Tunali Y, Karaca H, Isikdag I. Antimicrobial activity and a SAR study of some novel benzimidazole derivatives bearing hydrazone moiety. Eur. J. Med. Chem., 2010, 45, 3293-3298.
    95. Pandey J, Pal R, Dwivedi A, Hajela K. Synthesis of some new diaryl and triaryl hydrazone derivatives as possible estrogen receptor modulators. Arzneimittelforschung. 2002, 52, 39-44.
    96. Pavan FR, Maia PIS, Leite SRA, Deflon VM, Batista AA, Sato DN, Franzblau SG, Leite CQF. Thiosemicarbazones, semicarbazones, dithiocarbazates and hydrazide/ hydrazones: Anti-Mycobacterium tuberculosis activity and cytotoxicity, Eur. J. Med. Chem., 2010, 45, 1898-1905.
    97. Radhwan MAA, Ragab EA, Sabry NM, El-Shenawy SM. Synthesis and biological evaluation of new 3-substituted indole derivatives as potential antiinflammatory and analgesic agents. Bioorg. Med. Chem., 2007, 15: 3832-41.
    98. Ragavendran J, Sriram D, Patel S, Reddy I, Bharathwajan N, Stables, J, Yogeeswari P. Design and synthesis of anticonvulsants from a combined phthalimide-GABA-anilide and hydrazone pharmacophore. Eur. J. Med. Chem., 2007, 42, 146-151.
    99. Raja AS, Agarwal AK, Mahajan N, Pandeya SN, Ananthan A. Antibacterial and antitubercular activity of some diphenyl hydrazone and semicarbazone, Ind. J. Chem., 2010, 49B, 1384-1388.
    100. Rajitha G, Saideepa N, Praneetha P. Synthesis and evaluation of N-(α- benzamidocinnamoyl)aryl hydrazone Activities of Hydrazones derivative for anti-inflammatory and antioxidant activities, Ind. J. Chem., 2011, 50B, 729-733.
    101. Rando D, Sato, D.N, Siqueira, L, Malvezzi, A, Leite, C.Q.F, Amaral, A.T, Ferreira, E.I, Tavares, L.C. Potential tuberculostatic agents. Topliss application on benzoic acid ((5-Nitrothiophene-2-yl) methylene) hydrazide series. Bioorg. Med. Chem., 2002, 10, 557-560.
    102. Rane RA, Telvekar VN. Synthesis and evaluation of novel chloropyrrole molecules designed by molecular hybridization of common pharmacophores as potential antimicrobial agents. Bioorg. Med. Chem. Lett., 2010, 20, 5681–5685.
    103. Rasras MJA, Al-Tel HT, Al-Aboudi FA, Al-Qawasmeh AR. Synthesis and antimicrobial activity of cholic acid hydrazone analogues. Eur. J. Med. Chem., 2010, 45, 2307-2313.
    104. Rollas S, Gulerman N, Erdeniz H. Synthesis and antimicrobial activity of some new hydrazones of 4-fluorobenzoic acid hydrazide and 3-acetyl-2,5-disubstituted-1,3,4-oxadiazolines. Farmaco, 2002, 57, 171-174.
    105. Rollas S, Kucukguzel SG. Biological Activities of Hydrazone Derivatives. Molecules, 2007, 12, 1910-1939.
    106. Romeiro NC, Aguirre G, Hernandez P, González M, Cerecetto H, Aldana I, Silanes SP, Monge A, Barreiro EJ, Lima LM. Synthesis, trypanocidal activity and docking studies of novel quinoxaline-N-acylhydrazones, designed as cruzain inhibitors candidates, Bioorg. Med. Chem., 2009, 17, 641-652.
    107. Salgın-Gokşen, U, Gokhan-Kelekci, N, Goktas, O, Koysal, Y, Kılıc, E, Isık, S, Aktay, G, Özalp, M. 1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones, 1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: Synthesis, analgesic-anti-inflammatory and antimicrobial activities. Bioorg. Med. Chem., 2007, 15, 5738-5751.
    108. Savini L, Chiasserini, L, Gaeta, A, Pellerano, C. Synthesis and Anti-tubercular Evaluation of Quinolyl hydrazones.Bioorg. Med. Chem., 2002, 10, 2193-2198.
    109. Savini L, Chiasserini, L, Travagli, V, Pellerano, C, Novellino, E, Cosentino, S, Pisano, M.B. New α-heterocyclic hydrazones: evaluation of anticancer, anti-HIV and antimicrobial activity. Eur.J.Med.Chem., 2004, 39,113-122.
    110. Scior T, Garcés-Eisele SJ. Isoniazid is not a lead compound for its pyridyl ring derivatives, isonicotinoyl amides, hydrazides and hydrazones: A critical review. Curr. Med. Chem., 2006, 13, 2205-2219.
    111. Sharma RN, Sharma KP, Dikshit SN. Synthesis, Characterization and biological activities of some new hypophosphorousadducts of acid hydrazones derived from 2-((N-benzoyl) 2,3-dichloroanilido) acetohydrazide. Arch Appl Sci Res., 2011, 3, 415-424.
    112. Shindikar AV, Viswanathan CL. Novel fluoroquinolones: design, synthesis, and in vivo activity in mice against Mycobacterium tuberculosis H37 Rv. Bioorg. Med. Chem Lett., 2005, 15, 1803-1806.
    113. Shiradkar MR, Murahari KK, Gangadasu HR, Suresh T, Kalyan CC, Panchal D, Kaur R, Burange P, Ghogare J, Mokale V, Raut M. Synthesis of new S-derivatives of clubbed triazolyl thiazole as anti-Mycobacterium tuberculosis agents. Bioorg. Med. Chem., 2007, 15, 3997-4008.
    114. Siddiqui SM, Salahuddin A, Azam A. Synthesis, characterization and antiamoebic activity of some hydrazone and azole derivatives bearing pyridyl moiety as a promising heterocyclic scaffold. Eur. J. Med. Chem., 2012, 49, 411-416.
    115. Silva AG, Zapata-Suto G, Kummerle AE, Fraga CAM, Barreiro EJ, Sudo RT.Synthesis and vasodilatory activity of new N-acylhydrazone derivatives, designed as LASS Bio-alogues. Bioorg. Med. Chem., 2005, 13, 3431-37.
    116. Silva GA, Costa LMM, Brito FCF, Miranda ALP, Barreiro EJ, Fraga CAM. New class of potent antinociceptive and antiplatelet 10H-phenothiazine-1-acylhydrazone derivatives. Bioorg. Med. Chem, 2004, 12, 3149-3158.
    117. Sinha N Jain S, Tilekar A, Upadhayaya RS, Kishore N, Jana GH, Arora SK. Synthesis of isonicotinic acid N′-Arylidene-N-(2-oxo-2-(4-aryl-piperazin-1-yl)ethyl)hydrazides as antituberculosis agents. Bioorg. Med. Chem Lett., 2005, 15, 1573-1576.
    118. Sivakumar KK, Rajasekaran A, Ponnilavarasan I, Somasundaram A, Sivasakthi R, Kamalaveni S. Antimicrobial and analgesic activity of some (4Z)-3-methyl-1-((2-oxo-2H-chromen-4-yl)carbonyl)-1H-pyrzole-4,5-dione 4-((4-substitutedphenyl) hydrazone). Scholars Res Lib., 2010, 2(1), 211-19.
    119. Smalley TL Jr, Peat AJ, Boucheron JA, Dickerson S, Garrido D, Preugschat F, Schweiker SL, Thomson SA, Wang TY. Synthesis and evaluation of novel heterocylclic Inhibitors of GSK-3. Bioorg. Med. Chem. Lett., 2006, 16, 2091-94.
    120. Sriram D, Yogeeswari P, Devakaram RV. Synthesis, in vitro and in vivo antimycobacterial activities of diclofenac acid hydrazones and amides. Bioorg. Med. Chem., 2006, 14, 3113-3118.
    121. Sriram D, Yogeeswari P, Madhu K. Synthesis and in vitro and in vivo antimycobacterial activity of isonicotinoyl hydrazones. Bioorg. Med. Chem. Lett., 2005, 15, 4502-4505.
    122. Sriram D, Yogeeswari P, Madhu K. 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., 2006, 14, 876-878.
    123. Srivastava R, Pandeya SN, Singh AK, Sam A. Synthesis of some new acid hydrazone and their activity against mycobacterium. Inter J Chem Res, 2010, 2(1), 18-19.
    124. Terzioğlu N, Gursoy A. Synthesis and anticancer evaluation of some new hydrazone derivatives of 2,6-dimethylimidazo(2,1-b)-(1,3,4)thiadiazole-5-carbohydrazide. Eur. J. Med. Chem., 2003, 38, 781-786.
    125. Thomas KD, Adhikari AV, Telkar S, Chowdhury IH, Mahmood R, Pal KN, Rowd G, Sumesh E. Design, synthesis and docking studies of new quinoline-3-carbohydrazide derivatives as antitubercular agents, Eur. J. Med. Chem., 2011, 46, 5283-5292.
    126. Todeschini AR, Miranda AL, Silva CM, Parrini SC, Barreiro EJ. Synthesis and evaluation of analgesic, anti-inflammatory and antiplatelet properties of new 2- pyridylarylhydrazone derivatives. Eur. J. Med. Chem., 1998, 33, 189-99.
    127. Turan-Zitouni G, Blache Y, Guven K. Synthesis and antimicrobial activity of some imidazo-(1,2-a] pyridine-2-carboxylic acid arylidenehydrazide derivatives. Boll. Chim. Farm. 2001, 140, 397-400.
    128. Ulusoy N, Çapan G, Ötük G, Kiraz M. Synthesis and antimicrobial activity of new 6- phenylimidazo(2,1-b)thiazole derivatives. Boll. Chim. Farm, 2000, 139, 167-172.
    129. Ulusoy N, Gürsoy A, Otuk G, Kiraz M. Synthesis and antimicrobial activity of some 1,2,4-triazole-3-mercaptoacetic acid derivatives. Farmaco, 2001, 56, 947-952.
    130. Uppal G, Bala S, Kamboj S, Saini M. Therapeutic Review Exploring Antimicrobial Potential of Hydrazones as Promising Lead. Der Pharma Chemica, 2011, 3, 250-268.
    131. Vaio MAFVD, Freitas ACC, Castro HC, Albuquerque S.D, Cabral LM, Rodrigues CR, Albuquerque MG, Martins RCA, Henriques MGMO, Dias LRS. Synthesis, antichagasic in vitro evaluation, cytotoxicity assays, molecular modeling and SAR/QSAR studies of a 2-phenyl-3-(1-phenyl-1Hpyrazol-4-yl)-acrylic acid benzylidenecarbohydrazide series, Bioorg. Med. Chem., 2009, 17, 295-302.
    132. Vavrikova E, Polanc S, Kocevar M, Horvati K, Bosze S, Stolarikova J, Vavrova K, Vinsova J. New fluorinecontaining hydrazones active against MDR-tuberculosis, Eur. J. Med. Chem., 2011, 46, 4937-4945.
    133. Vicini P, Incerti M, Doytchinova I, La Colla P, Busonera B, Loddo R. Synthesis and antiproliferative activity of benzo(d)isothiazole hydrazones. Eur. J.Med. Chem., 2006, 41, 624-632.
    134. Vicini P, Zani F, Cozzini P, Doytchinova I. Hydrazones of 1,2-benzisothiazole hydrazides: synthesis, antimicrobial activity and QSAR investigations. Eur. J. Med. Chem., 2002, 37, 553-564.
    135. Vijesh AM, Isloor MA, Prabhu V, Ahmad S, Malladi S. Synthesis, characterization and anti-microbial studies of some novel 2,4-disubstituted thiazoles, Eur. J. Med. Chem., 2010, 45, 5460-5464.
    136. Visbal G, Marchan E, Maldonado, A, Simoni, Z, Navarro, M. Synthesis and characterization of platinum-sterol hydrazone complexes with biological activity against Leishmania (L.) mexicana. J. Inorg. Biochem., 2008, 102, 547-54.
    137. Walcourt A, Loyevsky M, Lovejoy DB, Gordeuk, V. R, Richardson, D.R. Novel aroylhydrazone and thiosemicarbazone iron chelators with anti-malarial activity against chloroquine-resistant and -sensitive parasites. Int. J. Biochem. Cell Biol., 2004, 36, 401-407.
    138. Zareef M, Iqbal R, Mirza B, Khan KM, Manan A, Asim F, Khan W. Synthesis and antimicrobial activity of some derivatives of acylhydrazine including novel benzenidiazasulfonamides. Eur. J. Med. Chem., 2008, 141-52.
    139. Zhang H, Drewe J, Tseng B Kasibhatla S, Cai SX. Discovery and SAR of indole-2- carboxylic acid benzylidenehydrazides as a new series of potent apoptosis inducers using a cellbased HTS assay. Bioorg. Med. Chem., 2004, 12, 3649-3655.
    140. Zheng L-W, Wu L-L, Zhao B-X, Dong W-L, Miao J-Y. Synthesis of novel substituted pyrazole-5-carbohydrazide hydrazone derivatives and discovery of a potent apoptosis inducer in A549 lung cancer cells. Bioorg. Med. Chem., 2009, 17, 1957–1962.

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    Asif, M. (2014). Pharmacologically potentials of hydrazonone containing compounds: a promising scaffold. International Journal of Advanced Chemistry, 2(2), 85-103. https://doi.org/10.14419/ijac.v2i2.2301

    Received date: 2014-03-26

    Accepted date: 2014-04-26

    Published date: 2014-07-04