Table of Contents Author Guidelines Submit a Manuscript
International Journal of Medicinal Chemistry
Volume 2014, Article ID 761030, 11 pages
http://dx.doi.org/10.1155/2014/761030
Review Article

Therapeutic Potential of Hydrazones as Anti-Inflammatory Agents

M. M. College of Pharmacy, Maharishi Markandeshwar University, Mullana, Ambala, Haryana 133207, India

Received 8 August 2013; Accepted 20 December 2013; Published 4 March 2014

Academic Editor: Paola Fossa

Copyright © 2014 Anu Kajal et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. N. Ingale, V. Maddi, M. Palkar et al., “Synthesis and evaluation of anti-inflammatory and analgesic activity of 3-[(5-substituted-1,3,4-oxadiazol-2-yl-thio)acetyl]-2H-chromen-2-ones,” Medicinal Chemistry Research, vol. 21, no. 1, pp. 16–26, 2012. View at Publisher · View at Google Scholar · View at Scopus
  2. B. Rigas, “The use of nitric oxide-donating nonsteroidal anti-inflammatory drugs in the chemoprevention of colorectal neoplasia,” Current Opinion in Gastroenterology, vol. 23, no. 1, pp. 55–59, 2007. View at Publisher · View at Google Scholar · View at Scopus
  3. M. Venerito, T. Wex, and P. Malfertheiner, “Nonsteroidal anti-inflammatory drug-induced gastroduodenal bleeding: risk factors and prevention strategies,” Pharmaceuticals, vol. 3, no. 7, pp. 2225–2237, 2010. View at Publisher · View at Google Scholar · View at Scopus
  4. A. Lanas, L. A. García-Rodríguez, M. T. Arroyo et al., “Effect of antisecretory drugs and nitrates on the risk of ulcer bleeding associated with nonsteroidal anti-inflammatory drugs, antiplatelet agents, and anticoagulants,” The American Journal of Gastroenterology, vol. 102, no. 3, pp. 507–515, 2007. View at Publisher · View at Google Scholar · View at Scopus
  5. S. Prakash, B. N. Gupta, and N. S. H. Moorthy, “Synthesis and physicochemical characterization ofmutual prodrug of indomethacin,” Trends in Applied Science Research, vol. 2, no. 2, pp. 165–169, 2007. View at Publisher · View at Google Scholar
  6. J. P. Cornelissen, J. H. Van Diemen, L. R. Groeneveld, J. G. Haasnoot, A. L. Spek, and J. Reedijk, “Synthesis and properties of isostructural transition-metal (copper, nickel, cobalt, and iron) compounds with 7,7′,8,8′-tetracyanoquinodimethanide(1-) in an unusual monodentate coordination mode. Crystal structure of bis(3,5-bis(pyridin-2-yl)-4-amino-1,2,4-triazole)bis(7,7′,8,8′- tetracyanoquinodimethanido)copper(II),” Inorganic Chemistry, vol. 31, no. 2, pp. 198–202, 1992. View at Publisher · View at Google Scholar · View at Scopus
  7. M. B. Smith and M. Jerry, March’s Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, John Wiley & Sons, Milton, Australia, 6th edition, 2007.
  8. R. Lazny and A. Nodzewska, “N,N-dialkylhydrazones in organic synthesis. From simple N,N-dimethylhydrazones to supported chiral auxiliaries,” Chemical Reviews, vol. 110, no. 3, pp. 1386–1434, 2010. View at Publisher · View at Google Scholar · View at Scopus
  9. S. N. P. Belskaya, W. Dehaen, and V. A. Bakuleva, “Synthesis and properties of hydrazones bearing amide, thioamide and amidine functions,” Arkivoc, vol. 2010, no. 1, pp. 275–332, 2010. View at Google Scholar · View at Scopus
  10. R. Brehme, D. Enders, R. Fernandez, and J. M. Lassaletta, “Aldehyde N,N-dialkylhydrazones as neutral acyl anion equivalents: umpolung of the imine reactivity,” European Journal of Organic Chemistry, vol. 2007, no. 34, pp. 5629–5660, 2007. View at Publisher · View at Google Scholar · View at Scopus
  11. I. S. Berdinskii, “The chemistry of hydrazones,” Chemistry of Heterocyclic Compounds, vol. 15, no. 2, p. 238, 1979. View at Publisher · View at Google Scholar
  12. P. A. S. Smith, “Hydrazones,” in Derivatives of Hydrazine and Other Hydronitrogens Having N-N Bonds, pp. 43–74, Benjamin/Cummings, Reading, Mass, USA, 1983. View at Google Scholar
  13. V. Polshettiwar and R. S. Varma, “Polystyrene sulfonic acid catalyzed greener synthesis of hydrazones in aqueous medium using microwaves,” Tetrahedron Letters, vol. 48, no. 32, pp. 5649–5652, 2007. View at Publisher · View at Google Scholar · View at Scopus
  14. N. Belkheiri, B. Bouguerne, F. Bedos-Belval et al., “Synthesis and antioxidant activity evaluation of a syringic hydrazones family,” European Journal of Medicinal Chemistry, vol. 45, no. 7, pp. 3019–3026, 2010. View at Publisher · View at Google Scholar · View at Scopus
  15. M. A. A. Radwan, E. A. Ragab, N. M. Sabry, and S. M. El-Shenawy, “Synthesis and biological evaluation of new 3-substituted indole derivatives as potential anti-inflammatory and analgesic agents,” Bioorganic & Medicinal Chemistry, vol. 15, no. 11, pp. 3832–3841, 2007. View at Publisher · View at Google Scholar · View at Scopus
  16. A. Almasirad, M. Tajik, D. Bakhtiari et al., “Synthesis and analgesic activity of N-arylhydrazone derivatives of mefenamic acid,” Journal of Pharmacy & Pharmaceutical Sciences, vol. 8, no. 3, pp. 419–425, 2005. View at Google Scholar · View at Scopus
  17. S. K. Sridhar, S. N. Pandeya, J. P. Stables, and A. Ramesh, “Anticonvulsant activity of hydrazones, Schiff and Mannich bases of isatin derivatives,” European Journal of Pharmaceutical Sciences, vol. 16, no. 3, pp. 129–132, 2002. View at Publisher · View at Google Scholar · View at Scopus
  18. D. Kaushik, S. A. Khan, G. Chawla, and S. Kumar, “N'-[(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene] 2/4-substituted hydrazides: synthesis and anticonvulsant activity,” European Journal of Medicinal Chemistry, vol. 45, no. 9, pp. 3943–3949, 2010. View at Publisher · View at Google Scholar · View at Scopus
  19. C. D. Duarte, E. J. Barreiro, and C. A. M. Fraga, “Privileged structures: a useful concept for the rational design of new lead drug candidates,” Mini-Reviews in Medicinal Chemistry, vol. 7, no. 11, pp. 1108–1119, 2007. View at Publisher · View at Google Scholar · View at Scopus
  20. U. Salgin-Gökşen, N. Gökhan-Kelekçi, Ö. Göktaş et al., “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,” Bioorganic & Medicinal Chemistry, vol. 15, no. 17, pp. 5738–5751, 2007. View at Publisher · View at Google Scholar · View at Scopus
  21. A. Deeb, F. El-Mariah, and M. Hosny, “Pyridazine derivatives and related compounds—part 13: synthesis and antimicrobial activity of some pyridazino[3′,4′:3,4]pyrazolo[5,1-c]- 1,2,4-triazines,” Bioorganic & Medicinal Chemistry Letters, vol. 14, no. 19, pp. 5013–5017, 2004. View at Publisher · View at Google Scholar · View at Scopus
  22. A. J. M. Rasras, T. H. Al-Tel, A. F. Al-Aboudi, and R. A. Al-Qawasmeh, “Synthesis and antimicrobial activity of cholic acid hydrazone analogues,” European Journal of Medicinal Chemistry, vol. 45, no. 6, pp. 2307–2313, 2010. View at Publisher · View at Google Scholar · View at Scopus
  23. Y. Özkay, Y. Tunali, H. Karaca, and I. Işikdaǧ, “Antimicrobial activity and a SAR study of some novel benzimidazole derivatives bearing hydrazone moiety,” European Journal of Medicinal Chemistry, vol. 45, no. 8, pp. 3293–3298, 2010. View at Publisher · View at Google Scholar · View at Scopus
  24. D. Kumar, N. M. Kumar, S. Ghosh, and K. Shah, “Novel bis(indolyl)hydrazide-hydrazones as potent cytotoxic agents,” Bioorganic & Medicinal Chemistry Letters, vol. 22, no. 1, pp. 212–215, 2012. View at Publisher · View at Google Scholar · View at Scopus
  25. K. Effenberger, S. Breyer, and R. Schobert, “Modulation of doxorubicin activity in cancer cells by conjugation with fatty acyl and terpenyl hydrazones,” European Journal of Medicinal Chemistry, vol. 45, no. 5, pp. 1947–1954, 2010. View at Publisher · View at Google Scholar · View at Scopus
  26. M. E. Caputto, L. E. Fabian, D. Benítez et al., “Thiosemicarbazones derived from 1-indanones as new anti-Trypanosoma cruzi agents,” Bioorganic & Medicinal Chemistry, vol. 19, no. 22, pp. 6818–6826, 2011. View at Publisher · View at Google Scholar · View at Scopus
  27. M. A. S. Aslam, S.-U. Mahmood, M. Shahid, A. Saeed, and J. Iqbal, “Synthesis, biological assay in vitro and molecular docking studies of new Schiff base derivatives as potential urease inhibitors,” European Journal of Medicinal Chemistry, vol. 46, no. 11, pp. 5473–5479, 2011. View at Publisher · View at Google Scholar · View at Scopus
  28. O. I. El-Sabbagh, M. A. Shabaan, H. H. Kadry, and E. S. Al-Din, “New octahydroquinazoline derivatives: synthesis and hypotensive activity,” European Journal of Medicinal Chemistry, vol. 45, no. 11, pp. 5390–5396, 2010. View at Publisher · View at Google Scholar · View at Scopus
  29. M. Catto, R. Aliano, A. Carotti et al., “Design, synthesis and biological evaluation of indane-2-arylhydrazinylmethylene-1,3-diones and indol-2-aryldiazenylmethylene-3-ones as β-amyloid aggregation inhibitors,” European Journal of Medicinal Chemistry, vol. 45, no. 4, pp. 1359–1366, 2010. View at Publisher · View at Google Scholar · View at Scopus
  30. A. K. Jordão, P. C. Sathler, V. F. Ferreira et al., “Synthesis, antitubercular activity, and SAR study of N-substituted- phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides,” Bioorganic & Medicinal Chemistry, vol. 19, no. 18, pp. 5605–5611, 2011. View at Publisher · View at Google Scholar · View at Scopus
  31. A. Mahajan, L. Kremer, S. Louw, Y. Guéradel, K. Chibale, and C. Biot, “Synthesis and in vitro antitubercular activity of ferrocene-based hydrazones,” Bioorganic & Medicinal Chemistry Letters, vol. 21, no. 10, pp. 2866–2868, 2011. View at Publisher · View at Google Scholar · View at Scopus
  32. C. A. Y. Jin, Z. Tan, M. He et al., “SAR and molecular mechanism study of novel acylhydrazone compounds targeting HIV-1 CA,” Bioorganic & Medicinal Chemistry, vol. 18, no. 6, pp. 2135–2140, 2010. View at Publisher · View at Google Scholar · View at Scopus
  33. A. M. Wu and P. D. Senter, “Arming antibodies: prospects and challenges for immunoconjugates,” Nature Biotechnology, vol. 23, no. 9, pp. 1137–1146, 2005. View at Publisher · View at Google Scholar · View at Scopus
  34. D. Enders and H. Eichenauer, “Enantioselective alkylation of aldehydes via metalated chiral hydrazones,” Tetrahedron Letters, vol. 18, no. 2, pp. 191–194, 1977. View at Google Scholar · View at Scopus
  35. D. M. Livermore, “Antibiotic resistance in staphylococci,” International Journal of Antimicrobial Agents, vol. 16, Supplement 1, pp. S3–S10, 2000. View at Google Scholar · View at Scopus
  36. A. S. de Miranda, W. B. Júnior , Y. K. C. da Silva et al., “Design, synthesis, antinociceptive and anti-inflammatory activities of novel piroxicam analogues,” in Molecules, vol. 17, no. 12, pp. 14126–14145, 2012. View at Publisher · View at Google Scholar
  37. G. Mehtap, U. Semra, and K. Esra, “Synthesis and analgesic and anti-inflammatory activities 6-substituted-3(2H)-pyridazinone-2-acetyl-2-(p-substituted/nonsubstituted benzal)hydrazone derivatives,” European Journal of Medicinal Chemistry, vol. 44, no. 9, pp. 3760–3764, 2009. View at Publisher · View at Google Scholar · View at Scopus
  38. A. K. Wahi, A. K. Singh, and A. Singh, “Design and synthesis of novel schiff's bases having N-(4H-1, 2,4-triazole-4-yl)benzamido moiety as antimicrobial and anti-inflammatory agents,” Der Pharma Chemica, vol. 3, no. 5, pp. 146–154, 2011. View at Google Scholar · View at Scopus
  39. S. M. Sondhi, M. Dinodia, and A. Kumar, “Synthesis, anti-inflammatory and analgesic activity evaluation of some amidine and hydrazone derivatives,” Bioorganic & Medicinal Chemistry, vol. 14, no. 13, pp. 4657–4663, 2006. View at Publisher · View at Google Scholar · View at Scopus
  40. Y. K. C. da Silva, C. V. Augusto, M. L. D. C. Barbosa et al., “Synthesis and pharmacological evaluation of pyrazine N-acylhydrazone derivatives designed as novel analgesic and anti-inflammatory drug candidates,” Bioorganic & Medicinal Chemistry, vol. 18, no. 14, pp. 5007–5015, 2010. View at Publisher · View at Google Scholar · View at Scopus
  41. E. Venkateshwarlu, J. V. Rao, K. Umasankar, and G. Dheeraj, “Study of anti-inflammatory, analgesic and antipyretic activity of novel isatin derivatives,” Asian Journal of Pharmaceutical and Clinical Research, vol. 5, no. 4, pp. 187–190, 2012. View at Google Scholar
  42. R. B. Lacerda, L. L. da Silva, C. K. F. de Lima et al., “Discovery of novel orally active anti-inflammatory N-phenylpyrazolyl-N-glycinyl-hydrazone derivatives that inhibit TNF-α production,” PLoS ONE, vol. 7, no. 10, article e46925, 2012. View at Publisher · View at Google Scholar
  43. S. Bala, G. Uppal, S. Kamboj, V. Saini, and D. N. Prasad, “Design, characterization, computational studies, and pharmacological evaluation of substituted-N′-[(1E) substitutedphenylmethylidene]benzohydrazide analogs,” Medicinal Chemistry Research, vol. 22, no. 6, pp. 2755–2767, 2013. View at Publisher · View at Google Scholar
  44. A. M. Isloor, B. Kalluraya, and K. S. Pai, “Synthesis, characterization and biological activities of some new benzo[b]thiophene derivatives,” European Journal of Medicinal Chemistry, vol. 45, no. 2, pp. 825–830, 2010. View at Publisher · View at Google Scholar · View at Scopus
  45. W. B. Júnior, M. S. Alexandre-Moreira, M. A. Alves et al., “Analgesic and anti-inflammatory activities of salicylaldehyde 2-chlorobenzoyl hydrazone (H2LASSBio-466), salicylaldehyde 4-chlorobenzoyl hydrazone (H2LASSBio-1064) and their zinc(II) complexes,” Molecules, vol. 16, no. 8, pp. 6902–6915, 2011. View at Publisher · View at Google Scholar · View at Scopus
  46. R. Narang, B. Narasimhan, S. Sharma et al., “Substituted naphthalen-1-γl-acetic acid hydrazides: synthesis, antimicrobial evaluation and QSAR analysis,” Medicinal Chemistry Research, vol. 9, no. 2, pp. 249–274, 2013. View at Google Scholar
  47. R. Narang, B. Narasimhan, S. Sharma et al., “Synthesis, antimycobacterial, antiviral, antimicrobial activities, and QSAR studies of nicotinic acid benzylidene hydrazide derivatives,” Medicinal Chemistry Research, vol. 21, no. 8, pp. 1557–1576, 2012. View at Publisher · View at Google Scholar · View at Scopus
  48. R. Narang, B. Narasimhan, S. Sharma et al., “Nicotinic acid benzylidene/phenyl-ethylidene hydrazides: synthesis, antimicrobial evaluation and QSAR studies,” Letters in Drug Design & Discovery, vol. 8, no. 8, pp. 733–749, 2011. View at Publisher · View at Google Scholar · View at Scopus
  49. R. Narang, B. Narasimhan, and S. Sharma, “(Naphthalen-1-yloxy)-acetic acid benzylidene/(1-phenyl-ethylidene)-hydrazide derivatives: synthesis, antimicrobial evaluation, and QSAR studies,” Medicinal Chemistry Research, vol. 21, no. 9, pp. 2526–2547, 2012. View at Publisher · View at Google Scholar · View at Scopus
  50. R. Narang, S. Sharma, and B. Narasimhan, “Evaluation of anti-inflammatory activity of acid Hydrazide derivatives,” Hygeia, vol. 4, no. 2, pp. 21–26, 2012. View at Google Scholar
  51. S. M. M. Ali, M. Jesmin, M. A. K. Azad, M. K. Islam, and R. Zahan, “Anti-inflammatory and analgesic activities of acetophenonesemicarbazone and benzophenonesemicarbazone,” Asian Pacific Journal of Tropical Biomedicine, vol. 2, no. 2, Supplement, pp. S1036–S1039, 2012. View at Publisher · View at Google Scholar
  52. R. D. Hunashal, P. M. Ronad, V. S. Maddi, D. Satyanarayana, and M. A. Kamadod, “Synthesis, anti-inflammatory and analgesic activity of 2-[4-(substituted benzylideneamino)-5-(substituted phenoxymethyl)-4H-1,2,4-triazol-3-yl thio] acetic acid derivatives,” Arabian Journal of Chemistry, 2011. View at Publisher · View at Google Scholar · View at Scopus
  53. N. A. Hamdy, H. A. Abdel-Aziz, G. M. Kamel, and I. M. I. Fakhr, “Convenient synthesis, anti-inflammatory, analgesicand ulcerogenicactivites of some new bis-hydrazonesand pyrazole derivatives,” Acta Poloniae Pharmaceutica, vol. 70, no. 3, pp. 469–480, 2013. View at Google Scholar
  54. Z. A. Kaplancikli, M. D. Altintop, A. Özdemir, G. Turan-Zitouni, S. I. Khan, and N. Tabanca, “Synthesis and biological evaluation of some hydrazone derivatives as anti-inflammatory agents,” Letters in Drug Design & Discovery, vol. 9, no. 3, pp. 310–315, 2012. View at Publisher · View at Google Scholar · View at Scopus
  55. P. Hernández, M. Cabrera, M. L. Lavaggi et al., “Discovery of new orally effective analgesic and anti-inflammatory hybrid furoxanyl N-acylhydrazone derivatives,” Bioorganic & Medicinal Chemistry, vol. 20, no. 6, pp. 2158–2171, 2012. View at Publisher · View at Google Scholar · View at Scopus
  56. C. M. Moldovan, O. Oniga, A. Pârvu et al., “Synthesis and anti-inflammatory evaluation of some new acyl-hydrazones bearing 2-aryl-thiazole,” European Journal of Medicinal Chemistry, vol. 46, no. 2, pp. 526–534, 2011. View at Publisher · View at Google Scholar · View at Scopus
  57. A. Kajal, S. Bala, S. Kamboj, and V. Saini, “Synthesis, characterization, and computational studies on phthalicanhydride-based benzylidene-hydrazide derivatives as novel, potential anti-inflammatory agents,” Medicinal Chemistry Research, 2013. View at Publisher · View at Google Scholar