Advertisement

Medicinal Chemistry Research

, Volume 24, Issue 7, pp 2862–2870 | Cite as

Synthesis of some pyrazolylaldehyde N-isonicotinoyl hydrazones and 2,5-disubstituted 1,3,4-oxadiazoles as DNA photocleaving agents

  • M. Kumar
  • V. KumarEmail author
  • V. Beniwal
Original Research

Abstract

In search of potential biologically active compounds, some novel 2,5-disubstituted 1,3,4-oxadiazole derivatives have been prepared conveniently via oxidation of newly synthesized pyrazolylaldehyde N-isonicotinoyl hydrazones by (diacetoxyiodo)benzene in dichloromethane under mild reaction conditions. Compounds were obtained in excellent yields, and their structures have been established on the basis of their FT-IR, 1H, 13C NMR, and mass spectral data. The DNA photocleavage potential for all the synthesized compounds was evaluated using agarose gel electrophoresis. It has been observed that oxadiazole derivatives showed a significant level of DNA photocleavage activity when compared with their corresponding hydrazones, and some modifications in the basic structure may lead to construct some potential chemotherapeutic agents in future.

Keywords

Pyrazole Oxadiazole Hydrazone Isonicotine DNA photocleavage (Diacetoxyiodo)benzene 

Notes

Acknowledgments

The authors are grateful to the Chairman, Maharishi Markandeshwar University, Mullana (Ambala), for providing the necessary research facilities. We are also grateful to Manish Kumar and Avtar Singh of the SAIF, Panjab University, Chandigarh, for providing IR, 1H, 13C NMR, mass spectra, and elemental analysis.

References

  1. Aggarwal R, Kumar R, Kumar V (2007) A facile and rapid one-pot synthesis of 1,4-diaryl-2-mercaptoimidazoles under solvent-free conditions. J Sulfur Chem 28:617–623CrossRefGoogle Scholar
  2. Al-Ayed AS (2011) Synthesis of new substituted chromen[4,3-c]pyrazol-4-ones and their antioxidant activities. Molecule 16:10292–10302CrossRefGoogle Scholar
  3. Aziz MA, Rohma GE, Hassan AA (2009) Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activity. Eur J Med Chem 44:3480–3487PubMedCrossRefGoogle Scholar
  4. Bakht MA, Yar MS, Abdel-Hamid SGS, Al Qasoumi I, Samad A (2010) Molecular properties prediction, synthesis and antimicrobial activity of some newer oxadiazole derivatives. Eur J Med Chem 45:5862–5869PubMedCrossRefGoogle Scholar
  5. Bekhit AA, Ashour HM, Bekhit AD, Bekhit SA (2009) Synthesis and biological evaluation of novel pyrazole derivatives as anti-inflammatory antimicrobial agents. Med Chem 5:103–117PubMedCrossRefGoogle Scholar
  6. Bondock S, Naser T, Ammar YA (2013) Synthesis of some new 2-(3-pyridyl)-4,5-disubstituted thiazoles as potent antimicrobial agents. Eur J Med Chem 62:270–279PubMedCrossRefGoogle Scholar
  7. Chandrakantha B, Shetty P, Nambiyar V, Isloor N, Isloor AM (2010) Synthesis, characterization and biological activity of some new 1,3,4-oxadiazole bearing 2-flouro-4-methoxyphenyl moiety. Eur J Med Chem 45:1206–1210PubMedCrossRefGoogle Scholar
  8. Dash S, Kumar BA, Singh J, Maiti BC, Maity TK (2011) Synthesis of some novel 3,5-disubstituted 1,3,4-oxadiazole derivatives and anticancer activity on EAC animal model. Med Chem Res 20:1206–1213CrossRefGoogle Scholar
  9. Deep A, Malhotra M, Sharma S (2012) Synthesis, characterization and antimicrobial evaluation of novel derivatives of isoniazid. Med Chem Res 21:1237–1244CrossRefGoogle Scholar
  10. Deodhar M, Nigade G, Chavan P (2012) Synthesis and analgesic activity of new pyridine-based heterocyclic derivatives. Med Chem Res 21:27–37CrossRefGoogle Scholar
  11. Elguero J, Katritzky AR, Rees CW, Scriven EFV (eds) (1996) Comprehensive heterocyclic chemistry II. Pergamon Press, Oxford, p 70Google Scholar
  12. Gowda SKR, Naik BHS, Kumar VB, Sudhomani CN, Naik RTR, Krishnamurthy G (2013) Synthesis, antimicrobial, DNA-binding and photocleavage studies of cobalt (III) and nickel (II) Schiff base complexes. Spectrochim Acta A 105:229–237CrossRefGoogle Scholar
  13. Gupta GK, Kumar V, Kumar V (2011) Pyrazoles as potential anti-obesity agents: a review. Res J Chem Environ 15:90–103Google Scholar
  14. Gupta GK, Saini V, Khare R, Kumar V (2014) 1, 4-Diaryl-2-mercaptoimidazoles derivatives as a novel class of antimicrobial agents: design, synthesis, and computational studies. Med Chem Res 23:4209–4220CrossRefGoogle Scholar
  15. Hanumanagoud H, Basavaraja KM (2012) Synthesis, antibacterial, antifungal activity and DNA cleavage study of 3-(7-methoxy-benzofuran-2-yl)-5-aryl-4H-[1,2,4]triazoles. J Chem Pharm Res 4:5165–5171Google Scholar
  16. Hassan GS, El-Messery SM, Al-Omary FAM, El-Subbagh HI (2012) Substituted thiazoles VII. Synthesis and antitumor activity of certain 2-(substituted amino)-4-phenyl-1,3-thiazole analogs. Bioorg Med Chem Lett 22:6318–6323PubMedCrossRefGoogle Scholar
  17. Jha KK, Samad A, Kumar Y, Shaharyar M, Khosa RL et al (2010) Design, synthesis and biological evaluation of 1,3,4-oxadiazole derivatives. Eur J Med Chem 45:4963–4967PubMedCrossRefGoogle Scholar
  18. Joshi D, Parikh KS (2014) Synthesis and antimicrobial evaluation of 1,3,4-oxadiazole-based chalcone derivatives. Med Chem Res 23:1855–1864CrossRefGoogle Scholar
  19. Judge V, Narasimhan B, Ahuja M (2012a) Isoniazid: the magic molecule. Med Chem Res 21:3940–3957CrossRefGoogle Scholar
  20. Judge V, Narasimhan B, Ahuja M, Sriram D, Yogeeswari P (2012b) Synthesis, antimycobacterial, antiviral, antimicrobial activities, and QSAR studies of isonicotinic acid-1-(substituted phenyl)-ethylidene/cyclohep-tylidene hydrazides. Med Chem Res 21:1935–1952CrossRefGoogle Scholar
  21. Kaur K, Kumar V, Gupta GK, Sharma AK (2014) Isoxazoline containing natural products as anticancer agents: a review. Eur J Med Chem 77:121–133PubMedCrossRefGoogle Scholar
  22. Kulkarni AKD, Patil SA, Naik VH, Badam PS (2011) DNA cleavage and antimicrobial investigation of Co (II), Ni (II), and Cu (II) complexes with triazole Schiff bases: synthesis and spectral characterization. Med Chem Res 20:346–354CrossRefGoogle Scholar
  23. Kumar P (2012) An environmentally benign and solvent-free synthesis of 3-aryl[1,2,4]triazolo[4,3-a]pyridines and 1-aryl-5-methyl[1,2,4]triazolo[4,3-a]quinolines using phenyliodine bis-(trifluoroacetate) or iodobenzene diacetate. J Heterocycl Chem 47:1237–1243CrossRefGoogle Scholar
  24. Kumar V, Aggarwal R, Tyagi P, Singh SP (2005) Synthesis and antibacterial activity of some new 1-heteroar-yl-5-amino-4-phenyl-3-trifluoromethylpyrazoles. Eur J Med Chem 40:922–927PubMedCrossRefGoogle Scholar
  25. Kumar H, Malhotra D, Sharma R, Sausville E, Malhotra M (2011) Synthesis, characterization and evaluation of isoniazid analogues as potent anticancer agents. Pharmacologyonline 3:337–343Google Scholar
  26. Kumar V, Kaur K, Gupta GK, Sharma AK (2013a) Pyrazole containing natural products: synthetic preview and biological significance. Eur J Med Chem 69:735–753PubMedCrossRefGoogle Scholar
  27. Kumar V, Kaur K, Gupta GK, Gupta AK, Kumar S (2013b) Developments in synthesis of the anti-inflammatory drug, celecoxib: a review. Recent Pat Inflamm Allergy Drug Discov 7:124–134PubMedCrossRefGoogle Scholar
  28. Kurdekar GS, Puttanagouda SM, Kulkarni NV et al (2011) Synthesis, characterization, antibiogram and DNA binding studies of novel Co (II), Ni (II), Cu (II), and Zn (II) complexes of Schiff base ligands with quinoline core. Med Chem Res 20:421–429CrossRefGoogle Scholar
  29. Lu X, Liu X, Wan B (2012) Synthesis and evaluation of anti-tubercular and antibacterial activities of new 4-(2,6-dichlorobenzyloxy)phenyl thiazole, oxazole and imidazole derivatives. Eur J Med Chem 49:164–171PubMedCrossRefGoogle Scholar
  30. Manjunatha K, Poojary B, Lobo LP, Fernandes JN, Kumari S (2010) Synthesis and biological evaluation of some 1,3,4-oxadiazole derivatives. Eur J Med Chem 45:5225–5233PubMedCrossRefGoogle Scholar
  31. Martins F, Santos S, Ventura C, Elvas-Leitao R, Santos L, Vitorino S, Reis M, Miranda V, Correia HF, Richardson DR, Bernhardt PV (1999) Crystal and molecular structure of 2-hydroxy-1-naphthaldehyde isonicotinoylhydrazone (NIH) and its iron (III) complex: an iron chelator with anti-tumour activity. J Biol Inorg Chem 4:266–273CrossRefGoogle Scholar
  32. Merugu KS, Kurnool A, Kumar V, Pujari LJN et al (2011) Synthesis, characterization and biological activities of 2,5-disubstituted-1,3,4-oxadiazoles. Der Pharma Chem 3:130–137Google Scholar
  33. Mohareb RM, El-Sayed NNE, Abdelaziz MA (2012) Uses of cyanoacetylhydrazine in heterocyclic synthesis: novel synthesis of pyrazole derivatives with anti-tumor activities. Molecule 17:8449–8463CrossRefGoogle Scholar
  34. Nikaljea APG, Pathana M, Ghodkea M, Rajanib D (2012) Synthesis of novel N-(2-substituted-4-oxothiazolidin-3-yl) isonicotinamide derivatives as anti-mycobacterial agents. Der Pharma Sin 3:488–493Google Scholar
  35. Oliveira CSD, Lira BF, Falcao-Silva VS, Siqueira-Junior JP, Barbosa-Filho JM (2012) Synthesis, molecular properties prediction, and anti-staphylococcal activity of N-acylhydrazones and new 1,3,4-oxadiazole derivatives. Molecule 17:5095–5107CrossRefGoogle Scholar
  36. Pal R, Kumar V, Gupta AK, Beniwal V (2014) Synthesis, characterization and DNA photocleavage study of a novel dehydroacetic acid based hydrazone Schiff’s base and its metal complexes. Med Chem Res 23:3327–3335CrossRefGoogle Scholar
  37. Prakash O, Kumar M, Kumar R, Sharma C, Aneja KR (2010) Hypervalent iodine (III) mediated synthesis of novel unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles as antibacterial and antifungal agents. Eur J Med Chem 45:4252–4257PubMedCrossRefGoogle Scholar
  38. Prakash O, Hussain K, Aneja DK, Sharma C, Aneja KR (2011) A facile iodine (III)-mediated synthesis of 3-(3-aryl-1-phenyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridines via oxidation of 2-((3-aryl-1-phenyl-1H-pyrazol-4-yl)methylene)-1-(pyridin-2-yl)hydrazines and their antimicrobial evaluations. Org Med Chem Lett 1:1–9PubMedCrossRefPubMedCentralGoogle Scholar
  39. Rajput AP, Rajput SS (2011) A novel method for the synthesis of formyl pyrazoles using Vilsmeier–Haack reaction. Int J Pharm Pharm Sci 3:346–351Google Scholar
  40. Raman N, Raja SJJ (2007) DNA cleavage, structural elucidation and anti-microbial studies of three novel mixed ligand Schiff base complexes of copper (II). Serb Chem Soc 72:983–992CrossRefGoogle Scholar
  41. Ravala JP, Shaha AB, Patela NH (2011) Synthesis and anti-tubercular activity of novel pyrazol-5(H)-one derivatives. Eur J Med Chem 2:238–242CrossRefGoogle Scholar
  42. Ríkova EV, Polanc S, Kocevar M, Kosmrlj J, Horváti K, Bosze S, Stolaríkova J, Imramovsky A, Vinsova J (2011) New series of isoniazid hydrazones linked with electron-withdrawing substituents. Eur J Med Chem 46:5902–5909CrossRefGoogle Scholar
  43. Rostamizadeh S, Ghamkhar SA (2008) Mild and facile method for one pot synthesis of 2,5-di-substituted 1,3,4-oxadiazoles at room temperature. Chin Chem Lett 19:639–642CrossRefGoogle Scholar
  44. Sharma A, Kumar V, Khare R, Gupta GK, Beniwal V (2014) Synthesis, docking study, and DNA photocleavage activity of some pyrimidinyl hydrazones and 3-(quinolin-3-yl)-5,7-dimethyl-1,2,4-triazolo[4,3-a]pyrimidine derivatives. Med Chem Res. doi: 10.1007/s00044-014-1265-9 Google Scholar
  45. Sousa J, Kovalishyn V, Latino DARS, Ramos J, Viveiros M (2014) Design, synthesis and biological evaluation of novel isoniazid derivatives with potent antitubercular activity. Eur J Med Chem 81:119–138CrossRefGoogle Scholar
  46. Sriram D, Thimmappa HM, Yogeeswari P (2011) Microwave assisted one-pot synthesis of highly potent novel isoniazid analogues. Bioorg Med Chem Lett 21:2125–2128PubMedCrossRefGoogle Scholar
  47. Sriram D, Venkata RA, Arumalla M, Lakshmi IV, Gopisetti K, Jangala V, Ullas JV, Thimmappa MH, Yogeeswari P (2012) Synthesis of highly potent novel anti-tubercular isoniazid analogues with preliminary pharmacokinetic evaluation. Bioorg Med Chem Lett 22:2764–2767PubMedCrossRefGoogle Scholar
  48. Taj T, Kamble RR, Kattimani PP, Badami BV (2012) Synthetic utility of sydnones: synthesis of pyrazolines derivatized with 1,2,4-triazoles as antihyperglymic, antioxidant agents and their DNA cleavage study. Med Chem Res 21:3709–3719CrossRefGoogle Scholar
  49. Tang J, Lv X, Wanga X, Sun LJ, Zhang Y et al (2012) Synthesis, biological evaluation and molecular modeling of novel 1,3,4-oxadiazole derivatives based on vanillic acid as potential immunosuppressive agents. Bioorg Med Chem 20:4226–4236PubMedCrossRefGoogle Scholar
  50. Vorvoglis A (1997) Chemical transformation using hypervalent iodine reagents. Tetrahedron 53:1179–1255CrossRefGoogle Scholar
  51. Yang R, Dai L (1993) Hypervalent iodine oxidation of N-acylhydrazones and N-phenylsemicarbazone: an efficient method for the synthesis of derivatives of 1,3,4-oxadiazoles and Δ3-1,3,4-oxadiazolines. J Org Chem 58:3381–3383CrossRefGoogle Scholar
  52. Zhang ZM, Zhang X, Zhao Z, Yan R et al (2012) Synthesis, biological evaluation and molecular docking studies of 1,3,4-oxadiazole derivatives as potential immunosuppressive agents. Bioorg Med Chem Lett 20:3359–3367CrossRefGoogle Scholar
  53. Zhdankin W (2009) Hypervalent iodine (III) reagents in organic synthesis. Arkivoc 1:1–62CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  1. 1.Department of ChemistryMaharishi Markandeshwar University, MullanaAmbalaIndia
  2. 2.Department of BiotechnologyMaharishi Markandeshwar University, MullanaAmbalaIndia

Personalised recommendations