Skip to main content
SpringerLink
Log in

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

  • Original Research
  • Published:
Medicinal Chemistry Research Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2

Similar content being viewed by others

References

  • 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 28:617–623

    Article  CAS  Google Scholar 

  • Al-Ayed AS (2011) Synthesis of new substituted chromen[4,3-c]pyrazol-4-ones and their antioxidant activities. Molecule 16:10292–10302

    Article  CAS  Google Scholar 

  • Aziz MA, Rohma GE, Hassan AA (2009) Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activity. Eur J Med Chem 44:3480–3487

    Article  PubMed  Google Scholar 

  • 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 45:5862–5869

    Article  CAS  PubMed  Google Scholar 

  • Bekhit AA, Ashour HM, Bekhit AD, Bekhit SA (2009) Synthesis and biological evaluation of novel pyrazole derivatives as anti-inflammatory antimicrobial agents. Med Chem 5:103–117

    Article  CAS  PubMed  Google Scholar 

  • 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 62:270–279

    Article  CAS  PubMed  Google Scholar 

  • 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 45:1206–1210

    Article  CAS  PubMed  Google Scholar 

  • 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 20:1206–1213

    Article  CAS  Google Scholar 

  • Deep A, Malhotra M, Sharma S (2012) Synthesis, characterization and antimicrobial evaluation of novel derivatives of isoniazid. Med Chem Res 21:1237–1244

    Article  Google Scholar 

  • Deodhar M, Nigade G, Chavan P (2012) Synthesis and analgesic activity of new pyridine-based heterocyclic derivatives. Med Chem Res 21:27–37

    Article  Google Scholar 

  • Elguero J, Katritzky AR, Rees CW, Scriven EFV (eds) (1996) Comprehensive heterocyclic chemistry II. Pergamon Press, Oxford, p 70

    Google Scholar 

  • 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 105:229–237

    Article  Google Scholar 

  • Gupta GK, Kumar V, Kumar V (2011) Pyrazoles as potential anti-obesity agents: a review. Res J Chem Environ 15:90–103

    Google Scholar 

  • 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 23:4209–4220

    Article  CAS  Google Scholar 

  • 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 4:5165–5171

    CAS  Google Scholar 

  • 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 22:6318–6323

    Article  CAS  PubMed  Google Scholar 

  • 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 45:4963–4967

    Article  CAS  PubMed  Google Scholar 

  • Joshi D, Parikh KS (2014) Synthesis and antimicrobial evaluation of 1,3,4-oxadiazole-based chalcone derivatives. Med Chem Res 23:1855–1864

    Article  CAS  Google Scholar 

  • Judge V, Narasimhan B, Ahuja M (2012a) Isoniazid: the magic molecule. Med Chem Res 21:3940–3957

    Article  CAS  Google Scholar 

  • 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 21:1935–1952

    Article  CAS  Google Scholar 

  • Kaur K, Kumar V, Gupta GK, Sharma AK (2014) Isoxazoline containing natural products as anticancer agents: a review. Eur J Med Chem 77:121–133

    Article  CAS  PubMed  Google Scholar 

  • 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 20:346–354

    Article  CAS  Google Scholar 

  • 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 47:1237–1243

    Article  CAS  Google Scholar 

  • 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 40:922–927

    Article  CAS  PubMed  Google Scholar 

  • Kumar H, Malhotra D, Sharma R, Sausville E, Malhotra M (2011) Synthesis, characterization and evaluation of isoniazid analogues as potent anticancer agents. Pharmacologyonline 3:337–343

    Google Scholar 

  • Kumar V, Kaur K, Gupta GK, Sharma AK (2013a) Pyrazole containing natural products: synthetic preview and biological significance. Eur J Med Chem 69:735–753

    Article  CAS  PubMed  Google Scholar 

  • 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 7:124–134

    Article  CAS  PubMed  Google Scholar 

  • 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 20:421–429

    Article  CAS  Google Scholar 

  • 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 49:164–171

    Article  CAS  PubMed  Google Scholar 

  • 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 45:5225–5233

    Article  CAS  PubMed  Google Scholar 

  • 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 4:266–273

    Article  Google Scholar 

  • 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 3:130–137

    CAS  Google Scholar 

  • Mohareb RM, El-Sayed NNE, Abdelaziz MA (2012) Uses of cyanoacetylhydrazine in heterocyclic synthesis: novel synthesis of pyrazole derivatives with anti-tumor activities. Molecule 17:8449–8463

    Article  CAS  Google Scholar 

  • 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 3:488–493

    Google Scholar 

  • 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 17:5095–5107

    Article  Google Scholar 

  • 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 23:3327–3335

    Article  CAS  Google Scholar 

  • 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 45:4252–4257

    Article  CAS  PubMed  Google Scholar 

  • 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 1:1–9

    Article  PubMed  PubMed Central  Google Scholar 

  • Rajput AP, Rajput SS (2011) A novel method for the synthesis of formyl pyrazoles using Vilsmeier–Haack reaction. Int J Pharm Pharm Sci 3:346–351

    CAS  Google Scholar 

  • 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 72:983–992

    Article  CAS  Google Scholar 

  • Ravala JP, Shaha AB, Patela NH (2011) Synthesis and anti-tubercular activity of novel pyrazol-5(H)-one derivatives. Eur J Med Chem 2:238–242

    Article  Google Scholar 

  • 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 46:5902–5909

    Article  Google Scholar 

  • 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 19:639–642

    Article  CAS  Google Scholar 

  • 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 

  • 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 81:119–138

    Article  Google Scholar 

  • Sriram D, Thimmappa HM, Yogeeswari P (2011) Microwave assisted one-pot synthesis of highly potent novel isoniazid analogues. Bioorg Med Chem Lett 21:2125–2128

    Article  PubMed  Google Scholar 

  • 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 22:2764–2767

    Article  PubMed  Google Scholar 

  • 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 21:3709–3719

    Article  CAS  Google Scholar 

  • 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 20:4226–4236

    Article  CAS  PubMed  Google Scholar 

  • Vorvoglis A (1997) Chemical transformation using hypervalent iodine reagents. Tetrahedron 53:1179–1255

    Article  Google Scholar 

  • 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 58:3381–3383

    Article  CAS  Google Scholar 

  • 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 20:3359–3367

    Article  CAS  Google Scholar 

  • Zhdankin W (2009) Hypervalent iodine (III) reagents in organic synthesis. Arkivoc 1:1–62

    Article  Google Scholar 

Download references

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.

Author information

Authors and Affiliations

  1. Department of Chemistry, Maharishi Markandeshwar University, Mullana, Ambala, 133207, India

    M. Kumar & V. Kumar

  2. Department of Biotechnology, Maharishi Markandeshwar University, Mullana, Ambala, 133207, India

    V. Beniwal

Authors
  1. M. Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. Beniwal
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. Kumar.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kumar, M., Kumar, V. & Beniwal, V. Synthesis of some pyrazolylaldehyde N-isonicotinoyl hydrazones and 2,5-disubstituted 1,3,4-oxadiazoles as DNA photocleaving agents. Med Chem Res 24, 2862–2870 (2015). https://doi.org/10.1007/s00044-015-1340-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00044-015-1340-x

Keywords

Search

Navigation