Article Sidebar

Download
PDF

Main Article Content

Abstract

In search of new antibacterial and antifungal agents with improved and broad spectrum potency, we designed and synthesized a series of novel N-benzylidene-4-(5-methyl-1H-tetrazol-1-yl)benzenamines (6a-j). All the synthesized compounds were evaluated for their in vitro antibacterial against Grampositive and Gram-negative bacteria. The antifungal activities of the synthesized compounds were also evaluated. Some of the compounds (6e, 6i, 6j) showed better activities towards bacterial pathogens. Among the synthesized compounds, compound 6f exhibited potent antibacterial activity against Gramnegative Salmonella abony, Salmonella typhi, Escherichia coli and Gram-positive Bacillus subtilis bacteria. Compound 6f also shows potent antifungal activities against all the fungal pathogens.

Keywords

Benzenamines Microbial activities Schiff base Tetrazole

Article Details

How to Cite
G. Vedpathak, S., K. Kakade, G., P. Dixit, P., & S. Ingle, V. (2018). Synthesis of N-Benzylidene-4-(5-methyl-1H-tetrazol-1-yl)benzenamines as Potent Antibacterial and Antifungal Agents. Asian Journal of Organic & Medicinal Chemistry, 3(3), 69–74. https://doi.org/10.14233/ajomc.2018.AJOMC-P102
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX

References

  1. I. Berber, C. Cokmus and E. Atalan, Characterization of Staphylococcus species by SDS-PAGE of Whole-Cell and Extracellular Proteins, Microbiology, 72, 42 (2003); https://doi.org/10.1023/A:1022221905449.
  2. Z.A. Kaplancikli, G. Turan-Zitouni, A. Özdemir and G. Revial, New Triazole and Triazolothiadiazine Derivatives as Possible Antimicrobial Agents, Eur. J. Med. Chem., 43, 155 (2008); https://doi.org/10.1016/j.ejmech.2007.03.019.
  3. M.K. Khera, I.A. Cliffe, T. Mathur and O. Prakash, Synthesis and in vitro Activity of Novel 1,2,4-Triazolo[4,3-a]pyrimidine Oxazolidinone Antibacterial Agents, Bioorg. Med. Chem. Lett., 21, 2887 (2011); https://doi.org/10.1016/j.bmcl.2011.03.075.
  4. W.M. Basyouni, K.A.M. El-Bayouki, W.M. Tohamy and S.Y. Abbas, Silica Sulfuric Acid: An Efficient, Reusable, Heterogeneous Catalyst for the One-Pot, Five-Component Synthesis of Highly Functionalized Piperidine Derivatives, Synth. Commun., 45, 1073 (2015); https://doi.org/10.1080/00397911.2015.1005632.
  5. J.N. Pendleton, S.P. Gorman and B.F. Gilmore, Clinical Relevance of the ESKAPE Pathogens, Expert Rev. Anti Infect. Ther., 11, 297 (2013); https://doi.org/10.1586/eri.13.12.
  6. A. Khalafi-Nezhad, M.N. Soltani Rad, H. Mohabatkar, Z. Asrari and B. Hemmateenejad, Design, Synthesis, Antibacterial and QSAR Studies of Benzimidazole and Imidazole Chloroaryloxyalkyl Derivatives, Bioorg. Med. Chem., 13, 1931 (2005); https://doi.org/10.1016/j.bmc.2005.01.014.
  7. L. Shi, H.-M. Ge, S.-H. Tan, H.-Q. Li, Y.-C. Song, H.-L. Zhu and R.-X Tan, Synthesis and Antimicrobial Activities of Schiff bases Derived from 5-Chloro-salicylaldehyde, Eur. J. Med. Chem., 42, 558 (2007); https://doi.org/10.1016/j.ejmech.2006.11.010.
  8. J. Kumar, A. Rai and V. Raj, A Comprehensive Review on the Pharma-cological Activity of Schiff Base Containing Derivatives, Org. Med. Chem., 1, 555564 (2017); https://doi.org/10.19080/OMCIJ.2017.01.555564.
  9. Z.H. El-Wahab and M.R. El-Sarrag, Derivatives of Phosphate Schiff Base Transition Metal Complexes: Synthesis, Studies and Biological Activity, Spectrochim. Acta Part A: Mol. Biomol. Spectrosc., 60, 271 (2004); https://doi.org/10.1016/S1386-1425(03)00216-6.
  10. S.-J. Lin, W.-J. Tsai, W.-F. Chiou, T.-H. Yang and L.-M. Yang, Selective COX-2 Inhibitors. Part 2: Synthesis and Biological Evaluation of 4-Benzylideneamino- and 4-Phenyliminomethyl-benzenesulfonamides, Bioorg. Med. Chem., 16, 2697 (2008); https://doi.org/10.1016/j.bmc.2007.11.033.
  11. S.M. Sondhi, N. Singh, A. Kumar, O. Lozach and L. Meijer, Synthesis, Anti-Inflammatory, Analgesic and Kinase (CDK-1, CDK-5 and GSK-3) Inhibition Activity Evaluation of Benzimidazole/Benzoxazole Deriv-atives and Some Schiff’s Bases, Bioorg. Med. Chem., 14, 3758 (2006); https://doi.org/10.1016/j.bmc.2006.01.054.
  12. S. Gemma, L. Savini, M. Altarelli, P. Tripaldi, L. Chiasserini, S.S. Coccone, V. Kumar, C. Camodeca, G. Campiani, E. Novellino, S. Clarizio, G. Delogu and S. Butini, Development of Antitubercular Compounds based on a 4-Quinolylhydrazone Scaffold. Further Structure-Activity Relationship Studies, Bioorg. Med. Chem., 17, 606 (2009); https://doi.org/10.1016/j.bmc.2009.06.051.
  13. C.V. Deliwala, J.D. Modi and S.S. Sabnis, Antitumor Agents. Schiff Cases from Benzaldehyde Nitrogen Mustards and 2-Phenyl-4-[(3-amino-4-methoxy)phenyl]thiazole, J. Med. Chem., 14, 450 (1971); https://doi.org/10.1021/jm00287a022.
  14. D. Sriram, P. Yogeeswari and T.G. Kumar, Microwave Assisted Synthesis, AntiHIV and AntiYFV Activities of Schiff Bases of N-Hydroxy-N¢-aminoguanidine Tosylate, Indian J. Pharm. Sci., 67, 493 (2005).
  15. L. Cheng, J. Tang, H. Luo, X. Jin, F. Dai, J. Yang, Y. Qian, X. Li and B. Zhou, Antioxidant and Antiproliferative Activities of Hydroxyl-Substituted Schiff Bases, Bioorg. Med. Chem. Lett., 20, 2417 (2010); https://doi.org/10.1016/j.bmcl.2010.03.039.
  16. M. Bhattacharya, S.A. Iqbal and S. Malik, Physicochemical Study of Furosemide Salicyldehyde Schiff Base Complex with Hg(II) and Ag(I) Metal Ion, Mater. Sci. Res. Ind., 3, 85 (2005).
  17. V.P. Singh, A. Katiyar and S. Singh, Synthesis, Characterization of Some Transition Metal(II) Complexes of Acetone p-Amino Acetophenone Salicyloyl Hydrazone and their Antimicrobial Activity, BioMetals, 21, 491 (2008); https://doi.org/10.1007/s10534-008-9136-9.
  18. V.B. Badwaik, R.D. Deshmukh and A.S. Aswar, Synthesis, Structural, and Biological Studies of Some Bivalent Metal Ion Complexes with the Tridentate Schiff Base Ligand, Russ. J. Coord. Chem., 35, 247 (2009); https://doi.org/10.1134/S1070328409040034.
  19. S.C.S. Bugalho, E.M.S. Macoas, M. Lurdes S. Cristiano and R. Fausto, Low Temperature Matrix-Isolation and Solid State Vibrational Spectra of Tetrazole, Phys. Chem. Chem. Phys., 3, 3541 (2001); https://doi.org/10.1039/b103344c.
  20. C. Liljebris, S.D. Larsen, D. Ogg, B.J. Palazuk and J.E. Bleasdale, Investigation of Potential Bioisosteric Replacements for the Carboxyl Groups of Peptidomimetic Inhibitors of Protein Tyrosine Phosphatase 1B: Identification of a Tetrazole-Containing Inhibitor with Cellular Activity, J. Med. Chem., 45, 1785 (2002); https://doi.org/10.1021/jm011100y.
  21. G. Costantino, K. Maltoni, M. Marinozzi, E. Camaioni, L. Prezeau, J.-P. Pin and R. Pellicciari, Synthesis and Biological Evaluation of 2-(3¢-(1H-tetrazol-5-yl)bicyclo[1.1.1]pent-1-yl)glycine (S-TBPG), A Novel mGlu1 Receptor Antagonist, Bioorg. Med. Chem., 9, 221 (2001); https://doi.org/10.1016/S0968-0896(00)00270-4.
  22. M. Ankersen, B. Peschke, B.S. Hansen and T.K. Hansen, Investigation of Bioisosters of the Growth Hormone Secretagogue L-692,429, Bioorg. Med. Chem. Lett., 7, 1293 (1997); https://doi.org/10.1016/S0960-894X(97)00216-3.
  23. C.J. Gardner, D.R. Armour, D.T. Beattie, J.D. Gale, A.B. Hawcock, G.J. Kilpatrick, D.J. Twissell and P. Ward, GR205171: A Novel Anta-gonist with High Affinity for the Tachykinin NK1 Receptor, and Potent Broad-Spectrum Anti-Emetic Activity, Regul. Pept., 65, 45 (1996); https://doi.org/10.1016/0167-0115(96)00071-7.
  24. S.H. Park, J.H. Kim, S.S. Bae, K.W. Hong, D.S. Lee, J.Y. Leem, B.T. Choi and H.K. Shin, Protective Effect of the Phosphodiesterase III Inhibitor Cilostazol on Amyloid b-Induced Cognitive Deficits Associated with Decreased Amyloid b-Accumulation, Biochem. Biophys. Res. Commun., 408, 602 (2011); https://doi.org/10.1016/j.bbrc.2011.04.068.
  25. G.W. Counts, D. Gregory, D. Zeleznik and M. Turck, Cefazaflur, A New Parenteral Cephalosporin: in vitro Studies, Antimicrob. Agents Chemother., 11, 708 (1977); https://doi.org/10.1128/AAC.11.4.708.
  26. S.G. Vedpathak, R.G. Momle, G.K. Kakade and V.S. Ingle, An Improved and Convenient Route for yhe Synthesis of 5-methyl-1H-tetrazol-1-yl Substituted Benzenamines, World J. Pharm. Res., 5, 1049 (2016).
  27. S.G. Vedpathak, G.K. Kakade and V.S. Ingle, An Improved One-pot Method for the Synthesis of 1,5-Disubstituted Tetrazoles from Secondary Amides using Titanium Tetrachloride (TiCl4), IRA-Int. J. Appl. Sci. (Faisalabad), 3, 16 (2016); https://dx.doi.org/10.21013/jas.v3.n1.p3.
  28. G.B. Bagihalli, P.S. Badami and S.A. Patil, Synthesis, Spectral Charact-erization and in vitro Biological Studies of Co(II), Ni(II) and Cu(II) Complexes with 1,2,4-Triazole Schiff Bases, J. Enzyme Inhib. Med. Chem., 24, 381 (2008); https://doi.org/10.1080/14756360802187901.
  29. G. Shanmugam, S. Elavarasan, M. Bhakiaraj and M. Gopalakrishnan, Simple and Efficient Method for the Preparation of Novel Tetrazole Derivatives Spectral Characterization and its Antibacterial Activities, Der Pharm. Chem., 5, 183 (2013).
  30. V. Dhayanithi, S. Shafi, K. Kumaran, S. Jai, V. Ragavan, K. Goud, S. Kumari and H. Pati, Synthesis of Selected 5-Thio-Substituted Tetrazole Derivatives and Evaluation of Their Antibacterial and Antifungal Activities, J. Serb. Chem. Soc., 76, 165 (2011); https://doi.org/10.2298/JSC090421001D.
  31. D. Varadaraji, S.S. Suban, V.R. Ramasamy, K. Kubendiran, J.S.K.G. Raguraman, S.K. Nalilu and H.N. Pati, Synthesis and Evaluation of a Series of 1-Substituted Tetrazole Derivatives as Antimicrobial Agents, Org. Commun., 3, 45 (2010).
  32. G.B. Patel, Y.A. Pawar, B.V. Sivakumar and D.H. More, Synthesis and Biological Evaluation of Some New N-Substituted Benzimidazoles Containing Tetrazoles Moiety, J. Pharm. Res., 4, 4377 (2011).
  33. A.C. Scott, eds.: J.G. Collee, J.P. Duguid, A.G. Fraser and B.P. Marmion, Laboratory Control of Antimicrobial Therapy, In: Mackie and Mac-Cartney Practical Medical Microbiology, Churchill, Livingstone, edn 13, vol. 2, p. 161 (1989).