Antibacterial and cytotoxic activities of Schiff base analogues of 4-aminoantipyrine

  • Mohammad Sayed Alam
  • Dong-Ung Lee
  • Md. Latiful Bari
Article
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Abstract

Schiff base is the class of compounds showing wide range of biological activities having the azomethine (-N=CH-) active pharmacophore, which play major roles in their significant bio-activities. A series of Schiff base analogues of 4-aminoantipyrine analogues have been tested for bactericidal and cytotoxic activities against selected bacterial strains and brine shrimp (Artemia salina) nauplii, respectively. Of the compounds tested, two compounds showed a good inhibition of bacterial growth against E. coli and C. sakazakii, whereas three compounds demonstrated high cytotoxicity with LC50 values of 225, 480, and 581 ppm, in a short term bioassay using A. salina. Qualitative structure-cytotoxic activity relationships were studied using physicochemical parameters; a good correlation between clogP and cytotoxic activity was observed.

Keywords

antibacterial activity brine shrimp toxicity crystal structure pyrazole-3-ones Schiff base 
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References

  1. Abd Rehim SS, Ibrahim MAM, and Khalid KF. (2001) The inhibition of 4-(2- amino-5-methylphenylazo)antipyrine on corrosion of mild steel in HCl solution. Mater Chem Phys 70, 268–73.CrossRefGoogle Scholar
  2. Adams JP. (2000) Nitro and related compounds. J Chem Soc Perkin Trans 1, 3695–705.CrossRefGoogle Scholar
  3. Agarwal RK and Prasad S. (2005) Synthesis, spectroscopic and physicochemical characterization and biological activity of Co(II) and Ni(II) coordination compounds with 4-aminoantipyrine thiosemicarbazone. Bioinorg Chem Appli 3, 271–88.CrossRefGoogle Scholar
  4. Alam MS and Lee DU. (2011) Cytotoxic and antimicrobial properties of furoflavones and furochalcones. J Korean Soc Appl Biol Chem 54, 725–30.CrossRefGoogle Scholar
  5. Alam MS and Lee DU. (2012) Synthesis, molecular structure and antioxidant activity of (E)-4-[benzylideneamino]-1,5-dimethyl-2-phenyl-1H-pyrazol- 3(2H)-one, a Schiff base ligand of 4-aminoantipyrine. J Chem Crystallogr 42, 93–102.CrossRefGoogle Scholar
  6. Alam MS, Choi JH, and Lee DU. (2012) Synthesis of novel Schiff base analogues of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one and their evaluation for antioxidant and anti-inflammatory activity. Bioorg Med Chem 20, 4103–8.CrossRefGoogle Scholar
  7. Alam MS, Nam YJ, and Lee DU. (2013) Synthesis and evaluation of (Z)-2,3- diphenylacrylo- nitrile analogs as anti-cancer and anti-microbial agents. Eur J Med Chem 69, 790–7.CrossRefGoogle Scholar
  8. Ali MA, Mirza AH, Butcher RJ, Tarafder MTH, Keat TB, and Ali AM. (2002) Biological activity of palladium(II) and platinum(II) complexes of the acetone Schiff bases of S-methyl- and S-benzyldithiocarbazate and the X-ray crystal structure of the [Pd(asme)2] (asme=anionic form of the acetone Schiff base of S-methyldithiocarbazate) complex. J Inorg Biochem 92, 141–8.CrossRefGoogle Scholar
  9. Ali P, Meshra J, Sheikh J, Tiwar V, Rajendra Dongre R, and Ben Hadda T. (2012) Predictions and correlations of structure activity relationship of some aminoantipyrine derivatives on the basis of theoretical and experimental ground. Med Chem Res 21, 157–64.CrossRefGoogle Scholar
  10. Bashkatova NV, Korotkova EI, Karbainov YA, Yagovkin AY, and Bakibaev AA. (2005) Electrochemical, quantum-chemical and antioxidant properties of antipyrine and its derivatives. J Pharm Biomed Anal 37, 1143–7.CrossRefGoogle Scholar
  11. Bauer AW, Kirby WMM, Sherris JC, and Turck M. (1966) Antibiotic susceptibility testing by a standardized single disk method. Amer J Clin Pathol 45, 493–6.Google Scholar
  12. Bey P and Vevert JP. (1977) Synthesis of α-alkyl and α-functionalized methyl-α-amino acids. Tetrahedron Lett 18, 1455–8.CrossRefGoogle Scholar
  13. Bruker SMART (Version 5.625) for Windows NT. (2000) Bruker AXS Inc., USA.Google Scholar
  14. Burdulene D, Palaima A, Stumbryavichyute Z, and Talaikite Z. (1999) Synthesis and antiinflammatory activity of 4-aminoantipyrine derivatives of succinamides. Pharm Chem J[Khim-Farm Zh] 33, 20–2.Google Scholar
  15. Costa D, Marques AP, Reis RL, Lima JLFC, and Fernandes E. (2006) Inhibition of human neutrophil oxidative burst by pyrazolone derivatives. Free Radical Biol Med 40, 632–40.CrossRefGoogle Scholar
  16. Cukurovali A, Yilmaz I, Ozmen H, and Ahmedzade M. (2002) Cobalt(II), copper(II), nickel(II) and zinc(II) complexes of two novel Schiff base ligands and their antimicrobial activity. Transition Met Chem 27, 171–6.CrossRefGoogle Scholar
  17. Ei Ashry ESH, Awad LF, Ibrahim EI, and Bdeewy OK. (2007) Synthesis of antipyrine derivatives derived from dimedone. Chinese J Chem 25, 570–3.CrossRefGoogle Scholar
  18. Ertl P, Rohde B, and Selzer P. (2000) Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties. J Med Chem 43, 3714–7.CrossRefGoogle Scholar
  19. Finney DJ. (1978) In Statistical Method in Biological Assay, (3rd ed.), Charles Griffin and Company, England.Google Scholar
  20. Hartl M and Humpf HU. (2000) Toxicity assessment of fumonisins using the brine shrimp (Artemia salina) bioassay. Food Chem Toxicol 38, 1097–102.CrossRefGoogle Scholar
  21. Higuchi M and Yamamoto K. (1999) Selective synthesis of cyclic phenylazomethines. Org Lett 1, 1881–3.CrossRefGoogle Scholar
  22. Hu TP. (2006) (E)-4-[4-(4-Chlorobenzyloxy)benzylideneamino]-1,5-dimethyl- 2-phenyl-1H-pyrazol-3(2H)-one. Acta Cryst E62, o2270–1.Google Scholar
  23. Ismail KZ. (2000) Synthesis, spectroscopic, magnetic and biological activity studies of copper(II) complexes of an antipyrine schiff base. Transition Met Chem 25, 522–8.CrossRefGoogle Scholar
  24. Jarrahpour A, Motamedifar M, Pakshir K, Hadi N, and Zarei M. (2004) Synthesis of novel azo Schiff bases and their antibacterial and antifungal activities. Molecules 9, 815–24.CrossRefGoogle Scholar
  25. Kees KL, Fitzgerald JJ, Steiner KE, Mattes JF, Mihan B, Tosi T, Mondoro D, and McCalebr ML. (1996) New potent antihyperglycemic agents in db/db mice: synthesis and structure-activity relationship studies of (4- substituted benzyl) (trifluoromethyl)pyrazoles and-pyrazolones. J Med Chem 39, 3920–8.CrossRefGoogle Scholar
  26. Layer RW. (1963) The chemistry of imines. Chem Rev 63, 489–510.CrossRefGoogle Scholar
  27. Li ZX and Zhang XL. (2006) 1,5-Dimethy-4-[(3-nitro-benzylidene)amino]-2- pheyl-1,2-dihydro-pyrazol-3-one. Chinese J Struct Chem 25, 29–32.Google Scholar
  28. Liu SX, Han JR, Zhen XL, and Tian X. (2006) (E)-4-[4-(2,4-Dichlorobenzyloxy) benzylideneamino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one. Acta Cryst E62, o5765–6.Google Scholar
  29. Macho V, Kralik M, and Hudec J. (2004) One stage preparation of Schiff’s bases from nitroarenes, aldehydes and carbon monoxide at presence of water. J Mol Catal A Chem 209, 69–73.CrossRefGoogle Scholar
  30. Mayer BN, Ferrigni NR, Putnam JE, Jacobsen LB, Nichols DE, and McLaughlin JL. (1982) Brine shrimp: a convenient general bioassay for active plant constituents. Planta Med 45, 31–4.CrossRefGoogle Scholar
  31. Montalvo-González R and Arizα-Castolo A. (2003) Molecular structure of diaryl-aldimines by multinuclear magneticresonance and X-ray diffraction. J Mol Structure 655, 375–89.CrossRefGoogle Scholar
  32. Santos MLP, Bagatin IA, Pereira EM, and Ferreira AMDC. (2001) Redox behaviour and reactivity of some di-Schiff base copper(II) complexes towards reduced oxygen species. J Chem Soc Dalton Trans, 838–44.Google Scholar
  33. Santos PMP, Antunes AMM, Noronha J, Fernandes E, and Vieira AJSC. (2010) Scavenging activity of aminoantipyrines against hydroxyl radical. Eur J Med Chem 45, 2258–64.CrossRefGoogle Scholar
  34. Sheldrick GM. (2008) A short history of SHELX. Acta Cryst A64, 112–22.CrossRefGoogle Scholar
  35. Stewart JJP. (2004) Optimization of parameters for semiempirical methods IV: extension of MNDO, AM1, and PM3 to more main group elements. J Mol Model 10, 155–64.CrossRefGoogle Scholar
  36. Testa B, Carrupt PA, Gaillard P, and Billois F. (1996) Lipophilicity in molecular modeling. Pharm Res 13, 335–43.CrossRefGoogle Scholar
  37. Türkeer L, Sener E, Yalçín I, Akbulut U, and Kayalidere I. (1990) QSAR of some antifungally active benzoxazoles employing quantum chemical parameters. Sci Pharm 58, 107–13.Google Scholar
  38. Weidenbörner M and Chandra Jha H. (1993) Antifungal activity of flavonoids and their mixtures against different fungi occurring on grain. Pestic Sci 38, 347–51.CrossRefGoogle Scholar
  39. Yadav PN, Demertzis MA, Kovalα-Demertzi D, Skoulika S, and West DX. (2003) Palladium(II) complexes of 4-formylantipyrine N(3)-substituted thiosemicarbazones: first example of X-ray crystal structure and description of bonding properties. Inorg Chim Acta 349, 30–6.CrossRefGoogle Scholar
  40. Zhang QZ, Zhao YL, Chen X, and Yu M. (2006) (E)-4-[2-(4-Chlorobenzyloxy) benzylideneamino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one. Acta Cryst E62, o5252–4.Google Scholar
  41. Zhao WN. (2007) A dinuclear manganese (II) complex with a 4-aminoantipyrine-derived Schiff base ligand. Acta Cryt E63, m2095.Google Scholar

Copyright information

© The Korean Society for Applied Biological Chemistry 2014

Authors and Affiliations

  • Mohammad Sayed Alam
    • 1
  • Dong-Ung Lee
    • 1
  • Md. Latiful Bari
    • 2
  1. 1.Division of BioscienceDongguk UniversityGyeongjuRepublic of Korea
  2. 2.Food analysis and Research laboratory, Centre for Advance Research in SciencesUniversity of DhakaDhakaBangladesh

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