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Ligand-assisted click reaction for the synthesis of new hybrid compounds based on 1,2,3-triazoles and 5,5-diphenylimidazolidine-2,4-dione and evaluation of their antibacterial activities

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Abstract

The new hybrid compounds based on 1,2,3-triazoles and 5,5-diphenylimidazolidine-2,4-dione were successfully synthesized by copper-catalyzed click reaction in the presence of water-soluble ligand, sodium 4-amino-5-hydroxy-7-sulfonaphthalene-2-sulfonate and copper salt. The click reaction of 5,5-diphenyl-3-(prop-2-yn-1-yl)imidazolidine-2,4-dione and 5,5-diphenyl-1,3-di(prop-2-yn-1-yl)imidazolidine-2,4-dione with aryl azides or sodium azide and benzyl chloride in water produced new 1,2,3-triazoles linked-5,5-diphenylimidazolidine-2,4-dione. The 4-amino-5-hydroxy-7-sulfonaphthalene-2-sulfonate was used as ligand, which enhanced the reactions and reduced the quantity of the toxic copper salt. The in vitro antibacterial activities of the all synthesized compounds were screened against the Gram-positive and Gram-negative bacteria, by the use of well diffusion method. The results showed that all compounds were active against both M. luteus and P. aeruginoasa bacteria.

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References

  1. Kolb HC, Sharpless KB (2003) Drug Discov Today 8:1128

    Article  CAS  PubMed  Google Scholar 

  2. Agalave SG, Maujan SR, Pore VS (2011) Chem Asian J 6:2696

    Article  CAS  PubMed  Google Scholar 

  3. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596

    Article  CAS  Google Scholar 

  4. Aher NG, Pore VS, Mishra NN, Kumar A, Shukla PK, Sharma A, Bhat MK (2009) Bioorg Med Chem Lett 19:759

    Article  CAS  PubMed  Google Scholar 

  5. Demaray JA, Thuener JE, Dawson MN, Sucheck SJ (2008) Bioorg Med Chem Lett 18:4868

    Article  CAS  PubMed  Google Scholar 

  6. Wang XL, Wan K, Zhou HC (2010) Eur J Med Chem 45:4631

    Article  CAS  PubMed  Google Scholar 

  7. Buckle DR, Outred DJ, Rockell CJM, Smith H, Spicer BA (1983) J Med Chem 26:251

    Article  CAS  PubMed  Google Scholar 

  8. Whiting M, Tripp JC, Lin YC, Lindstrom W, Olson AJ, Elder JH, Sharpless KB, Fokin VV (2006) J Med Chem 49:7697

    Article  CAS  PubMed  Google Scholar 

  9. Giffin MJ, Heaslet H, Brik A, Lin YC, Cauvi G, Wong CH, McRee DE, Elder JH, Stout CD, Torbett BE (2008) J Med Chem 51:6263

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Costa MS, Boechat N, Rangel EA, Silva FDCD, Souza AMTD, Rodrigues CR, Castro HC, Junior IN, Lourenc MCS, Wardell SMSV, Ferreirab VF (2006) Bioorg Med Chem 14:8644

    Article  CAS  PubMed  Google Scholar 

  11. Patpi SR, Pulipati L, Yogeeswari P, Sriram D, Jain N, Sridhar B, Murthy R, Anjana DT, Kalivendi SV, Kantevar S (2012) J Med Chem 55:3911

    Article  CAS  PubMed  Google Scholar 

  12. Simone RD, Chini MG, Bruno I, Riccio R, Mueller D, Werz O, Bifulco G (2011) J Med Chem 54:1565

    Article  PubMed  CAS  Google Scholar 

  13. Husain MI, Nasir M (1979) ChemInform 10:177

    Google Scholar 

  14. Kelbaugh RR, Sarges R (1979) Spiro-furanohydantoin derivatives. US Patent 4,147,797, Apr 3, 1979; (1979) Chem Abstr 91:20511

  15. Kelly TA, Sorcek RJ (2001) Novel N-(pyridin-4-yl) nitrogen heterocyclic compounds useful in the treatment of inflammatory disease. Patent WO 2001007048, Feb 1, 2001; (2001) Chem Abstr 134:131536

  16. Kieć-Kononowicz K, Szymańska E (2002) Farmaco 57:909

    Article  PubMed  Google Scholar 

  17. Rodgers TR, Lamontagne MP, Markove A, Ash AB (1977) J Med Chem 20:591

    Article  CAS  PubMed  Google Scholar 

  18. Valaviciene J, Blyum RA, Lutsenko VV, Stumbreviciute Z (1978) Chem Abstr 88:105221

    Google Scholar 

  19. Elokdah HM, Chai SY, Sulkowski TS, Strike DP (1997) Preparation of 2-thioxo-imidazolidin-4-ones for increasing HDL cholesterol concentration. Patent WO 9719932, Jun 5, 1997; (1997) Chem Abstr 127:81453

  20. Moloney GP, Martin GR, Mathews N, Milne A, Hobbs H, Dudsworth S, Sang PY, Knigh C, Williams M, Maxwell M, Glan RC (1999) J Med Chem 42:2504

    Article  CAS  PubMed  Google Scholar 

  21. Kolb HC, Finn MG, Sharpless KB (2001) Angew Chem Int Ed 40:2004

    Article  CAS  Google Scholar 

  22. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 1:2596

    Article  Google Scholar 

  23. Tornøe CW, Christensen C, Meldal M (2002) J Org Chem 67:3057

    Article  PubMed  CAS  Google Scholar 

  24. Rodionov VO, Presolski SI, Gardinier S, Lim Y-H, Finn MG (2007) J Am Chem Soc 129:12696

    Article  CAS  PubMed  Google Scholar 

  25. Donnelly PS, Zanatta SD, Zammit SC, White JM, Williams SJ (2008) Chem Commun 21:2459

    Article  CAS  Google Scholar 

  26. Ali AA, Chetia M, Sarma D (2016) Tetrahedron Lett 57:1711

    Article  CAS  Google Scholar 

  27. Özçubukçu S, Ozkal E, Jimeno C, Pericas MA (2009) Org Lett 11:4680

    Article  PubMed  CAS  Google Scholar 

  28. Rodionov VO, Presolski SI, Díaz Díaz D, Fokin VV, Finn M (2007) J Am Chem Soc 129:12705

    Article  CAS  PubMed  Google Scholar 

  29. Michaels HA, Zhu L (2011) Chem Asian J 6:2825

    Article  CAS  PubMed  Google Scholar 

  30. Candelon N, Lastecoueres D, Diallo AK, Aranzaes JR, Astruc D, Vincent J-M (2008) Chem Commun 6:741

    Article  Google Scholar 

  31. Thomas KD, Adhikari AV, Shetty NS (2010) Eur J Med Chem 45:3803

    Article  CAS  PubMed  Google Scholar 

  32. Kumar A, Ahmad I, Chhikara BS, Tiwari R, Mandal D, Parang K (2011) Bioorg Med Chem Lett 21:134246

    Google Scholar 

  33. Le Manach C, Baron A, Guillot R, Vauzeilles B, Beau JM (2011) Tetrahedron Lett 52:1462

    Article  CAS  Google Scholar 

  34. Keivanloo A, Kazemi SS, Nasr-Isfahani H, Bamoniri A (2017) Mol Divers 21:29

    Article  CAS  PubMed  Google Scholar 

  35. Keivanloo A, Kazemi SS, Nasr-Isfahani H, Bamoniri A (2016) Tetrahedron 72:6536

    Article  CAS  Google Scholar 

  36. Kazemi SS, Keivanloo A, Nasr-Isfahani H, Bamoniri A (2016) RSC Adv 6:92663

    Article  CAS  Google Scholar 

  37. Besharati-Seidani T, Keivanloo A, Kaboudin B, Yokomatsu T (2016) RSC Adv 6:83901

    Article  CAS  Google Scholar 

  38. Keivanloo A, Besharati-Seidani T, Kaboudin B, Yoshida A, Yokomatsu T (2018) Mol Divers 22:879

    Article  CAS  PubMed  Google Scholar 

  39. Keivanloo A, Fakharian M, Nabid MR, Amin AH (2019) J Iran Chem Soc 16:151

    Article  CAS  Google Scholar 

  40. Fakharian M, Keivanloo A, Nabid MR (2018) Helv Chim Acta 101:e1800004

    Article  CAS  Google Scholar 

  41. Abbaspour S, Keivanloo A, Bakherad M, Sepehri S (2019) Chem Biodivers 16:e1800410

    PubMed  Google Scholar 

  42. Keivanloo A, Abbaspour S, Bakherad M, Notash B (2019) ChemSelect 4:1366

    CAS  Google Scholar 

  43. Ashnagar A, Gharib NN, Amini M (2009) Asian J Chem 21:4976

    CAS  Google Scholar 

  44. Usifoh CO (2001) Arch Pharm 334:366

    Article  CAS  Google Scholar 

  45. Ghandour I, Bouayad A, Hökelek T, Haoudi A, Capet F, Renard C, Rodi YK (2019) Acta Cryst E 75:951

    Article  CAS  Google Scholar 

  46. Danielsson B, Johansson S (1965) Acta Pharm Suecica 2:155

    CAS  Google Scholar 

  47. Astruc D, Liang L, Rapakousiou A, Ruiz J (2011) Acc Chem Res 45:630

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgements

The authors are thankful to the Research Council of Shahrood University of Technology for the financial support of this work.

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Correspondence to Ali Keivanloo.

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Keivanloo, A., Lashkari, S., Sepehri, S. et al. Ligand-assisted click reaction for the synthesis of new hybrid compounds based on 1,2,3-triazoles and 5,5-diphenylimidazolidine-2,4-dione and evaluation of their antibacterial activities. Monatsh Chem 151, 935–943 (2020). https://doi.org/10.1007/s00706-020-02616-3

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