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.
Graphic abstract
Similar content being viewed by others
References
Kolb HC, Sharpless KB (2003) Drug Discov Today 8:1128
Agalave SG, Maujan SR, Pore VS (2011) Chem Asian J 6:2696
Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596
Aher NG, Pore VS, Mishra NN, Kumar A, Shukla PK, Sharma A, Bhat MK (2009) Bioorg Med Chem Lett 19:759
Demaray JA, Thuener JE, Dawson MN, Sucheck SJ (2008) Bioorg Med Chem Lett 18:4868
Wang XL, Wan K, Zhou HC (2010) Eur J Med Chem 45:4631
Buckle DR, Outred DJ, Rockell CJM, Smith H, Spicer BA (1983) J Med Chem 26:251
Whiting M, Tripp JC, Lin YC, Lindstrom W, Olson AJ, Elder JH, Sharpless KB, Fokin VV (2006) J Med Chem 49:7697
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
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
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
Simone RD, Chini MG, Bruno I, Riccio R, Mueller D, Werz O, Bifulco G (2011) J Med Chem 54:1565
Husain MI, Nasir M (1979) ChemInform 10:177
Kelbaugh RR, Sarges R (1979) Spiro-furanohydantoin derivatives. US Patent 4,147,797, Apr 3, 1979; (1979) Chem Abstr 91:20511
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
Kieć-Kononowicz K, Szymańska E (2002) Farmaco 57:909
Rodgers TR, Lamontagne MP, Markove A, Ash AB (1977) J Med Chem 20:591
Valaviciene J, Blyum RA, Lutsenko VV, Stumbreviciute Z (1978) Chem Abstr 88:105221
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
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
Kolb HC, Finn MG, Sharpless KB (2001) Angew Chem Int Ed 40:2004
Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 1:2596
Tornøe CW, Christensen C, Meldal M (2002) J Org Chem 67:3057
Rodionov VO, Presolski SI, Gardinier S, Lim Y-H, Finn MG (2007) J Am Chem Soc 129:12696
Donnelly PS, Zanatta SD, Zammit SC, White JM, Williams SJ (2008) Chem Commun 21:2459
Ali AA, Chetia M, Sarma D (2016) Tetrahedron Lett 57:1711
Özçubukçu S, Ozkal E, Jimeno C, Pericas MA (2009) Org Lett 11:4680
Rodionov VO, Presolski SI, Díaz Díaz D, Fokin VV, Finn M (2007) J Am Chem Soc 129:12705
Michaels HA, Zhu L (2011) Chem Asian J 6:2825
Candelon N, Lastecoueres D, Diallo AK, Aranzaes JR, Astruc D, Vincent J-M (2008) Chem Commun 6:741
Thomas KD, Adhikari AV, Shetty NS (2010) Eur J Med Chem 45:3803
Kumar A, Ahmad I, Chhikara BS, Tiwari R, Mandal D, Parang K (2011) Bioorg Med Chem Lett 21:134246
Le Manach C, Baron A, Guillot R, Vauzeilles B, Beau JM (2011) Tetrahedron Lett 52:1462
Keivanloo A, Kazemi SS, Nasr-Isfahani H, Bamoniri A (2017) Mol Divers 21:29
Keivanloo A, Kazemi SS, Nasr-Isfahani H, Bamoniri A (2016) Tetrahedron 72:6536
Kazemi SS, Keivanloo A, Nasr-Isfahani H, Bamoniri A (2016) RSC Adv 6:92663
Besharati-Seidani T, Keivanloo A, Kaboudin B, Yokomatsu T (2016) RSC Adv 6:83901
Keivanloo A, Besharati-Seidani T, Kaboudin B, Yoshida A, Yokomatsu T (2018) Mol Divers 22:879
Keivanloo A, Fakharian M, Nabid MR, Amin AH (2019) J Iran Chem Soc 16:151
Fakharian M, Keivanloo A, Nabid MR (2018) Helv Chim Acta 101:e1800004
Abbaspour S, Keivanloo A, Bakherad M, Sepehri S (2019) Chem Biodivers 16:e1800410
Keivanloo A, Abbaspour S, Bakherad M, Notash B (2019) ChemSelect 4:1366
Ashnagar A, Gharib NN, Amini M (2009) Asian J Chem 21:4976
Usifoh CO (2001) Arch Pharm 334:366
Ghandour I, Bouayad A, Hökelek T, Haoudi A, Capet F, Renard C, Rodi YK (2019) Acta Cryst E 75:951
Danielsson B, Johansson S (1965) Acta Pharm Suecica 2:155
Astruc D, Liang L, Rapakousiou A, Ruiz J (2011) Acc Chem Res 45:630
Acknowledgements
The authors are thankful to the Research Council of Shahrood University of Technology for the financial support of this work.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-020-02616-3