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Aspartic-acid-loaded starch-functionalized Mn–Fe–Ca ferrite magnetic nanoparticles as novel green heterogeneous nanomagnetic catalyst for solvent-free synthesis of dihydropyrimidine derivatives as potent antibacterial agents

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Abstract

Mn0.5Fe0.25Ca0.25Fe2O4@starch@aspartic acid magnetic nanoparticles (MNPs) as a new green nanocatalyst were designed and synthesized by a coprecipitation procedure. The structure of the aspartic-acid-loaded starch-functionalized Mn0.5Fe0.25Ca0.25Fe2O4 nanoparticles was evaluated by powder X-ray diffraction analysis, Fourier-transform infrared spectroscopy, vibrating-sample magnetometry, scanning electron microscopy, energy-dispersive X-ray spectroscopy, and thermogravimetric analysis. The ferrite magnetic nanoparticles exhibited superparamagnetic nature with saturation magnetization of 35 emu/g. The impact of the MnFeCaFe2O4@starch@aspartic acid MNPs was investigated in synthesis of 3,4-dihydropyrimidine derivatives by multicomponent reaction between thiourea/urea, acetylacetone, and various aryl aldehydes under solvent-free conditions. Facile workup, short reaction time, superb yield, and use of a reusable catalyst are the advantages of this method. The magnetic nanocatalyst was easily recovered and reused six times without considerable reduction in its catalytic activity. The in vitro antibacterial activity of all synthesized pyrimidine derivatives was studied by agar well diffusion assay technique against four pathogenic bacterial strains, namely Staphylococcus aureus (ATCC no. 6538) and Staphylococcus epidermidis (ATCC no. 12228) as Gram-positive bacteria and Pseudomonas aeruginosa (ATCC no. 9027) and Escherichia coli (ATCC no. 8739) as Gram-negative bacteria. All compounds exhibited greater antibacterial activity compared with the reference drug ciprofloxacin.

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References

  1. M.p. Reddy, W. Madhuri, K. Sadhana, I. Kim, K. Hui, K. Hui, K.S. Kumar, R.R. Reddy, J. Sol–Gel Sci. Technol. 70, 400 (2014)

    Article  CAS  Google Scholar 

  2. R. Kumar, H. Kumar, R.R. Singh, P. Barman, J. Sol–Gel Sci. Technol. 78, 566 (2016)

    Article  CAS  Google Scholar 

  3. S. Taghavi Fardood, A. Ramazani, J. Nanostruct. 6, 167 (2016)

    Google Scholar 

  4. F. Sadri, A. Ramazani, A. Massoudi, M. Khoobi, R. Tarasi, A. Shafiee, V. Azizkhani, L. Dolatyari, S.W. Joo, Green Chem. Lett. Rev. 7, 257 (2014)

    Article  CAS  Google Scholar 

  5. Y. Yang, H. Shi, Y. Wang, B. Shi, L. Guo, D. Wu, S. Yang, H. Wu, J. Biomater. Appl. 30, 810 (2016)

    Article  CAS  PubMed  Google Scholar 

  6. M. Ravichandran, G. Oza, S. Velumani, J.T. Ramirez, F. Garcia-Sierra, N.B. Andrade, M.A. Garza-Navarro, D.I. Garcia-Gutierrez, R. Lara-Estrada, E. Sacristán-Rock, RSC Adv. 5, 17223 (2015)

    Article  CAS  Google Scholar 

  7. V. Sudheesh, J. Nehra, A. Vinesh, V. Sebastian, N. Lakshmi, D.P. Dutta, V. Reddy, K. Venugopalan, A. Gupta, Mater. Res. Bull. 48, 698 (2013)

    Article  CAS  Google Scholar 

  8. S.C. McBain, H.H. Yiu, J. Dobson, Int. J. Nanomed. 3, 169 (2008)

    CAS  Google Scholar 

  9. M. Afradi, N. Foroughifar, H. Pasdar, H. Moghanian, RSC Adv. 6, 59343 (2016)

    Article  CAS  Google Scholar 

  10. K. Pušnik, M. Peterlin, I.K. Cigić, G. Marolt, K. Kogej, A. Mertelj, S.O. Gyergyek, D. Makovec, J. Phys. Chem. C 120, 14372 (2016)

    Article  CAS  Google Scholar 

  11. M. Sousa, J. Rubim, P. Sobrinho, F. Tourinho, J. Magn. Magn. Mater. 225, 67 (2001)

    Article  CAS  Google Scholar 

  12. M. Mikhaylova, D.K. Kim, C.C. Berry, A. Zagorodni, M. Toprak, A.S. Curtis, M. Muhammed, Chem. Mater. 16, 2344 (2004)

    Article  CAS  Google Scholar 

  13. Z. Durmus, H. Kavas, M.S. Toprak, A. Baykal, T.G. Altınçekiç, A. Aslan, A. Bozkurt, S. Coşgun, J. Alloys Compd. 484, 371 (2009)

    Article  CAS  Google Scholar 

  14. G. Marinescu, L. Patron, D.C. Culita, C. Neagoe, C.I. Lepadatu, I. Balint, L. Bessais, C.B. Cizmas, J. Nanopart. Res. 8, 1045 (2006)

    Article  CAS  Google Scholar 

  15. H. Qu, H. Ma, W. Zhou, C.J. O’Connor, Inorg. Chim. Acta 389, 60 (2012)

    Article  CAS  Google Scholar 

  16. J.Y. Park, E.S. Choi, M.J. Baek, G.H. Lee, Mater. Lett. 63, 379 (2009)

    Article  CAS  Google Scholar 

  17. D. Patel, Y. Chang, G.H. Lee, Curr. Appl. Phys. 9, S32 (2009)

    Article  Google Scholar 

  18. S.P. Schwaminger, P.F. García, G.K. Merck, F.A. Bodensteiner, S. Heissler, S. Günther, S. Berensmeier, J. Phys. Chem. C 119, 23032 (2015)

    Article  CAS  Google Scholar 

  19. J.-F. Lambert, Orig. Life Evol. Biosph. 38, 211 (2008)

    Article  CAS  PubMed  Google Scholar 

  20. J. Viota, F. Arroyo, A. Delgado, J. Horno, J. Colloid Interface Sci. 344, 144 (2010)

    Article  CAS  PubMed  Google Scholar 

  21. M.B. Gawande, A. Velhinho, I.D. Nogueira, C. Ghumman, O. Teodoro, P.S. Branco, RSC Adv. 2, 6144 (2012)

    Article  CAS  Google Scholar 

  22. A.H. Lu, E.E.L. Salabas, F. Schüth, Angew. Chem. Int. Ed. 46, 1222 (2007)

    Article  CAS  Google Scholar 

  23. Y. Deng, Y. Cai, Z. Sun, D. Zhao, Chem. Phys. Lett. 510, 1 (2011)

    Article  CAS  Google Scholar 

  24. A.M. Balu, B. Baruwati, E. Serrano, J. Cot, J. Garcia-Martinez, R.S. Varma, R. Luque, Green Chem. 13, 2750 (2011)

    Article  CAS  Google Scholar 

  25. J. Safari, Z. Zarnegar, J. Mol. Catal. A: Chem. 379, 269 (2013)

    Article  CAS  Google Scholar 

  26. D. Guin, B. Baruwati, S.V. Manorama, Org. Lett. 9, 1419 (2007)

    Article  CAS  PubMed  Google Scholar 

  27. M.G. Dehbalaei, N. Foroughifar, H. Pasdar, A. Khajeh-Amiri, N. Foroughifar, M. Alikarami, Res. Chem. Intermed. 43, 3035 (2017)

    Article  CAS  Google Scholar 

  28. M. Bahrami, A. Ramazani, Y. Hanifehpour, N. Fattahi, S. Taghavi Fardood, P. Azimzadeh Asiabi, S.W. Joo, Phosphorus Sulfur Silicon Relat. Elem. 191, 1368 (2016)

    Article  CAS  Google Scholar 

  29. A. Ramazani, Y. Ahmadi, N. Fattahi, H. Ahankar, M. Pakzad, H. Aghahosseini, A. Rezaei, S.T. Fardood, S.W. Joo, Phosphorus Sulfur Silicon Relat. Elem. 191, 1057 (2016)

    Article  CAS  Google Scholar 

  30. H. Nagarajaiah, A. Mukhopadhyay, J.N. Moorthy, Tetrahedron Lett. 57, 5135 (2016)

    Article  CAS  Google Scholar 

  31. R. Kaur, S. Chaudhary, K. Kumar, M.K. Gupta, R.K. Rawal, Eur. J. Med. Chem. 132, 108 (2017)

    Article  CAS  PubMed  Google Scholar 

  32. B.P. Kumar, G. Sankar, R.N. Baig, S. Chandrashekaran, Eur. J. Med. Chem. 44, 4192 (2009)

    Article  CAS  Google Scholar 

  33. D.A. Ibrahim, A.M. El-Metwally, Eur. J. Med. Chem. 45, 1158 (2010)

    Article  CAS  PubMed  Google Scholar 

  34. E. Klein, S. DeBonis, B. Thiede, D.A. Skoufias, F. Kozielski, L. Lebeau, Bioorg. Med. Chem. 15, 6474 (2007)

    Article  CAS  PubMed  Google Scholar 

  35. S.N. Mokale, S.S. Shinde, R.D. Elgire, J.N. Sangshetti, D.B. Shinde, Bioorg. Med. Chem. Lett. 20, 4424 (2010)

    Article  CAS  PubMed  Google Scholar 

  36. K.S. Atwal, G.C. Rovnyak, J. Schwartz, S. Moreland, A. Hedberg, J.Z. Gougoutas, M.F. Malley, D.M. Floyd, J. Med. Chem. 33, 1510 (1990)

    Article  CAS  PubMed  Google Scholar 

  37. G.C. Rovnyak, K.S. Atwal, A. Hedberg, S.D. Kimball, S. Moreland, J.Z. Gougoutas, B.C. O’Reilly, J. Schwartz, M.F. Malley, J. Med. Chem. 35, 3254 (1992)

    Article  CAS  PubMed  Google Scholar 

  38. J. Lloyd, H.J. Finlay, K. Atwal, A. Kover, J. Prol, L. Yan, R. Bhandaru, W. Vaccaro, T. Huynh, C.S. Huang, Bioorg. Med. Chem. Lett. 19, 5469 (2009)

    Article  CAS  PubMed  Google Scholar 

  39. S. Fatima, A. Sharma, R. Saxena, R. Tripathi, S.K. Shukla, S.K. Pandey, R. Tripathi, R.P. Tripathi, Eur. J. Med. Chem. 55, 195 (2012)

    Article  CAS  PubMed  Google Scholar 

  40. E. Rajanarendar, M.N. Reddy, K.R. Murthy, K.G. Reddy, S. Raju, M. Srinivas, B. Praveen, M.S. Rao, Bioorg. Med. Chem. Lett. 20, 6052 (2010)

    Article  CAS  PubMed  Google Scholar 

  41. E.W. Hurst, R. Hull, J. Med. Chem. 3, 215 (1960)

    Article  Google Scholar 

  42. A. Agarwal, K. Srivastava, S. Puri, P.M. Chauhan, Bioorg. Med. Chem. 13, 4645 (2005)

    Article  CAS  PubMed  Google Scholar 

  43. S. Chitra, D. Devanathan, K. Pandiarajan, Eur. J. Med. Chem. 45, 367 (2010)

    Article  CAS  PubMed  Google Scholar 

  44. R.W. Lewis, J. Mabry, J.G. Polisar, K.P. Eagen, B. Ganem, G.P. Hess, Biochemistry 49, 4841 (2010)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  45. K. Singh, T. Kaur, Med. Chem. Commun. 7, 749 (2016)

    Article  CAS  Google Scholar 

  46. U. Rashid, R. Sultana, N. Shaheen, S.F. Hassan, F. Yaqoob, M.J. Ahmad, F. Iftikhar, N. Sultana, S. Asghar, M. Yasinzai, Eur. J. Med. Chem. 115, 230 (2016)

    Article  CAS  PubMed  Google Scholar 

  47. R. Chikhale, S. Menghani, R. Babu, R. Bansode, G. Bhargavi, N. Karodia, M. Rajasekharan, A. Paradkar, P. Khedekar, Eur. J. Med. Chem. 96, 30 (2015)

    Article  CAS  PubMed  Google Scholar 

  48. K.L. Dhumaskar, S.N. Meena, S.C. Ghadi, S.G. Tilve, Bioorg. Med. Chem. Lett. 24, 2897 (2014)

    Article  CAS  PubMed  Google Scholar 

  49. R. Chikhale, R. Bhole, P. Khedekar, K. Bhusari, Eur. J. Med. Chem. 44, 3645 (2009)

    Article  CAS  PubMed  Google Scholar 

  50. H. Slimi, Y. Moussaoui, R. Ben Salem, Arab. J. Chem. 9, S510 (2016)

    Article  CAS  Google Scholar 

  51. Z. Radai, N.Z. Kiss, G. Keglevich, Curr. Org. Chem. 22, 533 (2018)

    Article  CAS  Google Scholar 

  52. S.S. Mansoor, S.S. Shafi, S.Z. Ahmed, Arab. J. Chem. 9, S846 (2016)

    Article  CAS  Google Scholar 

  53. A.M. Hakimi, N. Lashgari, S. Mahernia, G.M. Ziarani, M. Amanlou, Res. Pharm. Sci. 12, 353 (2017)

    Article  PubMed  PubMed Central  Google Scholar 

  54. H. Mehrabi, T. Yarahmadi, F.A. Bami, J. Chem. Res. 42, 326 (2018)

    Article  CAS  Google Scholar 

  55. D. Li, J. Wang, F. Chen, H. Jing, RSC Adv. 7, 4237 (2017)

    Article  CAS  Google Scholar 

  56. A. Maleki, A.A. Jafari, S. Yousefi, J. Iran. Chem. Soc. 14, 1801 (2017)

    Article  CAS  Google Scholar 

  57. N. Azizi, A. Mobinikhaledi, A.K. Amiri, H. Ghafuri, Res. Chem. Intermed. 38, 2271 (2012)

    Article  CAS  Google Scholar 

  58. H. Moghanian, M.A.B. Fard, A. Mobinikhaledi, N. Ahadi, Res. Chem. Intermed. 44, 4083 (2018)

    Article  CAS  Google Scholar 

  59. A. Mobinikhaledi, T. Mosleh, N. Foroughifar, Res. Chem. Intermed. 41, 2985 (2015)

    Article  CAS  Google Scholar 

  60. N. Azizi, F. Shirdel, Res. Chem. Intermed. 43, 3833 (2017)

    Article  CAS  Google Scholar 

  61. S. Shamim, K.M. Khan, U. Salar, F. Ali, M.A. Lodhi, M. Taha, F.A. Khan, S. Ashraf, Z. Ul-Haq, M. Ali, Bioorg. Chem. 76, 37 (2018)

    Article  CAS  PubMed  Google Scholar 

  62. W. Fan, Y. Queneau, F. Popowycz, Green Chem. 20, 485 (2018)

    Article  CAS  Google Scholar 

  63. T. Khatab, K.A. El-Bayouki, W. Basyouni, F. Sroor, Egypt. J. Chem. 56, 291 (2013)

    Article  Google Scholar 

  64. T. Ahmad, H. Bae, Y. Iqbal, I. Rhee, S. Hong, Y. Chang, J. Lee, D. Sohn, J. Magn. Magn. Mater. 381, 151 (2015)

    Article  CAS  Google Scholar 

  65. S. Abbasi-Pour, H.R. Shaterian, M. Afradi, A. Yazdani-Elah-Abadi, J. Magn. Magn. Mater. 438, 85 (2017)

    Article  CAS  Google Scholar 

  66. M.G. Dehbalaei, N. Foroughifar, H. Pasdar, A. Khajeh-Amiri, New J. Chem. 42, 327 (2018)

    Article  Google Scholar 

  67. K. Azizi, M. Karimi, H.R. Shaterian, A. Heydari, RSC Adv. 4, 42220 (2014)

    Article  CAS  Google Scholar 

  68. F. Nemati, M.M. Heravi, R.S. Rad, Chin. J. Catal. 33, 1825 (2012)

    Article  CAS  Google Scholar 

  69. E. Putilova, G. Zhdankina, N. Troitskii, S. Zlotin, Russ. J. Org. Chem. 41, 512 (2005)

    Article  CAS  Google Scholar 

  70. N.-E. Masoud, S.J. Hoseini, F. Mohammadi, Chin. J. Catal. 32, 1484 (2011)

    Article  CAS  Google Scholar 

  71. S. Agarwal, U. Aware, A. Patil, V. Rohera, M. Ghate, M. Jain, P. Patel, Bull. Korean Chem. Soc. 33, 377 (2012)

    Article  CAS  Google Scholar 

  72. M.F. Mady, G.E. Awad, K.B. Jørgensen, Eur. J. Med. Chem. 84, 433 (2014)

    Article  CAS  PubMed  Google Scholar 

  73. C. Perez, M. Pauli, P. Bazerque, Acta Biol. Med. Exp. 15, 113 (1990)

    Google Scholar 

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Acknowledgements

The authors thank Emad Darman Pars Pharmaceutical Company for financial support.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Pharmaceutical Chemistry, Tehran Medical Sciences, Islamic Azad University, Tehran, Iran

    Nahid Afradi

  2. Department of Chemistry, Tehran North Branch, Islamic Azad University, Tehran, Iran

    Naser Foroughifar & Hoda Pasdar

  3. Active Pharmaceutical Ingredient Research Center (APIRC), Pharmaceutical Sciences Branch, Islamic Azad University, Tehran, Iran

    Mahnaz Qomi

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  1. Nahid Afradi
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  2. Naser Foroughifar
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Afradi, N., Foroughifar, N., Pasdar, H. et al. Aspartic-acid-loaded starch-functionalized Mn–Fe–Ca ferrite magnetic nanoparticles as novel green heterogeneous nanomagnetic catalyst for solvent-free synthesis of dihydropyrimidine derivatives as potent antibacterial agents. Res Chem Intermed 45, 3251–3271 (2019). https://doi.org/10.1007/s11164-019-03791-7

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