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MgO nanoparticle-catalyzed, solvent-free Hantzsch synthesis and antibacterial evaluation of new substituted thiazoles

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Abstract

In this study, some novel 4-thiazolylpyrazoles were synthesized by modified Hantzsch method, under solvent-free conditions and in the presence of MgO nanoparticles as catalyst. Excellent yields in shorter reaction times were achieved under the new general protocol. Also, the in vitro antibacterial effects of synthesized compounds were evaluated against 21 gram-positive and gram-negative pathogenic bacterial strains and compared to antibiotics such as ceftriaxone and penicillin. The results were reported as inhibition zone diameter, minimum inhibitory concentration (MIC), and minimum bactericidal concentration (MBC) values. The compounds showed moderate to good antibacterial activities. Among the newly synthesized thiazoles, compounds 7b, f had inhibitory effects against eight pathogenic bacteria; besides, thioamide 6 with MIC and MBC values of 32 and 64 μg/mL against Streptococcus agalactiae was identified as the most effective antibacterial agent.

Graphical Abstract

MgO nanoparticle was prepared and successfully used as an efficient recyclable catalyst for the Hantzsch thiazole synthesis; reaction times and product yields were significantly improved in the presence of nanocatalyst.

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Acknowledgement

The authors would like to thank members of the University of Zabol especially Dr. Mansour Ghaffari-Moghaddam, dean of the faculty of science, for their support and assistance at the various stages of this project.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Zabol, Zabol, Iran

    Hamid Beyzaei, Reza Aryan, Hadi Molashahi & Alireza Samzadeh-Kermani

  2. Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK, S7N 5C9, Canada

    Mohammad Mehdi Zahedi

  3. Young Researchers and Elite Club, Neyshabur Branch, Islamic Azad University, Neyshabur, Iran

    Behzad Ghasemi

  4. Department of Chemistry, Faculty of Science, Kerman Branch, Islamic Azad University, Kerman, Iran

    Mohammadreza Moghaddam-Manesh

Authors
  1. Hamid Beyzaei
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  2. Reza Aryan
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  3. Hadi Molashahi
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  4. Mohammad Mehdi Zahedi
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  5. Alireza Samzadeh-Kermani
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  6. Behzad Ghasemi
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  7. Mohammadreza Moghaddam-Manesh
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Correspondence to Hamid Beyzaei.

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Beyzaei, H., Aryan, R., Molashahi, H. et al. MgO nanoparticle-catalyzed, solvent-free Hantzsch synthesis and antibacterial evaluation of new substituted thiazoles. J IRAN CHEM SOC 14, 1023–1031 (2017). https://doi.org/10.1007/s13738-017-1052-x

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  • DOI: https://doi.org/10.1007/s13738-017-1052-x

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