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MgO Nanoparticle-Catalyzed Synthesis and Broad-Spectrum Antibacterial Activity of Imidazolidine- and Tetrahydropyrimidine-2-Thione Derivatives

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Abstract

The biological properties of imidazolidine- and tetrahydropyrimidine-2-thione derivatives such as antiviral, antitumor, anti-inflammatory, and analgesic activities increase the demand for mild and efficient synthetic routes. In this regard, methods such as reaction of diaminoalkanes with carbon disulfide have been developed. However, this method usually suffers from relatively long reaction times, using excess reagents, vigorous reaction conditions, and emission of pernicious hydrogen sulfide gas. In this project, MgO nanoparticle was used as an efficient, non-toxic, recyclable, and economic catalyst to synthesize cyclic five- or six-membered thioureas 3a–h via reaction of 1:1 molar ratios of 1,2- or 1,3-diaminoalkanes 1a–h and carbon disulfide in ethanol at ambient temperature. More interestingly, no hydrogen sulfide emission was detected during the reaction progress. The in vitro antimicrobial properties of synthesized compounds were investigated against 14 different Gram-positive and Gram-negative pathogenic bacteria according to CLSI (Clinical and Laboratory Standards Institute) broth microdilution and disk diffusion methods. The results were compared to those of penicillin, gentamicin, and ceftriaxone, and reported as inhibition zone diameter (IZD), the minimum inhibitory concentration (MIC), and the minimum bactericidal concentration (MBC) values. The best inhibitory effects were observed with imidazolidine-2-thiones 3c and 3d. They were effective against 14 and 11 pathogens, respectively. The structure-activity relationships of the prepared heterocyclic compounds were also studied.

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Acknowledgements

The authors would like to thank the members of the University of Zabol especially Dr. Mohammad Allahbakhsh, deputy of Research and Technology, and Dr. Mansour Ghaffari-Moghaddam, dean of the Faculty of Science, for their support and assistance at the various stages this project.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Zabol, Zabol, 98613-35856, Iran

    Hamid Beyzaei, Somaye Kooshki, Reza Aryan & 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. Young Researchers and Elite Club, Kerman Branch, Islamic Azad University, Kerman, Iran

    Mohammadreza Moghaddam-Manesh

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  1. Hamid Beyzaei
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  2. Somaye Kooshki
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  4. Mohammad Mehdi Zahedi
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Correspondence to Hamid Beyzaei.

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Beyzaei, H., Kooshki, S., Aryan, R. et al. MgO Nanoparticle-Catalyzed Synthesis and Broad-Spectrum Antibacterial Activity of Imidazolidine- and Tetrahydropyrimidine-2-Thione Derivatives. Appl Biochem Biotechnol 184, 291–302 (2018). https://doi.org/10.1007/s12010-017-2544-y

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