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Efficient synthesis of functionalized dithiocarbamate derivatives through one-pot three-component reaction and evaluation of their antimicrobial activities

Journal of the Iranian Chemical Society volume 10, pages 725–732 (2013)Cite this article

Abstract

The one-pot three-component reaction of primary and secondary amines, carbon disulfide and β-nitrostyrene derivatives in neat condition at room temperature afforded functionalized dithiocarbamate derivatives in good to high yields. High bond-forming efficiency and easy work-up are advantages of this reaction. In vitro antimicrobial activities of synthesized compounds were studied against four Gram-positive bacteria, four Gram-negative bacteria and four fungi. The screening for the antimicrobial activity was performed by twofold serial dilution technique. Notably, some synthesized compounds displayed comparable or even better antibacterial and antifungal activities against some tested strains than the reference drugs ampicillin, streptomycin and amphotericin B, respectively.

Graphical abstract

A series of novel dithiocarbamates 4a-j have been synthesized via three-component reaction and compared pharmacologically concerning their antimicrobial and antibacterial activities as well as antifungal activity

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Scheme 1
Scheme 2
Fig. 1

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Acknowledgments

S.B gratefully acknowledges Iran National Science Foundation (INSF) for financial support. We thank Prof. R. Gleiter for his valuable discussions. We express our gratitude to Mr. M. Jalilevand, managing director of Kimia Exir Company for donation of the chemicals and financial support.

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Authors and Affiliations

  1. Peptide Chemistry Research Center, K. N. Toosi University of Technology, P. O. Box 15875-4416, Tehran, Iran

    Elmira Ghabraie, Saeed Balalaie & Morteza Bararjanian

  2. Microbial Biotechnology Lab, Department of Microbiology, School of Biology, College of Science, University of Tehran, Tehran, Iran

    Hamid Moghimi

  3. Organisch-Chemisches Institut, der Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany

    Frank Rominger

  4. Department of Chemistry, Tarbiat Modares University, P. O. Box 141115-175, Tehran, Iran

    Hamid Reza Bijanzadeh

Authors
  1. Elmira Ghabraie
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  2. Hamid Moghimi
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  3. Saeed Balalaie
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  4. Morteza Bararjanian
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Correspondence to Saeed Balalaie.

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Ghabraie, E., Moghimi, H., Balalaie, S. et al. Efficient synthesis of functionalized dithiocarbamate derivatives through one-pot three-component reaction and evaluation of their antimicrobial activities. J IRAN CHEM SOC 10, 725–732 (2013). https://doi.org/10.1007/s13738-012-0206-0

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