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Synthesis of novel three compound imidazole derivatives via Cu(II) catalysis and their larvicidal and antimicrobial activities

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Abstract

One-pot three-component reactions of 1-[[2-(furan-2-ylmethylene)hydrazinyl](phenyl)methyl]-1H-imidazole and other imidazole derivatives were synthesized by Mannich base method in the presence of Cu(II) catalysis. Cu(Phen)Cl2 catalysis was performed well compared with other Cu(II) catalysis. Synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, mass spectra, and elemental analysis. Synthesized compounds were evaluated by antimicrobial and larvicidal activities. 4-[[2-(Furan-2-ylmethylene)hydrazinyl](1H-imidazol-1-yl)methyl]-N,N-dimethylaniline was highly active (MIC: 0.5 µg/cm3) against Staphylococcus aureus compared with standard ciprofloxacin in antibacterial screening. 1-[(4-Chlorophenyl)[2-(furan-2-ylmethylene)hydrazinyl]methyl]-1H-imidazole was highly active (MIC: 0.25 µg/cm3) against Candida albicans compared with standard clotrimazole (MIC: 0.5 µg/cm3) in antifungal screening. Larvicidal activity was assessed to the urban mosquito, Culex quinquefasciatus, using a standard bioassay protocol. 1-[1-[2-(Furan-2-ylmethylene)hydrazinyl]-4,8-dimethylnona-3,7-dienyl]-1H-imidazole showed high toxicity levels of larvicidal activity based their half maximal lethal dose (LD 50) values. Therefore, some compounds are lead molecules for the growth of new classes of antimicrobial and larvicidal agents.

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Acknowledgments

We are very grateful to Saudi Biological Society and Prince Sultan Research Chair for Environment and Wildlife, Department of Botany and Microbiology, College of Sciences, King Saud University (KSU), Riyadh, Saudi Arabia for encouragement.

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Authors and Affiliations

  1. Department of Biology, College of Science and Arts, Albaha University, Baljurashi, Saudi Arabia

    Abdullah Alaklab

  2. P.G. and Research Department of Chemistry, Nehru Memorial College, Puthanampatti, Tiruchirappalli, 621007, Tamil Nadu, India

    Radhakrishnan Surendra Kumar & Akbar Idhayadhulla

  3. Prince Sultan Research Chair for Environment and Wildlife, Department of Botany and Microbiology, College of Sciences, King Saud University (KSU), Riyadh, Saudi Arabia

    Anis Ahamed & Ibrahim A. Arif

  4. Department of Medical Laboratory Sciences, College of Medicine and Human Health, Arba Minch University, Arba Minch, Ethiopia

    Aseer Manilal

  5. Department of Chemistry, School of Basic Sciences, VELS University, Chennai, 600117, Tamil Nadu, India

    Akbar Idhayadhulla

Authors
  1. Abdullah Alaklab
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  2. Radhakrishnan Surendra Kumar
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  3. Anis Ahamed
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  4. Ibrahim A. Arif
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  5. Aseer Manilal
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  6. Akbar Idhayadhulla
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Corresponding author

Correspondence to Akbar Idhayadhulla.

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Alaklab, A., Surendra Kumar, R., Ahamed, A. et al. Synthesis of novel three compound imidazole derivatives via Cu(II) catalysis and their larvicidal and antimicrobial activities. Monatsh Chem 148, 275–290 (2017). https://doi.org/10.1007/s00706-016-1746-2

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  • DOI: https://doi.org/10.1007/s00706-016-1746-2

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