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An efficient synthesis of benzimidazoles via a microwave technique and evaluation of their biological activities

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Abstract

A simple and practical protocol was developed for the synthesis of benzimidazoles. The protocol uses iminoester hydrochloride which is very useful in the reaction with 4,5-dichloro-1,2-phenylenediamine under microwave irradiation leading to the products with good yields and in short reaction times. This method can be used as a general technique for synthesizing benzimidazoles. The synthesized compounds were evaluated for their biological properties such as anti-lipase, antiviral, and antitumor activities. Five benzimidazol-1-acetic acid hydrazides showed slight antiviral activity at 25 μg/cm3 concentration despite their low toxicity. Substituted 2-benzylbenzimidazoles were active against adenocarcinoma (CT26) and melanoma (B16F10) cancer cell lines at concentrations below 10 μg/cm3. Six of the compounds showed anti-lipase activities at various concentrations; the IC50 value of one compound was 0.35 μg/cm3, which is similar activity to that of orlistat (0.32 μg/cm3).

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Acknowledgments

The authors gratefully acknowledge the financial support from the Scientific and Technical Research Council of Turkey (TÜBİTAK) through Project 108T356.

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Authors and Affiliations

  1. Department of Nutrition and Dietetics, Faculty of Health Sciences, Karadeniz Technical University, Trabzon, Turkey

    Bahittin Kahveci

  2. Department of Chemistry, Art and Science Faculty, Recep Tayyip Erdogan University, 53100, Rize, Turkey

    Emre Menteşe & Musa Özil

  3. Department of Biology, Faculty of Arts and Sciences, Recep Tayyip Erdogan University, 53100, Rize, Turkey

    Serdar Ülker

  4. Medical Microbiology, School of Medicine, Karadeniz Technical University, 61080, Trabzon, Turkey

    Murat Ertürk

Authors
  1. Bahittin Kahveci
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  2. Emre Menteşe
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  3. Musa Özil
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  4. Serdar Ülker
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  5. Murat Ertürk
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Correspondence to Bahittin Kahveci.

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Kahveci, B., Menteşe, E., Özil, M. et al. An efficient synthesis of benzimidazoles via a microwave technique and evaluation of their biological activities. Monatsh Chem 144, 993–1001 (2013). https://doi.org/10.1007/s00706-012-0916-0

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  • DOI: https://doi.org/10.1007/s00706-012-0916-0

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