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2-Morpholinoethyl-substituted N-heterocyclic carbene (NHC) precursors and their silver(I)NHC complexes: synthesis, crystal structure and in vitro anticancer properties

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Abstract

In this study, a series of unsymmetrically 2-morpholinoethyl-substituted benzimidazolium salts and their Ag(I)NHC complexes were synthesized. The 1,3-dialkylbenzimidazolium salts (1a–d) were synthesized in dimethylformamide at 80 °C temperature from the N-(2-morpholinoethyl)benzimidazole and alkyl halides. The Ag(I)NHC complexes (2a–d) were synthesized in dichloromethane at room temperature from the benzimidazolium salts and Ag2O. All compounds were characterized by spectroscopic techniques (NMR and FT-IR) and elemental analyses. Also, the salt 1c and complex 2c were characterized by single-crystal X-ray crystallography. Anticancer activities of 2-morpholinoethyl-substituted benzimidazolium salts and Ag(I)NHC complexes were investigated against the MCF-7 breast cancer cell line, and the IC30 and IC50 values of these compounds were found to be in the range of 241–490 and 6–14 µM, respectively.

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Acknowledgements

The authors acknowledge Dokuz Eylül University for the use of the Agilent Xcalibur Eos diffractometer (purchased under University Research Grant No: 2010.KB.FEN.13).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Arts and Sciences, Inönü University, 44280, Malatya, Turkey

    Aydın Aktaş, Ünzile Keleştemur, Yetkin Gök, Sevgi Balcıoğlu & Burhan Ateş

  2. Department of Physics, Dokuz Eylul University, 35160, Izmir, Turkey

    Muhittin Aygün

Authors
  1. Aydın Aktaş
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  2. Ünzile Keleştemur
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  3. Yetkin Gök
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  4. Sevgi Balcıoğlu
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Correspondence to Aydın Aktaş.

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Aktaş, A., Keleştemur, Ü., Gök, Y. et al. 2-Morpholinoethyl-substituted N-heterocyclic carbene (NHC) precursors and their silver(I)NHC complexes: synthesis, crystal structure and in vitro anticancer properties. J IRAN CHEM SOC 15, 131–139 (2018). https://doi.org/10.1007/s13738-017-1216-8

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  • DOI: https://doi.org/10.1007/s13738-017-1216-8

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