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


AKTAŞ A., KELEŞTEMUR U., GÖK Y., BALCIOGLU S., ATEŞ B., Aygun M.

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, vol.15, no.1, pp.131-139, 2018 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 15 Issue: 1
  • Publication Date: 2018
  • Doi Number: 10.1007/s13738-017-1216-8
  • Journal Name: JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.131-139
  • Keywords: N-Heterocyclic carbenes, Benzimidazolium salt, Silver(I)NHC complexes, Medical inorganic chemistry, Anticancer agents, X-ray diffraction, SILVER(I)-CARBENE COMPLEXES, BENZIMIDAZOLIUM SALTS, LIGANDS, PALLADIUM, FEATURES, GOLD(I)
  • Inonu University Affiliated: Yes

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 A degrees 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 A mu M, respectively.