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

Aktaş, Aydın; Keleştemür, Ünzile; Gök, Yetkın; Balcıoğlu, Sevgi; Ateş, Burhan; Aygün, Muhıttın

doi:10.1007/s13738-017-1216-8

Cited by 31 publications

(16 citation statements)

References 33 publications

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“…[6][7][8] Recently, studies on strong enzyme inhibition effects of NHC precursors have been published. [12][13][14][15][16][17] The studies on the structural and electronic properties of NHC precursors have just been published recently. [12][13][14][15][16][17] The studies on the structural and electronic properties of NHC precursors have just been published recently.…”

Section: Introductionmentioning

confidence: 99%

“…[9][10][11] NHC-metal complexes that have been synthesized from NHC ligands and transition metals exhibited very good biological activity as well as a strong catalytic effect. [12][13][14][15][16][17] The studies on the structural and electronic properties of NHC precursors have just been published recently. [18,19] In this study, we have investigated the structural and electronic properties of two new benzimidazolium salts (NHC precursors) using the single-crystal X-ray diffraction method and spectroscopic techniques.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, crystal structures, spectral FT‐IR, NMR and UV–Vis investigations and Hirshfeld surface analysis of two new 2‐hydroxyethyl‐substituted N‐heterocyclic carbene precursors

Aktaş

Celepci

Gök

2019

J Chinese Chemical Soc

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This study discusses the synthesis of two new 2‐hydroxyethyl substituted N‐heterocyclic carbene (NHC) precursors. The NHC precursors were prepared from 1‐(alkyl/aryl)benzimidazole and alkyl halides. They were characterized using 1H NMR, 13C NMR, FT‐IR, UV–Vis spectroscopy, and elemental analysis techniques. Molecular and crystal structures of 1 and 2 were determined using the single‐crystal X‐ray diffraction method. Crystal structure of the compounds features NHC precursors and chloride anions. Additionally in 2, the asymmetric unit has a water molecule, which forms a tetrameric chloride‐hydrate assembly with the chloride anion. The chloride anions play an important role in the stabilization of crystal structures to form a two‐dimensional supramolecular architecture. The 3D Hirshfeld surface and the associated 2D fingerprint plots were also drawn to gain insights into the behavior of the interactions in the compounds.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structures, spectral FT‐IR, NMR and UV–Vis investigations and Hirshfeld surface analysis of two new 2‐hydroxyethyl‐substituted N‐heterocyclic carbene precursors

Aktaş

Celepci

Gök

2019

J Chinese Chemical Soc

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“…This effect could be effective on biological activity . In the studies of biological activity related to NHC precursor and metal‐NHC complexes, it is observed that the molecules with bulky and lipophilic properties exhibit higher biological activity . In recent years, because of their great structural diversity and multitude of chemical properties, NHCs have been utilized in a variety of capacities.…”

Section: Introductionmentioning

confidence: 99%

meta‐Cyanobenzyl substituted benzimidazolium salts: Synthesis, characterization, crystal structure and carbonic anhydrase, α‐glycosidase, butyrylcholinesterase, and acetylcholinesterase inhibitory properties

Türker

Celepci

Aktaş

et al. 2018

Archiv der Pharmazie

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meta-Cyanobenzyl-substituted N-heterocyclic carbene (NHC) precursors were synthesized by the reaction of a series of N-(alkyl)benzimidazolium with 3-bromomethyl-benzonitrile. These benzimidazolium salts were characterized by using H NMR, C NMR, FTIR spectroscopy, and elemental analysis techniques. The molecular and crystal structures of 2f and 2g complexes were obtained by using the single-crystal X-ray diffraction method. The derivatives of these novel NHC precursors were effective inhibitors of α-glycosidase (AG), the cytosolic carbonic anhydrase I and II isoforms (hCA I and II), butyrylcholinesterase (BChE), and acetylcholinesterase (AChE) with K values in the range of 1.01-2.12 nM for AG, 189.56-402.44 nM for hCA I, 112.50-277.37 nM for hCA II, 95.45-352.58 nM for AChE, and 132.91-571.18 nM for BChE. In the last years, inhibition of the CA enzyme has been considered as a promising factor for pharmacologic intervention in a diversity of disturbances such as obesity, glaucoma, cancer, and epilepsy.

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“…The IC 30 and IC 50 values of these SCCs were found to be in the range of 241–490 and 6–14 μM, respectively. (Figure ) (Aktaş et al, ). However, anticancer activity is found to be increased as steric bulk at N‐substitution of the benzimidazole ring is increased.…”

Section: Anticancer Activities Of Silver‐nhcmentioning

confidence: 99%

Silver carbene complexes: An emerging class of anticancer agents

Kankala

Thota

Björkling

et al. 2018

Drug Development Research

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Cancer is a major global health problem with large therapeutic challenges. Although substantial progress has been made in cancer therapy, there still remains a need to develop novel and effective treatment strategies to treat several relapsed and refractory cancers. Recently, there has been growing demand for considering organometallics as antineoplastic agents. This review is focused on a group of organometallics, silver N‐heterocyclic carbene complexes (SCCs) and their anticancer efficacy in targeting multiple pathways in various in vitro cancer model systems. However, the precise molecular mechanism of SCCs anticancer properties remains unclear. Here, we discuss the SCCs chemistry, potential molecular targets, possible molecular mechanism of action, and their application in cancer therapies.

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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

Cited by 31 publications

References 33 publications

Synthesis, crystal structures, spectral FT‐IR, NMR and UV–Vis investigations and Hirshfeld surface analysis of two new 2‐hydroxyethyl‐substituted N‐heterocyclic carbene precursors

Synthesis, crystal structures, spectral FT‐IR, NMR and UV–Vis investigations and Hirshfeld surface analysis of two new 2‐hydroxyethyl‐substituted N‐heterocyclic carbene precursors

meta‐Cyanobenzyl substituted benzimidazolium salts: Synthesis, characterization, crystal structure and carbonic anhydrase, α‐glycosidase, butyrylcholinesterase, and acetylcholinesterase inhibitory properties

Silver carbene complexes: An emerging class of anticancer agents

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