19018-22-5Relevant academic research and scientific papers
Synthesis, characterization and anticancer activity of allyl substituted N-Heterocyclic carbene silver(I) complexes
?ahin, Neslihan,?ahin-B?lükba??, Serap,Tahir, Muhammad Nawaz,Ar?c?, Cengiz,?evik, Esranur,Gürbüz, Nevin,?zdemir, ?smail,Cummings, Brian S.
, p. 92 - 99 (2019)
Metal N-heterocyclic carbene (NHC) complexes have attracted considerable attention in biological fields for their potential applications in cancer and antimicrobial therapies. In this study, four new benzimidazole-based N-heterocyclic carbene salts (1a-d) and their silver (I) complexes (2a-d) were synthesized. All new compounds were characterized by elemental analysis, FT-IR, 1H NMR and, 13C NMR spectroscopy. Additionally, single crystal structural studies for complex 2d show that the benzene rings (C9–C14) and the central benzimidazole ring system make dihedral angles of 83.58(13)°. The Ag–Cl and Ag???C single bond lengths are 2.3267(8) and 2.087(3) ?, respectively. The C–Ag–Cl bond angle is 175.20(7)°. The prop-1-ene moiety attached at the second N-atom of benzimidazole is disordered at two set of sites with an occupancy ratio of 0.592(6): 0.408(6). There is one intramolecular hydrogen bond interaction between C22A-H22A … N2. The salts and Ag-complexes were further evaluated for their in vitro anticancer activities against DU-145 human prostate cancer cells, MCF-7, MDA-MB-231 human breast cancer cells and L-929 non-cancer cell for 24 h, 48 h and 72 h using the MTT assay. The Ag(I)–NHC complexes (2a-d) showed a dose and time-dependent cytotoxic activity against all cell lines. The IC50s for all Ag(I)–NHC complexes lower than 1 μM for 72 h time points on cancer cells. The results showed that complex 2d exhibited the highest activity against all cancer cell lines studied. Further, the complexes had relatively higher cytotoxicity to cancer cells than to non-cancer cell lines.
Novel N-heterocyclic carbene silver(I) complexes: Synthesis, structural characterization, and anticancer activity
?ahin-B?lükba??, Serap,?ahin, Neslihan,Tahir, Muhammad Nawaz,Ar?c?, Cengiz,?evik, Esranur,Gürbüz, Nevin,?zdemir, ?smail,Cummings, Brian S.
, p. 711 - 718 (2019)
In this study, we synthesized four novel unsymmetrically substituted NHC ligands (1a-d) and their Ag(I) complexes (2a-d). All new compounds were characterized using elemental analysis, FT-IR, 1H NMR, and 13C NMR spectroscopy and X-ray crystallography. The molecular structure of complex 2d was elucidated through single crystal X-ray diffraction analyses. Single crystal structural studies for complex 2d show that the benzene rings (C9–C14) and the central benzimidazole ring system make dihedral angles of 85.65(11)°. The Ag–Cl and Ag–C single bond lengths are 2.3553(7) and 2.096(2) ? respectively. The C–Ag–Cl bond angle is 168.27(7)°. Both salts and complexes were tested for their anti-cancer potential against three human cancer cell lines (DU-145, MCF-7, and MDA-MB-231) and non-cancer cells adipose from mouse (L-929) for 24 h, 48 h and 72 h using the MTT assays. However, the Ag(I)–NHC complexes (2a-d) showed a dose and time-dependent cytotoxic activity against all cell lines. MDA-MB-231 human breast carcinoma cells were the most sensitive to the Ag(I)–NHC complex displaying IC50 lower than 1 μM all time points. Further, the IC50s for Ag(I)–NHC were higher in non-cancer cells, suggesting that complexes possessed noteworthy selectivity for human cancer cells.
Synthesis and antitumour activity of trimethylsilylpropyl substituted benzimidazoles
Lukevics, Edmunds,Arsenyan, Pavel,Shestakova, Irina,Domracheva, Ilona,Nesterova, Alena,Pudova, Olga
, p. 507 - 515 (2001)
The quaternisation of N-substituted benzimidazoles by heating with various alkyl, allyl, propargyl and benzyl chlorides and bromides leads to the formation of benzimidazolinium salts. The interaction of N-monosubstituted benzimidazoles with various salts (CuCl2, ZnCl2, CoCl2, PdCl2 and AgNO3) yielded stable solid complexes. Potential cytotoxic activity of synthesised benzimidazolinium salts and benzimidazole metal complexes was tested in vitro on four monolayer tumour cell lines: MG-22A (mouse hepatoma), HT-1080 (human fibrosarcoma), B16 (mouse melanoma), Neuro 2A (mouse neuroblastoma) and normal mouse fibroblast cells. A preliminary analysis of the structure-activity relationship for the benzimidazole derivatives clearly indicates that the character of substituents in the benzimidazole ring has strong influence on the cytotoxic activity. The insertion of the silicon atom into the N-alkyl chain increases the cytotoxic activity of benzimidazolinium salts significantly, which show a very significant potency in vitro against all studied tumour cell lines, being particularly active in experiments with B16 (mouse melanoma). TD50 for the most active compounds are in the range 0.001-0.008 μg ml-1. Cytotoxicity of benzimidazole metal complexes (L2MX2) strongly depends on the metal nature. 1-(3-Trimethylsilylpropyl)benzimidazole in dose 1 mg kg-1 inhibits carcinoma S-180 tumour growth by 62% (on ICR mice).
Synthesis, characterization, and investigation of antiproliferative activity of novel Ag (I)-N-Heterocyclic Carbene (NHC) compounds
?evik-Y?ld?z, Esranur,?ahin, Neslihan,?ahin-B?lükba??, Serap
, (2020)
The aim of this study was to present the synthesis, characterization, and investigation of the antiproliferative activity of new metal N-Heterocyclic Carbene (NHC) salts (1a-c) and their Ag(I) complexes (2a-c). All synthesized compounds were characterized using elemental analysis, LC-MS, FT-IR, 1H NMR, and 13C NMR spectroscopy techniques. Salts and complexes were tested for antiproliferative activities on human breast and prostate cancer cell lines (MCF-7, MDA-MB-23, DU-145) and L-929 normal cells for 24 h, 48 h and 72 h using MTT assays. The Ag(I)-NHC complexes (2a-c) showed dose and time-dependent cytotoxic activity against all cell lines. MDA-MB-231 and MCF-7 human breast carcinoma cells were the most sensitive to displaying IC50 lower than 1 μM at all time points for 2a and 2b complexes respectively. The IC50s for Ag(I)-NHC were higher in normal cells especially compared to the breast cancer cells, suggesting that complexes possessed noteworthy selectivity for human breast cancer cells. Complex 2a showed high selectivity (≥13-fold) for MDA-MB-231 breast cancer cells at all time points. These results also demonstrated that complex 2b has 4-7-fold selectivity against MCF-7 breast cancer cells.
Activity analysis of new N-heterocyclic carbenes and silver N-heterocyclic carbene molecules against novel coronavirus by UV-vis, fluorescence spectroscopy and molecular docking
üstün, Elvan,?zdemir, Nam?k,?ahin, Neslihan
, p. 3109 - 3126 (2022/01/20)
The biggest pandemic that this generation has experienced is still continuing. While researchers concentrated on vaccine studies, development of treatment procedures and anti-viral drugs are other important parts of struggle against Severe Acute Respirato
Sustainable Synthesis of 2-Hydroxymethylbenzimidazoles using D-Fructose as a C2 Synthon
Raja, Dineshkumar,Philips, Abigail,Sundaramurthy, Devikala,Chandru Senadi, Gopal
supporting information, p. 3754 - 3759 (2021/10/14)
D-fructose, a biomass-derived carbohydrate has been identified as an environmentally benign C2 synthon in the preparation of synthetically useful 2-hydroxymethylbenzimidazole derivatives by coupling with 1,2-phenylenediamines. Proof of concept was established by synthesizing 23 examples using BF3.OEt2 (20 mol%), TBHP (5.5 M, decane) (1.0 equiv.) in CH3CN at 90 °C for 1 h. The pivotal features of this method include metal-free conditions, short time, good functional group tolerance, gram scale feasibility and the synthesis of benzimidazole fused 1,4-oxazine. Control studies with conventional C2 synthons did not produce the desired product, thus suggesting a new reaction pathway from D-fructose.
Metal-Free Synthesis of Benzimidazoles via Oxidative Cyclization of d -Glucose with o-Phenylenediamines in Water
Raja, Dineshkumar,Philips, Abigail,Palani, Pushbaraj,Lin, Wei-Yu,Devikala, Sundaramurthy,Senadi, Gopal Chandru
, p. 11531 - 11540 (2020/10/12)
d-Glucose has been identified as an efficient C1 synthon in the synthesis of benzimidazoles from o-phenylenediamines via an oxidative cyclization strategy. Isotopic studies with 13C6-d-glucose and D2O unambiguously confirmed the source of methine. The notable features of this method include the following: broad functional group tolerance, a biorenewable methine source, excellent reaction yields, a short reaction time, water as an environmentally benign solvent, and the synthesis of vitamin B12 component on the gram scale.
Visible-light-induced aerobic oxidative desulfurization of 2-mercaptobenzimidazolesviaa sulfinyl radical
Deng, Guo-Jun,Fu, Mei,Huang, Huawen,Ji, Xiaochen,Li, Yongtong
supporting information, p. 5594 - 5598 (2020/09/21)
A mild transition-metal-free non-toxic aerobic photoredox system was found to enable highly efficient desulfurization of 2-mercaptobenzimidazoles. This viable catalytic system includes Rose Bengal in a low catalyst loading as a photosensitizer and cheap, non-toxic NaCl in a catalytic amount as an additive, combined with an oxygen atmosphere. This protocol provides an important alternative access to a broad range of benzimidazole and deuterated benzimidazole products in generally high yields with good tolerance of various synthetically and pharmaceutically useful functionalities. The mechanistic studies reveal that both single electron transfer and energy transfer probably occur in the initial step and a sulfinyl radical intermediate is involved in the key desulfurization process.
Sustainable Palladium-Catalyzed Tsuji-Trost Reactions Enabled by Aqueous Micellar Catalysis
Braga, Felipe C.,Gallou, Fabrice,Lee, Nicholas R.,Lippincott, Daniel J.,Lipshutz, Bruce H.,Moghadam, Farbod A.,Zhu, Bingchun
supporting information, (2020/07/15)
Palladium-catalyzed allylic substitution, or "Tsuji-Trost"reactions, can be run under micellar catalysis conditions featuring not only chemistry in water but also numerous combinations of reaction partners that require low levels of palladium, typically on the order of 1000 ppm (0.1 mol %). These couplings are further characterized by especially mild conditions, leading to a number of cases not previously reported in an aqueous micellar medium. Inclusion of diverse nucleophiles, such as N-H heterocycles, alcohols, dicarbonyl compounds, and sulfonamides is described. Intramolecular cyclizations further illustrate the broad utility of this process. In addition to recycling studies, a multigram scale example is reported, indicative of the prospects for scale up.
First used of Alkylbenzimidazole-Cobalt(II) complexes as a catalyst for the N-Alkylation of amines with alcohols under solvent-free medium
?zdemir, ?smail,?zdemir, Nam?k,?ahin, Neslihan,Gürbüz, Nevin,Y?ld?r?m, ?lkay
, (2020/04/28)
In this study, alkylbenzimidazole-cobalt(II)-catalyzed direct N-alkylation reactions of amines with alcohols derivatives have been investigated under solvent-free medium. For this purpose, a series of cobalt(II) complexes bearing N-alkylbenzimidazole complexes have been synthesized and novel complexes fully characterized by elemental analysis, FT-IR, 1H NMR and, 13C{1H} NMR spectroscopies. Also, the structure of the complex 2a has been confirmed by X-ray crystallography. Generally, the N-alkylating reaction is usually performed in toluene with various metal complexes including cobalt. In this catalytic study of complexes, 2a-c has carried out in without solvent and alcohol acted both as solvent and reactant. Conversion and selectivity of amine products according to imine products for alkylation reactions have been seen high yield in medium solvent-free relative to in toluene.
