Synthesis, Characterization, Theoretical Analyses, and Investigation of Their Biological Activities of Acetovanillone-Derived Novel Benzyl Ethers

Calkilic, Nazire Merve; Alıcı, Hakan; Direkel, Şahin; Tahtacı, Hakan

doi:10.1080/10406638.2021.1950782

Cited by 6 publications

(6 citation statements)

References 52 publications

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“…The most significant evidence indicating the formation of the suggested compounds in the 1 H NMR spectra of these compounds is the disappearance of the –OH proton peaks observed as a broad singlet in the range of 4.83–4.75 ppm and the increase in peak intensity in the aliphatic region (1–5 ppm range) for compounds 7 – 15 and in the aromatic region (6.5–8.00 ppm) for compounds 16 – 24 . These data are in excellent agreement with similar studies in the literature. − , …”

Section: Results and Discussionsupporting

confidence: 93%

“…These data are in excellent agreement with similar studies in the literature. [65][66][67]71 The carbon peaks observed in the aliphatic region (60−10 ppm range) for compounds 7−15 and in the aromatic region (140−115 ppm range) for compounds 16−24 in the 13 C NMR spectra of the target compounds match the carbon counts of the proposed structures. Finally, the molecular ion peaks of the target compounds were observed as expected in the mass spectra, confirming the structures using all the spectroscopic methods used.…”

Section: Resultsmentioning

confidence: 54%

“…In the first step, ketone derivatives ( 3a – c ) were synthesized with varying yields between 51 and 62% by the reaction of imidazole ( 2 ) with various phenacyl bromide derivatives ( 1a – c ) in the presence of triethylamine, as described in the literature. , In this reaction, the proton of imidazole is removed by triethylamine in an acetone medium. Subsequently, a nucleophilic center, with a partially positive carbon atom, undergoes an SN 2 -type substitution reaction by attack from behind.…”

Section: Results and Discussionmentioning

confidence: 99%

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Imidazole-Derived Alkyl and Aryl Ethers: Synthesis, Characterization, In Vitro Anticancer and Antioxidant Activities, Carbonic Anhydrase I–II Inhibition Properties, and In Silico Studies

Faris,

Bostancı,

Özcan

et al. 2024

ACS Omega

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Imidazole derivatives display extensive applications in pharmaceutical chemistry and have been investigated as bioactive compounds for medicinal chemistry. In this study, besides the starting materials (3a−c and 4a−c), synthesis, characterization, and biological activity studies were conducted on a total of 18 compounds, nine of which are known and the other nine are original. The compounds investigated in the study are a series of alkyl (7−15) and aryl (16−24) ether derivatives bearing substituted phenyl and imidazole rings, which were characterized using various methods including 1 H NMR, 13 C NMR, FT-IR analysis, elemental analysis, and mass spectroscopy. Computeraided drug design studies have been carried out to predict the biological activities of compounds. Besides DFT calculations, the binding affinities of the compounds to EGFR, VEGFR2, FGFR1, HSP90, hCA I, and hCA II were investigated. Additionally, druglikeness and ADME analyses were performed on the compounds. Anticancer, antioxidant, and enzyme inhibition activity tests were performed in biological activity studies on the synthesized compounds. Among the synthesized compounds, compounds 17 and 19− 24 generally exhibited inhibition profiles against the widespread cytosolic hCA I isozyme with IC 50 values ranging from 4.13 to 15.67 nM and cytosolic hCA II isozyme with IC 50 values ranging from 5.65 to 14.84 nM. L929 (mouse fibroblast cell line) was used as the control healthy cell line, and MCF7 (breast cancer), C6 (rat glioblastoma), and HT-29 (colon cancer) cells were used in cell culture studies as cancer cell lines. Before the study on cancer cells, all compounds were examined on healthy cells, and their cytotoxicity was determined. As a result of these data, studies continued with six compounds determined to be nontoxic. On cancerous cells, it was determined that compounds 3a, 3b, 4a, 4b, 4c, and 7 had cytotoxic effects on both colon cancer and brain tumors. It was found that compound 3b had a more toxic effect than cisplatin on the glioma cell line with an IC 50 value of 10.721 ± 0.38 μM, and compound 3a had a more toxic effect on the colon cancer cell line with an IC 50 value of 20.88 ± 1.02 μM. However, it was determined that the same compounds did not have a statistically significant effect on breast cancer. Flow cytometry studies also showed that when the IC 50 dose of compound 3b was applied to the C6 cell line, the cells tended to early and late apoptosis. Additionally, it has been shown by flow cytometry that the cell cycle stops in the G0/G1 phase. A similar effect was observed in the colon cancer cell line with compound 3a. Compound 3b caused early and late apoptosis of the colon cancer cell line with the applied IC 50 dose and stopped the cell cycle in the G0/G1 phase. Finally, the FRAP method studied all synthesized compounds' antioxidant effects. According to the measured antioxidant power results, it was determined that no compound had a more effective reducing power than vitamin E.

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Section: Results and Discussionsupporting

confidence: 93%

Section: Resultsmentioning

confidence: 54%

Section: Results and Discussionmentioning

confidence: 99%

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Imidazole-Derived Alkyl and Aryl Ethers: Synthesis, Characterization, In Vitro Anticancer and Antioxidant Activities, Carbonic Anhydrase I–II Inhibition Properties, and In Silico Studies

Faris,

Bostancı,

Özcan

et al. 2024

ACS Omega

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“…In the 13 C NMR spectrum of compound 4 , the characteristic peak belonging to the carbonyl carbon (C=O) observed at 188.95 ppm disappeared and a new peak belonging to the carbon to which the −OH group was attached was observed at 71.67 ppm instead. This formation is a specific case showing the reduction of the carbonyl group in the 13 C NMR spectrum [16a,17] . Apart from this, since there was no change in the aromatic region, other carbon peaks were observed, similarly to the ketone compound.…”

Section: Resultsmentioning

confidence: 61%

Design, Synthesis, Characterization, Antiproliferative Activity, and In Silico Studies of Novel Alkyl Ether Derivatives Containing 1H‐1,2,4‐Triazole Ring

et al. 2022

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In this study, starting from 1H-1,2,4-triazole, a new series of aliphatic ether derivatives containing phenyl and 1H-1,2,4triazole groups together were synthesized using reduction and Williamson ether synthesis mechanisms, respectively. The molecular structures of the synthesized compounds were characterized by fourier-transform infrared spectroscopy (FT-IR), 1 H and 13 C nuclear magnetic resonance ( 1 H NMR and 13 C NMR), mass spectroscopy, and elemental analysis techniques. All synthesized compounds were screened against three different human cancer cell lines, including colon, lung, and liver cancer cells. Some of the compounds showed exceptionally high antiproliferative effects against all three cancer cell lines, with IC 50 values much lower than the positive control drug bendamustine. In addition, molecular docking studies were performed to support the in vitro results and the interaction types and amino acids that play key roles in the binding of the compounds to enzymes were identified. Finally, the potential of these compounds to be drugs and their drug-likeness properties were evaluated by absorption, distribution, metabolism, and excretion-toxicity (ADMET) calculations and it was determined that the compounds could be drug candidates with the capacity to be effective and safe drugs for use in the treatment of different diseases.

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“…Structurally, it resembles vanillin, hence it is often called acevanillion APO was isolated from the roots of the Canadian plant Apocynum cannabinum, from which it took its common name. It was also identified in the roots of another plant, Picrorhiza kurroa (Kutki) growing in the Himalayas [1][2][3][4][5][6]. The extract of this herb has long been used in India and Sri Lanka in traditional Indian medicine (Ayurveda).…”

Section: Introductionmentioning

confidence: 99%

Application of a Carbon Fiber Microelectrode as a Sensor for Apocynin Electroanalysis

Michalkiewicz,

Skorupa,

Jakubczyk

et al. 2024

Materials

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In this study, a carbon fiber microelectrode (CF) was applied for the investigation of the electrochemical behavior of the natural antioxidant, apocynin (APO). Given the limited solubility of APO in water, a mixture of anhydrous acetic acid (AcH) with 20%, v/v acetonitrile (AN) and 0.1 mol L−1 sodium acetate (AcNa) was used. The electrochemical properties of APO were examined through linear sweep voltammetry (LSV), differential pulse voltammetry (DPV), and cyclic voltammetry (CV). The anodic oxidation of APO, which is the basis of the method used, proved to be diffusion-controlled and proceeded with a two-electron and one proton exchange. Both radicals and radical cations, arising from the first and second step of electrode reactions, respectively, underwent subsequent chemical transformations to yield more stable final products (EqCiEiCi mechanism). Using optimized DPV conditions, the anodic peak current of APO at a potential of 0.925 V vs. Ag/AgCl showed a good linear response within the concentration range of 2.7 × 10−6–2.6 × 10−4 mol L−1. The detection and quantification limits were determined as 8.9 × 10−7 and 2.7 × 10−6 mol L−1, respectively. The developed DPV method enabled the successful determination of APO in herbal extracts and in dietary supplements. It should be noted that this is the first method to be used for voltammetric determination of APO.

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Synthesis, Characterization, Theoretical Analyses, and Investigation of Their Biological Activities of Acetovanillone-Derived Novel Benzyl Ethers

Cited by 6 publications

References 52 publications

Imidazole-Derived Alkyl and Aryl Ethers: Synthesis, Characterization, In Vitro Anticancer and Antioxidant Activities, Carbonic Anhydrase I–II Inhibition Properties, and In Silico Studies

Imidazole-Derived Alkyl and Aryl Ethers: Synthesis, Characterization, In Vitro Anticancer and Antioxidant Activities, Carbonic Anhydrase I–II Inhibition Properties, and In Silico Studies

Design, Synthesis, Characterization, Antiproliferative Activity, and In Silico Studies of Novel Alkyl Ether Derivatives Containing 1H‐1,2,4‐Triazole Ring

Application of a Carbon Fiber Microelectrode as a Sensor for Apocynin Electroanalysis

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