Synthesis and antimicrobial activity of some novel furyl and benzimidazole substituted benzyl ethers

Güven, Özden Özel; Erdoğan, Taner; Göker, Hakan; Yıldız, Sulhiye

doi:10.1002/jhet.5570440336

Cited by 26 publications

(3 citation statements)

References 7 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: 56%

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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: 56%

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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“…Natural biological substances such as purine bases and vitamin B 12 include benzimidazole moiety in their structure. Several benzimidazole derivatives are reported to exhibit antimicrobial , anticancer , antifungal , antiparasitic , antiviral , anti‐inflammatory , and antihistaminic activities.…”

Section: Introductionmentioning

confidence: 99%

Microwave‐assisted Synthesis of Hybrid Heterocyclics as Biological Potent Molecules

Srinivas¹,

Sunitha²,

Reddy³

et al. 2018

Journal of Heterocyclic Chem

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A series of novel 5‐((1H‐benzo[d]imidazol‐2‐yl)methyl)‐2‐((3aR,5S,6S,6aR)‐2,2‐dimethyl‐6‐((1‐phenyl‐1H‐1,2,3‐triazol‐4‐yl)methoxy)tetrahydrofuro[2,3‐d][1,3]dioxol‐5‐yl)‐3‐phenylthiazolidin‐4‐ones 9a–n has been synthesized from triazole‐linked thiazolidinone derivatives 8a–g with o‐phenylenediamine and characterized by IR, NMR, MS, and elemental analyses. Further, these compounds were screened for their antibacterial activity against Gram‐positive bacteria, namely, Bacillus subtilis (ATCC 6633), Staphylococcus aureus (ATCC 6538p), and Micrococcus luteus (IFC 12708), and Gram‐negative bacteria, namely, Proteus vulgaris (ATCC 3851), Salmonella typhimurium (ATCC 14028), and Escherichia coli (ATCC 25922). Among the screened compounds, compounds 9b, 9d, 9h, and 9i are highly active against almost all selected bacterial strains; the remaining compounds showed moderate to good activity and emerged as potential molecules for further development.

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