Synthesis, characterization, molecular docking and in vitro anti-cancer activity studies of new and highly selective 1,2,3-triazole substituted 4-hydroxybenzohyrdazide derivatives

Şenol, Halil; Ağgül, Ahmet Gökhan; Atasoy, Sezen; Güzeldemirci, Nuray Ulusoy

doi:10.1016/j.molstruc.2023.135247

Cited by 21 publications

(42 citation statements)

References 38 publications

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“…The imine carbon in arylidenehydrazide series was resonated at 148-149 ppm. In arylidene hydrazid series the hydrazid carbonyls resonated at 162-163 ppm in 13 C-APT NMR spectrums (Figure S24). When imine groups converter to thiazolidine-4-one ring, the hydrogen signal of imine group shifted from 8.5 to around 6 ppm.…”

Section: Characterization Of the Synthesized Compoundsmentioning

confidence: 99%

“…All the synthesized compounds were very well characterized by NMR ( 1 H, 13 C-APT) and HRMS spectroscopic techniques. In the 1 H-NMR spectrum of compound 2 (Figure S3), the furan ring resonated at 7.40 (d), 6.40 (d) and 6.32 (dd) ppm.…”

Section: Characterization Of the Synthesized Compoundsmentioning

confidence: 99%

“…Methylenic hydrogens of furfuryl moiety resonated at 4.95 ppm as singlet. In the 13 C-APT NMR spectrum of compound 2 (Figure S4), the ester carbonyl resonated at 168 ppm. The ester group was converted to hydrazid and compound 3 was synthesized.…”

Section: Characterization Of the Synthesized Compoundsmentioning

confidence: 99%

“…The ester group was converted to hydrazid and compound 3 was synthesized. In the 13 C-APT NMR spectrum of compound 3 (Figure S6), the hydrazid carbonyl resonated at 166 ppm. In addition, in the 1 H-NMR spectrum of compound 3 (Figure S5), due to the conversion of ester to hydrazide the ester methyl was not observed.…”

Section: Characterization Of the Synthesized Compoundsmentioning

confidence: 99%

“…They were characterized with NMR ( 1 H and 13 C-APT NMR) and HRMS spectroscopic techniques. The 1 H-NMR and 13 C-APT NMR spectra were measured using a Bruker Avance NEO NMR Spectrometer at 500 and 125 MHz, respectively, and coupling constant values were reported in Hertz (Hz) and chemical shifts were reported in parts per million (ppm) relative to the internal standard tetramethylsilane (δ = 0.00 ppm). The peak splittings were described as follows: s (singlet), d (doublet), t (triplet), q (quartet), m (multiplet), bs (broad singlet), dd (doublet of doublets) and dt (doublet of triplets).…”

Section: Experimental Section Chemical Materials and Devicesmentioning

confidence: 99%

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Synthesis, Characterization, Molecular Docking and in vitro Biological Studies of Thiazolidin‐4‐one Derivatives as Anti‐Breast‐Cancer Agents

2023

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In this study, 16 new compounds were synthesized starting from methylparaben. These new compounds consist of eight arylidenehydrazide derivatives and eight thiazolidin‐4‐on derivatives. All compounds were tested against MCF‐7 breast cancer cells and MCF10A breast healthy tissue to determine their anti‐cancer activity. Molecular docking studies were also carried out against receptor proteins related to the growth factor of cancer cells to understand inhibition mechanism. According to the results, 4‐furan‐2‐ylmethoxy)‐N‐(4‐oxo‐2‐phenylthiazolidin‐3‐yl)benzamide (5 a) and 4‐(furan‐2‐ylmethoxy)‐N‐(2‐(4‐nitrophenyl)‐4‐oxothiazolidin‐3‐yl)benzamide (5 e) were found as the highest selective and most active compounds against breast cancer cells.

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Section: Characterization Of the Synthesized Compoundsmentioning

confidence: 99%

Section: Characterization Of the Synthesized Compoundsmentioning

confidence: 99%

Section: Characterization Of the Synthesized Compoundsmentioning

confidence: 99%

Section: Characterization Of the Synthesized Compoundsmentioning

confidence: 99%

Section: Experimental Section Chemical Materials and Devicesmentioning

confidence: 99%

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Synthesis, Characterization, Molecular Docking and in vitro Biological Studies of Thiazolidin‐4‐one Derivatives as Anti‐Breast‐Cancer Agents

2023

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Novel quinazoline–chromene hybrids as anticancer agents: Synthesis, biological activity, molecular docking, dynamics and ADME studies

Tokalı,

Şenol,

Yetke

et al. 2023

Archiv der Pharmazie

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In this study, new quinazoline–chromene hybrid compounds were synthesized. The cytotoxic effects on cell viability of the hybrid compounds were tested against A549 human lung adenocarcinoma and BEAS‐2B healthy bronchial epithelial cell lines in vitro. In addition, the ability of the active compounds to inhibit cell migration was tested. Molecular docking studies were performed to evaluate the ligand–protein interactions, and molecular dynamics simulations were performed to determine the interactions and stability of ligand–protein complexes. In silico absorption, distribution, metabolism, and excretion (ADME) studies were conducted to estimate the drug‐likeness of the compounds. Compounds 4 (IC50 = 51.2 µM) and 5 (IC50 = 44.2 µM) were found to be the most active agents against A549 cells. They are found to be more selective against A549 cells than the reference drug doxorubicin. They also have the ability to significantly inhibit cell migration. They have the best docking scores against epidermal growth factor receptor (EGFR) (−11.300 and −11.226 kcal/mol) and vascular endothelial growth factor receptor 2 (VEGFR2) (−10.987 and −11.247 kcal/mol), respectively. In MD simulations, compounds 4 and 5 have strong hydrogen bond interactions above 80% of simulation times and showed a low ligand root mean square deviation (RMSD) around 2 Å. According to the ADME analysis, compounds 4 and 5 exhibit excellent drug‐likeness and pharmacokinetic characteristics.

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The anti‐breast cancer therapeutic potential of 1,2,3‐triazole‐containing hybrids

Song,

Zhang,

Zhang

et al. 2023

Archiv der Pharmazie

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Breast cancer, as one of the most common invasive malignancies and the leading cause of cancer‐related deaths in women globally, poses a significant challenge in the world health system. Substantial advances in diagnosis and treatment have significantly improved the survival rate of breast cancer patients, but the number of incidences and deaths of breast cancer are projected to increase by 40% and 50%, respectively, by 2040. Chemotherapy is one of the principal treatments for breast cancer therapy, but multidrug resistance and severe side effects remain the major obstacles to the success of treatment. Hence, there is a vital need to develop novel chemotherapeutic agents to combat this deadly disease. 1,2,3‐Triazole, which can be effectively constructed by click chemistry, not only can serve as a linker to connect different anti‐breast cancer pharmacophores but also is a valuable pharmacophore with anti‐breast cancer potential and favorable properties such as hydrogen bonding, moderate dipole moment, and enhanced water solubility. Particularly, 1,2,3‐triazole‐containing hybrids have demonstrated promising in vitro and in vivo anti‐breast cancer potential against both drug‐sensitive and drug‐resistant forms and possessed excellent selectivity by targeting different biological pathways associated with breast cancer, representing privileged scaffolds for the discovery of novel anti‐breast cancer candidates. This review concentrates on the latest advancements of 1,2,3‐triazole‐containing hybrids with anti‐breast cancer potential, including work published between 2020 and the present. The structure–activity relationships (SARs) and mechanisms of action are also reviewed to shed light on the development of more effective and multitargeted candidates.

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Synthesis, characterization, molecular docking and in vitro anti-cancer activity studies of new and highly selective 1,2,3-triazole substituted 4-hydroxybenzohyrdazide derivatives

Cited by 21 publications

References 38 publications

Synthesis, Characterization, Molecular Docking and in vitro Biological Studies of Thiazolidin‐4‐one Derivatives as Anti‐Breast‐Cancer Agents

Synthesis, Characterization, Molecular Docking and in vitro Biological Studies of Thiazolidin‐4‐one Derivatives as Anti‐Breast‐Cancer Agents

Novel quinazoline–chromene hybrids as anticancer agents: Synthesis, biological activity, molecular docking, dynamics and ADME studies

The anti‐breast cancer therapeutic potential of 1,2,3‐triazole‐containing hybrids

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