Structural, antioxidant, antiproliferative and in‒silico study of pyridine-based hydrazonyl‒selenazoles and their sulphur isosteres

Araškov, Jovana B.; Nikolić, Milan; Armaković, Sanja J.; Rodić, Marko V.; Višnjevac, Aleksandar; Padrón, José M.; Todorović, Tamara R.; Filipović, Nenad R.

doi:10.1016/j.molstruc.2021.130512

Cited by 19 publications

(22 citation statements)

References 84 publications

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“…The half-maximal growth inhibitory concentration (GI 50 ) values were calculated for each compound and presented in Table 7. In our previous study, we reported the antiproliferative activity of ligands HLS 1-3 on the same set of cell lines, 4 which is included in Table 7 for comparison purposes. The HLS 1 ligand itself appeared very potent against A549, HBL-100, HeLa, and SW1573 cells, while HLS 2 was totally inactive, despite the fact that favorable pharmacokinetic parameters were calculated for this compound.…”

Section: Antiproliferative Activity and Acute Lethality Studymentioning

confidence: 99%

“…N,N,N Tridentate coordination to various metal ions is characteristic of this class of ligands, [5][6][7][8][9][10] as it is for the structurally similar pyrazine-based TH. 11 Since ligands HLS 1-3 , 4 and their complexes with CoĲIII) 6 and CdĲII) 7 were shown to possess significant antiproliferative activity, we investigated whether the coordination to ZnĲII) may enhance the activity. In addition, due to the conjugate ligand systems used, we investigated the photophysical properties of the ligands and corresponding ZnĲII) complexes at both low (77 K) and room temperature (RT).…”

Section: Introductionmentioning

confidence: 99%

“…THs have shown anticancer and many other biological activities. 4 The biological activity of complexes has been studied to a much smaller extent in comparison to free ligands. Preparation of pyridine- and pyrazine-based complexes enhanced ligands' antimicrobial and anticancer activities, while several of them even induced apoptosis.…”

Section: Introductionmentioning

confidence: 99%

“…Since ligands HLS 1–3 , 4 and their complexes with Co( iii ) 6 and Cd( ii ) 7 were shown to possess significant antiproliferative activity, we investigated whether the coordination to Zn( ii ) may enhance the activity. In addition, due to the conjugate ligand systems used, we investigated the photophysical properties of the ligands and corresponding Zn( ii ) complexes at both low (77 K) and room temperature (RT).…”

Section: Introductionmentioning

confidence: 99%

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Zn(ii) complexes with thiazolyl–hydrazones: structure, intermolecular interactions, photophysical properties, computational study and anticancer activity

et al. 2022

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Section: Antiproliferative Activity and Acute Lethality Studymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Zn(ii) complexes with thiazolyl–hydrazones: structure, intermolecular interactions, photophysical properties, computational study and anticancer activity

et al. 2022

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“…Thus, the amino group is readily susceptible towards acylation, alkylation or condensation reactions. 3 4 , 15 16 17 18 The selenium analogs of 2-aminothiazoles have also attracted much attention as biologically active compounds. 19 Antibiotic and neuroprotective, 20 anticancer, 18 21 antifungal, 22 antimicrobial as well as anticonvulsant 23 24 activities have been reported, and high-affinity inhibitors of kinase CK2 and efficient phosphorescence biomarkers have also been described.…”

Section: Table 1 Yields (%) Of 4aa ...mentioning

confidence: 99%

One-Pot Syntheses of Substituted 2-Aminothiazoles and 2-Aminoselenazoles via Meerwein Arylation of Alkyl Vinyl Ketones

et al. 2022

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Both one-pot and two-step procedures for the synthesis of substituted 2-aminothiazoles and 2-aminoselenazoles are described. Anilines are first converted into arenediazonium bromides, which are then reacted with methyl vinyl ketone or cyclopropyl vinyl ketone in the presence of copper(II) bromide to give 4-aryl-3-bromobutan-2-ones (40–71%) and 3-aryl-2-bromo-1-cyclopropylpropan-1-ones (41–79%), respectively. These products are reacted, without prior isolation, with thiourea or selenourea to prepare 4-methyl- and 4-cyclopropyl-5-(R-benzyl)thiazol-2-amines (14 examples) and their selenium analogs (14 examples). The yields of the one-pot procedure are higher (40–81%) than those of the two-step procedure (32–70%).

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A detailed experimental and computational study of Cd complexes with pyridyl‐based thiazolyl hydrazones

Kokanov

Filipović

Višnjevac

et al. 2022

Applied Organom Chemis

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Interest in Cd complexes has been growing in recent years. Cd complexes are considered a potential solution in the search for novel antibiotics that can fight antimicrobial resistance. In addition, Cd complexes draw attention to material chemistry. The main objective of this work was to prepare the first Cd(II) complexes with anionic forms of pyridine‐based thiazolyl hydrazone (THs) ligands HLS2 [(E)‐4‐(4‐methoxyphenyl)‐2‐(2‐[pyridine‐2‐ylmethylene]hydrazinyl)thiazole] and HLS3 [(E)‐2‐(2‐[pyridine‐2‐ylmethylene]hydrazinyl)‐4‐(p‐tolyl)thiazole] and perform their structural and spectroscopic characterization, as well as stability in solution and upon heating. Studies related to their biological activities and possible electrochromic applications are also being conducted. Complexes [Cd(HLS2)2] (1) and [Cd(HLS3)2] (2) have been characterized by a single‐crystal X‐ray diffraction and computational analysis of intermolecular interactions responsible for their solid‐state structures was performed. Thermal stability of 1 and 2 in the solid‐state was analyzed by TGA/MS, where as their solution stability was determined by the spectrophotometric titration method. Electrochemical and in situ UV–Vis spectroelectrochemical analyses of 1 and 2 were carried out to determine redox mechanisms and the influence of the substituents and electrolytes on their redox responses. The antioxidant capacity of both complexes was tested in antioxidant assays, while their antimicrobial activity was tested against five Gram‐positive and four Gram‐negative bacteria, as well as against three fungi. The obtained results indicate their potent antioxidant capacity. The antimicrobial activity of investigated compounds on almost all tested bacterial strains was stronger than that of the standard antibiotic erythromycin. The results of docking studies indicate that the minor groove DNA is the possible biological target of 1 and 2.

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Structural, antioxidant, antiproliferative and in‒silico study of pyridine-based hydrazonyl‒selenazoles and their sulphur isosteres

Cited by 19 publications

References 84 publications

Zn(ii) complexes with thiazolyl–hydrazones: structure, intermolecular interactions, photophysical properties, computational study and anticancer activity

Zn(ii) complexes with thiazolyl–hydrazones: structure, intermolecular interactions, photophysical properties, computational study and anticancer activity

One-Pot Syntheses of Substituted 2-Aminothiazoles and 2-Aminoselenazoles via Meerwein Arylation of Alkyl Vinyl Ketones

A detailed experimental and computational study of Cd complexes with pyridyl‐based thiazolyl hydrazones

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