Coordination chemistry of pyrazine derivatives analogues of PZA: design, synthesis, characterization and biological activity

Ogryzek, Małgorzata; Chylewska, Agnieszka; Królicka, Aleksandra; Banasiuk, Rafał; Turecka, Katarzyna; Lesiak, Dorota; Nidzworski, Dawid; Makowski, Mariusz

doi:10.1039/c6ra03068h

Cited by 21 publications

(9 citation statements)

References 72 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This investigation was planned based on the knowledge acquired from the physicochemical properties of other pyrazine derivatives reported by us previously. 23,24,62 The initial step of the investigation included the preliminary determination of the relation between the HClO 4 molar concentration and the H o index. The obtained for 2HP results presented in Fig.…”

Section: Spectroscopic and Potentiometric Resultsmentioning

confidence: 99%

“…Some of these compounds including pyrazine-2aminoxime (PAOX), pyrazine-2-thiocarboxamide (PTCA), and 2-amine-5-bromo-3-(methylamine)pyrazine (ABMAP) were previously investigated by our group. [23][24][25] In the discovery of biologically active compounds, there are several important issues such as structure, tautomerism, acidbase equilibrium, hydrophobicity, and membrane permeability. Knowledge of these properties allows the potential biological and therapeutic activities and behavior of compounds in the body or environment to be predicted.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

When biomolecules meet 2-hydrazinopyrazine: from theory through experiment to molecular levels using a wide spectrum of techniques

et al. 2020

Self Cite

View full text Add to dashboard Cite

show abstract

Section: Spectroscopic and Potentiometric Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

When biomolecules meet 2-hydrazinopyrazine: from theory through experiment to molecular levels using a wide spectrum of techniques

et al. 2020

Self Cite

View full text Add to dashboard Cite

show abstract

“…The fight against infectious diseases, one aspect of this field, has seen great advances; however, antimicrobial resistance remains a major obstacle and continues to increase, and it is now considered a global public health problem [5]. Multiple investigations have been performed to test new free organic or metal coordination compounds, which can be precursors of more efficient and less toxic drugs by acting through different biological mechanisms [6–8].…”

Section: Introductionmentioning

confidence: 99%

Cu(II) and Ni(II) Complexes with New Tridentate NNS Thiosemicarbazones: Synthesis, Characterisation, DNA Interaction, and Antibacterial Activity

Polo-Cerón

2019

Bioinorganic Chemistry and Applications

View full text Add to dashboard Cite

This paper reports the synthesis and detailed characterisation of copper(II) and nickel(II) complexes with tridentate thiosemicarbazone ligands H2L1 and H2L2 derived from 2-acetylpyrazine. The ligands and their metal complexes were characterised by different physicochemical techniques, including elemental and thermogravimetric analysis; UV-Vis, IR, 1H-NMR, and 13C-NMR spectroscopy; molar conductance measurements; and mass spectrometry. The crystal structure of the H2L1 ligand was determined by single crystal X-ray diffraction studies. The spectral data showed that the thiosemicarbazone behaves as an NNS tridentate ligand through the nitrogen atoms of the azomethine group and pyrazine ring and the sulphur atom of the thioamide group. Elemental and thermal analyses indicated that the obtained metal complexes had a 1 : 1 stoichiometry (metal-ligand). The interactions between these complexes and calf thymus DNA (CT-DNA) were studied by electronic absorption and viscosity measurements. The activities of these compounds against oxidative DNA cleavage were examined by agarose gel electrophoresis. Cu(II) and Ni(II) complexes can wind DNA strands through groove interactions and promote strand breakage of the plasmid pmCherry under oxidative stress conditions. Moreover, all the complexes could interact more strongly with DNA than could with the free ligands. Finally, the antibacterial activities of the ligands and their complexes were determined by in vitro tests against Gram-positive bacterial strains (S. aureus ATCC 25923, L. monocytogenes ATCC 19115, and B. cereus ATCC 10876) and Gram-negative bacterial strains (E. coli ATCC 25922, S. typhimurium ATCC 14028, and K. pneumoniae ATCC BAA-2146) using the broth microdilution method. The metal complexes showed greater antimicrobial activities than the precursor ligands against some of the microorganisms.

show abstract

“…This endopeptidase is part of a complex proteolytic MMP enzyme family, where its over expression has been linked to several pathological processes [ 48 ]. As several articles had already described the coordination of metals by sulfur containing compounds [ 49 , 50 ], we investigated whether the sulfamethaoxazole in our compounds could coordinate the Zn 2+ ion in MMP-8. This could promote potential inhibitory activity on MMP-8, as presented by Tauro et al [ 48 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Sulfamethaoxazole 4-Thiazolidinone Hybrids and Their Biological Evaluation

et al. 2020

View full text Add to dashboard Cite

A search for potent antitubercular agents prompted us to design and synthesize sulfamethaoxazole incorporated 4-thiazolidinone hybrids (7a–l) by using a cyclocondensation reaction between 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide (4), aryl aldehyde (5a–l), and mercapto acetic acid (6) resulting in good to excellent yields. All the newly synthesized 4-thiazolidinone derivatives were screened for their in vitro antitubercular activity against M. Bovis BCG and M. tuberculosis H37Ra (MTB) strains. The compounds 7d, 7g, 7i, 7k, and 7l revealed promising antimycobacterial activity against M. Bovis and MTB strains with IC90 values in the range of 0.058–0.22 and 0.43–5.31 µg/mL, respectively. The most active compounds were also evaluated for their cytotoxicity against MCF-7, HCT 116, and A549 cell lines and were found to be non-cytotoxic. Moreover, the synthesized compounds were also analyzed for ADME (absorption, distribution, metabolism, and excretion) properties and showed potential as good oral drug candidates.

show abstract

Coordination chemistry of pyrazine derivatives analogues of PZA: design, synthesis, characterization and biological activity

Abstract: A novel Ru(iii) complexes were synthesized and characterized. Their stabilities were discussed in terms of aqueous and MeCN solutions. Antimicrobial properties of complexes studied were characterized against reference strains of bacteria and yeast.

Cited by 21 publications

References 72 publications

When biomolecules meet 2-hydrazinopyrazine: from theory through experiment to molecular levels using a wide spectrum of techniques

When biomolecules meet 2-hydrazinopyrazine: from theory through experiment to molecular levels using a wide spectrum of techniques

Cu(II) and Ni(II) Complexes with New Tridentate NNS Thiosemicarbazones: Synthesis, Characterisation, DNA Interaction, and Antibacterial Activity

Synthesis of Novel Sulfamethaoxazole 4-Thiazolidinone Hybrids and Their Biological Evaluation

Contact Info

Product

Resources

About