Aromatic hydrazones derived from nicotinic acid hydrazide as fluorimetric pH sensing molecules: Structural analysis by computational and spectroscopic methods in solid phase and in solution

Benković, Tomislav; Kenđel, Adriana; Parlov-Vuković, Jelena; Kontrec, Darko; Chiş, Vasile; Miljanić, Snežana; Galić, Nives

doi:10.1016/j.saa.2017.09.038

Cited by 24 publications

(9 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The 1 H NMR spectrum of 1 (d 6 -DMSO) (Supplementary material) showed an uncharacteristic downfield resonance for the amide H atom at 15.08 ppm, suggesting that H-bonding is taking place between it and the O atom of the ketone group on the backbone of the phendione moiety. H-bonding of this type has previously been documented for hydrazones of similar structure and it leads to keto-enol tautomerization (Benković et al 2018;Cheon et al 2002;Barbazán et al 2010). The 1 H NMR spectrum of 1 in d 4methanol shows additional peaks in the region 7.5-9.1 ppm compared to that recorded in d 6 -DMSO, indicating that the tautomerization process is more clearly observed in the former solvent.…”

Section: Chemical Synthesismentioning

confidence: 59%

Synthesis and antimicrobial activity of a phenanthroline-isoniazid hybrid ligand and its Ag+ and Mn2+ complexes

et al. 2019

View full text Add to dashboard Cite

Hydrazide ligand, (Z)-N'-(6-oxo-1,10phenanthrolin-5(6H)-ylidene)isonicotinohydrazide, 1 forms from a 1:1 Schiff base condensation reaction between isoniazid (INH) and 1,10-phenanthroline-5,6-dione (phendione). Ag ? and Mn 2? complexes with 1:2 metal:ligand stoichiometry are prepared: [Ag(1) 2 ]NO 3 , [Ag(1) 2 ]BF 4 and [Mn(1) 2 ](NO 3) 2. Polymeric {[Ag(1)(NO 3)]} n has 1:1 stoichiometry and forms upon infusion of CH 2 Cl 2 into a DMSO solution of [Ag(1) 2 ]NO 3. {[Ag(1)(NO 3)]} n was structurally characterized using X-ray crystallography. Metal-free 1 and its 1:2 complexes exhibit very good, broadspectrum antimicrobial activity and are not excessively toxic to mammalian cells (A549 lineage).

show abstract

Section: Chemical Synthesismentioning

confidence: 59%

Synthesis and antimicrobial activity of a phenanthroline-isoniazid hybrid ligand and its Ag+ and Mn2+ complexes

et al. 2019

View full text Add to dashboard Cite

show abstract

“… [66] reported the OH stretching vibration of the 8-hydroxyquinoline-2-carboxaldehyde isonicotinoylhydrazone at 3396 cm −1 . On the other hand, Benković et al [69] reported the stretching of the OH groups, involved in the intramolecular hydrogen bond with the nitrogen atom of the group C=N, of hydrazones with hydroxyl group in position 2 of phenyl ring at 3142 cm −1 . In the present study, the broad and very weak IR band at 3490 cm −1 have been assigned to stretching modes of OH involved in the intramolecular hydrogen bond for DD1 ( Figs.…”

Section: Resultsmentioning

confidence: 99%

5-((1H-imidazol-1-yl)methyl)quinolin-8-ol as potential antiviral SARS-CoV-2 candidate: Synthesis, crystal structure, Hirshfeld surface analysis, DFT and molecular docking studies

Douche

Sert

Brandán

et al. 2021

Journal of Molecular Structure

View full text Add to dashboard Cite

“…All obtained hydrazones were characterized by standard analytical procedures (UV/VIS, NMR, MS, HPLC, X-ray) [34,[37][38][39][40][41][42]. The physico-chemical properties of the compounds 1-12 were investigated and reported [32,36,38,39,41].…”

Section: Chemistrymentioning

confidence: 99%

“…In this regard, as part of our study on the analytical application of hydrazones and Schiff bases we prepared and characterized a series of differently substituted aroylhydrazones, both derived from nicotinic acid 1-12 ( Figure 1) [34][35][36][37][38][39][40][41] and isonicotinic acid hydrazide A-E ( Figure 2).…”

Section: Introductionmentioning

confidence: 99%

Cancer cell growth inhibition by aroylhydrazone derivatives

Илиев

Kontrec

Detcheva

et al. 2019

Biotechnology & Biotechnological Equipment

View full text Add to dashboard Cite

Hydrazones have versatile properties that make them promising for a range of possible applications. In this study, we examined a library of 17 aroylhydrazones derived from nicotinic acid hydrazide (1-12) and isonicotinic acid hydrazide (A-E) created by us for their biological activity. The antiproliferative activity of the compounds was investigated on non-tumour MCF-10A cells and cancer cell lines, MCF-7 and MDA-MB-231. Four compounds were selected as most active in cell growth inhibition of the tumour cell lines. These compounds, 5, 11, C and E, were tested on four additional cell lines: non-tumour BJ and cancer cell lines, HeLa, HepG2 and HT-29. Compounds 5 and E exhibited the highest selectivity index on cancer cell lines MDA-MB-231, HeLa and HepG2. High selectivity to MCF-7 cells was demonstrated with compound 5. Compound C was very selective to HepG2 cells as well as to MDA-MB-231 but to a lesser degree. Compound 11 showed selectivity against MDA-MB-231. The obtained results allow assessing the structure-activity relationship of the compounds and provide insight into the further development of this group of aroylhydrazones as more potent and selective anti-neoplastic agents.

show abstract

Aromatic hydrazones derived from nicotinic acid hydrazide as fluorimetric pH sensing molecules: Structural analysis by computational and spectroscopic methods in solid phase and in solution

Cited by 24 publications

References 38 publications

Synthesis and antimicrobial activity of a phenanthroline-isoniazid hybrid ligand and its Ag+ and Mn2+ complexes

Synthesis and antimicrobial activity of a phenanthroline-isoniazid hybrid ligand and its Ag+ and Mn2+ complexes

5-((1H-imidazol-1-yl)methyl)quinolin-8-ol as potential antiviral SARS-CoV-2 candidate: Synthesis, crystal structure, Hirshfeld surface analysis, DFT and molecular docking studies

Cancer cell growth inhibition by aroylhydrazone derivatives

Contact Info

Product

Resources

About