Acid–Base Properties and Kinetics of Hydrolysis of Aroylhydrazones Derived from Nicotinic Acid Hydrazide

Benković, Tomislav; Kontrec, Darko; Tomišić, Vladislav; Budimir, Ana; Galić, Nives

doi:10.1007/s10953-016-0504-8

Cited by 19 publications

(10 citation statements)

References 35 publications

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“…Only a slight decrease in r 1 values observed at lower pH conditions suggest that it may be due to the protonation of imino nitrogen atoms that led to increased chelating stability rather than stepwise dissociation of MnL Me under acidic conditions. This was further supported by the high protonation constant value ( K H >13) for imino nitrogen containing compound with similar (CH 3 )C=N‐NH‐CO moiety [37] . Notably, presence of methyl groups adjacent to imino nitrogen atoms facilitate to preserve the hydrogen bonding that stabilize the molecule at acidic conditions.…”

Section: Resultsmentioning

confidence: 78%

A Single‐Pot Template Reaction Towards a Manganese‐Based T₁ Contrast Agent

et al. 2021

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Manganese‐based contrast agents (MnCAs) have emerged as suitable alternatives to gadolinium‐based contrast agents (GdCAs). However, due to their kinetic lability and laborious synthetic procedures, only a few MnCAs have found clinical MRI application. In this work, we have employed a highly innovative single‐pot template synthetic strategy to develop a MnCA, MnLMe, and studied the most important physicochemical properties in vitro. MnLMe displays optimized r1 relaxivities at both medium (20 and 64 MHz) and high magnetic fields (300 and 400 MHz) and an enhanced r1b=21.1 mM−1 s−1 (20 MHz, 298 K, pH 7.4) upon binding to BSA (Ka=4.2×103 M−1). In vivo studies show that MnLMe is cleared intact into the bladder through renal excretion and has a prolonged blood half‐life compared to the commercial GdCA Magnevist. MnLMe shows great promise as a novel MRI contrast agent.

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Section: Resultsmentioning

confidence: 78%

A Single‐Pot Template Reaction Towards a Manganese‐Based T₁ Contrast Agent

et al. 2021

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“…Compounds 2, 6, 7, 11 and 12 showed good activity against multi-resistant clinical strains MRSA, ESBL+ E. coli and C. a. FLR+ , still lower than that of reference drugs. The same applies to compounds 11 and 12, which were highly active against S. aureus ATCC 6538 (both 11 and 12), C. albicans ATCC 10231 (11) and E. coli ATCC 10536 (11) but still not as active as the standard drugs. Compound 6 showed activity against the S. aureus ATCC 6538 strain with IC 90 range 6.0 ´ 10 -2 -0.48 µmol mL -1 , while compounds 11 and 12 showed even better antibacterial activity against S. aureus, with the lowest MIC value of 5.16 ´ 10 -3 µmol mL -1 (MIC range 5.16 ´ 10 -3 -0.2 µmol mL -1 for compound 11) as well as against the E. coli ATCC 10536 strain (IC 90 range 0.17-0.37 µmol mL -1 ).…”

Section: Resultsmentioning

confidence: 91%

“…Chemicals used in this study, such as acetic acid glacial (Panreac, Spain), dimethyl sulfoxide pure (Lach-Ner, Czech Republic), methanol (Merck KgaA, Germany), are commercially available and were used without further purification, while aroylhydrazone derivatives were synthesized by previously described procedures (11) and analyzed using standard analytical methods. Drugs used as positive controls were gentamicin sulphate and colistin purchased from Sigma-Aldrich, nystatin from PLIVA Hrvatska (Croatia), norfloxacin from Krka-Farma (Slovenia) and voriconazole from Pfizer (USA).…”

Section: Chemicalsmentioning

confidence: 99%

Antimicrobial assesment of aroylhydrazone derivatives in vitro

et al. 2019

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Aroylhydrazones 1–13 were screened for antimicrobial and antibiofilm activities in vitro. N′-(2-hydroxy-phenylmethylidene)-3-pyridinecarbohydrazide (2), N′-(5-chloro-2-hydroxyphenyl-methylidene)-3-pyridinecarbohydrazide (10), N′-(3,5-chloro-2-hydroxyphenylmethylidene)-3-pyridinecarbohydrazide (11), and N′-(2-hydroxy-5-nitrophenylmethylidene)-3-pyridinecarbohydrazide (12) showed antibacterial activity against Escherichia coli, with MIC values (in µmol mL−1) of 0.18–0.23, 0.11–0.20, 0.16–0.17 and 0.35–0.37, resp. Compounds 11 and 12, as well as N′-(2-hydroxy-3-methoxyphenylmethylidene)-3-pyridinecarbohydrazide (6) and N′-(2-hydroxy-5- methoxyphenylmethylidene)-3-pyridinecarbohydrazide (8) showed antibacterial activity against Staphylococcus aureus, with the lowest MIC values of 0.005–0.2, 0.05–0.12, 0.06–0.48 and 0.17–0.99 µmol mL−1. N′-(2-hydroxy-5-methoxyphenylmethylidene)-3-pyridinecarbohydrazide (7) showed antifungal activity against both fluconazole resistant and susceptible C. albicans strains with IC90 range of 0.18–0.1 µmol mL−1. Only compound 11 showed activity against C. albicans ATCC 10231 comparable to the activity of nystatin (the lowest MIC 4.0 ×10−2 vs. 1.7 × 10−2 µmol mL−1). Good activity regarding multi-resistant clinical strains was observed for compound 12 against MRSA strain (MIC 0.02 µmol mL−1) and compounds 2, 6 and 12 against ESBL+ E. coli MFBF 12794, with the lowest MIC for compound 12 (IC50 0.16 µmol mL−1). Anti-biofilm activity was found for compounds 2 (MBFIC 0.015–0.02 µmol mL−1 against MRSA) and 12 (MBFIC 0.013 µmol mL−1 against EBSL+ E. coli). In the case of compound 2 against MRSA biofilm formation, MBFIC values were comparable to those of gentamicin sulphate, whereas in the case of compound 12 and EBSL+ E. coli even more favourable activity compared to gentamicin was observed.

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“…Salicylaldehyde was obtained from Merck (Germany), o-vanillin, nicotinic acid and iso-nicotinic acid hydrazides were purchased from Fluka (Switzerland); benzaldehyde, 2,4-dihydroxybenzaldehyde, 2-hydroxy-4- chlorobenzaldehyde and 3,5-dichloro-2-hydroxy benzaldehyde purchased from Sigma (Switzerland). All hydrazones were synthesized in the University of Zagreb, according to previously described procedures [29,34,[42][43][44][45]. They were obtained by the condensation reaction of equimolar amounts of the corresponding aroylhydrazide (nicotinic hydrazide for 1-12 and isonicotinic hydrazide for A-E) and differently substituted aldehydes or ketones The reactions were carried out in dry alcohol (ethanol or ethanol) under argon atmosphere at 85 C for 20 h. The solvent was evaporated and the solids were suspended in CH 2 Cl 2 , filtered (G-3), rinsed with CH 2 Cl 2 (EtOH was used for 4, 5, 11 and 12), and dried at 50 C over 24 h.…”

Section: Chemistrymentioning

confidence: 99%

“…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%

Cancer cell growth inhibition by aroylhydrazone derivatives

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Kontrec

Detcheva

et al. 2019

Biotechnology & Biotechnological Equipment

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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.

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Acid–Base Properties and Kinetics of Hydrolysis of Aroylhydrazones Derived from Nicotinic Acid Hydrazide

Cited by 19 publications

References 35 publications

A Single‐Pot Template Reaction Towards a Manganese‐Based T₁ Contrast Agent

A Single‐Pot Template Reaction Towards a Manganese‐Based T₁ Contrast Agent

Antimicrobial assesment of aroylhydrazone derivatives in vitro

Cancer cell growth inhibition by aroylhydrazone derivatives

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Acid–Base Properties and Kinetics of Hydrolysis of Aroylhydrazones Derived from Nicotinic Acid Hydrazide

Cited by 19 publications

References 35 publications

A Single‐Pot Template Reaction Towards a Manganese‐Based T1 Contrast Agent

A Single‐Pot Template Reaction Towards a Manganese‐Based T1 Contrast Agent

Antimicrobial assesment of aroylhydrazone derivatives in vitro

Cancer cell growth inhibition by aroylhydrazone derivatives

Contact Info

Product

Resources

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A Single‐Pot Template Reaction Towards a Manganese‐Based T₁ Contrast Agent

A Single‐Pot Template Reaction Towards a Manganese‐Based T₁ Contrast Agent