4-Hydroxy-2-quinolones 132. Synthesis, chemical, and biological properties of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids 2-nitrobenzylidenehydrazides

Украинец, И. В.; Сидоренко, Л. В.; Golovchenko, Olga

doi:10.1007/s10593-007-0221-8

Cited by 7 publications

(4 citation statements)

References 5 publications

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“…Only in the single example of 2-aminoethanol amongst all of the variety of amines used in this study did the corresponding amide synthesis fail because the salt of ester 4 with this amino alcohol proved extremely stable to subsequent amidation. A similar selective inertness (but only with relation to ammonia) has been noted by us before in the ethyl 4-hydroxy-2-oxo- [4] and 4-chloro-2-oxo- [6] 1,2-dihydroquinoline-3-carboxylates. Moreover, factors determining this observed effect were then identified not so much as the properties of the individual functional groups or their reactivity but overall as the steric structure of the interacting molecules approaching one another (as a key to a lock) and in this way forming extremely stable adducts to further reaction.…”

supporting

confidence: 85%

“…Original article submitted June 8, 2007. amine because of the clear acidic properties of the 2-OH group in ester 4 since at least an equimolar amount of amine was tied up as the salt 5 but has not proved not strictly correct. The experiments carried out showed that such ammonium salts are quite stable when formed under normal conditions and, in contrast to analogous salts formed by 4-hydroxy-2-oxo-3-ethoxycarbonyl-1,2-dihydroquinolines [4], can be readily separated and characterized. …”

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confidence: 96%

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4-Hydroxy-2-quinolones 144. Alkyl-, arylalkyl-, and arylamides of 2-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid and their diuretic properties

Украинец

Tugaibei

Bereznyakova

et al. 2008

Chem Heterocycl Comp

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Keywords: amides, 2-hydroxy-4-oxo-4H-pyrido-[1,2-a]pyrimidine-3-carboxylic acids, tricarbonylmethane heterocyclic derivatives, diuretic activity, X-ray structural analysis.The problem of discovering novel classes of chemical substances capable of diuretic action, and particularly important, those which are highly efficient and safe diuretic medicines has not lost its urgency even over recent decades. Interesting substances investigated within this scheme are amidated 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids derivatives [2,3]. Although for a long time high diuretic activity has not been considered a characteristic of quinolone compounds, several of these materials proved extremely promising and have been subjected to broad pharmacological investigation to this time. With this in mind we have carried out the synthesis and biological screening to reveal the ability of the series of structurally related 2-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid N-R-amides 1-3 to increase the diuretic kidney function.It was found that the alkylamides 1a-u (Table 1) can be prepared by the reaction of ethyl 2-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylate (4) with a two, or better three, fold excess of the corresponding alkylamine in refluxing ethanol. It was initially proposed that it was necessary to use quite a large excess of the _______ * For Communication 143 see [1].

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confidence: 85%

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confidence: 96%

4-Hydroxy-2-quinolones 144. Alkyl-, arylalkyl-, and arylamides of 2-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid and their diuretic properties

Украинец

Tugaibei

Bereznyakova

et al. 2008

Chem Heterocycl Comp

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“…With the transfer to alkyl 1-R-4-hydroxy-2,2-dioxo-1H-2λ 6 ,1-benzothiazine-3-carboxylates the powerful acidifying effect of the sulfo group so greatly increases 4-ОН-acidity that the ordinary salt formation begins to prevent amidation. By comparison -the salts of alkyl 1-R-4-hydroxy-2-oxo-1,2dihydroquinoline-3-carboxylates are extremely unstable with amines and rapidly decompose even by carbon dioxide of the air [83]; and, as a rule, they do not cause problems in amidation. On the contrary the similar salts of their 2-sulfo analogs can be readily isolated and characterized.…”

Section: -R-4-hydroxy-22-dioxo-1h-2λ61-benzothiazine-3-carboxamidesmentioning

confidence: 99%

4-Hydroxyquinolin-2-ones and their Close Structural Analogues as a New Source of Highly Effective Pain-Killers

Украинец¹,

Gorokhova²,

Jaradat³

et al. 2014

Pain and Treatment

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Until recently 4-hydroxyquinolin-2-ones have not even mentioned as analgesics in scientific literature. Only some years ago the situation turned over when based on preliminary virtual screening we obtained hydrochlorides of [(alkylamino)alkyl]amides of 1-allyl-4-hydroxy-6,7dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid as potential opioid receptor antagonists [24]. Further pharmacological research has confirmed the presence of "calculated" Pain and Treatment 22 Pain and Treatment 24 Pain and Treatment 28

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“…They possess lots of biological activities such as antibacterial (Pomarnacka et al, 2006), antituberculosis (Bedia et al, 2006) and anticonvulsant (Ragavendran et al, 2007). It is stated in some papers and patents in the literature that pyridine-based hydrazones possess important pharmacological properties such as antimicrobial (Neuman, 2018;Soujanya et al, 2017;Ukrainets et al, 2007), antifungal (Backes et al, 2015), antibacterial (Ali et al, 2020;Morjan et al, 2014) and anti-inflammatory (Khalil et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

Yeni Piridin Bazlı N-Açil Hidrazon Türevlerinin Sentezi ve Spektroskopik Karakterizasyonu ve Glukozamin-6-Fosfat Üzerine Moleküler Yerleştirme Çalışmaları

Vural

Keskin

2023

Karadeniz Fen Bilimleri Dergisi

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Antimicrobial resistance in infectious diseases caused by organisms such as bacteria, fungi, viruses, and parasites has led to an increase in studies and demands for new antimicrobial drug development. The compounds including pyridine and N-acylhydrazone skeletons in their structures have a large application area in drug discovery due to their anticancer, anti-tubercular, anti-bacterial and anti-fungal activities. Here, the novel N-acyl-hydrazone derivatives, (E)-2-oxo-N'-(2,3,4-trimethoxybenzylidene)-1,2-dihydropyridine-3-carbohydrazide and (E)-N'-(1-(4-bromophenyl) ethylidene)-2-oxo-1,2-dihydropyridine-3-carbohydrazide were synthesized through a multistep reaction sequence. The structures of newly synthesized compounds were established on the basis of IR, 1D and 2D NMR spectra and mass spectral data. The theoretical electronic structure analysis was performed by density functional theory (DFT) at the B3LYP level with the 6-311++G(d,p) basis set in the gas phase of synthesized compounds. The newly synthesized compounds were docked on glucosamine-6 phosphate synthase to determine potential interactions between the analyzed compounds and its active site due to its role in microbial cell wall synthesis. The possibilities of these compounds to being active for antimycobacterial and antituberculosis have been found as quite high, and their interactions in the binding site have been determined with the range of binding affinity, [-7.1, -7.3] kcal/mol, respectively.

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4-Hydroxy-2-quinolones 132. Synthesis, chemical, and biological properties of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids 2-nitrobenzylidenehydrazides

Cited by 7 publications

References 5 publications

4-Hydroxy-2-quinolones 144. Alkyl-, arylalkyl-, and arylamides of 2-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid and their diuretic properties

4-Hydroxy-2-quinolones 144. Alkyl-, arylalkyl-, and arylamides of 2-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylic acid and their diuretic properties

4-Hydroxyquinolin-2-ones and their Close Structural Analogues as a New Source of Highly Effective Pain-Killers

Yeni Piridin Bazlı N-Açil Hidrazon Türevlerinin Sentezi ve Spektroskopik Karakterizasyonu ve Glukozamin-6-Fosfat Üzerine Moleküler Yerleştirme Çalışmaları

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