Synthesis and Intramolecular Cyclization of N-acyl- and N-allyl-N'-(2-oxo-1,2-dihydro-pyridin-3-yl)thiourea

Кулаков, И. В.; Nikitina, O. S.; Fisyuk, A. S.; Goncharov, D. S.; Shulgau, Zarina; Gulyaev, A. E.

doi:10.1007/s10593-014-1519-y

Cited by 23 publications

(9 citation statements)

References 18 publications

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“…In recent years, there has been a pronounced drive to investigate the topology and conformational aspects of these thioureas prior to their use in various applied fields [17,18]. A strong prevalence of intramolecular hydrogen bonding [19] largely dictates their aptitude towards complexation [20], cyclization reactions [21], anion recognition [22][23][24], and drug design [25,26]. More recently, we have reported [27] that Hirshfeld surfaces analysis [28][29][30] is an impressive tool for evaluating intermolecular interactions in a small cluster of 1-(adamantane-1-carbonyl) thioureas.…”

Section: Introductionmentioning

confidence: 99%

Recent developments in chemistry, coordination, structure and biological aspects of 1-(acyl/aroyl)-3-(substituted) thioureas

et al. 2016

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1-(Acyl/aroyl)-3-(substituted)thioureas are privileged architectures that have received remarkable attention of researchers in view of their variable topological aspects, binding modes and broad spectrum promising pharmacological properties. Reactivity of acyl thiourea derivatives has presented various organic transformations into other demanding scaffolds and this is an attractive strategy for synthetic chemists to access heterocyclic cores. Multiple binding sites make them flexible ligands for complexation with transition metals thus occupying a distinct position in coordination chemistry. 1-(Acyl/aroyl)-3-(substituted)thioureas have also emerged as attractive candidates in various fields such as ion sensors, corrosion inhibitors, molecular electronics, in metal extraction and in pharmaceuticals. The medicinal chemistry of this organo-sulfur framework and the derived metal complexes has witnessed fantastic progress in the current era. In continuation of our efforts to compile data on the structural aspects and numerous applications of 1-(acyl/aroyl)-3-(substituted)thiourea analogs, continuous advances have prompted us to present an overview of the last 2 years literature on this exciting family of compounds through this review article.

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Section: Introductionmentioning

confidence: 99%

Recent developments in chemistry, coordination, structure and biological aspects of 1-(acyl/aroyl)-3-(substituted) thioureas

et al. 2016

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“…The 1 H and 13 C NMR spectra of the investigated compounds were recorded with JEOL JNM-ECA-400 or Bruker DRX-400 instruments (400 and 100 MHz, respectively) with TMS as internal standard. 13 С NMR signals were assigned by using the APT (Attached Proton Test). IR spectra were recorded with an INFRALUM FT-801 spectrophotometer.…”

Section: Methodsmentioning

confidence: 99%

“…11 Recently, we have used this approach for the synthesis of 3-amino-4arylpyridin-2(1H)-ones 12 5 and 6, and some their derivatives. 13 These compounds may be convenient starting materials for the preparation of benzo [c] [1,7]naphthyridin-4(3H)-ones. Previously, the Bischler-Napieralski reaction was used for the formation of the pyridine ring in the synthesis of dibenzo [c,f]-1,7-naphthyridines.…”

Section: Paper Syn Thesismentioning

confidence: 99%

A New Approach to the Synthesis of Benzo[c][1,7]naphthyridin-4(3H)-ones

et al. 2017

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A simple and efficient approach has been developed for the synthesis of previously inaccessible 6-arylbenzo[c][1,7]naphthyridin-4(3H)-ones, which is based on the interaction of 3-amino-6-methyl-4-arylpyridin-2(1H)-ones and aromatic aldehydes in a strong acidic media (trifluoroacetic, phosphorous or polyphosphorous acids) under heating. The initial imine derivatives undergo Pictet–Spengler condensation to form intermediate 6-aryl-5,6-dihydrobenzo[c]-1,7-naphthyridin-4(3H)-ones, which are oxidized by atmospheric oxygen to give 3-amino-6-methyl-4-arylpyridin-2(1H)-ones as the final products.

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“…Some 3-aminopyridin-2(1H)-one derivatives show antiviral activity, including against the AIDS virus [5,6]. The presence of an "embedded" amino acid fragment makes them attractive building blocks for the synthesis of novel derivatives with promising biological applications [7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Cytoprotective Activity of Newly Synthesized 3-(arylmethyl)-6-methyl-4-phenylpyridin-2(1H)-ones derivatives

Sergazy¹,

Shulgau²,

Zhulikeyeva³

et al. 2022

Preprint

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Currently, studies are being conducted on the possible role of the cytoprotective effect of biologically active substances in conditions of cerebral hypoxia or cardiomyopathies. At the same time, oxidative stress is considered as one of the important mechanisms of cellular cytotoxicity and a target for the action of cytoprotectors. The aim of this study is to search for derivatives of 3-(arylmethyl)-6-methyl-4-phenylpyridin-2(1H)-ones. The probability of cytoprotective action was assessed by two tests by measuring cell viability (with neutral red dye and MTT test). It was found that some derivatives of 3-(arylmethyl)-6-methyl-4-phenylpyridin-2(1H)-ones under the conditions of our experiment have a pronounced cytoprotective activity, providing better cell survival in vitro, including the MTT test and conditions of blood hyperviscosity. To correlate the obtained results in vitro, molecular docking of the synthesized derivatives was also carried out. The standard drug omeprazole (co-crystallized with the enzyme) was used as a standard. It was shown that all synthesized derivatives of 3-(arylmethyl)-6-methyl-4-phenylpyridin-2(1H)-ones had higher affinity for the selected protein than the standard gastro-cytoprotector omeprazole. The studied derivatives of 3-(arylmethyl)-6-methyl-4-phenylpyridin-2(1H)-ones also fully satisfy Lipinski's rule of thumb of five (RO5), which increases their chances for possible use as orally active drugs with a good ability to absorption and moderate lipophilicity. Thus, the results obtained make it possible to evaluate derivatives of 3-(arylmethyl)-6-methyl-4-phenylpyridin-2(1H)-ones as having a relatively high cytoprotective potential.

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Synthesis and Intramolecular Cyclization of N-acyl- and N-allyl-N'-(2-oxo-1,2-dihydro-pyridin-3-yl)thiourea

Cited by 23 publications

References 18 publications

Recent developments in chemistry, coordination, structure and biological aspects of 1-(acyl/aroyl)-3-(substituted) thioureas

Recent developments in chemistry, coordination, structure and biological aspects of 1-(acyl/aroyl)-3-(substituted) thioureas

A New Approach to the Synthesis of Benzo[c][1,7]naphthyridin-4(3H)-ones

Cytoprotective Activity of Newly Synthesized 3-(arylmethyl)-6-methyl-4-phenylpyridin-2(1H)-ones derivatives

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