Synthesis and antiradical activity of 4-aryl(hetaryl)-substituted 3-aminopyridin-2(1Н)-ones

Кулаков, И. В.; Matsukevich, Mariya V.; Shulgau, Zarina; Sergazy, Shyngys; Сейлханов, Т. М.; Пузари, Амрит; Fisyuk, A. S.

doi:10.1007/s10593-016-1809-7

Cited by 30 publications

(13 citation statements)

References 28 publications

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“…Here we report our studies into the possibility of applying 3-amino-4-(2-thienyl)pyridin-2(1H)-one ( 9), developed by us earlier, 17 in the synthesis of novel thieno[3,2c] [1,7]naphthyridin-4 (3H)-ones 12 by the Picket-Spengler reaction.…”

Section: Methodsmentioning

confidence: 99%

“…In our opinion, the inaccessibility of 6-arylbenzo[c] [1,7]naphthyridin-4(3H)-ones 6 is due to the difficulty of synthesizing the initial 3-amino-4-arylpyridin-2(1H)ones 4. We previously reported 17 an effective method for the synthesis of a whole series of 4-(het)aryl-substituted 3aminopyridin-2(1H)-ones based on the Gewald method. 18 The known methods for the preparation of 3-aminopyridin-2(1H)-ones are based on the condensation of unsymmetrical 1,3-diketones 7 with amides of α-functionalized acetic acids (by Knoevenagel reaction of amides as the CH acid component at the more-active carbonyl group of the unsymmetrical 1,3-diketone, followed by heterocyclization of the resulting intermediate) resulting, for example, in 4alkyl-6-arylpyridin-2(1H)-ones 8 when using 1-alkyl 3-aryl 1,3-diketones (Scheme 2).…”

Section: Letter Syn Lett Schemementioning

confidence: 99%

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Synthesis of the First Representatives of Thieno[3,2-c][1,7]naphthyridine Derivatives Based on 3-Amino-6-methyl-4-(2-thienyl) pyridin-2(1H)-one

Кулаков

Matsukevich

Levin

et al. 2018

Synlett

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A one-pot method for obtaining novel thieno[3,2-c][1,7]naphthyridine derivatives based on the reaction of 3-amino-4-(thien-2-yl)pyridin-2(1H)-one with aromatic aldehydes in 80% phosphoric acid at 130 °C has been developed. The formation of the thieno[3,2-c][1,7]naphthyridine ring was due to the intermediate generation of the corresponding azomethine, which underwent intramolecular cyclization with electrophilic attack of the β-carbon atom of the thiophene core under Pictet–Spengler conditions. The isolated 5,7-dihydrothieno[3,2-c][1,7]naphthyridin-4(3H)-ones underwent oxidative aromatization in air to give thieno[3,2-c][1,7]naphthyridin-6(7H)-ones. A two-step synthesis of thieno[3,2-c][1,7]naphthyridines involving the isolation of the intermediate imine did not lead to a significant increase in the product yield.

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Section: Methodsmentioning

confidence: 99%

Section: Letter Syn Lett Schemementioning

confidence: 99%

Synthesis of the First Representatives of Thieno[3,2-c][1,7]naphthyridine Derivatives Based on 3-Amino-6-methyl-4-(2-thienyl) pyridin-2(1H)-one

Кулаков

Matsukevich

Levin

et al. 2018

Synlett

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“…Previously we have reported the method for the preparation of 4-aryl(hetaryl)-substituted 3-aminopyridin-2(1H)-ones based on the intramolecular cyclization of N-(3-oxoalkenyl)amides. Almost all of the obtained 3-aminopyridin-2(1H)-ones possess a high antiradical activity [1]. In addition, 3-aminopyridin-2(1H)-one derivatives are of interest as potential biologically active compounds [2,3].…”

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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“…In clinical practice, 5‐amino‐[3,4′‐bipyridin]‐6(1 H )‐one 4 , known as the cardiotonic drug Amrinone, is used [17] . In addition, 3‐aminopyridin‐2(1 H )‐ones are used in the synthesis more complex biologically active compounds [18a–m] …”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3‐Aminopyrido[2,1‐a]isoquinolin‐4‐one Derivatives via Condensation of Azlactones with 1‐Alkyl‐3,4‐dihydroisoquinolines

et al. 2021

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Reactions of available 1-alkyl-3,4-dihydroisoquinolines with 4-(2,2,2-trifluoroacetyl)-, 4-acetyl-or 4-(ethoxy-methylene)-2-aryloxazol-5(4H)-ones were studied. A series of new 3-amino-6,7dihydro-4H-pyrido[2,1-a]isoquinolin-4-one derivatives was synthesized. The intermediates formed as a result of the addition of azlactone to 1-methyl-3,4-dihydroisoquinoline were isolated. The effect of the nature of the substituents, as well as the reaction conditions on the yield and structure of the title products was revealed.

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Synthesis and antiradical activity of 4-aryl(hetaryl)-substituted 3-aminopyridin-2(1Н)-ones

Cited by 30 publications

References 28 publications

Synthesis of the First Representatives of Thieno[3,2-c][1,7]naphthyridine Derivatives Based on 3-Amino-6-methyl-4-(2-thienyl) pyridin-2(1H)-one

Synthesis of the First Representatives of Thieno[3,2-c][1,7]naphthyridine Derivatives Based on 3-Amino-6-methyl-4-(2-thienyl) pyridin-2(1H)-one

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

Synthesis of 3‐Aminopyrido[2,1‐a]isoquinolin‐4‐one Derivatives via Condensation of Azlactones with 1‐Alkyl‐3,4‐dihydroisoquinolines

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