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Synthesis and Analgesic Activity of bis(3,4-dihydroquinoxalin-2(1H)-one) and bis(3,4-dihydro-2H-1,4-benzoxazin-2-one) Derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

An ester condensation between 3,5-diacetyl-2,6-dimethylpyridine and an excess of diethyl oxalate was used for the preparation of 4,4'(2,6-dimethylpyridine-3,5-diyl)bis(2-hydroxy-4-oxobut-2-enoate). The synthesized hydroxyester was shown to readily react with о-phenylenediamine and о-aminophenol with the formation of bis(3,4-dihydroquinoxalin-2(1H)-one) and bis(3,4-dihydro-2H-1,4benzoxazin-2-one) derivatives, which showed superior in vivo analgesic activity compared to the reference drug, metamizole sodium.

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This study received financial support from the Ministry of Education and Science of the Russian Federation (project 4.1657.2017 / 4.6).

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Authors and Affiliations

  1. F. M. Dostoevskii Omsk State University, 55a Mira Ave., Omsk, 644077, Russia

    Ivan V. Kulakov, Anastasiya A. Karbainova & Alexander S. Fisyuk

  2. Republican State Enterprise “National Center for Biotechnology”, Committee of Science, Ministry of Education and Science of Kazakhstan, 13/5 Kurgalzhynskoye Road, Astana, Kazakhstan, 010000

    Zarina T. Shulgau

  3. Kokshetau State University named after Sh. Ualikhanov, 76 Abaya St., Kokshetau, Kazakhstan, 020000

    Tulegen M. Seilkhanov

  4. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk, 630090, Russia

    Yurii V. Gatilov

  5. Novosibirsk State University, 2 Pirogova St., Novosibirsk, 630090, Russia

    Yurii V. Gatilov

  6. Laboratory of New Organic Materials, Omsk State Technical University, 11 Mira St., Omsk, 644050, Russia

    Alexander S. Fisyuk

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  1. Ivan V. Kulakov
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  2. Anastasiya A. Karbainova
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  3. Zarina T. Shulgau
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  4. Tulegen M. Seilkhanov
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  5. Yurii V. Gatilov
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  6. Alexander S. Fisyuk
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Correspondence to Ivan V. Kulakov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(10), 1094–1097

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Kulakov, I.V., Karbainova, A.A., Shulgau, Z.T. et al. Synthesis and Analgesic Activity of bis(3,4-dihydroquinoxalin-2(1H)-one) and bis(3,4-dihydro-2H-1,4-benzoxazin-2-one) Derivatives. Chem Heterocycl Comp 53, 1094–1097 (2017). https://doi.org/10.1007/s10593-017-2178-6

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  • DOI: https://doi.org/10.1007/s10593-017-2178-6

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