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Synthesis of 2H-pyrano[3,2-g]quinolin-2-ones containing a pyrimidinone moiety and characterization of their anticoagulant activity via inhibition of blood coagulation factors Xa and XIa

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Chemistry of Heterocyclic Compounds Aims and scope

The reactions of 7-hydroxy-1,2,2,4-tetramethylhydroquinoline-6-carbaldehydes with methyl 3-oxopentanedioate were used to synthesize 3-oxo-3-(6,8,8,9-tetramethyl-2-oxo-2H-pyrano[3,2-g]quinolin-3-yl)propanoates with various degrees of hydrogenation in the pyridine ring, the condensation of which with carboximidamides provided a series of new 6,8,8,9-tetramethyl-3-(6-oxo-1,6-dihydropyrimidin-4-yl)-2H-pyrano[3,2-g]quinolin-2-ones. It was found that some compounds of this class exhibited relatively high inhibitory activity against the blood coagulation factors Xа and XIa.

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Authors and Affiliations

  1. Voronezh State University, 1 Universitetskaya Sq, Voronezh, 394018, Russia

    Andrei Yu. Potapov, Mikhail A. Potapov, Irina V. Ledenyova, Nadezhda V. Stolpovskaya & Khidmet S. Shikhaliev

  2. Belgorod State National Research University, 85 Pobedy St, Belgorod, 308015, Russia

    Boris V. Paponov

  3. Center for Theoretical Problems of Physico-Chemical Pharmacology, Russian Academy of Sciences, 30 Srednyaya Kalitnikovskaya St, Moscow, 109029, Russia

    Nadezhda A. Podoplelova & Mikhail A. Panteleev

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  1. Andrei Yu. Potapov
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  2. Boris V. Paponov
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  3. Nadezhda A. Podoplelova
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  4. Mikhail A. Panteleev
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  5. Mikhail A. Potapov
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Correspondence to Andrei Yu. Potapov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(5), 574–80

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Potapov, A.Y., Paponov, B.V., Podoplelova, N.A. et al. Synthesis of 2H-pyrano[3,2-g]quinolin-2-ones containing a pyrimidinone moiety and characterization of their anticoagulant activity via inhibition of blood coagulation factors Xa and XIa. Chem Heterocycl Comp 57, 574–580 (2021). https://doi.org/10.1007/s10593-021-02945-z

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