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Synthesis and Anticoagulant Activity of New Ethylidene and Spiro Derivatives of Pyrrolo[3,2,1-ij]quinolin-2-ones

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Abstract

The reaction of pyrrolo[3,2,1-ij]quinoline-1,2-diones with methyl (het)aryl ketones gave the corresponding 1-(het)arylmethylidenepyrroloquinolin-2-ones, and 1,3-dipolar cycloaddition of the latter to azomethine ylide generated from sarcosine and paraformaldehyde afforded 4-acyl-1,4′,4′,6′-tetramethylspiro[pyrrolidine-3,1′-pyrrolo[3,2,1-ij]quinolin]-2′(4′H)-ones. The synthesized compounds were evaluated for inhibitory activity against blood coagulation factors Xa and XIa.

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Funding

This study was performed under financial support by the Russian Science Foundation (project no. 18-74-10097).

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Authors and Affiliations

  1. Voronezh State University, 394018, Voronezh, Russia

    N. P. Novichikhina, A. A. Skoptsova, A. S. Shestakov, A. Yu. Potapov, E. A. Kosheleva, O. A. Kozaderov, I. V. Ledenyova & Kh. S. Shikhaliev

  2. Rogachev National Medical Research Center of Pediatric Hematology, Oncology, and Immunology, 117997, Moscow, Russia

    N. A. Podoplelova

  3. Center for Theoretical Problems of Physicochemical Pharmacology, Russian Academy of Sciences, 109029, Moscow, Russia

    M. A. Panteleev

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  1. N. P. Novichikhina
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Correspondence to Kh. S. Shikhaliev.

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Novichikhina, N.P., Skoptsova, A.A., Shestakov, A.S. et al. Synthesis and Anticoagulant Activity of New Ethylidene and Spiro Derivatives of Pyrrolo[3,2,1-ij]quinolin-2-ones. Russ J Org Chem 56, 1550–1556 (2020). https://doi.org/10.1134/S1070428020090080

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