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Synthesis and properties of novel hybrid molecules bearing 4H-pyrrolo[3,2,1-ij]quinolin-2-one and thiazole moieties

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Abstract

A reaction of 2-(4,4,6-trimethyl-2-oxo-4H-pyrrolo[3,2,1-ij]quinoline-1-ylidene)-hydrazinocarbothioamides with α-halocarbonyl compounds, such as ethyl bromocetate and 2-bromoacetophenone derivatives, afforded a series of novel 4,4,6-trimethyl-2-oxo-4H-pyrrolo[3,2,1-ij]quinoline-1(2H)-ylidene)hydrazinylidene)thiazolidin-4-ones and 4,4,6-trimethyl-1-(2-(4-arylthiazol-2-yl)hydrazinylidene)-4H-pyrrolo[3,2,1-ij]quinolin-2(1H)-ones. The synthesized compounds exist in the form of Z-isomers. Primary screening in vitro of inhibitory activity towards blood clotting factors Xa and XIa was carried out, revealing that the thiazole derivative bearing the 4-chlorophenyl substituent at the thiazole moiety exhibits a sufficiently high anticoagulant activity towards these blood clotting factors.

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Authors and Affiliations

  1. Voronezh State University, 1 Universitetskaya pl., 394018, Voronezh, Russian Federation

    N. P. Novichikhina, Z. E. Ashrafova, N. V. Stolpovskaya, I. V. Ledenyova, M. G. Kholyavka & Kh. S. Shikhaliev

  2. Dmitry Rogachev National Medical Research Center of Pediatric Hematology, Oncology, and Immunology, 1 ul. Samory Mashela, 111799, Moscow, Russian Federation

    N. A. Podoplelova

  3. Center for Theoretical Problems of Physical and Chemical Pharmacology, Russian Academy of Sciences, 30 ul. Srednyaa Kalitnikovskaya, 109029, Moscow, Russian Federation

    M. A. Panteleev

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  1. N. P. Novichikhina
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  2. Z. E. Ashrafova
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  3. N. V. Stolpovskaya
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  8. Kh. S. Shikhaliev
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Correspondence to Kh. S. Shikhaliev.

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This work was financially supported by the Russian Science Foundation (Project No. 18-74-10097, https://rscf.ru/project/21-74-03011/).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1969–1975, September, 2022.

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Novichikhina, N.P., Ashrafova, Z.E., Stolpovskaya, N.V. et al. Synthesis and properties of novel hybrid molecules bearing 4H-pyrrolo[3,2,1-ij]quinolin-2-one and thiazole moieties. Russ Chem Bull 71, 1969–1975 (2022). https://doi.org/10.1007/s11172-022-3615-y

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