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Synthesis of 8-carboxamide-substituted angelicin derivatives

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Abstract

A method for the synthesis of 4-methyl-2-oxo-9-phenyl-2H-furo[2,3-h]chromene-8-carboxylic acid amides combining in the structure the angelicin core with heterocyclic fragments at the amide nitrogen atom was developed. The cytotoxic activity of the obtained amides against the MCF7 (breast adenocarcinoma), A549 (non-small cell lung cancer), VA-13 (embryonic lung fibroblast cells) and HEK293T (embryonic kidney cells) cell lines was studied. In contrast to the previously described highly toxic angelicin derivatives with aryl- and hetarylcarbonyl substituents at position 8, the synthesized amides demonstrated in in vitro experiments in these cell lines the IC50abs values ranging within 2–100 µmol L−1. The cytotoxicity and selectivity of the action of this group of derivatives were found to be significantly affected by the substituent at position 5′ of the angelicin moiety.

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Authors and Affiliations

  1. Department of Chemistry, Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    S. R. Klyatskina, A. S. Olshanova, N. D. Dagaev, N. I. Vorozhtsov, D. A. Skvortsov, D. A. Vasilenko, E. B. Averina, N. V. Zyk & E. K. Beloglazkina

Authors
  1. S. R. Klyatskina
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  2. A. S. Olshanova
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  3. N. D. Dagaev
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  4. N. I. Vorozhtsov
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  5. D. A. Skvortsov
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  6. D. A. Vasilenko
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  7. E. B. Averina
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  8. N. V. Zyk
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  9. E. K. Beloglazkina
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Corresponding author

Correspondence to E. K. Beloglazkina.

Additional information

This work was financially supported by the Russian Science Foundation (Project No. 22-14-00099, evaluation of the cytotoxicity of synthesized compounds). The synthesis of isoxazole 9 and 14 was carried out within the framework of the Russian state assignment on the topic “Molecular design, synthesis, and study of physiologically active substances, development of the methodology of medical chemistry, chemoinformatics, and directed chemical synthesis” (No. TsITIS 121021000105-7, TsITIS is the Center for Information Technologies and Systems), the synthesis of other compounds was carried out within the framework of the Russian state assignment on the topic “Synthesis and study of physical, chemical and biological properties of organic and organo-element compounds” (No. TsITIS AAAA-A21-121012290046-4).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 7, pp. 1598–1605, July, 2023.

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Klyatskina, S.R., Olshanova, A.S., Dagaev, N.D. et al. Synthesis of 8-carboxamide-substituted angelicin derivatives. Russ Chem Bull 72, 1598–1605 (2023). https://doi.org/10.1007/s11172-023-3939-2

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  • DOI: https://doi.org/10.1007/s11172-023-3939-2

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