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First enantioselective synthesis of tetrahydrochromeno[2,3-b]carbazolylacetaldehyde via trienamine catalysis and its biological activity

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Chemistry of Heterocyclic Compounds Aims and scope

The first enantioselective synthesis of a tetrahydrochromeno[2,3-b]carbazole derivative via trienamine catalysis is presented. This molecule reduced the anxiety-like behavior in mice. On the contrary, its enantiomer showed low activity, demonstrating the importance of the stereochemisty in the corresponding cycloadduct. On the other hand, both enantiomers showed low antidepressant-like activity.

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Authors and Affiliations

  1. Departamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S/N, Guanajuato, Gto. 36050, México

    Carlos E. Castillo-Espinoza, Tushar Janardan Pawar, Miguel A. Vázquez, David Cruz Cruz & Clarisa Villegas Gómez

  2. Departamento de Farmacia, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S/N, Guanajuato, Gto. 36050, México

    Angel Josabad Alonso-Castro

  3. Red de Estudios Moleculares Avanzados, Instituto de Ecología AC, Carretera Antigua a Coatepec 351, El Haya, Xalapa, Ver. 91070, México

    José Luis Olivares-Romero

Authors
  1. Carlos E. Castillo-Espinoza
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  2. Tushar Janardan Pawar
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  3. Angel Josabad Alonso-Castro
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  4. José Luis Olivares-Romero
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  5. Miguel A. Vázquez
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  6. David Cruz Cruz
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  7. Clarisa Villegas Gómez
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Corresponding authors

Correspondence to David Cruz Cruz or Clarisa Villegas Gómez.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(6/7), 358–362

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Castillo-Espinoza, C.E., Pawar, T.J., Alonso-Castro, A.J. et al. First enantioselective synthesis of tetrahydrochromeno[2,3-b]carbazolylacetaldehyde via trienamine catalysis and its biological activity. Chem Heterocycl Comp 58, 358–362 (2022). https://doi.org/10.1007/s10593-022-03098-3

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