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Synthesis of bicyclic 1,4-thiazepines as novel anti-Trypanosoma brucei brucei agents.

ABSTRACT: 1,4-Thiazepines derivatives are pharmacologically important heterocycles with different applications in medicinal chemistry. In the present work, we describe the preparation of new bicyclic thiazolidinyl-1,4-thiazepines 3 by reaction between azadithiane compounds and Michael acceptors. The reaction scope was explored and the yields were optimized. The activity of the new compounds was evaluated against Nippostrongylus brasiliensis and Caenorhabditis elegans as anthelmintic models and Trypanosoma brucei brucei. The most active compound was 3l, showing an EC50 = 2.8 ± 0.7 ?M against T. b. brucei and a selectivity index >71.

SUBMITTER: Vairoletti F

PROVIDER: S-EPMC6786244 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature

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Synthesis of bicyclic 1,4-thiazepines as novel anti-Trypanosoma brucei brucei agents.

Vairoletti Franco F Medeiros Andrea A Fontán Pablo P Meléndrez Jennifer J Tabárez Carlos C Salinas Gustavo G Franco Jaime J Comini Marcelo A MA Saldaña Jenny J Jancik Vojtech V Mahler Graciela G Saiz Cecilia C

MedChemComm 20190611 8

1,4-Thiazepines derivatives are pharmacologically important heterocycles with different applications in medicinal chemistry. In the present work, we describe the preparation of new bicyclic thiazolidinyl-1,4-thiazepines 3 by reaction between azadithiane compounds and Michael acceptors. The reaction scope was explored and the yields were optimized. The activity of the new compounds was evaluated against Nippostrongylus brasiliensis and Caenorhabditis elegans as anthelmintic m ...[more]

PMID: 31673311

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