0582840 - ÚOCHB 2025 RIV GB eng J - Článek v odborném periodiku
Špaková Raschmanová, J. - Fábian, M. - Sudzina, A. - Martinková, M. - Bago Pilátová, M. - Cvačka, Josef - Kofroňová, Edita - Mezencev, R.
An approach to pyrrolidine-containing sphingomimetics based on L-tartaric acid chiron.
Tetrahedron. Roč. 153, March (2024), č. článku 133843. ISSN 0040-4020. E-ISSN 1464-5416
Institucionální podpora: RVO:61388963
Klíčová slova: sphingomimetics * pyrrolidine skeleton * heterosigmatropic rearrangement * olefin cross-metathesis reaction * anticancer profile * sphingolipids * synthesis * cancer
Obor OECD: Organic chemistry
Impakt faktor: 2.1, rok: 2023
Způsob publikování: Omezený přístup
https://doi.org/10.1016/j.tet.2024.133843

A short synthetic approach to constructing pyrrolidine-containing sphingolipid-like derivatives has been accomplished. The cornerstone feature of the synthesis was a [3,3]-heterosigmatropic rearrangement of an imidate derived from L -tartaric acid chiron, which completed the core motif of the target sphingomimetics carrying three consecutive stereocentres and a terminal vinyl. A late -stage olefin cross metathesis reaction installed an alkyl side chain with the flexibility for analogue construction. The results obtained from biological screening have completed the structure -activity relationships in a series of eight prepared stereoisomeric C -alkyl pyrrolidinediols and elucidated the role of the stereochemistry on the heterocyclic skeleton towards the studied anticancer profile.
Trvalý link: https://hdl.handle.net/11104/0350893