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CC BY 4.0 · SynOpen 2024; 08(01): 68-75
DOI: 10.1055/a-2264-8302
paper

Synthesis of 3,4-Disubstituted Pyrroline Nitroxides Containing Diphenylphosphane or Diphenylphosphane Oxide Substituents

Áron Balázsi
a   Institute of Organic and Medicinal Chemistry, Faculty of Pharmacy, University of Pécs, Honvéd st. 1, 7624 Pécs, Hungary
,
Balázs Bognár
a   Institute of Organic and Medicinal Chemistry, Faculty of Pharmacy, University of Pécs, Honvéd st. 1, 7624 Pécs, Hungary
,
József Jekő
b   Department of Chemistry, University of Nyíregyháza, Sóstói st. 31/b, 4400 Nyíregyháza, Hungary
,
Tamás Kálai  ∗
a   Institute of Organic and Medicinal Chemistry, Faculty of Pharmacy, University of Pécs, Honvéd st. 1, 7624 Pécs, Hungary
c   Szentágothai Research Centre, Ifjúság st. 20, 7624 Pécs, Hungary
› InstitutsangabenFinancial support from the Hungarian National Research, Development and Innovation Office (NKFI K 137793) and Molecular Scale Biophysics Research Infrastructure Transnational Access (TNA-MOSBRI-2023-166) are greatly acknowledged.
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Dedicated to the memory of Prof. Ferenc Fülöp

Abstract

(Methyl 4-(diphenylphosphoryl)-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxylate-1-yl)oxydanyl was obtained as a key intermediate of the reaction starting from 3,4-dibromo-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-1-yloxydanyl or (methyl 2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxylate-1-yl)oxidanyl. This key compound could be converted into an azido-specific Staudinger ligation-inducing spin label, amino- and thiol-specific spin label, or MITO-CP-like antiproliferative agent.

Key words

free radicals - MITO-CP - lithiation - phosphane - Staudinger ligation - spin labeling

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2264-8302.
  • Supporting Information


Publikationsverlauf

Eingereicht: 09. Dezember 2023

Angenommen nach Revision: 08. Januar 2024

Accepted Manuscript online:
08. Februar 2024

Artikel online veröffentlicht:
01. März 2024

© 2024. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)

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