Synthesis of Anti-oxidant Steroids by Hybridisation with Nitroxides

Carl P. Soltau; Naomi E. Weir; Alexander P. Martyn; Steven E. Bottle

doi:10.1055/a-2232-8240

Synthesis, Table of Contents

Synthesis 2024; 56(21): 3289-3296
DOI: 10.1055/a-2232-8240

paper

Special Issue PSRC-10 (10th Pacific Symposium on Radical Chemistry)

Synthesis of Anti-oxidant Steroids by Hybridisation with Nitroxides

Carl P. Soltau

^aSchool of Chemistry and Physics, Queensland University of Technology, 2 George St, Brisbane, QLD 4000, Australia

,

Naomi E. Weir

^aSchool of Chemistry and Physics, Queensland University of Technology, 2 George St, Brisbane, QLD 4000, Australia

,

Alexander P. Martyn

^aSchool of Chemistry and Physics, Queensland University of Technology, 2 George St, Brisbane, QLD 4000, Australia

^bCancer & Ageing Research Program, Centre for Genomics and Personalised Health at The Translational Research Institute (TRI), 37 Kent St, Woolloongabba, QLD 4102, Australia

,

Steven E. Bottle∗

^aSchool of Chemistry and Physics, Queensland University of Technology, 2 George St, Brisbane, QLD 4000, Australia

› Author Affiliations

Abstract

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Abstract

Steroidal–nitroxide hybrid molecules and non-radical controls were synthesised in good yields using simple carbodiimide coupling. An unexpected product arose from reactions between the nitroxide moiety and the solvent THF. Methoxyamine derivatives of the nitroxide drug hybrids were produced using Fenton chemistry without side reactions occurring on the steroid. The hybrid compounds bind to the glucocorticoid receptor and are relevant for the study of radical biological chemistry and redox-related disease processes.

Key words

nitroxides - anti-oxidants - steroids - glucocorticoid - radicals

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References

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