Abstract
Integrin inhibitors based on the tripeptide sequence Arg-Gly-Asp (RGD) are potential therapeutics for the treatment of idiopathic pulmonary fibrosis (IPF). Herein, we describe an expeditious three-step synthetic sequence of Horner-Wadsworth-Emmons olefination, diimide reduction, and global deprotection to synthesise cores for these compounds in high yields (63-83% over 3 steps) with no need for chromatography. Key to this transformation is the phosphoramidate protecting group, which is stable to metalation steps.
| Original language | English |
|---|---|
| Pages (from-to) | 1617-1626 |
| Number of pages | 10 |
| Journal | Beilstein Journal of Organic Chemistry |
| Volume | 16 |
| DOIs | |
| Publication status | Published - 8 Jul 2020 |
Funding
Financial support for this work was provided by GSK via the GSK/University of Strathclyde Centre for Doctoral Training in Synthetic and Medicinal Chemistry. We thank EPSRC for further funding via Prosperity Partnership EP/S035990/1.
Keywords
- arginine
- Horner-Wadsworth-Emmons
- integrin
- phosphoramidate
- tetrahydronaphthyridine
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Dive into the research topics of 'Facile synthesis of 7-alkyl-1,2,3,4-tetrahydro-1,8-naphthyridines as arginine mimetics using a Horner-Wadsworth-Emmons-based approach'. Together they form a unique fingerprint.Projects
- 1 Finished
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PP: Accelerated Discovery and Development of New Medicines: Prosperity Partnership for a Healthier Nation
Murphy, J. (Co-investigator) & Bell, J. (Researcher)
1/01/19 → 31/12/23
Project: Research
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