Facile synthesis of 7-alkyl-1,2,3,4-tetrahydro-1,8-naphthyridines as arginine mimetics using a Horner–Wadsworth–Emmons-based approach
| Autor: | Tim N. Barrett, John A. Murphy, Rhys A. Lippa |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
tetrahydronaphthyridine Arginine Chemistry Metalation Stereochemistry integrin phosphoramidate Organic Chemistry Phosphoramidate arginine Tripeptide Full Research Paper lcsh:QD241-441 chemistry.chemical_compound lcsh:Organic chemistry Diimide lcsh:Q QD lcsh:Science Protecting group Alkyl Horner–Wadsworth–Emmons |
| Zdroj: | Beilstein Journal of Organic Chemistry Beilstein Journal of Organic Chemistry, Vol 16, Iss 1, Pp 1617-1626 (2020) |
| ISSN: | 1860-5397 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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