Facile synthesis of 7-alkyl-1,2,3,4-tetrahydro-1,8-naphthyridines as arginine mimetics using a Horner-Wadsworth-Emmons-based approach

Lippa, Rhys A. and Murphy, John A. and Barrett, Tim N. (2020) Facile synthesis of 7-alkyl-1,2,3,4-tetrahydro-1,8-naphthyridines as arginine mimetics using a Horner-Wadsworth-Emmons-based approach. Beilstein Journal of Organic Chemistry, 16. pp. 1617-1626. ISSN 1860-5397 (https://doi.org/10.3762/BJOC.16.134)

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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.

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• Item metadata

  Item type:	Article
  ID code:	74202
  Dates:	Date Event 8 July 2020 Published 29 June 2020 Accepted
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Pure Administrator
  Date deposited:	09 Oct 2020 15:27
  Last modified:	03 Feb 2025 19:54
  Related URLs:	Scopus publication
  URI:	https://strathprints.strath.ac.uk/id/eprint/74202