Synthesis of the Key Intermediate of SM-406 (Xevinapant) and Its Analogues

J Org Chem. 2022 Oct 7;87(19):13315-13321. doi: 10.1021/acs.joc.2c01173. Epub 2022 Sep 15.

Abstract

Efficient methods for the synthesis of three dipeptide mimetics with diazabicycloalkanone amino acid scaffolds were developed. Among them, compound 3, which contains a 1,5-diazabicyclo[6,3,0]dodecanone amino acid core structure, was used as the key intermediate of a clinical staged IAP inhibitor SM-406 (Xevinapant). Compared with the reported methods for the synthesis of compound 3 and its derivatives, our method is more efficient and more suitable for large scale preparation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids
  • Antineoplastic Agents* / pharmacology
  • Azocines
  • Benzhydryl Compounds
  • Dipeptides / chemistry

Substances

  • Amino Acids
  • Antineoplastic Agents
  • Azocines
  • Benzhydryl Compounds
  • Dipeptides
  • N-benzhydryl-5-(2-(methylamino)propanamido)-3-(3-methylbutanoyl)-6-oxodecahydropyrrolo(1,2-a)(1,5)diazocine-8-carboxamide