Synthesis and evaluation of 1-arylsulfonyl-3-piperazinone derivatives as factor Xa inhibitors(1-6) VI. A series of new derivatives containing N,S- and N,SO2-spiro acetal scaffolds

Chem Pharm Bull (Tokyo). 2007 Feb;55(2):317-23. doi: 10.1248/cpb.55.317.

Abstract

In the course of development of factor Xa (FXa) inhibitors, we have found unique compounds containing an N,O- and an N,N-spiro acetal structure. It appeared that the difference in overall conformation due to the N,X-spiro acetal structure might be important for FXa inhibitory activity. Therefore, other N,X-spiro acetal structures, an N,S- and an N,SO2-spiro acetal, were developed as analogues of the N,X-spiro acetal structure. Compound 7b (N,S-spiro acetal structure) was found to have the strongest activity in these series of N,X-spiro acetal compounds, which had ever been synthesized.(4,5)).

Publication types

  • Evaluation Study

MeSH terms

  • Acetals / chemistry*
  • Anticoagulants / pharmacology
  • Antithrombin III / chemical synthesis*
  • Antithrombin III / pharmacology
  • Molecular Conformation
  • Molecular Structure
  • Nitrogen / chemistry*
  • Oxygen / chemistry*
  • Piperidines / chemical synthesis*
  • Piperidines / pharmacology
  • Serine Proteinase Inhibitors / pharmacology
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / pharmacology

Substances

  • Acetals
  • Anticoagulants
  • Piperidines
  • Serine Proteinase Inhibitors
  • Spiro Compounds
  • Antithrombin III
  • Nitrogen
  • Oxygen