Synthesis of a reported calpain inhibitor isolated from Streptomyces griseus

Bioorg Med Chem Lett. 2001 Oct 8;11(19):2647-9. doi: 10.1016/s0960-894x(01)00524-8.

Abstract

The reported diketopiperazine calpain inhibitor, cis-L-L-3,6-bis-(4-hydroxybenzyl)-1,4-dimethylpiperazine-2,5-dione 1, and its analogues 3 and 4 were synthesized from the corresponding amino acids. The previously assigned structure of 1 is confirmed but neither synthetic 1 nor its N-methylphenylalanine analogues 3 and 4 inhibit porcine erythrocyte calpain I.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Calpain / antagonists & inhibitors*
  • Calpain / metabolism
  • Cysteine Proteinase Inhibitors / chemical synthesis
  • Cysteine Proteinase Inhibitors / chemistry
  • Cysteine Proteinase Inhibitors / pharmacology
  • Erythrocytes / drug effects
  • Erythrocytes / enzymology
  • Glycoproteins / chemical synthesis*
  • Glycoproteins / chemistry
  • Glycoproteins / isolation & purification
  • Glycoproteins / pharmacology
  • Magnetic Resonance Spectroscopy
  • Piperazines / chemical synthesis*
  • Piperazines / chemistry
  • Piperazines / pharmacology
  • Streptomyces griseus / chemistry*
  • Swine
  • Tyrosine / analogs & derivatives*
  • Tyrosine / chemical synthesis*
  • Tyrosine / chemistry
  • Tyrosine / pharmacology

Substances

  • 3,6-bis(4-hydroxyphenylmethyl)-1,4-dimethyl-2,5-diketopiperazine
  • Cysteine Proteinase Inhibitors
  • Glycoproteins
  • Piperazines
  • calpain inhibitors
  • Tyrosine
  • Calpain