Synthesis of a reported calpain inhibitor isolated from Streptomyces griseus.
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.
Donkor
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Department of Pharmaceutical Sciences, The University of Tennessee Health Science Center, Memphis, TN 38163, USA. idonkor@utom.edu
Sanders
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D000818:Animals; D002154:Calpain / Q000037:antagonists & inhibitors* / Q000378:metabolism; D015853:Cysteine Proteinase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004912:Erythrocytes / Q000187:drug effects / Q000201:enzymology; D006023:Glycoproteins / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013305:Streptomyces griseus / Q000737:chemistry*; D013552:Swine; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
C091113:3,6-bis(4-hydroxyphenylmethyl)-1,4-dimethyl-2,5-diketopiperazine; D015853:Cysteine Proteinase Inhibitors; D006023:Glycoproteins; D010879:Piperazines; C039304:calpain inhibitors; D014443:Tyrosine; D002154:Calpain