The first synthesis of an epidiselenodiketopiperazine.
Epidithiodiketopiperazines (ETPs) are natural products (e.g., gliotoxin) with varied and important biological activity, which often is attributed to the redox properties of the disulfide moiety. As such, analogs with altered redox properties and similar structural characteristics would be of value to biological investigations. The use of an ETP as the point of departure in the first synthesis of an epidiselenodiketopiperazine (ESeP) and its activity against Mycobacterium tuberculosis (MTB) is reported.
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Travis C
TC
McMahon
Sarah
S
Stanley
Edward
E
Kazyanskaya
Deborah
D
Hung
John L
JL
Wood
D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D054659:Diketopiperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004220:Disulfides / Q000737:chemistry; D005912:Gliotoxin / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010084:Oxidation-Reduction
D000995:Antitubercular Agents; D054659:Diketopiperazines; D004220:Disulfides; D016566:Organoselenium Compounds; C579062:epidiselenodiketopiperazine; D005912:Gliotoxin