53348-47-3Relevant academic research and scientific papers
Synthesis and biological evaluation of epidithio-, epitetrathio-, and bis-(methylthio)diketopiperazines: Synthetic methodology, enantioselective total synthesis of epicoccin G, 8,8′-epi-ent-rostratin B, gliotoxin, gliotoxin G, emethallicin E, and haematocin and discovery of new antiviral and antimalarial agents
Nicolaou, K. C.,Lu, Min,Totokotsopoulos, Sotirios,Heretsch, Philipp,Giguere, Denis,Sun, Ya-Ping,Sarlah, David,Nguyen, Thu H.,Wolf, Ian C.,Smee, Donald F.,Day, Craig W.,Bopp, Selina,Winzeler, Elizabeth A.
supporting information, p. 17320 - 17332,13 (2020/09/02)
An improved sulfenylation method for the preparation of epidithio-, epitetrathio-, and bis-(methylthio)diketopiperazines from diketopiperazines has been developed. Employing NaHMDS and related bases and elemental sulfur or bis[bis(trimethylsilyl)amino]trisulfide (23) in THF, the developed method was applied to the synthesis of a series of natural and designed molecules, including epicoccin G (1), 8,8′-epi-ent-rostratin B (2), gliotoxin (3), gliotoxin G (4), emethallicin E (5), and haematocin (6). Biological screening of selected synthesized compounds led to the discovery of a number of nanomolar antipoliovirus agents (i.e., 46, 2,2′-epi-46, and 61) and several low-micromolar anti-Plasmodium falciparum lead compounds (i.e., 46, 2,2′-epi-46, 58, 61, and 1).
NEW Co-METABOLITES OF GLIOTOXIN IN GLIOCLADIUM VIRENS
Kirby, Gordon W.,Rao, Ghanakota V.,Robins, David J.
, p. 301 - 304 (2007/10/02)
Chromatographic separation of extracts of Gliocladium virens, grown on a medium containing sulphate, has led to the identification of 5 co-metabolites of gliotoxin (1a), new to this fungus, viz. the epitrisulphide, gliotoxin E (1b), the 3-hydroxymethylbut-2-enyl ether (3c), didehydrogliotoxin (5), bis-N-norgliovictin (6), and the 3-methylbut-2-enyl ether of cyclo-(glycyl-L-tyrosyl) (7); the metabolites (3c), (6), and (7) are new natural products.The synthesis of the epitri- and epitetrasulphides, gliotoxin E (1b) and gliotoxin G (1c), from gliotoxin (1a) is described, as is that of the 3-methylbut-2-enyl ether (7) from cyclo-(glycyl-L-tyrosyl).The biosynthetic significance of the dioxopiperazines (6) and (7) is briefly discussed.
