89291-86-1Relevant academic research and scientific papers
The first synthesis of an epidiselenodiketopiperazine
McMahon, Travis C.,Stanley, Sarah,Kazyanskaya, Edward,Hung, Deborah,Wood, John L.
supporting information, p. 4534 - 4536 (2012/10/30)
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 s
Observations on the reactivity of thiyl radicals derived from 3,6-epidithiodiketopiperazine-2,5-diones and related congeners
Hilton,Motherwell,Potier,Pradet,Selwood
, p. 2239 - 2242 (2007/10/03)
A range of thiyl radicals derived from the reduced form of epidithiodiketopiperazines (ETPs) act as polarity reversal catalysts for the hydrosilylation of an enol lactone but not for H-atom abstraction from a model ribose ester.
Synthesis and Activity of New Epipolythiopiperazine-2,5-dione Compounds. I
Jiang, Hui,Newcombe, Nicole,Sutton, Philip,Lin, Qing Hui,Muellbacher, Arno,Waring, Paul
, p. 1743 - 1754 (2007/10/02)
The new lipophilic epipolythiopiperazine-2,5-diones 1,4-dibutylepidithiopiperazine-2,5-dione, 1,4-dibenzylepidithiopiperazine-2,5-dione, 1-benzyl-4-methylepidithiopiperazine-2,5-dione and 3,3'-dithiobis(1,4-dimethylpiperazine-2,5-dione) were synthesized.Unlike the parent compound, the fungal toxin and immunomodulating agent gliotoxin, these compounds did not affect macrophage adherence and cell proliferation in vitro.Like the reduced form of gliotoxin and other simple analogues, these new compounds induce oxidative damage to naked DNA.We conclude that an increase in lipophilicity plays no part in the biological activity of these compounds and in fact abrogates almost all activity.We also synthesized an intermolecular disulfide analogue which also lacked activity.
Monosubstitution of Symmetric Piperazine-2,5-dione Derivatives
Badran, Terry W.,Easton, Christopher J.
, p. 1455 - 1459 (2007/10/02)
Bromination and methanolysis of derivatives of glycine anhydride affords the corresponding 3-bromo- and 3-methoxy-substituted piperazine-2,5-dione derivatives in a simple one-pot procedure.
Divergent, Generalized Synthesis of Unsymmetrically Substituted 2,5-Piperasinediones
Williams, Robert M.,Armstrong, Robert W.,Maruyama, Lynn K.,Dung, Jen-Sen,Anderson, Oren P.
, p. 3246 - 3253 (2007/10/02)
N,N'-Disubstituted 2,5-piperazinediones (12) can be 3,6-dibrominated followed by displacement with sodium 2-mercaptopyridine to furnish syn-1,4-disubstituted 3,6-bis(2'-thiopyridyl)-2,5-piperazinediones (8) in high yield.Precomplexation of these sulfides with silver(I) triflate followed by addition of trimethylsilyl enol ethers leads to chemoselective C-C bond formation, furnishing the homologated piperazinediones 10.The remaining sulfide functionality of 10 is relatively inert to a second substitution.These electrophylic 2,5-piperazinediones provide access to relatively inaccessible, unsymmetrical 2,5-piperazinediones and provide advantages over the corresponding well-known enolate anion approach.Substrates that contain N-p-methoxybenzyl residues can be deprotected to the lipophobic N,N'-unsubstituted 2,5-piperazinediones with aqueous ceric ammonium nitrate.The diastereoselectivity observed in the coupling reactions is discussed in the context of a single crystal X-ray structure determination of 20.
TOTAL SYNTHESIS OF BICYCLOMYCIN
Nakatsuka, Shin-ichi,Yamada, Kozi,Yoshida, Kumi,Asano, Osamu,Murakami, Yoshihiro,Goto, Toshio
, p. 5627 - 5630 (2007/10/02)
Total synthesis of (+/-)-bicyclomycin was achieved in 19 steps starting from diketopyperazine.
