53338-36-6

Usage

Chemical class

Diazabicyclo compounds

Structure

Bicyclic with two nitrogen atoms and two sulfur atoms in the ring

Heterocyclic compound

Contains sulfur and nitrogen atoms

Common use

Organic synthesis and as a ligand in coordination chemistry

Applications

Potential use in pharmaceuticals, materials science, and catalysis

Reactivity

Versatile

Stability

Stable

Importance

Valuable and important in the field of organic and inorganic chemistry

Upstream product

• 73333-77-4 3,6-Dimercapto-1,3,4,6-tetramethyl-piperazine-2,5-dione 
• 81411-35-0 1,3,4,6-tetramethyl-3,6-bis(acetylthio)-2,5-piperazinedione 
• 50501-00-3 1,4-dimethyl-3,6-dimethylene-2,5-piperazinedione 
• 73333-71-8 1,3-Dimethyl-3-methoxy-6-methylene-2,5-dioxopiperazine 
• 73333-74-1 1,4,6-Trimethyl-3-methylene-6-methoxy-2,5-dioxopiperazine 
• 73333-68-3 1-(Benzyloxy)-3-methylene-4,6-dimethyl-2,5-dioxo-piperazine 
• 61760-34-7 3r,6c-bis-methoxymethylsulfanyl-1,3,4,6t-tetramethyl-piperazine-2,5-dione 
• 59319-27-6 3,6-dimethoxy-1,3,4,6-tetramethyl-piperazine-2,5-dione 

Relevant academic research and scientific papers

Synthesis of New Diketopiperazines, Thiolation to Thiodiketopiperazines, and Examination of Their ROS-Generating Properties

A variety of new symmetrical and unsymmetrical diketopiperazines have been prepared from free amino acids by using a previously developed microwave-assisted protocol. This included the successful incorporation of L-pyroglutamic acid as an unusual building block. The diketopiperazines were then thiolated electrophilically to the corresponding bis(methylthio)- and epidithiodiketopiperazines. Initial experiments showed a promising activity towards the generation of reactive oxygen species in HeLa cells. A variety of novel symmetrical and unsymmetrical thiodiketopiperazines have been prepared by methyl dichlorophosphite assisted dimerization of free amino acids and by thiolation of the resulting cyclic dipeptides with elemental sulfur and NaHMDS. Some of the sulfur compounds showed interesting activity in the generation of reactive oxygen species in HeLa cells.

TOTAL SYNTHESIS OF GLIOTOXIN, DEHYDROGLIOTOXIN AND HYALODENDRIN

Two general methods, Method A and Method B in Scheme 19, to synthesize epidithiapiperazinediones, are described.A total synthesis of racemic and optically active gliotoxin (1) and of racemic dehydrogliotoxin (53) was achieved by using Method A, whereas a total synthesis of racemic hyalodendrin (52) was completed by using Method B.

Synthesis of dehydroamino acids and didehydrodioxopiperazines and their conversion into α-mercapto-α-amino acid derivatives

A synthesis of α,β-dehydroamino acid derivatives 12 is described, which is of possible general applicability and might be useful for the preparation of peptides which have such a moiety in their sequence.I addition, several didehydrodioxopiperazines (13-1