4774-22-5

Usage

Uses

Used in Pharmaceutical Industry:
Piperazine-2,6-dione is used as a pharmaceutical compound for the prevention or treatment of apoptosis. Apoptosis is a process of programmed cell death that plays a crucial role in various diseases, including cancer, neurodegenerative disorders, and autoimmune diseases. Piperazine-2,6-dione has been found to modulate the apoptotic pathways, making it a promising candidate for therapeutic intervention in these conditions.
In addition to its direct therapeutic applications, Piperazine-2,6-dione can also be used as a building block or intermediate in the synthesis of various bioactive molecules, including drugs, agrochemicals, and other specialty chemicals. Its unique chemical structure and reactivity make it a valuable component in the development of novel compounds with diverse applications.

InChI:InChI=1/C4H6N2O2/c7-3-1-5-2-4(8)6-3/h5H,1-2H2,(H,6,7,8)

Upstream product

• 7365-83-5 N-carbamoylmethyl-glycine 
• 21954-96-1 2,2′-iminobis(acetamide) 
• 32253-74-0 iminodiacetic acid monoammonium salt 
• 683-57-8 bromo-acetic acid amide 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 123-91-1 1,4-dioxane 
• 79-07-2 Chloroacetamide 
• 883886-67-7 amino-acetic acid methyl ester hydrochloride salt 

Downstream Products

• 110-85-0 piperazine 
• 860765-20-4 4-nitro-piperazine-2,6-dione 
• 1309367-36-9 3,5-dioxopiperazine-1-carbodithioic acid 3-cyano-3,3-diphenylpropyl ester 
• 1239362-96-9 (S)-4-{6-chloro-2-[1-(4-fluorophenyl)ethylamino]pyrimidin-4-yl}piperazine-2,6-dione 
• 501127-89-5 4-tert-butoxycarbonylpiperazine-2,6-dione 

Relevant academic research and scientific papers

Synthesis, docking study and inhibitory activity of 2,6-diketopiperazines derived from α-amino acids on HDAC8

Diketopiperazines (DKPs) have been regarded as an important scaffold from the viewpoint of synthesis due to their biological properties for the treatment of several diseases, including cancer. In this work, two novel series of enantiomeric 2,6-DKPs derived from α-amino acids were synthesized through nucleophilic substitution and intramolecular cyclization reactions. All the compounds were docked against histone deacetylase 8 (HDAC8), which is a promising target for the development of anticancer drugs. These compounds bound into the active site of HDAC8 in a similar way to Trichostatin A (TSA), which is an HDAC8 inhibitor. This study showed that the conformation of the 2,6-DKP ring, stereochemistry, and the type of substituent on the chiral center had an important role in the binding modes. The Gibbs free energies and dissociation constants values of HDAC8-ligand complexes showed that compounds (S)-4hBn, (S)-4m, (R)-4h, and (R)-4m were more stable and affine towards HDAC8 than TSA. The inhibitory activities of 4a, (S)-4h, (S)- and (R)-4(g, l, m) were evaluated in vitro on HDAC8. It was found that compounds (R)-4g (IC50 = 21.54 nM) and (R)-4m (IC50 = 10.81 nM) exhibited better inhibitory activities than TSA (IC50 = 28.32 nM). These results suggested that 2,6-DKPs derivatives may be promising anticancer agents for further biological studies.

Synthesis and structure-activity relationships of A novel class of dithiocarbamic acid esters as anticancer agent

Based on a novel lead compound 4-methylpiperazine-1-carbodithioic acid 3-cyano-3,3-diphenylpropyl ester 1, the systematic structural modification was carried out. All the synthesized compounds were evaluated for their in-vitro anticancer activities on four to six different cell lines at three different concentrations. Most of the tested compounds could selectively inhibit the growth of HL-60 and Bel-7402 cell lines at a medium concentration. Four compounds (3f, 3g, 3n, and 5) were selected for the IC50 test, and the results revealed that three compounds (3g, 3n, and 5) showed almost the same or a slightly weaker activity than compound 1 against HL-60, and three compounds (3f, 3g, and 3n) showed >2-fold higher potency than compound 1 against Bel-7402. The in-vivo efficacy of 3n · HCl was evaluated with transplanted hepatocyte carcinoma 22 as an in-vivo test model. It was found that 3n · HCl could inhibit significantly the growth of tumor, and that this effect was dose-dependent. Meanwhile, the compound 3n · HCl showed low toxicity compared with compound 1 · HCl as evidenced by the little body-weight loss. These results confirmed that compound 3n · HCl is more potent than the lead compound 1 · HCl. Preliminary structure-activity relationships indicated that: a) Both nitrile group and the cyclic amine containing at least two nitrogens were indispensable moieties to keep the activity; b) substitution of the piperazine ring is unfavorable for the improvement of activity; c) the suitable linker joining the piperazinyl dithiocarboxyl and diphenylacetonitril group should be ethylene; d) a non-coplanar arrangement of the two benzene rings appears to be essential for activity. Based on a novel lead compound 4-methyl-piperazine-1-carbodithioic acid 3-cyano-3,3-diphenyl-propyl ester 1, the systematic structural modification was carried out. Compounds 3g and 3n were found to show more potent biological activities than lead compound 1. Some useful SARs were revealed Copyright

Process for preparing (S)(+)-4,4'(methyl-1,2-ethanediyl)-bis(2,6-piperazinedione)

The compound (S)(+)-4,4'-(1-methyl-1,2-ethanediyl)-bis(2,6-piperazinedione) is prepared by treating propylenediamine tetraacetic tetraamide in a dipolar aprotic solvent with an alkali metal derivative of dimethyl sulfoxide to form a dialkali metal salt of (S)(+)-4,4'-(1-methyl-1,2-ethanediyl)-bis(2,6-piperazinedione); and neutralizing the dialkali metal salt.