2,5-Piperazinedione

Details

Stereochemistry	ACHIRAL
Molecular Formula	C4H6N2O2
Molecular Weight	114.1026
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1CNC(=O)CN1

InChI

InChIKey=BXRNXXXXHLBUKK-UHFFFAOYSA-N

InChI=1S/C4H6N2O2/c7-3-1-5-4(8)2-6-3/h1-2H2,(H,5,8)(H,6,7)

HIDE SMILES / InChI

Molecular Formula	C4H6N2O2
Molecular Weight	114.1026
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Alaptide from synchrotron powder diffraction data.	2010-03-13	21580652
(S)-alpha-methyl,alpha-amino acids: a new stereocontrolled synthesis.	2010-03	19363669
Chiral piperazine-2,5-dione derivatives as effective alpha-glucosidase inhibitors. Part 4.	2010-01	20087993
Detection and quantitation of 2,5-diketopiperazines in wheat sourdough and bread.	2009-10-28	19807105
Cytotoxic piperazine-2,5-dione derivatives from marine fungus Gliocladium sp.	2009-09	19827308
N-(4-Meth-oxy-2-nitro-phen-yl)-N-(methyl-sulfon-yl)acetamide.	2009-04-02	21583985
Novel HDAC6 isoform selective chiral small molecule histone deacetylase inhibitors.	2009-02-01	19111466
N-(4-Chloro-2-nitro-phen-yl)-N-(methyl-sulfon-yl)acetamide.	2008-10-11	21580956
Three-dimensional frameworks built from piperazine-2,5-dione and simple metal salts (M = Co, Ni, Cu and Ag).	2008-08	18682639
2-Chloro-N-(4-fluoro-phen-yl)acetamide.	2008-06-07	21202836
NEXAFS spectroscopy of homopolypeptides at all relevant absorption edges: polyisoleucine, polytyrosine, and polyhistidine.	2007-08-23	17663583
Oxidation of cyclic dipeptides by photoinduced H-atom abstraction. A laser flash FT EPR and optical spectroscopy study.	2007-06-14	17516635
A new piperazine-2,5-dione from the marine fungus Gliocladium sp.	2007-06	17663202
Identification of the endogenous key substrates of the human organic cation transporter OCT2 and their implication in function of dopaminergic neurons.	2007-04-25	17460754
The use of the Ugi four-component condensation.	2007	17406624
Janthinolide A-B, two new 2,5-piperazinedione derivatives from the endophytic Penicillium janthinellum isolated from the soft coral Dendronephthya sp.	2006-12	17283665
1,3,5-Triazepane-2,6-diones as structurally diverse and conformationally constrained dipeptide mimetics: identification of malaria liver stage inhibitors from a small pilot library.	2006-11-15	16927352
1H and 13C assignments of cyclo[N-(Lys-Phe)-Orn-Val], a semicyclic imide tetrapeptide from Burkholderia cepacia.	2006-10	16826554
2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists. 3. Synthesis, pharmacokinetics, and in vivo potency.	2006-07-13	16821776
2,5-Diketopiperazines as potent and selective oxytocin antagonists 1: Identification, stereochemistry and initial SAR.	2005-05-16	15863320
Combinatorial approaches towards the discovery of new tryptase inhibitors.	2005-03-15	15745817
Interaction of molybdocene dichloride with cysteine-containing peptides: coordination, regioselective hydrolysis, and intramolecular aminolysis.	2005-02-21	15859290
Piperazine-2,5-dione-oxalic acid-water (1/1/2) and a redetermination of piperazine-2,5-dione, both at 120 K: hydrogen-bonded sheets containing multiple ring types.	2005-02	15695910
Kinetics of degradation and oil solubility of ester prodrugs of a model dipeptide (Gly-Phe).	2004-08	15265509
Noncovalent self-assembly of bicyclo[4.2.2]diketopiperazines: influence of saturation in the bridging carbacyclic ring.	2004-02-05	14748580
An efficient synthesis of 2,5-diketopiperazine derivatives by the Ugi four-center three-component reaction.	2003	15068092
Five- and six-membered ring opening of pyroglutamic diketopiperazine.	2002-03-22	11895398
Entry to new conformationally constrained amino acids. First synthesis of 3-unsubstituted 4-alkyl-4-carboxy-2-azetidinone derivatives via an intramolecular N(alpha)-C(alpha)-cyclization strategy.	2001-05-18	11348142

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:10:02 GMT 2025` Edited by `admin` on `Mon Mar 31 19:10:02 GMT 2025`
Record UNII	240L69DTV7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2,5-Piperazinedione

Systematic Name

English

NSC-26345

Preferred Name

English

.ALPHA.,.GAMMA.-DIACIPIPERAZINE

Common Name

English

2,5-DIOXOPIPERAZINE

Systematic Name

English

DIGLYCOLYLDIAMIDE

Systematic Name

English

CYCLOGLYCYLGLYCINE

Common Name

English

GLYCYLGLYCINE LACTAM

Common Name

English

2,5-DIKETOPIPERAZINE

Systematic Name

English

2,5-PIPERAZINEDIONE [MI]

Common Name

English

GLYCINE ANHYDRIDE

Common Name

English

Code System Code Type Description

PUBCHEM

7817