36357-32-1

Basic information

• Product Name: Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methyl-, (3S,8aS)- (9CI)
• Synonyms: Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methyl-, (3S,8aS)- (9CI);Cyclo(L-Ala-L-Pro);(3S,8aS)-Hexahydro-3-methylpyrrolo[1,2-a]pyrazine-1,4-dioneNumbers: 61949-27-7;Cyclo(alanylproline);Cyclo-(L-alanine-L-proline);cyclo(Pro-Ala);L-Prolyl-L-alanine diketopiperazine
• CAS NO: 36357-32-1
• Molecular Formula: C₈H₁₂N₂O₂
• Molecular Weight: 168.19308
• Product Categories: PYRROLE
• Mol File: 36357-32-1.mol
• Article Data: 18

Chemical Properties

• Melting Point: 178-181℃ (methanol )
• Appearance: /
• CAS DataBase Reference: Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methyl-, (3S,8aS)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methyl-, (3S,8aS)- (9CI)(36357-32-1)
• EPA Substance Registry System: Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methyl-, (3S,8aS)- (9CI)(36357-32-1)

Safety Data

• Hazardous Substances Data: 36357-32-1(Hazardous Substances Data)

Usage

Description

Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methyl-, (3S,8aS)(9CI) is a heterocyclic chemical compound with the molecular formula C8H10N2O2. It features a fused pyrazine and pyrrole ring structure, along with a hexahydro-3-methyl group. As a chiral molecule, it exists in two enantiomeric forms, (3S,8aS)and (3R,8aR)-. This cyclic organic compound is notable for its potential applications in pharmaceuticals and biochemical research due to its unique structural characteristics and the possibility of exhibiting biological activity.

Uses

Used in Pharmaceutical Industry:
Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methyl-, (3S,8aS)(9CI) is utilized as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique heterocyclic structure allows it to serve as a building block for the development of new drugs with potential therapeutic applications.
Used in Biochemical Research:
In the field of biochemical research, Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methyl-, (3S,8aS)(9CI) is employed as a compound of interest for studying its biological activity. Its structural features make it a candidate for investigating interactions with biological targets, which could lead to the discovery of new therapeutic agents or a better understanding of biological processes.

Upstream product

• 71067-42-0 alanylproline methyl ester hydrochloride 
• 22209-85-4 (2S,2'R)-N-(N-Benzyloxycarbonylalanyl)proline methyl ester 
• 61430-03-3 (S)-1-((S)-2-Amino-propionyl)-pyrrolidine-2-carboxylic acid amide 
• 129474-02-8 Cbz-D-Ala-L-Pro-NH₂ 
• 22610-33-9 (2S,2'S)-N-(N-Benzyloxycarbonylalanyl)proline methyl ester 
• 27446-57-7 benzyl N-(1S)-2-[(2S)-2-(aminocarbonyl)tetrahydro-1H-pyrrol-1-yl]-1-methyl-2-oxoethylcarbamate 
• 176018-79-4 (5R,8aS)-5-Methyl-hexahydro-3a,6,7-triaza-azulene-4,8-dione 
• 6422-36-2 L-prolyl-L-alanine 
• 76399-73-0 (S)-1-((S)-2-Amino-propionyl)-pyrrolidine-2-carboxylic acid amide; hydrochloride 
• 3082-75-5 L-Alanine ethyl ester 
• 81377-00-6 α-L-Ala-L-Pro-methyl ester 
• 916504-59-1 (3S,8aS)-6,7,8,8a-tetrahydro-1-methoxy-3-methylpyrrolo[1,2-a]pyrazin-4(3H)-one 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 2491-20-5 L-alanine methyl ester hydrochloride 

Downstream Products

• 1072102-45-4 C₈H₁₆N₂ 
• 128425-02-5 L-FDAA-L-Pro 

Relevant articles and documents

Mechanism of 2,5-dioxopiperazine formation

The cyclization of H-Ala-Pro-NH2 to the 2,5-dioxopiperazine (DKP) has been Studied as a model for the spontaneous cleavage of the peptide bond with concomitant formation of 2,5-dioxopiperazine that can occur at the N-terminus of a polypeptide chain. The reaction involves pre-equilibrium attack of the N-terminal amino group on the carbonyl carbon of the second residue giving a zwitterionic intermediate, T(±) which is in acid-base equilibrium with various forms characterized by the different grades of protonation, T0, T+ and T-. The Bronsted plot for the base-catalysis and the pH-rate profile give pK(a) ~ 7 and ~ 13 for the equilibria T- + H+ ? T(±) + T(-) + H(+) ? T0 respectively. The reaction is subjects to general base and general acid cataysis on different steps. Departure of the amino group from T0 and T- by two parallel routes gives the product. The bifunctional acid catalyst HCO3- strongly increase the reaction rate and at high concentrations cause a of the rate-limiting step. At high pH, the overall reaction rate is limited by the trans - cis isomerization of the Ala-Pro peptide bond.

Cyclo(l-proline-l-serine) Dipeptide Suppresses Seed Borne Fungal Pathogens of Rice: Altered Cellular Membrane Integrity of Fungal Hyphae and Seed Quality Benefits

Five proline-containing diketopiperazines (Pro-DKPs) produced by antagonistic microorganisms as secondary metabolites were selected and synthesized under laboratory conditions. Out of five synthesized Pro-DKPs, cyclo(l-Pro-l-Ser) (DKP-6) revealed the best inhibition of fungal pathogens (Fusarium verticillioides and Fusarium fujikuroi) of rice under in vitro conditions with effective doses lower than standard fungicide carbendazim. DKP-6 induced stress on the fungal cell membrane integrity, which was revealed by calcofluor white and propidium iodide assays, endorsed by ultra-microscopic details and soluble protein leakage assays. In vivo seed treatment of infested rice seeds with DKP-6 at 2000 μg/mL for 10 h of seed treatment inflicted best reduction in seed rot and seedling blight with respect to control and carbendazim. Significant enhancement in seedling quality parameters were also observed. The work presented the strong influence of cyclo(l-Pro-l-Ser) as a mycocidal seed treatment agent better than synthetic toxic fungicides for rice.

Cyclols Revisited: Facile Synthesis of Medium-Sized Cyclic Peptides

Medium-sized rings, particularly the corresponding cyclic peptides, are challenging synthetic targets. In the present study, we report an approach to medium-sized cyclic peptides through targeted formation and collapse of cyclol intermediates. This methodology operates on β-amino imides derived from 2,5-diketopiperazines and offers a straightforward transition from frequently examined scaffolds in drug discovery to a rarely visited class of medium-sized rings.

AGRICULTURAL CHEMICAL CONTAINING 2,5-DIKETOPIPERAZINE DERIVATIVE AS ACTIVE INGREDIENT

Disclosed herein is an agricultural agent containing a 2,5-diketopiperazine derivative capable of controlling plant diseases and promoting plant growth or an agriculturally acceptable salt thereof as an active ingredient.