27483-18-7

Basic information

• Product Name: (3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione
• Synonyms: (3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione;Cyclo(D-Val-L-Pro);(3R,8aS)-Hexahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione;Cyclo(L-prolyl-D-valine);Cyclo(L-prolyl-D-valyl);Cyclo-(S-Pro-R-Val);D-Valyl-L-proline diketopiperazine
• CAS NO: 27483-18-7
• Molecular Formula: C10H16N2O2
• Molecular Weight: 196.25
• Mol File: 27483-18-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 153-155℃
• Appearance: /
• CAS DataBase Reference: (3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione(27483-18-7)
• EPA Substance Registry System: (3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione(27483-18-7)

Safety Data

• Hazardous Substances Data: 27483-18-7(Hazardous Substances Data)

Usage

Description

(3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione is a pyrrolopyrazine derivative with a molecular formula C10H16N2O2. It is a cyclic compound that features a pyrrolidine ring and a pyrazine ring, with a carbonyl group attached to the pyrazine ring. (3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione is known for its potential as a precursor in the synthesis of pharmaceuticals and agrochemicals, and it may also be utilized in drug discovery and development due to its capacity to influence biological processes. Its diverse properties, such as antioxidant, antimicrobial, or anticancer activities, make it a promising candidate for further research in medicinal chemistry.

Uses

Used in Pharmaceutical and Agrochemical Industries:
(3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione is used as a precursor in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides.
Used in Drug Discovery and Development:
(3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione is utilized in drug discovery and development processes due to its ability to modulate biological processes, which can lead to the creation of novel therapeutic agents.
Used in Medicinal Chemistry Research:
(3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione is used as a subject of interest in medicinal chemistry research, where its antioxidant, antimicrobial, and anticancer properties are explored for potential applications in the treatment and prevention of various diseases.

Upstream product

• 22838-58-0 Boc-D-Val-OH 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 916504-58-0 (8aS)-6,7,8,8a-tetrahydro-1-methoxypyrrolo[1,2-a]pyrazin-4(3H)-one 
• 916504-70-6 (3R,8aS)-6,7,8,8a-tetrahydro-1-methoxy-3-(1-methyethyl)pyrrolo[1,2-a]pyrazin-4(3H)-one 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 13734-41-3 t-Boc-L-valine 
• 3705-27-9 (S)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 

Relevant articles and documents

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The use of Nbb resin in cyclic dipeptide ('diketopiperazine') synthesis

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Unambiguous stereochemical assignment of cyclo(Phe-pro), cyclo(leu-pro), and cyclo(val-pro) by electronic circular dichroic spectroscopy

2,5-diketopiperazines (DKPs) are cyclic dipeptides ubiquitously found in nature. In particular, cyclo(Phe-Pro), cyclo(Leu-Pro), and cyclo(Val-Pro) are frequently detected in many microbial cultures. Each of these DKPs has four possible stereoisomers due to the presence of two chirality centers. However, absolute configurations of natural DKPs are often ambiguous due to the lack of a simple, sensitive, and reproducible method for stereochemical assignment. This is an important problem because stereochemistry is a key determinant of biological activity. Here, we report a synthetic DKP library containing all stereoisomers of cyclo(Phe-Pro), cyclo(Leu-Pro), and cyclo(Val-Pro). The library was subjected to spectroscopic characterization using mass spectrometry, NMR, and electronic circular dichroism (ECD). It turned out that ECD can clearly differentiate DKP stereoisomers. Thus, our ECD dataset can serve as a reference for unambiguous stereochemical assignment of cyclo(Phe-Pro), cyclo(Leu-Pro), and cyclo(Val-Pro) samples from natural sources. The DKP library was also subjected to a biological screening using assays for E. coli growth and biofilm formation, which revealed distinct biological effects of cyclo(D-Phe-L-Pro).

Diastereoselective alkylation of a proline-derived bicyclic lactim ether

N-Boc-protected L-proline (6) was converted into the bicyclic lactim ether (8aS)-6,7,8,8a-tetrahydro-1-methoxypyrrolo[1,2-a]pyrazin-4(3H)-one (5) in four steps (Scheme 1). Deprotonation with LDA or LHMDS and subsequent alkylation resulted in the diastereoisomeric products cis- and trans-9. The diastereoselectivity was mainly dependent on the electrophile. Whereas small alkyl halides gave preferably cis-9, sterically more-demanding alkyl halides resulted in cisltrans mixtures. Electrophiles bearing a π-system favored the trans-products 9. Some isolated cis- and tranx-lactim ethers 9 were converted to the corresponding diketopiperazines cis- and trans-10 by acid hydrolysis. The structures and configurations of several compounds were confirmed by NMR and NOE experiments, as well as by X-ray crystallography (Figs. 1-4).