14705-60-3

Basic information

• Product Name: Pyrrolo(2,1-F)pyrazine-1,4-dione, 2,3,6,7,8,8A-hexahydro-3-(phenylmethyl)-
• Synonyms: 3-(Phenylmethyl)-2,3,6,7,8,8A-hexahydropyrrolo(2,1-F)pyrazine-1,4-dione;Pyrrolo(2,1-F)pyrazine-1,4-dione, 2,3,6,7,8,8A-hexahydro-3-(phenylmethyl)-;Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(phenylmethyl)-;Hexahydro-3-(phenylmethyl)pyrrolo[1,2-a]pyrazine-1,4-dione
• CAS NO: 14705-60-3
• Molecular Formula: C₁₄H₁₆N₂O₂
• Molecular Weight: 244.28904
• Mol File: 14705-60-3.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 509.5°Cat760mmHg
• Flash Point: 262°C
• Appearance: /
• Density: 1.26g/cm³
• PKA: 13.21±0.40(Predicted)
• CAS DataBase Reference: Pyrrolo(2,1-F)pyrazine-1,4-dione, 2,3,6,7,8,8A-hexahydro-3-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrolo(2,1-F)pyrazine-1,4-dione, 2,3,6,7,8,8A-hexahydro-3-(phenylmethyl)-(14705-60-3)
• EPA Substance Registry System: Pyrrolo(2,1-F)pyrazine-1,4-dione, 2,3,6,7,8,8A-hexahydro-3-(phenylmethyl)-(14705-60-3)

Safety Data

• Hazardous Substances Data: 14705-60-3(Hazardous Substances Data)

Usage

General Description

Pyrrolo(2,1-F)pyrazine-1,4-dione, 2,3,6,7,8,8A-hexahydro-3-(phenylmethyl)- is a chemical compound with the molecular formula C18H20N2O2. It is a heterocyclic compound containing a pyrrolopyrazine ring system and a phenylmethyl group. Pyrrolo(2,1-F)pyrazine-1,4-dione, 2,3,6,7,8,8A-hexahydro-3-(phenylmethyl)- has a hexahydro structure, meaning it contains six carbon atoms in a saturated ring. It is commonly used in medicinal chemistry and drug development for its potential pharmacological properties, such as antiviral and antibacterial activity. Additionally, it has been studied for its potential role as a catalyst in organic synthesis. However, it is important to note that this compound may have potential hazards, and proper safety precautions should be taken when handling it.

Upstream product

• 13589-02-1 L-prolyl-L-phenylalanine 
• 3705-26-8 L-Phenylalanyl-L-prolin-lactam 
• 955095-22-4 1-(3,4,5-tris(octadecyloxy)benzyl)-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine 
• 23631-72-3 N-carbobenzoxy-L-prolyl-L-phenylalanine methyl ester 
• 54793-80-5 (S)-proline-(S)-phenylalanine methyl ester 
• 75286-51-0 C₃₄H₃₈N₄O₆S₂ 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 126706-63-6 L-prolyl-L-phenylalanine benzyl ester hydrochloride 
• 74257-60-6 (S)-tert-butyl 2-((S)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-ylcarbamoyl)pyrrolidine-1-carboxylate 
• 63-91-2 L-phenylalanine 
• 1403821-04-4 C₂₇H₂₆N₂O₄ 
• 2133-40-6 methyl pyrrolidine-2-carboxylate hydrochloride 
• 95753-55-2 N-α-FMOC-4-nitro-L-phenylalanine 

Downstream Products

• 3919-02-6 N-L-prolyl-L-phenylalanine 
• 78452-05-8 [(S)-1-((S)-3-Benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-carbamic acid tert-butyl ester 
• 78452-05-8 [(S)-1-((S)-3-Benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-carbamic acid tert-butyl ester 
• 78452-06-9 [(S)-1-((S)-3-Benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-carbamic acid benzyl ester 
• 81531-47-7 [(S)-2-((S)-3-Benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-1-benzyloxymethyl-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 3705-26-8 L-Phenylalanyl-D-prolin-lactam 
• 50868-53-6 N-(d-Lysergyl-L-valyl)-L-phenylalanyl-L-prolin-lactam 
• 78452-06-9 [(S)-1-((3S,8aS)-3-Benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-carbamic acid benzyl ester 
• 96625-34-2 N--Phe-Pro-Lactam 
• 50868-53-6 N-(d-Lysergyl-L-valyl)-L-phenylalanyl-L-prolin-lactam 
• 78452-05-8 [(S)-1-((3S,8aS)-3-Benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-carbamic acid tert-butyl ester 
• 81531-47-7 N--Phe-Pro-Lactam 
• 914771-44-1 (3S,8aS)-3-benzyloctahydropyrrolo[1,2-a]pyrazine 

Relevant articles and documents

Synthesis of 3-Benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione

3-Benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione [cyclo(Pro-Phe)] was synthesized by cyclization of prolylphenylalanine and phenylalanylproline methyl esters which were prepared from the corresponding Boc-protected amino acids.

A facile pathway to synthesize diketopiperazine derivatives

Eighteen diketopiperazines (DKPs) were synthesized in good yields by a solid-phase protocol. This synthesis reveals that the OPac linker between the peptidyl and resin support is favorable to DKP-ring formation and offers a facile and effective way to prepare diverse DKP libraries for combinatorial chemistry.

Antidiabetic in vitro and in vivo evaluation of cyclodipeptides isolated from Pseudomonas fluorescens IB-MR-66e

Three cyclodipeptides [cyclo(l-Pro-l-Leu), 1; cyclo(l-Pro-l-Val), 2; and cyclo(l-Pro-l-Phe), 3] were isolated from Pseudomonas fluorescens IB-MR-66e. The structures were established by spectral means and corroborated by synthesis. The antidiabetic potential of compounds 1-3 was explored in vivo, in vitro and in silico. The three peptides showed important inhibitory activity against the α-glucosidase enzyme. Further analysis in vivo using a sucrose tolerance test corroborated that compounds 1 and 3 (1-30 mg kg-1) significantly reduced the postprandial state. Peptide 1 (1-30 mg kg-1) also reduced the postprandial peak after a glucose challenge and exhibited significant hypoglycemia during an insulin tolerance test; thus, its antidiabetic action involved also an improvement of insulin utilization not related to Akt phosphorylation nor to an increment in mitochondrial bioenergetics nor insulin secretion.

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).

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.