14705-60-3

Usage

Uses

Used in Pharmaceutical Industry:
Pyrrolo(2,1-F)pyrazine-1,4-dione, 2,3,6,7,8,8A-hexahydro-3-(phenylmethyl)is utilized as a pharmaceutical agent for its antiviral and antibacterial properties, making it a candidate for the development of new drugs to combat various infectious diseases. Its unique structure and activity profile contribute to the search for novel therapeutics.
Used in Organic Synthesis:
In the field of organic synthesis, Pyrrolo(2,1-F)pyrazine-1,4-dione, 2,3,6,7,8,8A-hexahydro-3-(phenylmethyl)serves as a catalyst to facilitate chemical reactions. Its role in catalysis can enhance the efficiency and selectivity of certain organic transformations, which is crucial for the production of complex organic molecules and pharmaceutical intermediates.

Upstream product

• 3588-57-6 Z-DL-Phe-OH 
• 67-64-1 acetone 
• 955095-22-4 1-(3,4,5-tris(octadecyloxy)benzyl)-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine 
• 69936-03-4 (1S)-methyl 2-[(S)-2-amino-3-phenylpropanoyl]cyclopentanecarboxylate 
• 35446-32-3 (S)-3-((Ξ)-benzylidene)-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione 
• 100665-27-8 (5S,6aR,10bR,10cS)-5-Benzyl-10b-hydroxy-hexahydro-8-thia-3a,5a,10a-triaza-cyclopenta[c]fluorene-4,6,10-trione 
• 57177-79-4 (S)-tert-butyl 2-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl)pyrrolidine-1-carboxylate 
• 214849-88-4 (S)-3-[(Z)-benzylidene]hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 87900-97-8 N-(N-phenylacetyl-Ala)-cyclo-(Phe-Pro) 
• 54793-80-5 (S)-proline-(S)-phenylalanine methyl ester 
• 13589-02-1 L-prolyl-L-phenylalanine 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 

Downstream Products

• 3919-02-6 N-L-prolyl-L-phenylalanine 
• 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 
• 32021-26-4 3-benzylhexahydropyrrolo[1,2-a]pyrazin-1,4-dione 
• 95713-60-3 L-Phe-L-FDAA 
• 147-85-3 L-proline 
• 95713-61-4 L-FDAA-D-Phe 
• 128425-02-5 L-FDAA-L-Pro 
• 673-06-3 D-(R)-phenylalanine 

Relevant academic research and scientific papers

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.

One-pot synthesis of symmetrical and unsymmetrical diketopiperazines from unprotected amino acids

An efficient synthesis of symmetrical and unsymmetrical proline-type diketopiperazines using a phosphite-promoted coupling was used to generate diketopiperazines with overall good yields from unprotected amino acids. Georg Thieme Verlag Stuttgart.

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.

Site-site interactions within high-loading PAMAM dendrimer resin beads

Combinatorial chemistry and solid-phase synthesis have revolutionised the process of drug discovery in the last decade. Ever since the concept of split and mix synthesis was introduced in 1988, and in particular the concept of one bead one compound, this approach has been associated with the possibility of generating thousands or millions of compounds in only a relatively small number of synthetic steps. The demand for high loading resins has therefore increased over the last few years. Our research has focussed on bead-loading enhancement via a dendrimerisation process. Dendrimer resin beads have shown compatibility for many chemical conditions, however high functional group density could produce undesirable site-site interactions.

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).

Molecular capture and conformational change of diketopiperazines containing proline residues by epigallocatechin-3-O-gallate in water

The addition of an aqueous solution of diketopiperazine cyclo(Pro-Xxx) (Xxx: amino acid residue) to an aqueous solution of (?)-epigallocatechin-3-O-gallate (EGCg) led to precipitation of the complex of EGCg and cyclo(Pro-Xxx). The molecular capture abilities of cyclo(Pro-Xxx) using EGCg were evaluated by the ratio of the amount of cyclo(Pro-Xxx) included in the precipitates of the complex with EGCg to that of the total cyclo(Pro-Xxx) used. Stronger hydrophobicity of the side chain of the amino acid residue of cyclo(Pro-Xxx) led to a higher molecular capture ability. Furthermore, the molecular capture ability decreased when the side chain of the amino acid residue had a hydrophilic hydroxyl group. When diketopiperazine cyclo(Pro-Xxx), excluding cyclo(D-Pro-L-Ala), was taken into the hydrophobic space formed by the three aromatic A, B, and B′ rings of EGCg, and formed a complex, their conformation was maintained in the hydrophobic space. Based on nuclear Overhauser effect (NOE) measurement, the 3-position methyl group of cyclo(D-Pro-L-Ala) in D2O was axial, whereas that of cyclo(L-Pro-L-Ala) was equatorial. When cyclo(D-Pro-L-Ala) was taken into the hydrophobic space of EGCg and formed a 2:2 complex, its 3-position methyl group changed from the axial position to the equatorial position due to steric hindrance by EGCg.

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.

Evaluation of two cyclic di-peptides as inhibitors of CCL2 induced chemotaxis

Monocyte chemoattractant protein (CCL2) plays a major role in the recruitment of monocytes during inflammation. In this study we analysed properties of synthetic CCL2 inhibitors in inhibiting CCL2 mediated monocyte migration. Using trans-endothelial chemotaxis assays compounds C1 and C5 were found to significantly reduce CCL2 mediated migration. Flow based adhesion assays showed reduction in adhesion to VCAM-1 in the presence of 10 nM CCL2 and 50 μM C5 (p 0.05). Further studies with these compounds can aid in their development as anti-inflammatory therapies. The Royal Society of Chemistry 2013.

Solid-phase synthesis of phenylalanine containing peptides using a traceless triazene linker

The use of a triazene function to anchor phenylalanine to a polymeric support through its side chain is reported. To prove the usefulness of this strategy in solid-phase peptide synthesis, several bioactive peptides have been prepared including cyclic, C-modified, and protected peptides. The triazene linkage is formed by coupling the diazonium salt of Fmoc-Phe(pNH 2)-OAllyl to a MBHA-polystyrene resin previously functionalized with isonipecotic acid (90%). Further assembly of the peptide chain, cleavage from the resin using 2-5% TFA in DCM, and reduction of the resulting diazonium salt of the peptide with FeSO4-7H2O in DMF afforded the desired products in high purities (73-94%).