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14705-60-3

14705-60-3 Structure

14705-60-3 Structure
IdentificationBack Directory
[Name]

Pyrrolo(2,1-F)pyrazine-1,4-dione, 2,3,6,7,8,8A-hexahydro-3-(phenylmethyl)-
[CAS]

14705-60-3
[Synonyms]

Cyclo(D-phenylalanyl-L-prolyl)
Hexahydro-3-(phenylmethyl)pyrrolo[1,2-a]pyrazine-1,4-dione
Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(phenylmethyl)-
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)-
[Molecular Formula]

C14H16N2O2
[MDL Number]

MFCD00101617
[MOL File]

14705-60-3.mol
[Molecular Weight]

244.29
Chemical PropertiesBack Directory
[Boiling point ]

509.5±39.0 °C(Predicted)
[density ]

1.26±0.1 g/cm3(Predicted)
[solubility ]

DMF: 1 mg/ml; Ethanol: 1 mg/ml
[form ]

A solid
[pka]

13.21±0.40(Predicted)
[color ]

White to off-white
[Sequence]

Cyclo(Phe-Pro)
Hazard InformationBack Directory
[Uses]

Cyclo(Phe-Pro) (Cyclo(phenylalanylprolyl)) is a quorum-sensing molecule of Vibrio vulnificus that specifically interacts with RIG-I, inhibiting RIG-I polyubiquitination, suppressing IRF-3 activation, and reducing type I interferon production. Cyclo(Phe-Pro) enhances susceptibility to HCV and influenza virus and also alleviates plant aluminum toxicity stress. The mechanism of Cyclo(Phe-Pro) involves the regulation of host immune signaling pathways, bacterial virulence gene expression, and plant antioxidant systems, making it a promising candidate for research in viral infections, bacterial virulence regulation, and agricultural stress resistance[1][2][3].
[in vivo]

Cyclo(Phe-Pro) (50 mg/kg, i.v., once daily for 3 days) promoted HCV replication and suppressed poly(I:C)-induced antiviral response in the HCV-infected Huh7 subcutaneous xenograft NOD/SCID mouse model[1].

Animal Model:Subcutaneous xenograft model of HCV-infected Huh7 cells in NOD/SCID mice[1]
Dosage:50 mg/kg
Administration:Intravenous injection (i.v.), once daily for 3 days
Result:Reversed poly(I:C)-induced HCV RNA reduction, restoring serum HCV RNA levels.
[References]

[1] Lee W, et al. Vibrio vulnificus quorum-sensing molecule cyclo(Phe-Pro) inhibits RIG-I-mediated antiviral innate immunity. Nat Commun. 2018 Apr 23;9(1):1606. DOI:10.1038/s41467-018-04075-1
[2] Bina XR, et al. The cyclic dipeptide cyclo(Phe-Pro) inhibits cholera toxin and toxin-coregulated pilus production in O1 El Tor Vibrio cholerae. J Bacteriol. 2010 Jul;192(14):3829-32. DOI:10.1128/JB.00191-10
[3] Wang Y, et al. Novel application of cyclo(-Phe-Pro) in mitigating aluminum toxicity through oxidative stress alleviation in wheat roots. Environ Pollut. 2024 Dec 15;363(Pt 2):125241. DOI:10.1016/j.envpol.2024.125241
Spectrum DetailBack Directory
[Spectrum Detail]

Pyrrolo(2,1-F)pyrazine-1,4-dione, 2,3,6,7,8,8A-hexahydro-3-(phenylmethyl)-(14705-60-3)1HNMR
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