Pyrrophenone

Modify Date: 2024-01-02 23:43:31

Pyrrophenone Structure
Pyrrophenone structure
Common Name Pyrrophenone
CAS Number 341973-06-6 Molecular Weight 849.962
Density 1.4±0.1 g/cm3 Boiling Point N/A
Molecular Formula C49H37F2N3O5S2 Melting Point N/A
MSDS N/A Flash Point N/A

 Use of Pyrrophenone


Pyrrophenone is a potent and specific cytosolic phospholipase A2α (cPLA2α) inhibitor with an IC50 value of 4.2 nM[1].

 Names

Name Pyrrophenone
Synonym More Synonyms

 Pyrrophenone Biological Activity

Description Pyrrophenone is a potent and specific cytosolic phospholipase A2α (cPLA2α) inhibitor with an IC50 value of 4.2 nM[1].
Related Catalog
Target

cPLA2α:4.2 nM (IC50)

In Vitro Pyrrophenone shows potent inhibition of arachidonic acid release, prostaglandin E2, thromboxane B2, and leukotriene B4 formation in human whole blood[1]. Pyrrophenone inhibits the production of arachidonic acid (AA) (IC50=24±1.7 nM), PGE2 (IC50=25±19 nM),, and LTC4 (IC50=14±6.7 nM),from THP-1 cells stimulated with A23187[1]. Pyrrophenone inhibits the production of AA (IC50=0.19±0.068 μM), PGE2 (IC50=0.20±0.047 μM), TXB2 (IC50=0.16±0.093 μM),and LTB4 (IC50=0.32±0.24 μM) from human whole blood stimulated with A23187[1]. Pyrrophenone (0.1-0.5 μM, 48 h) inhibits the growth of PC-PTC3 and PCCl3 cells[2]. Cell Proliferation Assay[2] Cell Line: PC-PTC3 and PCCl3 cells Concentration: 0.1, 0.3, and 0.5 μM Incubation Time: 48 hours Result: Significantly inhibited basal PC-PTC3 cell proliferation at concentrations as low as 0.1 μM. Basal cell proliferation of normal PCCl3 cells was also inhibited by 0.5 μM, although to a lesser extent.
In Vivo Pyrrophenone (administered i.p. at 20 mg/kg 30 min before LPS injection.) suppresses bronchoalveolar lavage (BAL) levels of leukotriene B4 (LTB4) and platelet activating factor (PAF)[3]. Animal Model: Specific pathogen-free female BALB/c mice[3] Dosage: 20 mg/kg Administration: Administered i.p. 30 min before LPS injection Result: Suppressed the recruitment of neutrophils and eosinophils, but not macrophages.
References

[1]. K Seno, et al. Pyrrolidine inhibitors of human cytosolic phospholipase A2. Part 2: synthesis of potent and crystallized 4-triphenylmethylthio derivative 'pyrrophenone'. Bioorg Med Chem Lett. 2001 Feb 26;11(4):587-90.

[2]. Stefania Mariggiò, et al. Cytosolic phospholipase A2 alpha regulates cell growth in RET/PTC-transformed thyroid cells. Cancer Res. 2007 Dec 15;67(24):11769-78.

[3]. C-H Lee, et al. Mechanism of glutamine inhibition of cytosolic phospholipase a2 (cPLA2 ): Evidence of physical interaction between glutamine-Induced mitogen-activated protein kinase phosphatase-1 and cPLA2. Clin Exp Immunol. 2015 Jun;180(3):571-80.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Molecular Formula C49H37F2N3O5S2
Molecular Weight 849.962
Exact Mass 849.214294
PSA 163.25000
LogP 6.28
Index of Refraction 1.721

 Synonyms

N-{[(2S,4R)-1-[2-(2,4-Difluorobenzoyl)benzoyl]-4-(tritylsulfanyl)-2-pyrrolidinyl]methyl}-4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]benzamide
N-{[(2S,4R)-1-[2-(2,4-difluorobenzoyl)benzoyl]-4-(tritylsulfanyl)pyrrolidin-2-yl]methyl}-4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]benzamide
Benzamide, N-[[(2S,4R)-1-[2-(2,4-difluorobenzoyl)benzoyl]-4-[(triphenylmethyl)thio]-2-pyrrolidinyl]methyl]-4-[(Z)-(2,4-dioxo-5-thiazolidinylidene)methyl]-