341973-06-6

Basic information

• Product Name: Pyrrophenone
• Synonyms: Pyrrophenone;N-[[(2S,4R)-1-[2-(2,4-difluorobenzoyl)benzoyl]-4-tritylsulfanylpyrrolidin-2-yl]methyl]-4-[(E)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]benzamide
• CAS NO: 341973-06-6
• Molecular Formula: C49H37F2N3O5S2
• Molecular Weight: 849.9619864
• Mol File: 341973-06-6.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Pyrrophenone(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrophenone(341973-06-6)
• EPA Substance Registry System: Pyrrophenone(341973-06-6)

Safety Data

• Hazardous Substances Data: 341973-06-6(Hazardous Substances Data)

Usage

Description

Pyrrophenone is a compound that selectively inhibits the group IVA phospholipase A2 (PLA2), also known as calcium-dependent cytosolic PLA2 (cPLA2), which plays a central role in initiating the synthesis of prostaglandins (PGs) and leukotrienes (LTs). It effectively blocks the release of arachidonic acid (AA) and the production of PGE2 and LTC4 in cells, with its action being reversible and selective.

Uses

Used in Pharmaceutical Industry:
Pyrrophenone is used as an inhibitor for cPLA2α, which is crucial in the synthesis of prostaglandins and leukotrienes. Its application is significant in enzyme assays, where it demonstrates potent inhibition with an IC50 of 4.2 nM. It also blocks the release of AA and the production of PGE2 and LTC4 in cells, with IC50 values of 24, 25, and 14 nM, respectively.
Used in Anti-inflammatory Applications:
Pyrrophenone is used as an anti-inflammatory agent due to its ability to inhibit the production of PGE2, LTs, and platelet-activating factor by human neutrophils. It can be particularly useful in managing inflammation-related conditions and diseases.
Used in Cell Signaling Research:
Pyrrophenone is used as a research tool to study the role of cPLA2α in cellular processes, such as AA release and PGE2 synthesis, which are essential for understanding the underlying mechanisms of various diseases and conditions.
Used in Drug Development:
Pyrrophenone can be utilized in the development of new drugs targeting cPLA2α for the treatment of inflammation, pain, and other related conditions. Its selective and reversible inhibition of cPLA2α makes it a promising candidate for drug development.

Upstream product

• 188111-05-9 4-(2,4-dioxothiazolidin-5-ylidenemethyl)benzoic acid 
• 85-44-9 phthalic anhydride 
• 372-18-9 1,3-Difluorobenzene 
• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 
• 619-66-9 4-Carboxybenzaldehyde 
• 121147-93-1 (2S,4S)-2-methyl N-Boc-4-((methylsulfonyl)oxy)pyrrolidine-2-carboxylate 
• 135030-72-7 2-(2,4-difluorobenzoyl)benzoic acid 
• 393792-04-6 (2S,4R)-2-azidomethyl-4-tritylsulfanylpyrrolidine 
• 337307-10-5 (2S,4R)-2-Hydroxymethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 337307-11-6 (2S,4R)-2-azidomethyl-4-tritylsulfanylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 176306-17-5 (2S,4R)-4-tritylsulfanylpyrrolidine-1,2-dicarboxylic acid 1-tert-butyl-2-methyl diester 
• 393791-87-2 (2S,4R)-2-methanesulfonyloxymethyl-4-tritylsulfanylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 337307-12-7 ((2S,4R)-2-Azidomethyl-4-tritylsulfanyl-pyrrolidin-1-yl)-[2-(2,4-difluoro-benzoyl)-phenyl]-methanone 

Relevant articles and documents

Pyrrolidine inhibitors of human cytosolic phospholipase A2. Part 2: Synthesis of potent and crystallized 4-triphenylmethylthio derivative 'pyrrophenone'

We synthesized a potent and crystallized human cytosolic phospholipase A2α inhibitor, pyrrophenone (6) which inhibits the isolated enzyme with an IC50 value of 4.2 nM. Pyrrophenone shows potent inhibition of arachidonic acid release, prostaglandin E2, thromboxane B2, and leukotriene B4 formation in human whole blood. The magnitudes of prostaglandin E2 and thromboxane B2 inhibition are the same as those of indomethacin.