Pyrrophenone

• CAT Number: R064407
• CAS Number: 341973-06-6
• Molecular Formula: C49H37F2N3O5S2
• Molecular Weight: 849.96
• Purity: ≥95%
• Synonyms: N-[[(2S,4R)-1-[2-(2,4-difluorobenzoyl)benzoyl]-4-tritylsulfanylpyrrolidin-2-yl]methyl]-4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]benzamide
• InChI: InChI=1S/C49H37F2N3O5S2/c50-36-24-25-41(42(51)27-36)44(55)39-18-10-11-19-40(39)47(58)54-30-38(28-37(54)29-52-45(56)32-22-20-31(21-23-32)26-43-46(57)53-48(59)60-43)61-49(33-12-4-1-5-13-33,34-14-6-2-7-15-34)35-16-8-3-9-17-35/h1-27,37-38H,28-30H2,(H,52,56)(H,53,57,59)/b43-26-/t37-,38+/m0/s1
• InChIKey: XSCZRVUQXBBTRO-GYCZXHFISA-N
• SMILES: C1C(CN(C1CNC(=O)C2=CC=C(C=C2)C=C3C(=O)NC(=O)S3)C(=O)C4=CC=CC=C4C(=O)C5=C(C=C(C=C5)F)F)SC(C6=CC=CC=C6)(C7=CC=CC=C7)C8=CC=CC=C8

Pyrrophenone (Cat No.: R064407) is a potent and selective inhibitor of cytosolic phospholipase A2α (cPLA2α), an enzyme responsible for releasing arachidonic acid from membrane phospholipids, leading to the production of pro-inflammatory mediators. By blocking cPLA2α activity, pyrrophenone has been widely used in research to study inflammation, immune responses, and signaling pathways linked to eicosanoid biosynthesis. It is valuable in investigating disease mechanisms such as arthritis, asthma, and neuroinflammation. Although not a therapeutic drug, pyrrophenone remains an important pharmacological tool in inflammation research.

Reference

[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.
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[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.
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[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.
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