866028-26-4

Basic information

• Product Name: INF39
• Synonyms: INF39
• CAS NO: 866028-26-4
• Molecular Formula: C₁₂H₁₃ClO₂
• Molecular Weight: 224.68342
• EINECS: -0
• Mol File: 866028-26-4.mol

Chemical Properties

• Boiling Point: 309.3±30.0 °C(Predicted)
• Appearance: /
• Density: 1.131±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C
• CAS DataBase Reference: INF39(CAS DataBase Reference)
• NIST Chemistry Reference: INF39(866028-26-4)
• EPA Substance Registry System: INF39(866028-26-4)

Safety Data

• Hazardous Substances Data: 866028-26-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
INF39 is used as an anti-inflammatory agent for the treatment of inflammatory bowel disease. It helps in reducing inflammation and alleviating symptoms associated with the condition by inhibiting the NLRP3 inflammasome pathway.

Biochem/physiol Actions

INF39 is an orally active acrylate derivative and a non-cytotoxic INF4E analog (no toxicity at 100 μM in THP-1 cultures vs. TC50 = 65 μM with INF4E) that acts as an irreversible inhibitor against NLRP3 (NACHT, LRR and PYD domains-containing protein 3) ATPase activity (52% inhibition in 15 min by 100 μM INF39; 105 ng human NLP3 & 250 μM ATP) essential for the NLRP3 inflammasome assembly and activation. INF39 effectively decreases 5 mM (30 min) ATP-induced interleukin-1β (IL-1β) release and pyroptosis of murine bone marrow-derived macrophages in cultures (by 55-58% and 43-65%, respectively, with 1-hr 10 μM INF39 pretreatment of LPS-primed BMDM) and alleviates gut-associated inflammation in a rat model of 2,4-dinitrobenzenesulfonic acid (DNBS)-induced colitis in vivo (12.5-50 mg/kg/day in 0.2 mL olive oil p.o.).

Upstream product

• 682813-61-2 ethyl 3-(acetoxy(2-chlorophenyl)methyl)-2-oxobut-3-enoate 
• 88039-46-7 ethyl 2-((2-chlorophenyl)(hydroxy)methyl)acrylate 
• 611-17-6 1-bromomethyl-2-chlorobenzene 
• 50-00-0 formaldehyd 
• 866028-25-3 ethyl 3-(2-chlorophenyl)-2-(diethoxyphosphoryl)propanoate 

Relevant articles and documents

Development of an Acrylate Derivative Targeting the NLRP3 Inflammasome for the Treatment of Inflammatory Bowel Disease

Pharmacological inhibition of NLRP3 inflammasome activation may offer a new option in the treatment of inflammatory bowel disease. In this work, we report the design, synthesis, and biological screening of a series of acrylate derivatives as NLRP3 inhibitors. The in vitro determination of reactivity, cytotoxicity, NLRP3 ATPase inhibition, and antipyroptotic properties allowed the selection of 11 (INF39), a nontoxic, irreversible NLRP3 inhibitor able to decrease interleukin-1β release from macrophages. Bioluminescence resonance energy transfer experiments proved that this compound was able to directly interfere with NLRP3 activation in cells. In vivo studies confirmed the ability of the selected lead to alleviate the effects of colitis induced by 2,4-dinitrobenzenesulfonic acid in rats after oral administration.

Design, Synthesis, and Evaluation of Acrylamide Derivatives as Direct NLRP3 Inflammasome Inhibitors

NLRP3 inflammasome plays a key role in the intracellular activation of caspase-1, processing of pro-inflammatory interleukin-1β (IL-1β), and pyroptotic cell death cascade. The overactivation of NLRP3 is implicated in the pathogenesis of autoinflammatory d

ALPHA-(ARYL-OR HETEROARYL-METHYL)-BETA-PIPERIDINOPROPANOIC ACID COMPOUNDS AS ORL1-RECEPTOR ANTAGONISTS

This invention provides the compounds of formula (I): or a pharmaceutically acceptable ester or salt thereof, wherein R1 and R2 independently represent hydrogen or the like; R3 represents aryl or the like; -X-Y- represents

ALPHA ARYL OR HETEROARYL METHYL BETA PIPERIDINO PROPANAMIDE COMPOUNDS AS ORL1-RECEPTOR ANTAGONIST

This invention provides the compounds of formula (I): or a pharmaceutically acceptable ester of such compound, or a pharmaceutically acceptable salt thereof, wherein Ri and R2 independently represent a hydrogen atom or the like; R3 represents a hydrogen atom, or the like; R4 represents a hydrogen atom or the like; (formula II) represents one of the following or the like; R5 represents an aryl group having from 6 to 10 ring atoms or the like; X represents an oxygen atom, or the like; Y represents an oxgen atom or the like and n represents an integer 0, 1 or 2. These compounds have ORL1-receptor antagonist activity; and therefore, are useful to treat diseases or conditions such as pain, various CNS diseases etc.