107829-09-4

Basic information

• Product Name: N-(3-nitrophenyl)butanamide
• Synonyms: N-(3-nitrophenyl)butanamide
• CAS NO: 107829-09-4
• Molecular Formula: C₁₀H₁₂N₂O₃
• Molecular Weight: 208.21388
• Mol File: 107829-09-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(3-nitrophenyl)butanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-nitrophenyl)butanamide(107829-09-4)
• EPA Substance Registry System: N-(3-nitrophenyl)butanamide(107829-09-4)

Safety Data

• Hazardous Substances Data: 107829-09-4(Hazardous Substances Data)

Upstream product

• 141-75-3 butyryl chloride 
• 99-09-2 3-nitro-aniline 
• 98326-78-4 N-(butyl)-3-nitroaniline 
• 106-31-0 butanoic acid anhydride 

Downstream Products

• 423735-93-7 ML₁₆₁ 
• 925049-62-3 N-(3-butyramidophenyl)-3-chlorobenzamide 
• 75125-56-3 N-[2-(2,6-Dicyano-4-nitro-phenylazo)-5-diethylamino-phenyl]-butyramide 
• 124515-92-0 N-[2-(2-Bromo-6-cyano-4-nitro-phenylazo)-5-diethylamino-phenyl]-butyramide 
• 76751-08-1 3-Butyramido-N,N-diethyl-anilin 
• 98326-78-4 N-(butyl)-3-nitroaniline 
• 93469-29-5 3-butyrylaminoaniline 

Relevant articles and documents

Characterization of Protease-Activated Receptor (PAR) ligands: Parmodulins are reversible allosteric inhibitors of PAR1-driven calcium mobilization in endothelial cells

Several classes of ligands for Protease-Activated Receptors (PARs) have shown impressive anti-inflammatory and cytoprotective activities, including PAR2 antagonists and the PAR1-targeting parmodulins. In order to support medicinal chemistry studies with hundreds of compounds and to perform detailed mode-of-action studies, it became important to develop a reliable PAR assay that is operational with endothelial cells, which mediate the cytoprotective effects of interest. We report a detailed protocol for an intracellular calcium mobilization assay with adherent endothelial cells in multiwell plates that was used to study a number of known and new PAR1 and PAR2 ligands, including an alkynylated version of the PAR1 antagonist RWJ-58259 that is suitable for the preparation of tagged or conjugate compounds. Using the cell line EA.hy926, it was necessary to perform media exchanges with automated liquid handling equipment in order to obtain optimal and reproducible antagonist concentration-response curves. The assay is also suitable for study of PAR2 ligands; a peptide antagonist reported by Fairlie was synthesized and found to inhibit PAR2 in a manner consistent with reports using epithelial cells. The assay was used to confirm that vorapaxar acts as an irreversible antagonist of PAR1 in endothelium, and parmodulin 2 (ML161) and the related parmodulin RR-90 were found to inhibit PAR1 reversibly, in a manner consistent with negative allosteric modulation.

Discovery of 1,3-diaminobenzenes as selective inhibitors of platelet activation at the PAR1 receptor

A high-throughput screen of the NIH-MLSMR compound collection, along with a series of secondary assays to identify potential targets of hit compounds, previously identified a 1,3-diaminobenzene scaffold that targets protease-activated receptor 1 (PAR1). We now report additional structure-activity relationship (SAR) studies that delineate the requirements for activity at PAR1 and identify plasma-stable analogues with nanomolar inhibition of PAR1-mediated platelet activation. Compound 4 was declared as a probe (ML161) with the NIH Molecular Libraries Program. This compound inhibited platelet aggregation induced by a PAR1 peptide agonist or by thrombin but not by several other platelet agonists. Initial studies suggest that ML161 is an allosteric inhibitor of PAR1. These findings may be important for the discovery of antithrombotics with an improved safety profile.