659730-32-2

Basic information

• Product Name: Amg 517
• Synonyms: Amg 517;N-[4-[[6-[4-(Trifluoromethyl)phenyl]-4-pyrimidinyl]oxy]-2-benzothiazolyl]acetamide;AcetaMide, N-[4-[[6-[4-(trifluoroMethyl)phenyl]-4-pyriMidinyl]oxy]-2-benzothiazolyl]-;N-[4-[[6-[4-(Trifluoromethyl)phenyl]-4-pyrimidinyl]oxy]-2-benzothiazolyl]acetamide AMG517;N-(4-((6-(4-(Trifluoromethyl)phenyl)pyrimidin-4-yl)oxy)benzo[d]thiazol-2-yl)acetamide
• CAS NO: 659730-32-2
• Molecular Formula: C₂₀H₁₃F₃N₄O₂S
• Molecular Weight: 430.41
• Product Categories: API;Inhibitors
• Mol File: 659730-32-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 227℃
• Appearance: /
• Density: 1.458
• Solubility: ≥21.5 mg/mL in DMSO; insoluble in H2O; ≥4.93 mg/mL in EtOH
• PKA: 10.19±0.70(Predicted)
• CAS DataBase Reference: Amg 517(CAS DataBase Reference)
• NIST Chemistry Reference: Amg 517(659730-32-2)
• EPA Substance Registry System: Amg 517(659730-32-2)

Safety Data

• Hazardous Substances Data: 659730-32-2(Hazardous Substances Data)

Usage

Uses

AMG-517 is a novel TRPV1 antagonist.

Upstream product

• 7471-03-6 2-amino-4-hydroxybenzothiazole 
• 659729-09-6 4-chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine 
• 659730-31-1 4-[6-(4-trifluoromethylphenyl)pyrimidin-4-yloxy]benzothiazol-2-ylamine 
• 108-24-7 acetic anhydride 

Relevant articles and documents

Novel vanilloid receptor-1 antagonists: 2. Structure-activity relationships of 4-oxopyrimidines leading to the selection of a clinical candidate

A series of novel 4-oxopyrimidine TRPV1 antagonists was evaluated in assays measuring the blockade of capsaicin or acid-induced influx of calcium into CHO cells expressing TRPV1. The investigation of the structure-activity relationships in the heterocyclic A-region revealed the optimum pharmacophoric elements required for activity in this series and resulted in the identification of subnanomolar TRPV1 antagonists. The most potent of these antagonists were thoroughly profiled in pharmacokinetic assays. Optimization of the heterocyclic A-region led to the design and synthesis of 23, a compound that potently blocked multiple modes of TRPV1 activation. Compound 23 was shown to be effective in a rodent "on-target" biochemical challenge model (capsaicin-induced flinch, ED50 = 0.33 mg/kg p.o.) and was antihyperalgesic in a model of inflammatory pain (CFA-induced thermal hyperalgesia, MED = 0.83 mg/kg, p.o.). Based on its in vivo efficacy and pharmacokinetic profile, compound 23 (N-{4-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl} -acetamide; AMG 517) was selected for further evaluation in human clinical trials.