N-[3-(2-bromobenzamido)phenyl]furan-2-carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[3-(2-bromobenzamido)phenyl]furan-2-carboxamide
• 英文别名: N-[3-[(2-bromobenzoyl)amino]phenyl]furan-2-carboxamide
• 化学式: C₁₈H₁₃BrN₂O₃
• 分子量: 385.217
• InChiKey: FWNHNUDMJPPIIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  糠酸（呋喃甲酸） 、 N-(3-aminophenyl)-2-bromobenzamide hydrochloride 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以44%的产率得到N-[3-(2-bromobenzamido)phenyl]furan-2-carboxamide
  参考文献：
  名称：

  The parmodulin NRD-21 is an allosteric inhibitor of PAR1 Gq signaling with improved anti-inflammatory activity and stability

  摘要：

  Novel analogs of the allosteric, biased PAR1 ligand ML161 (parmodulin 2, PM2) were prepared in order to identify potential anti-thrombotic and anti-inflammatory compounds of the parmodulin class with improved properties. Investigations of structure-activity relationships of the western portion of the 1,3-diaminobenzene scaffold were performed using an intracellular calcium mobilization assay with endothelial cells, and several heterocycles were identified that inhibited PAR1 at sub-micromolar concentrations. The oxazole NRD-21 was profiled in additional detail, and it was confirmed to act as a selective, reversible, negative allosteric modulator of PAR1. In addition to inhibiting human platelet aggregation, it showed superior anti-inflammatory activity to ML161 in a qPCR assay measuring the expression of tissue factor in response to the cytokine TNF-alpha in endothelial cells. Additionally, NRD-21 is much more plasma stable than ML161, and is a promising lead compound for the parmodulin class for anti-thrombotic and anti-inflammatory indications.

  DOI：

  10.1016/j.bmc.2019.06.043

文献信息

• US9422262B2
  申请人：——

  公开号：US9422262B2

  公开（公告）日：2016-08-23
• [EN] COMPOUNDS AND METHODS FOR TREATING DISEASES MEDIATED BY PROTEASE ACTIVATED RECEPTORS<br/>[FR] COMPOSÉS ET MÉTHODES DE TRAITEMENT DE MALADIES À MÉDIATION PAR DES RÉCEPTEURS ACTIVÉS PAR UNE PROTÉASE
  申请人：BROAD INST INC

  公开号：WO2012040636A2

  公开（公告）日：2012-03-29

  The invention relates to the use of a compound of Formula I for the treatment of protease-activated receptor mediated diseases by the administration of a compound of Formula I or a prodrug or metabolite thereof.