6-bromo-8-(4-methoxybenzamido)-4-oxo-4H-chromene-2-carboxylic acid | 1443367-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-bromo-8-(4-methoxybenzamido)-4-oxo-4H-chromene-2-carboxylic acid
• 英文别名: 6-Bromo-8-(4-methoxybenzamido)-4-oxo-4h-chromene-2-carboxylic acid；6-bromo-8-[(4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid
• CAS: 1443367-20-1
• 化学式: C₁₈H₁₂BrNO₆
• 分子量: 418.2
• InChiKey: TZKQFDIFVZAYER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  8-amino-6-bromo-4-oxo-4H-chromene-2-carboxylic acid ethyl ester 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 48.0h， 生成 6-bromo-8-(4-methoxybenzamido)-4-oxo-4H-chromene-2-carboxylic acid
  参考文献：
  名称：

  8-Benzamidochromen-4-one-2-carboxylic Acids: Potent and Selective Agonists for the Orphan G Protein-Coupled Receptor GPR35

  摘要：

  8-Amido-chromen-4-one-2-carboxylic acid derivatives were identified as novel agonists at the G protein-coupled orphan receptor GPR35. They were characterized by a beta-arrestin recruitment assay and optimized to obtain agonists with nanomolar potency for the human GPR35. The compounds were found to exhibit high selectivity versus the related GPR55. The most potent agonists were 6-bromo-8-(4-methoxybenzamido)-4-oxo-4H-chromene-2-carboxylic acid (85, EC50 12.1 nM) and 6-bromo-8-(2-chloro-4-methoxybenzamido)-4-oxo-4H-chromene-2-carboxylic acid (90, EC50 11.1 nM), both of which were >1700 fold selective versus GPR55. Most compounds were considerably less potent at rat and mouse than at human GPR35. 6-Bromo-8-(2-methoxybenzamido)-4-oxo-4H-chromene-2-carboxylic acid (87) was the only derivative that activated GPR35 of all three species at similar, low micromolar concentration. Compounds 85 and 90 are the most potent agonists at the human GPR35 known to date and might thus serve as powerful pharmacological tools to further elucidate the receptor's (patho)physiological role and its potential as a future drug target.

  DOI：

  10.1021/jm400587g

文献信息

• [EN] TL1A PATIENT SELECTION METHODS, SYSTEMS, AND DEVICES<br/>[FR] MÉTHODES, SYSTÈMES ET DISPOSITIFS DE SÉLECTION DE PATIENT TL1A
  申请人：PROMETHEUS BIOSCIENCES INC

  公开号：WO2020232125A1

  公开（公告）日：2020-11-19

  Provided are methods, systems, and kits for selecting a patient for treatment with a therapeutic agent based on a presence of a genotype associated with a positive therapeutic response to the therapeutic agent. The therapeutic agent, in some embodiments, is an inhibitor of TL1A activity or expression, such as for example, an anti-TL1A antibody.
• 8-Benzamidochromen-4-one-2-carboxylic Acids: Potent and Selective Agonists for the Orphan G Protein-Coupled Receptor GPR35
  作者：Mario Funke、Dominik Thimm、Anke C. Schiedel、Christa E. Müller

  DOI：10.1021/jm400587g

  日期：2013.6.27

  8-Amido-chromen-4-one-2-carboxylic acid derivatives were identified as novel agonists at the G protein-coupled orphan receptor GPR35. They were characterized by a beta-arrestin recruitment assay and optimized to obtain agonists with nanomolar potency for the human GPR35. The compounds were found to exhibit high selectivity versus the related GPR55. The most potent agonists were 6-bromo-8-(4-methoxybenzamido)-4-oxo-4H-chromene-2-carboxylic acid (85, EC50 12.1 nM) and 6-bromo-8-(2-chloro-4-methoxybenzamido)-4-oxo-4H-chromene-2-carboxylic acid (90, EC50 11.1 nM), both of which were >1700 fold selective versus GPR55. Most compounds were considerably less potent at rat and mouse than at human GPR35. 6-Bromo-8-(2-methoxybenzamido)-4-oxo-4H-chromene-2-carboxylic acid (87) was the only derivative that activated GPR35 of all three species at similar, low micromolar concentration. Compounds 85 and 90 are the most potent agonists at the human GPR35 known to date and might thus serve as powerful pharmacological tools to further elucidate the receptor's (patho)physiological role and its potential as a future drug target.