1-[(7-methoxy-2-oxo-2H-chromen-4-yl)methyl]-3,5,7-triaza-1-azoniatricyclo[3.3.1.1³,⁷]decane bromide | 157170-71-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 1-[(7-methoxy-2-oxo-2H-chromen-4-yl)methyl]-3,5,7-triaza-1-azoniatricyclo[3.3.1.1³,⁷]decane bromide
• CAS: 157170-71-3
• 化学式: Br*C₁₇H₂₁N₄O₃
• 分子量: 409.283
• InChiKey: PPPFEXPAYVABMW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.19
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  49.16
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-[(7-methoxy-2-oxo-2H-chromen-4-yl)methyl]-3,5,7-triaza-1-azoniatricyclo[3.3.1.1³,⁷]decane bromide 在 盐酸 作用下， 以 水 为溶剂， 反应 2.5h， 以95%的产率得到(7-methoxy-2-oxo-2H-chromen-4-yl)methanaminium chloride
  参考文献：
  名称：

  Designing Anti-inflammatory Drugs from Parasitic Worms: A Synthetic Small Molecule Analogue of the Acanthocheilonema viteae Product ES-62 Prevents Development of Collagen-Induced Arthritis

  摘要：

  In spite of increasing evidence that parasitic worms may protect humans from developing allergic and autoimmune diseases and the continuing identification of defined helminth-derived immunomodulatory molecules, to date no new anti-inflammatory drugs have been developed from these organisms. We have approached this matter in a novel manner by synthesizing a library of drug-like small molecules based upon phosphorylcholine, the active moiety of the anti-inflammatory Acanthocheilonema viteae product, ES-62, which as an immunogenic protein is unsuitable for use as a drug. Following preliminary in vitro screening for inhibitory effects responses, a sulfone-containing phosphorylcholine analogue (11a) was selected for testing in collagen-induced arthritis (CIA). Testing revealed that 11a was as effective as ES-62 in protecting DBA/1 mice from developing CIA and mirrored its mechanism of action in downregulating the TLR/IL-1R transducer, MyD88. 11a is thus a novel prototype for anti-inflammatory drug development. on relevant macrophage cytokine an in vivo model of inflammation,

  DOI：

  10.1021/jm401251p
• 作为产物：
  描述：

  4-溴甲基-7-甲氧基香豆素 、 乌洛托品 生成 1-[(7-methoxy-2-oxo-2H-chromen-4-yl)methyl]-3,5,7-triaza-1-azoniatricyclo[3.3.1.1³,⁷]decane bromide
  参考文献：
  名称：

  Designing Anti-inflammatory Drugs from Parasitic Worms: A Synthetic Small Molecule Analogue of the Acanthocheilonema viteae Product ES-62 Prevents Development of Collagen-Induced Arthritis

  摘要：

  In spite of increasing evidence that parasitic worms may protect humans from developing allergic and autoimmune diseases and the continuing identification of defined helminth-derived immunomodulatory molecules, to date no new anti-inflammatory drugs have been developed from these organisms. We have approached this matter in a novel manner by synthesizing a library of drug-like small molecules based upon phosphorylcholine, the active moiety of the anti-inflammatory Acanthocheilonema viteae product, ES-62, which as an immunogenic protein is unsuitable for use as a drug. Following preliminary in vitro screening for inhibitory effects responses, a sulfone-containing phosphorylcholine analogue (11a) was selected for testing in collagen-induced arthritis (CIA). Testing revealed that 11a was as effective as ES-62 in protecting DBA/1 mice from developing CIA and mirrored its mechanism of action in downregulating the TLR/IL-1R transducer, MyD88. 11a is thus a novel prototype for anti-inflammatory drug development. on relevant macrophage cytokine an in vivo model of inflammation,

  DOI：

  10.1021/jm401251p