N-[2-(dimethylamino)ethyl](2-naphthyl)methanesulfonamide | 1496553-78-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[2-(dimethylamino)ethyl](2-naphthyl)methanesulfonamide
• 英文别名: N-[2-(dimethylamino)ethyl]-1-naphthalen-2-ylmethanesulfonamide
• CAS: 1496553-78-6
• 化学式: C₁₅H₂₀N₂O₂S
• 分子量: 292.402
• InChiKey: HPMNWFMPZNONRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(氯甲基)萘 在 sodium sulphite-heptahydrate 、 五氯化磷 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 3.75h， 生成 N-[2-(dimethylamino)ethyl](2-naphthyl)methanesulfonamide
  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

文献信息

• Designing Anti-inflammatory Drugs from Parasitic Worms: A Synthetic Small Molecule Analogue of the <i>Acanthocheilonema viteae</i> Product ES-62 Prevents Development of Collagen-Induced Arthritis
  作者：Lamyaa Al-Riyami、Miguel A. Pineda、Justyna Rzepecka、Judith K. Huggan、Abedawn I. Khalaf、Colin J. Suckling、Fraser J. Scott、David T. Rodgers、Margaret M. Harnett、William Harnett

  DOI：10.1021/jm401251p

  日期：2013.12.27

  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,