3-[(4-Bromophenyl)methylsulfonyl]propan-1-ol | 1285171-28-9

• 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: 3-[(4-Bromophenyl)methylsulfonyl]propan-1-ol
• 英文别名: 3-[(4-bromophenyl)methylsulfonyl]propan-1-ol
• CAS: 1285171-28-9
• 化学式: C₁₀H₁₃BrO₃S
• 分子量: 293.181
• InChiKey: OTWCJMQSDFADSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(4-Bromophenyl)methylsulfonyl]propan-1-ol 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 1-(3-((4-bromobenzyl)sulfonyl)propyl)pyrrolidine
  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：

  3-[(4-Bromophenyl)methylsulfanyl]propan-1-ol 在 间氯过氧苯甲酸 作用下， 反应 20.0h， 以78%的产率得到3-[(4-Bromophenyl)methylsulfonyl]propan-1-ol
  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