3-chloro-5-hexyl-2,6-dimethoxybenzoic acid | 1143527-05-2

• 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-chloro-5-hexyl-2,6-dimethoxybenzoic acid
• 英文别名: 3-Chloro-5-hexyl-2,6-dimethoxybenzoic acid
• CAS: 1143527-05-2
• 化学式: C₁₅H₂₁ClO₄
• 分子量: 300.782
• InChiKey: RNUVAUWSHCOTSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-chloro-5-hexyl-2,6-dimethoxybenzoic acid 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 苯 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Revised Structure and Synthesis of Celastramycin A, A Potent Innate Immune Suppressor

  摘要：

  After searching for natural substances that regulate innate immunity using the ex vivo Drosophila culture system, a benzoyl pyrrole-type compound, celastramycin A, was identified and isolated as a potent suppressor. By synthesizing the previously reported structure 1 and another benzoyl pyrrole-type compound 2 reported in a Japanese patent, the correct structure of celastramycin A was confirmed to be 2. Compound 2 suppressed the production of IL-8 (IC50 0.06 mu g/mL) in human umbilical vein endothelial cells (HUVECs).

  DOI：

  10.1021/ol9002306
• 作为产物：
  描述：

  3-hexyl-2,6-dimethoxybenzoic acid 在 磺酰氯 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 3.0h， 以70%的产率得到3-chloro-5-hexyl-2,6-dimethoxybenzoic acid
  参考文献：
  名称：

  Revised Structure and Synthesis of Celastramycin A, A Potent Innate Immune Suppressor

  摘要：

  After searching for natural substances that regulate innate immunity using the ex vivo Drosophila culture system, a benzoyl pyrrole-type compound, celastramycin A, was identified and isolated as a potent suppressor. By synthesizing the previously reported structure 1 and another benzoyl pyrrole-type compound 2 reported in a Japanese patent, the correct structure of celastramycin A was confirmed to be 2. Compound 2 suppressed the production of IL-8 (IC50 0.06 mu g/mL) in human umbilical vein endothelial cells (HUVECs).

  DOI：

  10.1021/ol9002306

文献信息

• Revised Structure and Synthesis of Celastramycin A, A Potent Innate Immune Suppressor
  作者：Haruhisa Kikuchi、Mizuki Sekiya、Yasuhiro Katou、Kazunori Ueda、Takahiro Kabeya、Shoichiro Kurata、Yoshiteru Oshima

  DOI：10.1021/ol9002306

  日期：2009.4.16

  After searching for natural substances that regulate innate immunity using the ex vivo Drosophila culture system, a benzoyl pyrrole-type compound, celastramycin A, was identified and isolated as a potent suppressor. By synthesizing the previously reported structure 1 and another benzoyl pyrrole-type compound 2 reported in a Japanese patent, the correct structure of celastramycin A was confirmed to be 2. Compound 2 suppressed the production of IL-8 (IC50 0.06 mu g/mL) in human umbilical vein endothelial cells (HUVECs).