3-{hydroxy-[1-(4-methylsulfonyl)-1H-indol-2-yl]methyl}-indole-1-carboxylic acid tert-butyl ester | 352674-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-{hydroxy-[1-(4-methylsulfonyl)-1H-indol-2-yl]methyl}-indole-1-carboxylic acid tert-butyl ester
• CAS: 352674-31-8
• 化学式: C₂₉H₂₈N₂O₅S
• 分子量: 516.618
• InChiKey: CQUZDYCWHXKLKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  37.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  90.53
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-{hydroxy-[1-(4-methylsulfonyl)-1H-indol-2-yl]methyl}-indole-1-carboxylic acid tert-butyl ester 在 sodium 、 三氯氧磷 作用下， 以 四氢呋喃 、 氨 、 正戊烷 为溶剂， 生成 Malassezin
  参考文献：
  名称：

  Malassezin—a novel agonist of the Arylhydrocarbon receptor from the yeast Malassezia furfur

  摘要：

  The yeast Malassezia furfur converts tryptophan into several indole compounds. One of three malassezin, was identified as 2-( 1H-indol-3-ylmethl)- 1 H-indole-3-carbaldehyde (I). It was synthesized from N-Boc-indole-3-carbaldehyde in five steps with 12% overall yield. The compound easily cyclizes to indolo[3.2-b]carbazole (7) which is known to interact with the arylhydrocarbon receptor (AHR). Similarly, malassezin was found to induce cytochrome P450 as an agonist of AHR(EC50 = 1.57 muM) in rat hepatocytes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00319-9
• 作为产物：
  描述：

  3-吲哚甲醛 在 4-二甲氨基吡啶 、 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.25h， 生成 3-{hydroxy-[1-(4-methylsulfonyl)-1H-indol-2-yl]methyl}-indole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Malassezin—a novel agonist of the Arylhydrocarbon receptor from the yeast Malassezia furfur

  摘要：

  The yeast Malassezia furfur converts tryptophan into several indole compounds. One of three malassezin, was identified as 2-( 1H-indol-3-ylmethl)- 1 H-indole-3-carbaldehyde (I). It was synthesized from N-Boc-indole-3-carbaldehyde in five steps with 12% overall yield. The compound easily cyclizes to indolo[3.2-b]carbazole (7) which is known to interact with the arylhydrocarbon receptor (AHR). Similarly, malassezin was found to induce cytochrome P450 as an agonist of AHR(EC50 = 1.57 muM) in rat hepatocytes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00319-9