3-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-methylindole | 88973-00-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-methylindole
• 英文别名: 2,6-Di-tert-butyl-4-(2-methyl-1H-indol-3-yl)phenol；2,6-ditert-butyl-4-(2-methyl-1H-indol-3-yl)phenol
• CAS: 88973-00-6
• 化学式: C₂₃H₂₉NO
• 分子量: 335.489
• InChiKey: HWDKWDLUQNIFDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯胺 、 4-(2-bromopropionyl)-2,6-di-tert-butylphenol 以9%的产率得到
  参考文献：
  名称：

  ISOMURA, YASUO;ITO, NORIKI;HOMMA, HIROSHIGE;ABE, TETSUSHI;KUBO, KAZUO, CHEM. AND PHARM. BULL., 1983, 31, N 9, 3168-3178

  摘要：

  DOI：

文献信息

• Studies on the synthesis and anti-inflammatory activity of 2,6-di-tert-butylphenols with a heterocyclic group at the 4-position. I.
  作者：YASUO ISOMURA、NORIKI ITO、HIROSHIGE HOMMA、TETSUSHI ABE、KAZUO KUBO

  DOI：10.1248/cpb.31.3168

  日期：——

  A number of 2, 6-di-tert-butylphenols with a heterocyclic group at the 4-position were prepared. The heterocyclic groups were as follows : benzoxazole, benzothiazole, benzimidazole, indole, imidazo [1, 2-a] pyridine and imidazo [1, 2-a] pyrimidine. Anti-inflammatory activity of these compounds was examined by using the adjuvant-induced arthritis (A. A) assay. Some compounds were further tested in carrageenin-induced rat paw edema (CIPE) assay and AcOH-induced writhing (AIW) assay in mice. The anti-inflammatory activity was greatly dependent on the value of the heterocyclic group. Among these compounds, 2-(3, 5-di-tert-butyl-4-hydroxyphenyl)-benzoxazole (IIa) and 2-(3, 5-di-tert-butyl-4-hydroxyphenyl) indole (Xg) showed very potent activity. Both IIa and Xg had a minimum effective dose of 5 mg/kg (p. o.) in A. A assay and showed stronger activity than phenylbutazone in CIPE assay but weaker analgesic activity than aminopyrine in AIW assay.

  制备了一系列在4位含有杂环基团的2,6-二叔丁基苯酚。这些杂环基团包括：苯并噁唑、苯并噻唑、苯并咪唑、吲哚、咪唑[1,2-a]喹啉和咪唑[1,2-a]嘧啶。这些化合物的抗炎活性通过佐剂诱导的关节炎（A.A）测定进行评估。部分化合物在卡拉胶诱导的大鼠足肿胀（CIPE）测定和醋酸诱导的小鼠扭动（AIW）测定中进一步测试。这些化合物的抗炎活性在很大程度上取决于杂环基团的性质。在这些化合物中，2-(3,5-二叔丁基-4-羟基苯基)苯并噁唑（IIa）和2-(3,5-二叔丁基-4-羟基苯基)吲哚（Xg）表现出非常强的活性。IIa和Xg在A.A测定中的最小有效剂量为5 mg/kg（口服），在CIPE测定中显示出比苯基布托松更强的活性，但在AIW测定中的镇痛活性则弱于氨基吡啶。
• ISOMURA, YASUO;ITO, NORIKI;HOMMA, HIROSHIGE;ABE, TETSUSHI;KUBO, KAZUO, CHEM. AND PHARM. BULL., 1983, 31, N 9, 3168-3178
  作者：ISOMURA, YASUO、ITO, NORIKI、HOMMA, HIROSHIGE、ABE, TETSUSHI、KUBO, KAZUO

  DOI：——

  日期：——