5-Butyl-7-methoxy-1-methyl-1H-indol-4-ol, acetate (ester) | 99107-54-7

• 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: 5-Butyl-7-methoxy-1-methyl-1H-indol-4-ol, acetate (ester)
• 英文别名: 1H-Indol-4-ol, 5-butyl-7-methoxy-1-methyl-, 4-acetate；(5-butyl-7-methoxy-1-methylindol-4-yl) acetate
• CAS: 99107-54-7
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: JIUVITDMSXZWRL-UHFFFAOYSA-N

物化性质

• 沸点：
  425.6±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酸酐 、 1-己炔 、 alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 5-Butyl-7-methoxy-1-methyl-1H-indol-4-ol, acetate (ester)
  参考文献：
  名称：

  1,4-Dihydronaphthoquinones, hydroindoloquinones, benzofurans, and benzothiophenes as inhibitors of 5-lipoxygenase. Synthesis and structure-activity studies

  摘要：

  A series of substituted 1,4-dihydronaphthoquinones, hydroindoloquinones, benzofuran-4,7-dihydroquinones, and benzothiophene-4,7-dihydroquinones were synthesized and evaluated for inhibitory activity against 5-lipoxygenase. These compounds were found to be active in vitro for LTC4/D4 inhibition with the potencies (IC50's) ranging from 0.2 to 85 microM. Active 1,4-dihydronaphthoquinone acetates (IC50 less than 20 microM) were evaluated in an ex vivo LTB4 inhibition assay. The acetates of 1,4-dihydronaphthoquinones containing the alkyl substituent(s) (2-n-butyl, 11, and 2,3-diethyl, 15) exhibited the best activity in LTC4/D4 inhibition (IC50 = 0.2-0.4 microM, in vitro) as well as in LTB4 inhibition (60-75% inhibition).

  DOI：

  10.1021/jm00164a050

文献信息

• 1,4-Dihydronaphthoquinones, hydroindoloquinones, benzofurans, and benzothiophenes as inhibitors of 5-lipoxygenase. Synthesis and structure-activity studies
  作者：Ayako Yamashita、Robert G. Schaub、Michael K. Bach、Gordon J. White、Arthur Toy、Nabil B. Ghazal、Michael D. Burdick、John R. Brashler、Marilyn S. Holm

  DOI：10.1021/jm00164a050

  日期：1990.2

  A series of substituted 1,4-dihydronaphthoquinones, hydroindoloquinones, benzofuran-4,7-dihydroquinones, and benzothiophene-4,7-dihydroquinones were synthesized and evaluated for inhibitory activity against 5-lipoxygenase. These compounds were found to be active in vitro for LTC4/D4 inhibition with the potencies (IC50's) ranging from 0.2 to 85 microM. Active 1,4-dihydronaphthoquinone acetates (IC50 less than 20 microM) were evaluated in an ex vivo LTB4 inhibition assay. The acetates of 1,4-dihydronaphthoquinones containing the alkyl substituent(s) (2-n-butyl, 11, and 2,3-diethyl, 15) exhibited the best activity in LTC4/D4 inhibition (IC50 = 0.2-0.4 microM, in vitro) as well as in LTB4 inhibition (60-75% inhibition).
• Reaction of a pyrrole-carbene chromium complex with alkynes: a facile hydroindoloquinone formation with in-situ protection.
  作者：A. Yamashita、T.A. Scahill、A. Toy

  DOI：10.1016/s0040-4039(00)98594-0

  日期：1985.1
• YAMASHITA, A.;SCAHILL, T. A.;TOY, A., TETRAHEDRON LETT., 1985, 26, N 25, 2969-2972
  作者：YAMASHITA, A.、SCAHILL, T. A.、TOY, A.

  DOI：——

  日期：——