[(2S,3R,5R,6R)-5-(1H-indole-3-carbonyloxy)-6-[(2R)-5-methoxy-5-oxopentan-2-yl]oxy-2-methyloxan-3-yl] 1H-indole-3-carboxylate | 1172590-15-6

• 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: [(2S,3R,5R,6R)-5-(1H-indole-3-carbonyloxy)-6-[(2R)-5-methoxy-5-oxopentan-2-yl]oxy-2-methyloxan-3-yl] 1H-indole-3-carboxylate
• CAS: 1172590-15-6
• 化学式: C₃₀H₃₂N₂O₈
• 分子量: 548.593
• InChiKey: HHUTZTFDELQJSQ-GOTIHPCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2S,3R,5R,6R)-5-(1H-indole-3-carbonyloxy)-6-[(2R)-5-methoxy-5-oxopentan-2-yl]oxy-2-methyloxan-3-yl] 1H-indole-3-carboxylate 在 甲醇 、 sodium 、 溶剂黄146 、 三甲基硅烷化重氮甲烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 4.57h， 以26%的产率得到
  参考文献：
  名称：

  An Indole-Containing Dauer Pheromone Component with Unusual Dauer Inhibitory Activity at Higher Concentrations

  摘要：

  In Caenorhabditis elegans, the dauer pheromone, which consists of a number of derivatives of the 3,6-dideoxysugar ascarylose, is the primary cue for entry into the stress-resistant, "nonaging" dauer larval stage. Here, using activity-guided fractionation and NMR-based structure elucidation, a structurally novel, indole-3-carboxyl-modified ascaroside is identified that promotes dauer formation at low nanomolar concentrations but inhibits dauer formation at higher concentrations.

  DOI：

  10.1021/ol901011c
• 作为产物：
  描述：

  1H-吲哚-3-羰酰氯 、 methyl (4R)-4-[(2R,3R,5R,6S)-3,5-dihydroxy-6-methyloxan-2-yl]oxypentanoate 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.62h， 以83%的产率得到[(2S,3R,5R,6R)-5-(1H-indole-3-carbonyloxy)-6-[(2R)-5-methoxy-5-oxopentan-2-yl]oxy-2-methyloxan-3-yl] 1H-indole-3-carboxylate
  参考文献：
  名称：

  An Indole-Containing Dauer Pheromone Component with Unusual Dauer Inhibitory Activity at Higher Concentrations

  摘要：

  In Caenorhabditis elegans, the dauer pheromone, which consists of a number of derivatives of the 3,6-dideoxysugar ascarylose, is the primary cue for entry into the stress-resistant, "nonaging" dauer larval stage. Here, using activity-guided fractionation and NMR-based structure elucidation, a structurally novel, indole-3-carboxyl-modified ascaroside is identified that promotes dauer formation at low nanomolar concentrations but inhibits dauer formation at higher concentrations.

  DOI：

  10.1021/ol901011c

文献信息

• An Indole-Containing Dauer Pheromone Component with Unusual Dauer Inhibitory Activity at Higher Concentrations
  作者：Rebecca A. Butcher、Justin R. Ragains、Jon Clardy

  DOI：10.1021/ol901011c

  日期：2009.7.16

  In Caenorhabditis elegans, the dauer pheromone, which consists of a number of derivatives of the 3,6-dideoxysugar ascarylose, is the primary cue for entry into the stress-resistant, "nonaging" dauer larval stage. Here, using activity-guided fractionation and NMR-based structure elucidation, a structurally novel, indole-3-carboxyl-modified ascaroside is identified that promotes dauer formation at low nanomolar concentrations but inhibits dauer formation at higher concentrations.