N-(3-hydroxyethyl)-indole-3-carboxamide | 260981-71-3

• 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: N-(3-hydroxyethyl)-indole-3-carboxamide
• 英文别名: N-(2-hydroxy)ethyl indole-3-carboxamide；N-(2-hydroxyethyl)-1H-indole-3-carboxamide
• CAS: 260981-71-3
• 化学式: C₁₁H₁₂N₂O₂
• mdl: MFCD12178799
• 分子量: 204.228
• InChiKey: HCNTVRWDNCJMFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  65.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-hydroxyethyl)-indole-3-carboxamide 在 zinc diacetate 作用下， 反应 2.0h， 以84%的产率得到2-(3-吲哚基)-2-恶唑啉
  参考文献：
  名称：

  Biotransformation of the phytoalexin camalexin by the phytopathogen Rhizoctonia solani

  摘要：

  The unusual metabolism of the cruciferous phytoalexin camalexin by virulent and weakly virulent isolates of the root rot fungus Rhizoctonia solani Kuhn is reported. This biotransformation proceeded via 5-hydroxycamalexin, which was further biotransformed into more polar metabolites. Importantly, the metabolites resulting from transformation of camalexin were significantly less toxic to the pathogen than camalexin. Thus, it was concluded that R. solani can detoxify camalexin through oxidation of the indole ring. The chemistry involved in the structure determination of the intermediates of this pathway, their synthesis as well as antifungal activity is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00479-3
• 作为产物：
  描述：

  3-吲哚甲酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 N-(3-hydroxyethyl)-indole-3-carboxamide
  参考文献：
  名称：

  Yamada, Fumio; Yamada, Koji; Takeda, Hikari, Heterocycles, 2001, vol. 55, # 12, p. 2361 - 2368

  摘要：

  DOI：

文献信息

• Yamada, Fumio; Yamada, Koji; Takeda, Hikari, Heterocycles, 2001, vol. 55, # 12, p. 2361 - 2368
  作者：Yamada, Fumio、Yamada, Koji、Takeda, Hikari、Somei, Masanori

  DOI：——

  日期：——
• Biotransformation of the phytoalexin camalexin by the phytopathogen Rhizoctonia solani
  作者：M.Soledade C. Pedras、Abdul Q. Khan

  DOI：10.1016/s0031-9422(99)00479-3

  日期：2000.1

  The unusual metabolism of the cruciferous phytoalexin camalexin by virulent and weakly virulent isolates of the root rot fungus Rhizoctonia solani Kuhn is reported. This biotransformation proceeded via 5-hydroxycamalexin, which was further biotransformed into more polar metabolites. Importantly, the metabolites resulting from transformation of camalexin were significantly less toxic to the pathogen than camalexin. Thus, it was concluded that R. solani can detoxify camalexin through oxidation of the indole ring. The chemistry involved in the structure determination of the intermediates of this pathway, their synthesis as well as antifungal activity is described. (C) 2000 Elsevier Science Ltd. All rights reserved.