3-indolemethylthioacetate | 86204-54-8

• 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-indolemethylthioacetate
• 英文别名: indolyl-3-methyl thioacetate；3-indolylmethyl thioacetate；S-(1H-indol-3-ylmethyl) ethanethioate
• CAS: 86204-54-8
• 化学式: C₁₁H₁₁NOS
• 分子量: 205.28
• InChiKey: OHDQLGGJKAOMCI-UHFFFAOYSA-N

物化性质

• 沸点：
  379.9±25.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-indolemethylthioacetate 在 水 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.08h， 生成 吲哚-3-甲醇
  参考文献：
  名称：

  The cruciferous phytoalexins rapalexin A, brussalexin A and erucalexin: Chemistry and metabolism in Leptosphaeria maculans

  摘要：

  The interactions of the cruciferous phytoalexins rapalexin A (1), brussalexin A (2) and erucalexin (3) with the fungal plant pathogen Leptosphaeria maculans were analyzed and their inhibitory activities against this pathogen were determined. The reaction of L. maculans to N-methyl S-(indolyl-3-methyl) carbamodithioate, an analogue of brussalexin A, was also investigated. Rapalexin A was resistant to metabolism and was the most inhibitory of all compounds tested, suggesting that increasing concentrations of rapalexin A in Brassica species would improve their disease resistance to L. maculans. By contrast, erucalexin was quickly detoxified by reduction to yield 3-dihydroerucalexins. The relative configurations of the diastereomeric mixture of dihydroerucalexins were established by 1D H-1 nuclear Overhauser enhancement spectroscopy (NOE). Brussalexin A was chemically unstable decomposing mainly to indolyl-3-methanol, a product with anti-cancer properties. For this reason, brussalexin A might be of interest to use as a prodrug. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.020
• 作为产物：
  描述：

  1-(1H-indol-3-yl)-N,N,N-trimethylmethanaminium methyl sulfate 、 potassium thioacetate 以 水 为溶剂， 反应 0.25h， 以76%的产率得到3-indolemethylthioacetate
  参考文献：
  名称：

  Benghiat, Eric; Crooks, Peter A., Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 423 - 425

  摘要：

  DOI：

文献信息

• Efficient synthesis of brussalexin A, a remarkable phytoalexin from Brussels sprouts
  作者：M. Soledade C. Pedras、Qing-An Zheng、Mohammed G. Sarwar

  DOI：10.1039/b702156a

  日期：——

  The synthesis of brussalexin A, the first phytoalexin containing an allyl thiolcarbamate group, and its selective inhibitory activity against fungal plant pathogens is described.

  描述了布鲁萨利新 A 的合成，这是第一种含有烯丙基硫基氨基甲酸酯的植物抗菌素，以及其对植物真菌病原体的选择性抑制活性。
• Benghiat, Eric; Crooks, Peter A., Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 423 - 425
  作者：Benghiat, Eric、Crooks, Peter A.

  DOI：——

  日期：——
• The cruciferous phytoalexins rapalexin A, brussalexin A and erucalexin: Chemistry and metabolism in Leptosphaeria maculans
  作者：M. Soledade C. Pedras、Vijay K. Sarma-Mamillapalle

  DOI：10.1016/j.bmc.2012.05.020

  日期：2012.7

  The interactions of the cruciferous phytoalexins rapalexin A (1), brussalexin A (2) and erucalexin (3) with the fungal plant pathogen Leptosphaeria maculans were analyzed and their inhibitory activities against this pathogen were determined. The reaction of L. maculans to N-methyl S-(indolyl-3-methyl) carbamodithioate, an analogue of brussalexin A, was also investigated. Rapalexin A was resistant to metabolism and was the most inhibitory of all compounds tested, suggesting that increasing concentrations of rapalexin A in Brassica species would improve their disease resistance to L. maculans. By contrast, erucalexin was quickly detoxified by reduction to yield 3-dihydroerucalexins. The relative configurations of the diastereomeric mixture of dihydroerucalexins were established by 1D H-1 nuclear Overhauser enhancement spectroscopy (NOE). Brussalexin A was chemically unstable decomposing mainly to indolyl-3-methanol, a product with anti-cancer properties. For this reason, brussalexin A might be of interest to use as a prodrug. (C) 2012 Elsevier Ltd. All rights reserved.