N-methyl-S-(3-indolylmethyl)carbamodithioate | 1395069-51-8

• 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: N-methyl-S-(3-indolylmethyl)carbamodithioate
• 英文别名: 1H-indol-3-ylmethyl N-methylcarbamodithioate
• CAS: 1395069-51-8
• 化学式: C₁₁H₁₂N₂S₂
• 分子量: 236.362
• InChiKey: NIXSRAWVFMDSBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methyl-S-(3-indolylmethyl)carbamodithioate 在 水 作用下， 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：

  3-indolemethylthioacetate 在 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 N-methyl-S-(3-indolylmethyl)carbamodithioate
  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