S-methyl [(2-sulfanyl-1H-indolyl-3)methyl]carbamothioate | 1418290-91-1

• 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: S-methyl [(2-sulfanyl-1H-indolyl-3)methyl]carbamothioate
• 英文别名: S-methyl N-[(2-sulfanyl-1H-indol-3-yl)methyl]carbamothioate
• CAS: 1418290-91-1
• 化学式: C₁₁H₁₂N₂OS₂
• 分子量: 252.361
• InChiKey: VEEJKWLGBOZVPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 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：
  71.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-methyl [(2-sulfanyl-1H-indolyl-3)methyl]carbamothioate 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.08h， 以20%的产率得到S-methyl [(2-sulfanylmethyl-1H-indolyl-3)methyl]carbamothioate
  参考文献：
  名称：

  Unprecedented spirocyclization of 3-methyleneindoline-2-thiones during hydrolysis of the phytoalexin cyclobrassinin

  摘要：

  The phytoalexin cyclobrassinin is a plant defense that has additional importance since it inhibits brassinin hydrolase, a phytoalexin detoxifying enzyme produced by the plant pathogen Alternaria brassicicola. Hence, the 1,3-thiazino[6,5-b] indole scaffold of cyclobrassinin has great application as a lead structure to design potential inhibitors of brassinin detoxification. For this reason, it is necessary to determine whether A. brassicicola is able to transform cyclobrassinin. During this work new reactions of 1,3-thiazino[6,5-b] indoles and indoline-2-thiones and their unique [4+2] cycloaddition products were discovered and characterized. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.042
• 作为产物：
  描述：

  cyclobrassinin 在 Alternaria brassicicola cyclobrassinin hydrolase 作用下， 反应 2.0h， 生成 S-methyl [(2-sulfanyl-1H-indolyl-3)methyl]carbamothioate
  参考文献：
  名称：

  The phytoalexins brassilexin and camalexin inhibit cyclobrassinin hydrolase, a unique enzyme from the fungal pathogen Alternaria brassicicola

  摘要：

  Alternaria brassicicola is a fungal pathogen of many agriculturally important cruciferous crops. Cyclobrassinin hydrolase (CH) is an enzyme produced by A. brassicicola that catalyzes the transformation of the cruciferous phytoalexin cyclobrassinin into S-methyl[(2-sulfanyl-1H-indolyl-3)methyl]carbamothioate. The purification and characterization of CH was performed using a four-step chromatography method. SDS-PAGE and gel exclusion chromatography indicated that CH is a tetrameric protein with molecular mass of 330 kDa. Sequence analysis and chemical modification of CH with selective reagents suggested that the enzyme mediates hydrolysis of cyclobrassinin using a catalytic amino acid triad. Enzyme kinetic studies using cyclobrassinin and 1-methylcyclobrassinin as substrates revealed that CH displayed positive substrate cooperativity. Investigation of the effect of nine phytoalexins and two derivatives on the activity of CH indicated that six compounds displayed inhibitory activity: brassilexin, 1-methylbrassilexin, dioxibrassinin, camalexin, brassicanal A and sinalexin. The enzyme kinetics of CH strongly suggested that brassilexin and 1-methylbrassilexin are noncompetitive inhibitors of CH activity, and that camalexin is a competitive inhibitor while dioxibrassinin inhibits CH through a mixed mechanism. The phytoalexin brassilexin is the most effective inhibitor of CH (K-i = 32 +/- 9 mu M). These results suggest that crops able to accumulate higher concentration of brassilexin would display higher resistance levels to the fungus. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.005

文献信息

• Unprecedented spirocyclization of 3-methyleneindoline-2-thiones during hydrolysis of the phytoalexin cyclobrassinin
  作者：M. Soledade C. Pedras、Abbas Abdoli、Paulos B. Chumala、Pijus Saha、Gabriele Schatte

  DOI：10.1016/j.bmcl.2012.11.042

  日期：2013.1

  The phytoalexin cyclobrassinin is a plant defense that has additional importance since it inhibits brassinin hydrolase, a phytoalexin detoxifying enzyme produced by the plant pathogen Alternaria brassicicola. Hence, the 1,3-thiazino[6,5-b] indole scaffold of cyclobrassinin has great application as a lead structure to design potential inhibitors of brassinin detoxification. For this reason, it is necessary to determine whether A. brassicicola is able to transform cyclobrassinin. During this work new reactions of 1,3-thiazino[6,5-b] indoles and indoline-2-thiones and their unique [4+2] cycloaddition products were discovered and characterized. (C) 2012 Elsevier Ltd. All rights reserved.
• The phytoalexins brassilexin and camalexin inhibit cyclobrassinin hydrolase, a unique enzyme from the fungal pathogen Alternaria brassicicola
  作者：M. Soledade C. Pedras、Zoran Minic

  DOI：10.1016/j.bmc.2013.11.005

  日期：2014.1

  Alternaria brassicicola is a fungal pathogen of many agriculturally important cruciferous crops. Cyclobrassinin hydrolase (CH) is an enzyme produced by A. brassicicola that catalyzes the transformation of the cruciferous phytoalexin cyclobrassinin into S-methyl[(2-sulfanyl-1H-indolyl-3)methyl]carbamothioate. The purification and characterization of CH was performed using a four-step chromatography method. SDS-PAGE and gel exclusion chromatography indicated that CH is a tetrameric protein with molecular mass of 330 kDa. Sequence analysis and chemical modification of CH with selective reagents suggested that the enzyme mediates hydrolysis of cyclobrassinin using a catalytic amino acid triad. Enzyme kinetic studies using cyclobrassinin and 1-methylcyclobrassinin as substrates revealed that CH displayed positive substrate cooperativity. Investigation of the effect of nine phytoalexins and two derivatives on the activity of CH indicated that six compounds displayed inhibitory activity: brassilexin, 1-methylbrassilexin, dioxibrassinin, camalexin, brassicanal A and sinalexin. The enzyme kinetics of CH strongly suggested that brassilexin and 1-methylbrassilexin are noncompetitive inhibitors of CH activity, and that camalexin is a competitive inhibitor while dioxibrassinin inhibits CH through a mixed mechanism. The phytoalexin brassilexin is the most effective inhibitor of CH (K-i = 32 +/- 9 mu M). These results suggest that crops able to accumulate higher concentration of brassilexin would display higher resistance levels to the fungus. (C) 2013 Elsevier Ltd. All rights reserved.