brassitine | 113866-42-5

• 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: brassitine
• 英文别名: brassitin；S-methyl N-(1H-indol-3-ylmethyl)carbamothioate
• CAS: 113866-42-5
• 化学式: C₁₁H₁₂N₂OS
• 分子量: 220.295
• InChiKey: GHGDPZHQDKPWOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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：
  70.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  芸薹宁 在 双氧水 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 以8%的产率得到brassitine
  参考文献：
  名称：

  Three sulphur-containing stress metabolites from Japanese radish

  摘要：

  Three new brassinin related stress metabolites, named brassitin, N-methoxyspirobrassinol methyl ether and N-methoxyspirobrassinol, were isolated from the Japanese radish 'Daikon' (Raphanus sativus var. hortensis) after inoculation with Pseudomonas cichorii. Their structures have been established on the basis of spectroscopic data and chemical reactions. N-Methoxyspitobrassinol has an unusual hemi-aminal structure, and occurs as a mixture of diastereomers. The occurrence of N-methoxyspirobrassinol methyl ether and N-methoxyspirobrassinol suggests the involvement of oxidized intermediates in the biosynthesis from brassinin to spirobrassinin.

  DOI：

  10.1016/0031-9422(95)00011-u

文献信息

• New syntheses of indole phytoalexins and related compounds
  作者：Peter Kutschy、Milan Dzurilla、Mitsuo Takasugi、Marcel Török、Ingrid Achbergerová、Renáta Homzová、Mária Rácová

  DOI：10.1016/s0040-4020(98)00088-x

  日期：1998.4

  brassinin, brassitin, cyclobrassinin and related compounds via 3-aminomethylindole and its 1-substituted derivatives obtained by nickel boride catalyzed reduction of corresponding aldoximes with sodium borohydride and via[1-(t-butoxycarbonyl)-indol-3-yl]methyl isothiocyanate, the first stable derivative of indol-3-ylmethyl isothiocyanate is described. Antifungal activity of the prepared compounds was examined

  通过3-氨基甲基吲哚及其由硼化镍获得的1-取代衍生物的合成，通过硼氢化钠催化相应的醛肟还原，并通过[1-（叔丁氧基羰基）-吲哚-3-基描述了异硫氰酸甲酯甲酯，吲哚-3-基甲基异硫氰酸酯的第一稳定衍生物。通过TLC生物测定法使用Leersiae双歧杆菌检查制备的化合物的抗真菌活性，并用选择的化合物进行定量筛选。
• Novel IDO inhibitors and methods of use thereof
  申请人：Prendergast C. George

  公开号：US20070105907A1

  公开（公告）日：2007-05-10

  Novel indoleamine 2,3-dioxygenase (IDO) inhibitors, compositions comprising the same, and methods of use thereof are disclosed.

  披露了新型的吲哚胺2,3-双加氧酶（IDO）抑制剂，包含该抑制剂的组合物以及使用它们的方法。
• Novel IDO Inhibitors and Methods of Use Thereof
  申请人：Prendergast George C.

  公开号：US20100166881A1

  公开（公告）日：2010-07-01

  Novel indoleamine 2,3-dioxygenase (IDO) inhibitors, compositions comprising the same, and methods of use thereof are disclosed.

  本发明揭示了新型的色氨酸2,3-双加氧酶（IDO）抑制剂、包含该抑制剂的组合物以及其使用方法。
• IDO inhibitors and methods of use thereof
  申请人：Lankenau Institute for Medical Research

  公开号：US07705022B2

  公开（公告）日：2010-04-27

  Novel indoleamine 2,3-dioxygenase (IDO) inhibitors, compositions comprising the same, and methods of use thereof are disclosed.

  本发明涉及新型吲哚胺2,3-二氧化酶（IDO）抑制剂，包括其组成成分和使用方法。
• Structure−Activity Study of Brassinin Derivatives as Indoleamine 2,3-Dioxygenase Inhibitors
  作者：Paul Gaspari、Tinku Banerjee、William P. Malachowski、Alexander J. Muller、George C. Prendergast、James DuHadaway、Shauna Bennett、Ashley M. Donovan

  DOI：10.1021/jm0508888

  日期：2006.1.1

  A screen of indole-based structures revealed the natural product brassinin to be a moderate inhibitor of indoleamine 2,3-dioxygenase (IDO), a new cancer immunosuppression target. A structure-activity study was undertaken to determine which elements of the brassinin structure could be modified to enhance potency. Three important discoveries have been made, which will impact future IDO inhibitor development: (i) The dithiocarbamate portion of the brassinin lead is a crucial moiety, which may be binding to the heme iron of IDO; (ii) an indole ring is not necessary for IDO inhibition; and (iii) substitution of the S-methyl group of brassinin with large aromatic groups provides inhibitors that are three times more potent in vitro than the most commonly used IDO inhibitor, 1-methyl-tryptophan.