(2S,3R)-N-(3,4-dichlorophenyl)-1-methoxy-2'-methylsulfanylspiro[2H-indole-3,5'-4H-1,3-thiazole]-2-amine | 1351000-37-7

• 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: (2S,3R)-N-(3,4-dichlorophenyl)-1-methoxy-2'-methylsulfanylspiro[2H-indole-3,5'-4H-1,3-thiazole]-2-amine
• CAS: 1351000-37-7
• 化学式: C₁₈H₁₇Cl₂N₃OS₂
• 分子量: 426.39
• InChiKey: ZKMBUJRGRUFRBT-WMZOPIPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  87.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲基[(1-甲氧基-1H-吲哚-3-基)甲基]二硫代氨基甲酸酯 在 溴 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.83h， 生成 (2S,3R)-N-(3,4-dichlorophenyl)-1-methoxy-2'-methylsulfanylspiro[2H-indole-3,5'-4H-1,3-thiazole]-2-amine 、 (2R,3R)-N-(3,4-dichlorophenyl)-1-methoxy-2'-methylsulfanylspiro[2H-indole-3,5'-4H-1,3-thiazole]-2-amine
  参考文献：
  名称：

  Stereoselective synthesis of 1-methoxyspiroindoline phytoalexins and their amino analogues

  摘要：

  The stereoselective synthesis of the spiroindoline phytoalexin (R)-(+)-1-methoxyspirobrassinin and its unnatural (S)-(-)-enantiomer were achieved by the bromine-induced spirocyclization of 1-methoxybrassinin using chiral auxiliaries (+)- and (-)-menthol, followed by oxidation of the obtained menthyl ethers. The TFA-catalyzed methanolysis of chiral 1-methoxyspirobrassinol menthyl ethers provided (2R,3R)-(-)-1-methoxyspirobrassinol methyl ether and its other three unnatural stereoisomers. The enantiomers of the 2-amino analogues of the indole phytoalexin (2R,3R)-(-)-1-methoxyspirobrassinol methyl ether were prepared by the TFA-catalyzed replacement of the chiral alkoxy group with an amine. The synthesized compounds were tested in vitro on cancer cell lines and examined with enantiopure 2-amino analogues of the indole phytoalexin (2R,3R)-(-)-1-methoxyspirobrassinol methyl ether, which showed in most cases, lower activity than the corresponding racemates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.07.006

文献信息

• Stereoselective synthesis of 1-methoxyspiroindoline phytoalexins and their amino analogues
  作者：Aneta Salayová、Zuzana Kudličková、Matej Baláž、Mariana Budovská、Martina Pilátová、Ján Mojžiš、Kenji Monde、Ján Petrovaj、Taťána Gondová

  DOI：10.1016/j.tetasy.2014.07.006

  日期：2014.9

  The stereoselective synthesis of the spiroindoline phytoalexin (R)-(+)-1-methoxyspirobrassinin and its unnatural (S)-(-)-enantiomer were achieved by the bromine-induced spirocyclization of 1-methoxybrassinin using chiral auxiliaries (+)- and (-)-menthol, followed by oxidation of the obtained menthyl ethers. The TFA-catalyzed methanolysis of chiral 1-methoxyspirobrassinol menthyl ethers provided (2R,3R)-(-)-1-methoxyspirobrassinol methyl ether and its other three unnatural stereoisomers. The enantiomers of the 2-amino analogues of the indole phytoalexin (2R,3R)-(-)-1-methoxyspirobrassinol methyl ether were prepared by the TFA-catalyzed replacement of the chiral alkoxy group with an amine. The synthesized compounds were tested in vitro on cancer cell lines and examined with enantiopure 2-amino analogues of the indole phytoalexin (2R,3R)-(-)-1-methoxyspirobrassinol methyl ether, which showed in most cases, lower activity than the corresponding racemates. (C) 2014 Elsevier Ltd. All rights reserved.