3-(2-isothiocyanato-phenyl)-4-methyl-thiazoline-2-thione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2-isothiocyanato-phenyl)-4-methyl-thiazoline-2-thione
• 英文别名: 3-(2-isothiocyanatophenyl)-4-methylthiazole-2(3H)-thione；3-(2-isothiocyanatophenyl)-4-methyl-1,3-thiazole-2-thione
• 化学式: C₁₁H₈N₂S₃
• 分子量: 264.396
• InChiKey: ZBWQBKRDCGSKAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  17.29
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(2-isothiocyanato-phenyl)-4-methyl-thiazoline-2-thione 、 2,4-二氯苯胺 以 乙腈 为溶剂， 反应 24.0h， 以62%的产率得到
  参考文献：
  名称：

  Novel phenyl(thio)ureas bearing (thio)oxothiazoline group as potential BACE-1 inhibitors: synthesis and biological evaluation

  摘要：

  We report the synthesis and the beta-site amyloid precursor protein cleaving enzyme-1 inhibitory properties of novel phenyl(thio) ureas bearing 2-(thio)oxothiazoline derivatives. A library of analogues was prepared according to specific synthetic schemes and the inhibitory activity was monitored using a fluorescence resonance energy transfer assay. Several analogues show potent inhibitory activities ranging between 1 and 0.01 mu M and the activity is related to the NH acidity of the (thio) urea motif. Our results illustrate once again the close relationship between molecular recognition, complexation of the active site in enzymatic system, and organocatalysis utilizing explicit hydrogen bonding.

  DOI：

  10.3109/14756366.2011.642375
• 作为产物：
  描述：

  N-(2-aminophenyl)-4-methyl-thiazoline-2-thione 在 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 3-(2-isothiocyanato-phenyl)-4-methyl-thiazoline-2-thione
  参考文献：
  名称：

  阻转异构硫脲的非对映异构体催化的醛的对映选择性氰基硅烷化

  摘要：

  合成并测试了新的双功能阻转异构硫脲1作为非对映异构体（a R / a S）-（R，R）-1的混合物以及作为单一非对映异构体（a R）-（R，R）-1和（a R）-（S，S）-1在一系列醛（芳族和脂族）的有机催化，对映选择性，氰基硅烷化反应中进行。获得了适度的对映体过量（至多69％ee）和定量收率。使用硫脲非对映异构体的混合物（R / aS）-（R，R）-1而不是单个非对映异构体。

  DOI：

  10.1016/j.tetasy.2006.03.008

文献信息

• Enantioselective cyanosilylation of aldehydes catalysed by a diastereomeric mixture of atropisomeric thioureas
  作者：Rebecca M. Steele、Chiara Monti、Cesare Gennari、Umberto Piarulli、Federico Andreoli、Nicolas Vanthuyne、Christian Roussel

  DOI：10.1016/j.tetasy.2006.03.008

  日期：2006.3

  New bifunctional atropisomeric thioureas 1 were synthesised and tested as both a mixture of diastereomers (aR/aS)-(R,R)-1 and as single diastereomers (aR)-(R,R)-1 and (aR)-(S,S)-1, in the organocatalysed, enantioselective, cyanosilylation of a range of aldehydes (aromatic and aliphatic). Moderate enantiomeric excesses (up to 69% ee) and quantitative yields were obtained. The best results were achieved

  合成并测试了新的双功能阻转异构硫脲1作为非对映异构体（a R / a S）-（R，R）-1的混合物以及作为单一非对映异构体（a R）-（R，R）-1和（a R）-（S，S）-1在一系列醛（芳族和脂族）的有机催化，对映选择性，氰基硅烷化反应中进行。获得了适度的对映体过量（至多69％ee）和定量收率。使用硫脲非对映异构体的混合物（R / aS）-（R，R）-1而不是单个非对映异构体。
• Novel phenyl(thio)ureas bearing (thio)oxothiazoline group as potential BACE-1 inhibitors: synthesis and biological evaluation
  作者：Federico Andreoli、Abdallah Larbi Doukara、Mohammed Amine Mehdid、Nicolas Vanthuyne、Christian Roussel、Jean Dessolin、Jean-Louis Kraus

  DOI：10.3109/14756366.2011.642375

  日期：2013.2.1

  We report the synthesis and the beta-site amyloid precursor protein cleaving enzyme-1 inhibitory properties of novel phenyl(thio) ureas bearing 2-(thio)oxothiazoline derivatives. A library of analogues was prepared according to specific synthetic schemes and the inhibitory activity was monitored using a fluorescence resonance energy transfer assay. Several analogues show potent inhibitory activities ranging between 1 and 0.01 mu M and the activity is related to the NH acidity of the (thio) urea motif. Our results illustrate once again the close relationship between molecular recognition, complexation of the active site in enzymatic system, and organocatalysis utilizing explicit hydrogen bonding.