2-methylthio-N-(2-aminophenyl)-4-methyl-thiazolium iodide | 877309-01-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-methylthio-N-(2-aminophenyl)-4-methyl-thiazolium iodide
• 英文别名: 3-(2-Aminophenyl)-4-methyl-2-(methylsulfanyl)-1,3-thiazol-3-ium iodide；2-(4-methyl-2-methylsulfanyl-1,3-thiazol-3-ium-3-yl)aniline;iodide
• CAS: 877309-01-8
• 化学式: C₁₁H₁₃N₂S₂*I
• 分子量: 364.274
• InChiKey: WTHKONBEMIUKQH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.36
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methylthio-N-(2-aminophenyl)-4-methyl-thiazolium iodide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以1.73 g的产率得到3-(2-aminophenyl)-4-methylthiazol-2(3H)-one
  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)-4,5-dimethyl-thiazoline-2-thione 、 碘甲烷 以 丙酮 为溶剂， 反应 24.0h， 生成 2-methylthio-N-(2-aminophenyl)-4-methyl-thiazolium iodide
  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

文献信息

• Access to <i>N</i>-Thioalkenyl and <i>N</i>-(<i>o</i>-Thio)aryl-benzimidazol-2-ones by Ring Opening of Thiazolobenzimidazolium and Benzimidazobenzothiazolium Salts and C–O Bond Cleavage of an Alkoxide
  作者：Federico Andreoli、Radia Kaid-Slimane、Fabien Coppola、Daniel Farran、Christian Roussel、Nicolas Vanthuyne

  DOI：10.1021/acs.joc.5b00221

  日期：2015.3.20

  We report herein the synthesis of highly functionalized 1,3-dihydro-2H-benzimidazol-2-ones via a ring opening of thiazolo[3,2-a]benzimidazolium or benzimidazo[2,1-b][1,3]benzothiazol-6-ium salts and an unusual C–O bond cleavage of an alkoxide. A large variety of benzimidazolones bearing an original N-thioalkenyl or N-(o-thio)aryl group was obtained in high yields. The developed chemistry provides efficient

  我们在这里报告通过噻唑并[3,2- a ]苯并咪唑鎓或苯并咪唑并[2,1- b ] [1,3]苯并噻唑的开环合成高度官能化的1,3-二氢-2H-苯并咪唑-2-酮-6-ium盐和醇盐异常的C–O键裂解。以高收率获得了多种带有原始N-硫代烯基或N-（邻硫代）芳基的苯并咪唑酮。先进的化学方法可快速有效地访问特权的苯并咪唑-2-酮骨架。
• New Route to 3-Alkylthiazolo[3,2-a]benzimidazole Derivatives
  作者：Christian Roussel、Federico Andreoli、Mihaela Roman、Maria Hristova、Nicolas Vanthuyne

  DOI：10.3390/10020327

  日期：——

  3-Alkyl-thiazolo[3,2-a]benzimidazole derivatives are obtained in high yields via the corresponding 4-alkyl-N-3-(2-aminophenyl)-thiazoline-2-thiones which are easily prepared from 1,2-diaminobenzene, CS(2) and halogenoketones. This new route compares advantageously with the classical mercaptobenzimidazole routes in term of simplicity,isolated yields and availability of the starting materials.

  3-烷基-噻唑并[3,2-a]苯并咪唑衍生物是通过相应的4-烷基-N-3-(2-氨基苯基)-噻唑啉-2-硫酮以高产率获得的，这些4-烷基-N-3-(2-氨基苯基)-噻唑啉-2-硫酮很容易从1,2-二氨基苯、CS(2) 和卤代酮。该新路线在简单性、分离产率和起始原料的可用性方面与经典的巯基苯并咪唑路线相比具有优势。
• 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.