2-[2-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydrobenzo-[b][1,4]thiazepin-4-yl]phenol | 873934-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并硫氮卓类
• 英文名称: 2-[2-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydrobenzo-[b][1,4]thiazepin-4-yl]phenol
• 英文别名: 2-[2-(1,3-Benzodioxol-5-yl)-2,3-dihydro-1,5-benzothiazepin-4-yl]phenol；2-[2-(1,3-benzodioxol-5-yl)-2,3-dihydro-1,5-benzothiazepin-4-yl]phenol
• CAS: 873934-69-1
• 化学式: C₂₂H₁₇NO₃S
• 分子量: 375.448
• InChiKey: WXVQTZUWIVVJBM-UHFFFAOYSA-N

物化性质

• 熔点：
  142 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  546.4±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基苯硫醇 、 2'-Hydroxy-3,4-methylenedioxychalkone 在 C₂₂H₃₂N₄⁽²⁺⁾*2CF₃O₃S^(1-) 作用下， 反应 1.33h， 以75%的产率得到2-[2-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydrobenzo-[b][1,4]thiazepin-4-yl]phenol
  参考文献：
  名称：

  Di-cationic Ionic Liquid Catalyzed Synthesis of 1,5-Benzothiazepines

  摘要：

  一种简单优雅的方法已被开发用于合成1,5-苯并噻嗪，采用双阳离子液体作为溶剂和催化剂，通过在温和反应条件下使邻氨基硫醇与多种查尔酮反应。此外，还研究了催化剂的重复使用性，进行了三轮实验。所有反应被提出是通过1,4-共轭迈克尔加成反应，然后进行环状缩合反应。

  DOI：

  10.14233/ajchem.2018.20920

文献信息

• In silico studies on 2,3-dihydro-1,5-benzothiazepines as cholinesterase inhibitors
  作者：Farzana Latif Ansari、Saima Kalsoom、Zaheer-ul-Haq、Zahra Ali、Farukh Jabeen

  DOI：10.1007/s00044-011-9754-6

  日期：2012.9

  In vitro studies on cholinesterase inhibitory potential on the three sets of 2,3-dihydro-1,5-benzothiazepines have been carried out. The compounds in Set 1 were unsubstituted on ring A, while those in Sets 2 and 3 had a 2'- and 3'-hydoxy substituent, respectively, in ring A. These studies revealed that they are mixed inhibitors of both AChE and BChE as reflected from their IC50 values. It was further observed that 3'-hydroxy substituted benzothiazepines (Set 3) were found to have stronger affinity for both AChE and BChE compared with those of Sets 1 and 2. Moreover, all the compounds in Set 3 were found to be stronger BChE inhibitors than AChE. These experimental observations were rationalized by conducting in silico studies using molecular docking tool of Molecular Operating Environment (MOE) software, thereby, a good correlation was observed between IC50 values and their binding interactions within the enzyme active site. We have observed that these interactions were electrostatic and hydrophobic in nature besides hydrogen bonding. The high BChE inhibitory potential of 3'-hydroxy substituted benzothiazepines was found to be cumulative effect of hydrogen bonding and pi-pi interactions between the ligand and BChE. These findings may serve as a guideline for synthesizing more potent ChE inhibitors for the treatment of Alzheimer's disease and related dementias.