4-(2-hydroxyphenyl)-2-(3-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepine

• 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: 4-(2-hydroxyphenyl)-2-(3-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepine
• 英文别名: 2-[2-(3-Methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4-yl]phenol
• 化学式: C₂₂H₁₉NO₂S
• 分子量: 361.464
• InChiKey: BEKZGXSAFLYQHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  67.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2'-羟基苯乙酮 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 4-(2-hydroxyphenyl)-2-(3-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepine
  参考文献：
  名称：

  Derivatives of 4-(2-hydroxylphenyl)-2-phenyl-2,3-dihydro-1,5-benzothiazepine

  摘要：

  In the structures of 2-(4-chlorophenyl)-4-(2-hydroxyphenyl)2,3- dihydro-1,5-benzothiazepine, C21H16ClNOS, 4-(2-hydroxyphenyl)2-( 4- tolyl)-2,3-dihydro-1,5-benzothiazepine, C22H19NOS, and 4-(2-hydroxyphenyl)-2-(3-methoxyphenyl)-2,3-dihydro1,5- benzothiazepine, C22H19NO2S, the central seven-membered heterocyclic rings adopt twist-boat conformations in which the N atoms are involved in strong intramolecular hydrogen bonds with the hydroxyl H atoms, resulting in six-membered rings.

  DOI：

  10.1107/s0108270103008345

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.