[3-Butyl-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzo[b]thiophen-3-yl}-methanone | 193962-63-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [3-Butyl-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzo[b]thiophen-3-yl}-methanone
• 英文别名: [3-Butyl-4-(2-pyrrolidin-1-ylethoxy)phenyl]-[2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-1-benzothiophen-3-yl]methanone
• CAS: 193962-63-9
• 化学式: C₃₇H₄₄N₂O₃S
• 分子量: 596.834
• InChiKey: HZFNILSQPHZRMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [3-Butyl-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzo[b]thiophen-3-yl}-methanone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 [3-Butyl-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzo[b]thiophen-3-yl}-methanol
  参考文献：
  名称：

  Dibasic benzo[b]thiophene derivatives as a novel class of active site directed thrombin inhibitors. 2. Exploring interactions at the proximal (S2) binding site

  摘要：

  In an effort to increase the thrombin inhibitory activity of a novel series of inhibitors (i.e., 1a), substituents were incorporated at the C-3" position of the C-3 aryl ring (2). Consistent with the X-ray crystallography studies, small hydrophobic groups at the C-3" site (Br and Me) enhanced thrombin inhibitory activity by 8-fold. However, a few more hydrophilic substituents (NO2 and OMe) also enhanced the potency of the series. The biological results are discussed in terms of molecular modeling studies. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00447-8
• 作为产物：
  描述：

  2-(4-甲氧基苯基)苯并噻吩 在 四(三苯基膦)钯 、 三氯化铝 、 四氯化钛 、 caesium carbonate 、 乙硫醇 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 23.0h， 生成 [3-Butyl-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzo[b]thiophen-3-yl}-methanone
  参考文献：
  名称：

  Dibasic benzo[b]thiophene derivatives as a novel class of active site directed thrombin inhibitors. 2. Exploring interactions at the proximal (S2) binding site

  摘要：

  In an effort to increase the thrombin inhibitory activity of a novel series of inhibitors (i.e., 1a), substituents were incorporated at the C-3" position of the C-3 aryl ring (2). Consistent with the X-ray crystallography studies, small hydrophobic groups at the C-3" site (Br and Me) enhanced thrombin inhibitory activity by 8-fold. However, a few more hydrophilic substituents (NO2 and OMe) also enhanced the potency of the series. The biological results are discussed in terms of molecular modeling studies. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00447-8

文献信息

• Dibasic benzo[b]thiophene derivatives as a novel class of active site directed thrombin inhibitors. 2. Exploring interactions at the proximal (S2) binding site
  作者：Daniel J. Sall、Stephen L. Briggs、Nickolay Y. Chirgadze、David K. Clawson、Donetta S. Gifford-Moore、Valentine J. Klimkowski、Jefferson R. McCowan、Gerald F. Smith、James H. Wikel

  DOI：10.1016/s0960-894x(98)00447-8

  日期：1998.9

  In an effort to increase the thrombin inhibitory activity of a novel series of inhibitors (i.e., 1a), substituents were incorporated at the C-3" position of the C-3 aryl ring (2). Consistent with the X-ray crystallography studies, small hydrophobic groups at the C-3" site (Br and Me) enhanced thrombin inhibitory activity by 8-fold. However, a few more hydrophilic substituents (NO2 and OMe) also enhanced the potency of the series. The biological results are discussed in terms of molecular modeling studies. (C) 1998 Elsevier Science Ltd. All rights reserved.