(4-[4-(1-pyrrolidinyl)butoxy]phenyl)-(2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]-thiophen-3-yl)ketone | 193963-46-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-[4-(1-pyrrolidinyl)butoxy]phenyl)-(2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]-thiophen-3-yl)ketone
• 英文别名: [4-(4-Pyrrolidin-1-ylbutoxy)phenyl]-[2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-1-benzothiophen-3-yl]methanone
• CAS: 193963-46-1
• 化学式: C₃₅H₄₀N₂O₃S
• 分子量: 568.78
• InChiKey: OQQBSOHNGKSINZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (4-[4-(1-pyrrolidinyl)butoxy]phenyl)-(2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]-thiophen-3-yl)ketone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 [4-(4-Pyrrolidin-1-yl-butoxy)-phenyl]-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-benzo[b]thiophen-3-yl}-methanol
  参考文献：
  名称：

  Diamino Benzo[b]thiophene Derivatives as a Novel Class of Active Site Directed Thrombin Inhibitors. 5. Potency, Efficacy, and Pharmacokinetic Properties of Modified C-3 Side Chain Derivatives

  摘要：

  A systematic investigation of the structure-activity relationships of the C-3 side chain of the screening hit la led to the identification of the potent thrombin inhibitors 23c, 28c, and 31c. Their activities (1240, 903, and 1271 x 10(6) L/mol, respectively) represent 2200- and 2900-fold increases in potency over the starting lead la. This activity enhancement was accomplished with an increase of thrombin selectivity. The in vitro anticoagulant profiles of derivatives 28c and 31c were determined, and they compare favorably with the clinical agent H-R-1-[4aS,-8aS]perhydroisoquinolyl-prolyl-arginyl aldehyde (D-Piq-Pro-Arg-H; 32). The more potent members of this series have been studied in an arterial/venous shunt (AV shunt) model of thrombosis and were found to be efficacious in reducing clot formation. However, their efficacy is currently limited by their rapid and extensive distribution following administration.

  DOI：

  10.1021/jm9903388
• 作为产物：
  描述：

  1-(2-(4-溴苯氧基)乙基)吡咯烷 在 四(三苯基膦)钯 、 四氯化钛 、 sodium hydride 、 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 8.25h， 生成 (4-[4-(1-pyrrolidinyl)butoxy]phenyl)-(2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]-thiophen-3-yl)ketone
  参考文献：
  名称：

  Diamino Benzo[b]thiophene Derivatives as a Novel Class of Active Site Directed Thrombin Inhibitors. 5. Potency, Efficacy, and Pharmacokinetic Properties of Modified C-3 Side Chain Derivatives

  摘要：

  A systematic investigation of the structure-activity relationships of the C-3 side chain of the screening hit la led to the identification of the potent thrombin inhibitors 23c, 28c, and 31c. Their activities (1240, 903, and 1271 x 10(6) L/mol, respectively) represent 2200- and 2900-fold increases in potency over the starting lead la. This activity enhancement was accomplished with an increase of thrombin selectivity. The in vitro anticoagulant profiles of derivatives 28c and 31c were determined, and they compare favorably with the clinical agent H-R-1-[4aS,-8aS]perhydroisoquinolyl-prolyl-arginyl aldehyde (D-Piq-Pro-Arg-H; 32). The more potent members of this series have been studied in an arterial/venous shunt (AV shunt) model of thrombosis and were found to be efficacious in reducing clot formation. However, their efficacy is currently limited by their rapid and extensive distribution following administration.

  DOI：

  10.1021/jm9903388

文献信息

• US6025382A
  申请人：——

  公开号：US6025382A

  公开（公告）日：2000-02-15
• US6251921B1
  申请人：——

  公开号：US6251921B1

  公开（公告）日：2001-06-26
• US6265575B1
  申请人：——

  公开号：US6265575B1

  公开（公告）日：2001-07-24