3,4-Difluorophenyl 2-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl Ketone | 193965-86-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-Difluorophenyl 2-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl Ketone
• 英文别名: (3,4-difluorophenyl)-[2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-1-benzothiophen-3-yl]methanone
• CAS: 193965-86-5
• 化学式: C₂₇H₂₃F₂NO₂S
• 分子量: 463.548
• InChiKey: VZOWFZHQKLBDTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-Difluorophenyl 2-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl Ketone 在 sodium tetrahydroborate 、 sodium hydride 、 二异丁基氢化铝 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 1-[2-[2-Fluoro-4-[[2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-1-benzothiophen-3-yl]methyl]phenoxy]ethyl]pyrrolidine
  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：

  3,4-二氟苯甲酰氯 、 2-[4-[2-(1-pyrrolidinyl)ethoxy]-phenyl]benzo[b]thiophene 在 四氯化钛 碳酸氢钠 、 乙酸乙酯 、 Sodium sulfate-III 、 SiO2 、 甲醇 、 氯仿 作用下， 以 1,2′dichloroethane 为溶剂， 反应 5.0h， 以to afford 1.7 g (3.7 mmol; 37%) of the ketone as a viscous oil的产率得到3,4-Difluorophenyl 2-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl Ketone
  参考文献：
  名称：

  Antithrombotic diamines

  摘要：

  本申请涉及使用式I所定义的二胺作为凝血酶抑制剂、凝血抑制剂和血栓性疾病药物的用途。它还提供了式I的新化合物、其制备的过程和中间体，以及包含式I的新药物制剂。

  公开号：

  US06265575B1

文献信息

• ANTITHROMBOTIC DIAMINES
  申请人：ELI LILLY AND COMPANY

  公开号：EP0863755B1

  公开（公告）日：2004-12-15
• 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
• 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.