5-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene | 193965-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 5-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene
• 英文别名: 1-[2-[4-(5-methoxy-1-benzothiophen-2-yl)phenoxy]ethyl]pyrrolidine
• CAS: 193965-31-0
• 化学式: C₂₁H₂₃NO₂S
• 分子量: 353.485
• InChiKey: JWQALNGXILYIHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene 在 三氯化铝 、 sodium hydride 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 生成 [5-methoxy-2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-1-benzothiophen-3-yl]-[4-[(1R,2R)-2-piperidin-1-ylcyclohexyl]oxyphenyl]methanone
  参考文献：
  名称：

  Dibasic benzo[b]thiophene derivatives as a novel class of active site directed thrombin inhibitors: 4. SAR studies on the conformationally restricted C3-side chain of hydroxybenzo[b]thiophenes

  摘要：

  A novel series of benzo[b]thiophene diamine thrombin inhibitors with a conformationally restricted C3-side chain 3 was investigated. The constrained C3-side chain by a cyclohexyl ring contributed to not only an additive but also a synergistic effect on the thrombin inhibitory activity. The SAR studies resulted in the discovery of a potent thrombin inhibitor 27 that was over 750-fold more potent than the initial lead compound 1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00076-1
• 作为产物：
  描述：

  5-溴苯并[b]噻吩 在 盐酸 、 四(三苯基膦)钯 、 正丁基锂 、 硼酸三异丙酯 、 sodium methylate 、 sodium carbonate 、 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene
  参考文献：
  名称：

  Dibasic benzo[b]thiophene derivatives as a novel class of active site directed thrombin inhibitors: 4. SAR studies on the conformationally restricted C3-side chain of hydroxybenzo[b]thiophenes

  摘要：

  A novel series of benzo[b]thiophene diamine thrombin inhibitors with a conformationally restricted C3-side chain 3 was investigated. The constrained C3-side chain by a cyclohexyl ring contributed to not only an additive but also a synergistic effect on the thrombin inhibitory activity. The SAR studies resulted in the discovery of a potent thrombin inhibitor 27 that was over 750-fold more potent than the initial lead compound 1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00076-1

文献信息

• Antithrombotic diamines
  申请人：Eli Lilly and Company

  公开号：US06025382A1

  公开（公告）日：2000-02-15

  This application relates to the use as thrombin inhibitors, coagulation inhibitors and thromboembolic disorder agents of diamines of formula I as defined herein. It also provides novel compounds of formula I, processes and intermediates for their preparation, and pharmaceutical formulations comprising the novel compounds of formula I.

  该应用涉及将I式中所定义的二胺用作凝血酶抑制剂、凝血抑制剂和血栓栓塞性疾病药剂。它还提供了I式的新化合物，其制备方法和中间体，以及包含这些新化合物的药物配方。
• 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