4-Hydroxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene | 193965-81-0

• 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: 4-Hydroxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene
• 英文别名: 2-[4-(2-Pyrrolidin-1-ylethoxy)phenyl]-1-benzothiophen-4-ol
• CAS: 193965-81-0
• 化学式: C₂₀H₂₁NO₂S
• 分子量: 339.458
• InChiKey: HQVKWTINBUIPNP-UHFFFAOYSA-N

物化性质

• 沸点：
  552.0±50.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对氟苯甲酰氯 、 4-Hydroxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene 在 三氯化铝 作用下， 以 1,2-二氯乙烷 为溶剂， 生成
  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：

  4-甲氧基苯并噻吩 在 盐酸 、 四(三苯基膦)钯 、 正丁基锂 、 三氯化铝 、 硼酸三异丙酯 、 sodium carbonate 、 乙硫醇 作用下， 生成 4-Hydroxy-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

• 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: 4. SAR studies on the conformationally restricted C3-side chain of hydroxybenzo[b]thiophenes
  作者：Kumiko Takeuchi、Todd J. Kohn、Daniel J. Sall、Michael L. Denney、Jefferson R. McCowan、Gerry F. Smith、Donetta S. Gifford-Moore

  DOI：10.1016/s0960-894x(99)00076-1

  日期：1999.3

  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.