6-benzyloxy-2-(dimethylamino)benzo[b]thiophen-3-yl 3,4-difluorophenyl ketone | 193965-24-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-benzyloxy-2-(dimethylamino)benzo[b]thiophen-3-yl 3,4-difluorophenyl ketone
• 英文别名: (3,4-difluorophenyl)-[2-(dimethylamino)-6-phenylmethoxy-1-benzothiophen-3-yl]methanone
• CAS: 193965-24-1
• 化学式: C₂₄H₁₉F₂NO₂S
• 分子量: 423.483
• InChiKey: DNEUWHFAIWMDAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  6-benzyloxy-2-(dimethylamino)benzo[b]thiophen-3-yl 3,4-difluorophenyl ketone 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 [3-fluoro-4-[(1R,2R)-2-piperidin-1-ylcyclohexyl]oxyphenyl]-[6-phenylmethoxy-2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-1-benzothiophen-3-yl]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：

  N,N-dimethyl-2-hydroxy-2-(4-benzyloxy)phenylthioacetamide 在 甲烷磺酸 作用下， 以 二氯甲烷 、 氯苯 为溶剂， 反应 3.0h， 生成 6-benzyloxy-2-(dimethylamino)benzo[b]thiophen-3-yl 3,4-difluorophenyl ketone
  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。
• [EN] ANTITHROMBOTIC DIAMINES<br/>[FR] DIAMINES ANTITHROMBOTIQUES
  申请人：ELI LILLY AND COMPANY

  公开号：WO1997025033A1

  公开（公告）日：1997-07-17

  (EN) 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).(FR) La présente invention concerne l'utilisation, comme inhibiteurs de thrombine, inhibiteurs de coagulation et agents destinés aux désordres de la thromboembolie, de diamines de formule I telle qu'elle est définie dans la description. L'invention concerne aussi des composés nouveaux de formule I, des procédés et des produits intermédiaires pour leur préparation, et des formulations pharmaceutiques comprenant les composés nouveaux de formule I.

  该应用涉及使用公式（I）所定义的二胺作为凝血酶抑制剂、凝血抑制剂和血栓栓塞疾病药物的用途。它还提供了公式（I）的新化合物、其制备过程和中间体，以及包含公式（I）的新药物配方。
• EP0863755A4
  申请人：——

  公开号：EP0863755A4

  公开（公告）日：1999-01-20
• ANTITHROMBOTIC DIAMINES
  申请人：ELI LILLY AND COMPANY

  公开号：EP0863755A1

  公开（公告）日：1998-09-16
• US6025382A
  申请人：——

  公开号：US6025382A

  公开（公告）日：2000-02-15