1-(5-chloro-thiophen-2-yl-methyl)-1H-indole-2,3-dione | 445455-63-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(5-chloro-thiophen-2-yl-methyl)-1H-indole-2,3-dione
• 英文别名: 1-((5-chlorothiophen-2-yl)methyl)indoline-2,3-dione；1-[(5-chloro-thien-2-yl)methyl]-2H-indole-2,3-dione；1-[(5-chloro-2-thienyl)Methyl]-2H-indole-2,3-dione；1-[(5-chloro-2-thienyl)methyl)-2H-indole-2,3-dione；1-[(5-chlorothiophen-2-yl)methyl]indole-2,3-dione
• CAS: 445455-63-0
• 化学式: C₁₃H₈ClNO₂S
• mdl: MFCD11524360
• 分子量: 277.731
• InChiKey: AAYZREZLTCRJHR-UHFFFAOYSA-N

物化性质

• 沸点：
  438.1±55.0 °C(Predicted)
• 密度：
  1.523±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  65.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(5-chloro-thiophen-2-yl-methyl)-1H-indole-2,3-dione 在 三乙基硅烷 、 水 、 异丙基氯化镁 、 三乙胺 、 三氟乙酸 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 50.5h， 生成
  参考文献：
  名称：

  Tetracyclic spirooxindole blockers of hNaV1.7: activity in vitro and in CFA-induced inflammatory pain model

  摘要：

  The structure-activity relationship of a new series of tetracyclic spirooxindoles led to the discovery of compound 25a, a potent hNa(V)1.7 blocker with improved ADME properties and in vivo efficacy in the CFA-induced inflammatory pain model.

  DOI：

  10.1007/s00044-012-0180-1
• 作为产物：
  描述：

  2-氯-5-氯甲基噻吩 在 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.08h， 以22%的产率得到1-(5-chloro-thiophen-2-yl-methyl)-1H-indole-2,3-dione
  参考文献：
  名称：

  WO2008/2946

  摘要：

  公开号：

文献信息

• Discovery of XEN907, a spirooxindole blocker of NaV1.7 for the treatment of pain
  作者：Sultan Chowdhury、Mikhail Chafeev、Shifeng Liu、Jianyu Sun、Vandna Raina、Ray Chui、Wendy Young、Rainbow Kwan、Jianmin Fu、Jay A. Cadieux

  DOI：10.1016/j.bmcl.2011.04.088

  日期：2011.6

  series of NaV1.7 blockers were developed. Following the elimination of undesirable structural features, preliminary optimization of the oxindole C-3 and N-1 substituents afforded the simplified analogue 9b, which demonstrated a 10-fold increase in target potency versus the original HTS hit. A scaffold rigidification strategy then led to the discovery of XEN907, a novel spirooxindole NaV1.7 blocker. This

  从通过高通量筛选活动确定的羟吲哚2a开始，开发了一系列Na V 1.7阻滞剂。在消除了不良的结构特征之后，对羟吲哚C-3和N-1取代基进行了初步优化，得到了简化的类似物9b，与原始HTS命中相比，该类似物的目标效能提高了10倍。脚手架的加固策略随后导致了XEN907的发现，XEN907是一种新型螺氧吲哚Na V 1.7阻滞剂。这种先导化合物的效能又提高了10倍，代表了进一步优化工作的有希望的结构。
• Use of GAL3 receptor antagonists for the treatment of depression and/or anxiety and compounds useful in such methods
  申请人：——

  公开号：US20030078271A1

  公开（公告）日：2003-04-24

  This invention is directed to pyrimidine and indolone derivatives which are selective antagonists for the GAL3 receptor. The invention provides a pharmaceutical composition comprising a therapeutically effective amount of a compound of the invention and a pharmaceutically acceptable carrier. This invention also provides a pharmaceutical composition made by combining a therapeutically effective amount of a compound of the invention and a pharmaceutically acceptable carrier. This invention further provides a process for making a pharmaceutical composition comprising combining a therapeutically effective amount of a compound of the invention and a pharmaceutically acceptable carrier. This invention also provides a method of treating a subject suffering from depression and/or anxiety which comprises administering to the subject an amount of a compound of the invention effective to treat the subject's depression and/or anxiety. This invention also provides a method of treating depression and/or anxiety in a subject which comprises administering to the subject a composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a GAL3 receptor antagonist.

  这项发明涉及嘧啶和吲哚酮衍生物，它们是选择性GAL3受体拮抗剂。该发明提供了一种包含该发明化合物的治疗有效量和药用载体的药物组合物。该发明还提供了通过结合该发明化合物的治疗有效量和药用载体制备的药物组合物。该发明进一步提供了一种制备药物组合物的方法，包括结合该发明化合物的治疗有效量和药用载体。该发明还提供了一种治疗患有抑郁症和/或焦虑症的受试者的方法，包括向受试者施用足以治疗受试者抑郁症和/或焦虑症的该发明化合物的量。该发明还提供了一种治疗受试者抑郁症和/或焦虑症的方法，包括向受试者施用包含药用载体和治疗有效量GAL3受体拮抗剂的组合物。
• GAL3 antagonists for the treatment of neuropathic pain
  申请人：——

  公开号：US20040092570A1

  公开（公告）日：2004-05-13

  This invention is directed to pyrimidine and indolone derivatives which are selective antagonists for the GAL3 receptor and are useful for the treatment of neuropathic pain and other abnormalities. This invention also provides a method of treating a subject suffering from an abnormality which comprises administering to the subject an amount of a compound of the invention effective to treat the subject's abnormality. This invention also provides a method of treating an abnormality in a subject which comprises administering to the subject a composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a GAL3 receptor antagonist.

  这项发明涉及嘧啶和吲哚酮衍生物，它们是选择性的GAL3受体拮抗剂，可用于治疗神经病痛和其他异常。这项发明还提供了一种治疗患有异常的受试者的方法，包括向受试者投予本发明中的化合物的有效剂量以治疗受试者的异常。这项发明还提供了一种治疗受试者异常的方法，包括向受试者投予包含药用载体和治疗有效量的GAL3受体拮抗剂的组合物。
• Indolone compounds useful to treat cognitive impairment
  申请人：Blackburn P. Thomas

  公开号：US20070135509A1

  公开（公告）日：2007-06-14

  This invention provides a method of treating a subject suffering from a cognitive impairment or a cognitive disorder which comprises administering to the subject an amount of an indolone compound effective to treat the subject's cognitive impairment or disorder.

  这项发明提供了一种治疗患有认知障碍或认知障碍的受试者的方法，包括向受试者施用一定量的吲哚酮化合物，以有效治疗受试者的认知障碍或障碍。
• Indolone Compounds Useful To Treat Cognitive Impairment
  申请人：Blackburn P. Thomas

  公开号：US20070135510A1

  公开（公告）日：2007-06-14

  This invention provides a method of treating a subject suffering from a cognitive impairment or a cognitive disorder which comprises administering to the subject an amount of an indolone compound effective to treat the subject's cognitive impairment or disorder.

  该发明提供了一种治疗患认知障碍或认知障碍的受试者的方法，包括向受试者施用有效治疗受试者认知障碍或障碍的吲哚酮化合物的剂量。