5-chloro-3-hydroxy-3-(4-methoxyphenyl)indolin-2-one | 383424-81-5

• 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: 5-chloro-3-hydroxy-3-(4-methoxyphenyl)indolin-2-one
• 英文别名: rac-5-chloro-3-hydroxy-3-(4-methoxy-phenyl)-1,3-dihydro-indol-2-one；5-Chloro-3-hydroxy-3-(4-methoxyphenyl)-1,3-dihydro-2H-indol-2-one；5-chloro-3-hydroxy-3-(4-methoxyphenyl)-1H-indol-2-one
• CAS: 383424-81-5
• 化学式: C₁₅H₁₂ClNO₃
• 分子量: 289.718
• InChiKey: GYRWDRCEOGOEDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-3-hydroxy-3-(4-methoxyphenyl)indolin-2-one 在 三乙基硅烷 、 三氟乙酸 作用下， 反应 24.0h， 以63.5%的产率得到rac-5-chloro-3-(4-methoxy-phenyl)-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Oxindole derivatives

  摘要：

  这项发明描述了一般式I的化合物或其药用盐，其中R1、R2、R3和X在此处描述，以及它们的制备方法、含有它们的药物以及将这些化合物用作药用活性剂的用途。这些化合物显示出抗增殖剂的活性，可能特别适用于癌症的治疗。

  公开号：

  US20060293319A1
• 作为产物：
  描述：

  5-chloro-2-(4-methoxyphenyl)-1H-indole 在 磷酸 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 5-chloro-3-hydroxy-3-(4-methoxyphenyl)indolin-2-one
  参考文献：
  名称：

  1,2,3,3a,4,8b-六氢吡咯并[3,2-b]吲哚核心的合成研究。1,2-芳基移位的异常断裂

  摘要：

  研究了 2-(3-oxindolin-2-yl) 乙腈的碱辅助转化。出乎意料的是，具有未受保护的氮原子的底物的尝试反应伴随着 2-芳基乙腈的不寻常挤出，随后发生 1,2-芳基转移以提供 3-羟基二氢吲哚-2-酮。另一方面，氧代二氢吲哚的N-烷基衍生物的反应采取了预期的路线，仅提供1​​,2,3,3a,4,8b-六氢吡咯并[3,2- b ]吲哚。

  DOI：

  10.1021/acs.joc.1c02753

文献信息

• 1,3-Dihydro-2H-Indole-2-One Compound and Pyrrolidine-2-One Compound Fused With Aromatic Heterocycle
  申请人：Sekiguchi Yoshinori

  公开号：US20080318923A1

  公开（公告）日：2008-12-25

  It is intended to provide a drug which is efficacious against pathological conditions relating to arginine-vasopressin V1b receptor. More particularly speaking, it is intended to provide a drug which has a therapeutic or preventive effect on depression, anxiety, Alzheimer's disease, Parkinson's disease, Huntington's chorea, eating disorders, hypertension, digestive diseases, drug addiction, epilepsy, brain infarction, brain ischemia, brain edema, head injury, inflammation, immune diseases, alopecia and so on. As the results of intensive studies, a novel 1,3-dihydro-2H-indol-2-one compound and a pyrrolidin-2-one compound fused with a heteroaromatic ring, which are highly selective antagonists of arginine-vasopressin V1b receptor, have high metabolic stabilities and show favorable brain penetration and high plasma concentrations, are found, thereby achieving the above objective.

  旨在提供一种对与精氨酸加压素V1b受体相关的病理状况具有疗效的药物。更具体地说，旨在提供一种对抑郁症、焦虑症、阿尔茨海默病、帕金森病、亨廷顿舞蹈症、进食障碍、高血压、消化系统疾病、药物成瘾、癫痫、脑梗死、脑缺血、脑水肿、头部损伤、炎症、免疫疾病、脱发等具有治疗或预防作用的药物。经过深入研究，发现了一种新颖的1,3-二氢-2H-吲哚-2-酮化合物和与杂芳环融合的吡咯烷-2-酮化合物，它们是高度选择性的精氨酸加压素V1b受体拮抗剂，具有高代谢稳定性，表现出有利的血脑屏障穿透和高血浆浓度，从而实现了上述目标。
• Novel 1,3-dihydro-2H-indol-2-one derivatives, process for preparing them and pharmaceutical compositions containing them
  申请人：Roux Richard

  公开号：US20050176770A1

  公开（公告）日：2005-08-11

  The invention relates to compounds of formula: and to solvates and/or hydrates thereof, with affinity for and selectivity towards the V 1b receptors or both the V 1b and V 1a receptors of arginine-vasopressin. The invention also relates to a process for preparing them, to the intermediate compounds of formula (II) which are useful for preparing them, to pharmaceutical compositions containing them and to their use for preparing medicinal products.

  本发明涉及式的化合物：以及其溶剂化物和/或水合物，具有亲和力和选择性，对精氨酸加压素的V1b受体或V1a和V1b受体均有亲和力。本发明还涉及制备它们的方法，用于制备它们的有用的式（II）的中间化合物，含有它们的制药组合物以及它们用于制备药物的用途。
• Novel 1,3-dihydro-2h-indol-2-one derivatives, method for preparing same and pharmaceutical compositions containing them
  申请人：——

  公开号：US20030162767A1

  公开（公告）日：2003-08-28

  The invention relates to compounds of formula: 1 and to solvates and/or hydrates thereof, with affinity for and selectivity towards the V 1b receptors or both the V 1b and V 1a receptors of arginine-vasopressin. The invention also relates to a process for preparing them, to the intermediate compounds of formula (II) which are useful for preparing them, to pharmaceutical compositions containing them and to their use for preparing medicinal products.

  本发明涉及式子1的化合物及其溶剂化物和/或水合物，它们具有亲和力和选择性，可作用于精氨酸加压素的V1b受体或V1a和V1b受体。本发明还涉及制备它们的方法，用于制备它们的有用中间体化合物（II），含有它们的制药组合物以及它们用于制备药物的用途。
• 1,3-dihydro-2H-indol-2-one derivatives, method for preparing same and pharmaceutical compositions containing them
  申请人：Roux Richard

  公开号：US06864277B2

  公开（公告）日：2005-03-08

  The invention relates to compounds of formula: and to solvates and/or hydrates thereof, with affinity for and selectivity towards the Vreceptors or both the V 1b and V 1a receptors of arginine-vasopressin. The invention also relates to a process for preparing them, to the intermediate compounds of formula (II) which are useful for preparing them, to pharmaceutical compositions containing them and to their use for preparing medicinal products.

  本发明涉及以下公式的化合物：以及其溶剂化物和/或水合物，具有亲和力和选择性，可与精氨酸加压素的V1B和/或V1A受体结合。本发明还涉及一种制备它们的方法，用于制备它们的有用中间体化合物（II）的方法，含有它们的制药组合物以及它们用于制备药物的用途。
• 1,3-dihydro-2H-indol-2-one derivatives, process for preparing them and pharmaceutical compositions containing them
  申请人：Sanofi-Aventis

  公开号：US07425566B2

  公开（公告）日：2008-09-16

  The invention relates to compounds of formula: and to solvates and/or hydrates thereof, with affinity for and selectivity towards the V1b receptors or both the V1b and V1a receptors of arginine-vasopressin. The invention also relates to a process for preparing them, to the intermediate compounds of formula (II) which are useful for preparing them, to pharmaceutical compositions containing them and to their use for preparing medicinal products.

  本发明涉及以下式的化合物：以及与其溶剂化合物和/或水合物，具有亲和力和选择性，可以结合到加压素的V1b受体或同时结合到V1b和V1a受体。本发明还涉及一种制备它们的方法，以及用于制备药物的中间化合物（II）和含有它们的制药组合物，以及它们的用途。