3-Benzyl-5-chloro-1,3-dihydro-3-hydroxyindol-2-one | 905081-72-3

• 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: 3-Benzyl-5-chloro-1,3-dihydro-3-hydroxyindol-2-one
• 英文别名: 3-benzyl-5-chloro-3-hydroxy-1,3-dihydro-2H-indol-2-one；3-benzyl-5-chloro-3-hydroxy-1H-indol-2-one
• CAS: 905081-72-3
• 化学式: C₁₅H₁₂ClNO₂
• 分子量: 273.719
• InChiKey: YSHZZTYDHXVNBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氯靛红 、 溴甲苯 在 氯化铵 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 以88%的产率得到3-Benzyl-5-chloro-1,3-dihydro-3-hydroxyindol-2-one
  参考文献：
  名称：

  An efficient and rapid synthesis of 3-hydroxy-3-alkyl-2-oxindoles via Zn-mediated barbier-type reaction under aqueous conditions

  摘要：

   介绍了一种从异汀类化合物中快速合成3-羟基-3-烷基-2-氧茚酮的方法。该方法在水溶液条件下引入了一种环保的、未活化的锌粉、固体$$\hbox {NH}_{4}\hbox {Cl}$$和底物，从而以中等到良好的收率生产出产品。在不使用柱层析的情况下，大部分化合物都以分析纯的形式分离出来。反应过程可以用肉眼观察到。摘要 描述了一种从异汀类化合物中快速合成 3-羟基-3-烷基-2-氧化吲哚的方法。该方法采用未活化的 Zn 粉尘、固体 $$\hbox {NH}_{4}\hbox {Cl}$$ 和底物在水溶液条件下进行合成，以中等至良好的收率得到了产物。

  DOI：

  10.1007/s12039-017-1329-8

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。
• 1,3-dihydroindol-2-one derivatives substituted in the 3-position by a
  申请人：Sanofi

  公开号：US05594023A1

  公开（公告）日：1997-01-14

  The present invention relates to compounds of formula (I) and salts thereof, where appropriate: ##STR1## These compounds have an affinity for the vasopressin and/or ocytocin receptors.

  本发明涉及式(I)化合物及其盐，如适用：这些化合物具有对加压素和/或催产素受体的亲和力。
• Indol-2-one derivatives
  申请人：Sanofi

  公开号：US05773612A1

  公开（公告）日：1998-06-30

  A compound of formula II' ##STR1## in which R.sub.I is an ethoxy group or a chlorine atom; R.sub.II is hydrogen, a chlorine atom or a methyl group; R.sub.III is a chlorophenyl group or a methoxyphenyl group; R.sub.IV is an amino group, a group NR.sub.9 R.sub.10 or NR.sub.9 R.sub.XI, or a piperazin-1-yl radical substituted in the 4-position by a (C.sub.2 -C.sub.10)alkylene group substituted by an amino group which is free or carries a protective group; R.sub.10 is (CH.sub.2).sub.p R.sub.35 or a (C.sub.2 -C.sub.10)alkylene group substituted by R.sub.21 ; R.sub.XI is a (C.sub.1 -C.sub.12)alkyl group or a group .omega.-R.sub.32 R.sub.33 N(C.sub.1 -C.sub.4)-alkylcarbonyl; and R.sub.21 is R.sub.36 ; a group OR.sub.37 ; a group NR.sub.32 R.sub.33 ; a cyano group; a group S(C.sub.1 -C.sub.7)alkyl; a group SO(C.sub.1 -C.sub.7)alkyl; or a group SO.sub.2 (C.sub.1 -C.sub.7)alkyl; R.sub.35 is a piperid-4-yl group which is unsubstituted or substituted in the 1-position by a (C.sub.1 -C.sub.7)alkoxycarbonyl group or by a (C.sub.1 -C.sub.7)alkyl group; or a pyrid-2-yl group; R.sub.37 is R.sub.13 ; a (C.sub.3 -C.sub.7)cycloalkyl group; a (C.sub.1 -C.sub.6)alkylene group substituted by R.sub.24 ; a (C.sub.2 -C.sub.6)alkylene group substituted by a hydroxyl or a (C.sub.1 -C.sub.7)alkoxy group; or a (C.sub.2 -C.sub.6)alkylene group substituted by an amino group which is free or substituted by one or two (C.sub.1 -C.sub.7)alkyl groups or by a protective group; R.sub.24 is a carboxyl group; a (C.sub.1 -C.sub.7)alkoxycarbonyl group; a benzyloxycarbonyl group; or a carbamoyl group which is free or substituted by one or two (C.sub.1 -C.sub.7)alkyl groups.

  化合物II'的化学式为##STR1## 其中R.sub.I为乙氧基或氯原子；R.sub.II为氢、氯原子或甲基基团；R.sub.III为氯苯基或甲氧基苯基；R.sub.IV为氨基、NR.sub.9 R.sub.10或NR.sub.9 R.sub.XI基团，或者在4-位置被取代的哌嗪-1-基基团，所取代的基团为(C.sub.2 -C.sub.10)烷基基团，该基团被氨基自由取代或带有保护基；R.sub.10为(CH.sub.2).sub.p R.sub.35或(C.sub.2 -C.sub.10)烷基基团，该基团被R.sub.21取代；R.sub.XI为(C.sub.1 -C.sub.12)烷基基团或.omega.-R.sub.32 R.sub.33 N(C.sub.1 -C.sub.4)-烷基羰基基团；R.sub.21为R.sub.36、OR.sub.37、NR.sub.32 R.sub.33、氰基、S(C.sub.1 -C.sub.7)烷基、SO(C.sub.1 -C.sub.7)烷基或SO.sub.2 (C.sub.1 -C.sub.7)烷基；R.sub.35为哌啶-4-基基团，该基团未取代或在1-位置被(C.sub.1 -C.sub.7)烷氧羰基基团或(C.sub.1 -C.sub.7)烷基基团取代；或者为吡啶-2-基基团；R.sub.37为R.sub.13、(C.sub.3 -C.sub.7)环烷基团、被R.sub.24取代的(C.sub.1 -C.sub.6)烷基基团、被羟基或(C.sub.1 -C.sub.7)烷氧基取代的(C.sub.2 -C.sub.6)烷基基团；或者被自由氨基或被一或两个(C.sub.1 -C.sub.7)烷基或保护基取代的(C.sub.2 -C.sub.6)烷基基团；R.sub.24为羧基、(C.sub.1 -C.sub.7)烷氧羰基、苄氧羰基或自由或被一或两个(C.sub.1 -C.sub.7)烷基取代的氨基基团。
• 1,3-dihydro-2H-indole-2-one compound and pyrrolidine-2-one compound fused with aromatic heterocycle
  申请人：Taisho Pharmaceutical Co., Ltd.

  公开号：US08030499B2

  公开（公告）日：2011-10-04

  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.

  本发明旨在提供一种对精氨酸加压素V1b受体相关的病理状况有效的药物。更具体地说，本发明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、饮食失调、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、免疫性疾病、脱发等具有治疗或预防作用的药物。经过密集研究，发现了一种新型的1,3-二氢吲哚-2-酮化合物和一种与杂环芳香环融合的吡咯烷-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、良好的脑穿透性和高血浆浓度，从而实现了上述目标。
• DERIVES DE 1,3-DIHYDROINDOL-2-ONE SUBSTITUES EN 3 PAR UN GROUPE AZOTE COMME AGONISTES ET/OU ANTAGONISTES DE LA VASOPRESSINE ET/OU DE L'OCYTOCINE
  申请人：SANOFI

  公开号：EP0687251A1

  公开（公告）日：1995-12-20