5-chloro-3-hydroxy-3-(1-naphthyl)-1,3-dihydro-2H-indol-2-one | 905103-50-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-chloro-3-hydroxy-3-(1-naphthyl)-1,3-dihydro-2H-indol-2-one
• 英文别名: 5-chloro-3-hydroxy-3-(naphtyl-1)indolin-2-one；5-chloro-3-hydroxy-3-naphthalen-1-yl-1H-indol-2-one
• CAS: 905103-50-6
• 化学式: C₁₈H₁₂ClNO₂
• 分子量: 309.752
• InChiKey: QMUODUNLFIIHNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-3-hydroxy-3-(1-naphthyl)-1,3-dihydro-2H-indol-2-one 在 N-甲基吗啉 、 2-[氨基(二甲基)甲硅烷基]-2-甲基丙烷 、 四氯化锡 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 以67%的产率得到2-amino-5-chloro-3-(naphtyl-1)indol-3-oI
  参考文献：
  名称：

  A Concise Silylamine Approach to 2-Amino-3-hydroxy-indoles with Potent in vivo Antimalaria Activity

  摘要：

  The development of a concise strategy to access 2-amino-3-hydroxy-indoles, which are disclosed as novel antimalarials with potent in vivo activity, is reported. Starting from isatins the target compounds are synthesized in 2 steps and in good yields via oxoindole intermediates by employing tert-butyldimethylsilyl amine (TBDMSNH(2)) as previously unexplored ammonia equivalent.

  DOI：

  10.1021/ol101566h
• 作为产物：
  描述：

  1-萘硼酸 、 5-氯靛红 在 亚磷酸三苯酯 、 acetylacetonatobis(ethylene)rhodium(I) 水 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以87%的产率得到5-chloro-3-hydroxy-3-(1-naphthyl)-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  [EN] 2-AMINOINDOLE COMPOUNDS AND METHODS FOR THE TREATMENT OF MALARIA
  [FR] COMPOSÉS 2-AMINOINDOLES ET MÉTHODES DE TRAITEMENT DE LA MALARIA

  摘要：

  公开号：

  WO2011053697A8

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-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。
• 2-Aminoindole Compounds And Methods For The Treatment Of Malaria
  申请人：Mazitschek Ralph

  公开号：US20120232063A1

  公开（公告）日：2012-09-13

  The present invention relates to methods of treating a subject with malaria comprising administering a 2-aminoindole compound represented by Formula: (I)—The values and preferred values of the variables in Structural Formula I are defined herein.

  本发明涉及治疗疟疾的方法，包括给予一种由公式(I)所表示的2-氨基吲哚化合物。公式I中变量的值和优选值在此定义。
• 2-AMINOINDOLE COMPOUNDS AND METHODS FOR THE TREATMENT OF MALARIA
  申请人：Genzyme Corporation

  公开号：EP2493305B1

  公开（公告）日：2015-03-25
• US8030499B2
  申请人：——

  公开号：US8030499B2

  公开（公告）日：2011-10-04