6-chloro-3-(4-chlorophenyl)-3-hydroxyindolin-2-one | 917917-42-1

• 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: 6-chloro-3-(4-chlorophenyl)-3-hydroxyindolin-2-one
• 英文别名: rac-6-chloro-3-(4-chloro-phenyl)-3-hydroxy-1,3-dihydro-indol-2-one；6-chloro-3-(4-chlorophenyl)-3-hydroxy-1H-indol-2-one
• CAS: 917917-42-1
• 化学式: C₁₄H₉Cl₂NO₂
• 分子量: 294.137
• InChiKey: SCIMVPXRFBSKQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  6-chloro-3-(4-chlorophenyl)-3-hydroxyindolin-2-one 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 生成
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of indolinone derivatives as novel ghrelin receptor antagonists

  摘要：

  The ghrelin receptor is a G-protein-coupled receptor (GPCR) widely expressed in the brain, stomach and the intestine. It was firstly identified during studies aimed to find synthetic modulators of growth hormone (GH) secretion. GHSR and its endogenous ligand ghrelin were found to be involved in hunger response. Through food intake regulation, they could affect body weight and adiposity. Thus GHSR antagonists rapidly became an attractive target to treat obesity and feeding disorders. In this study we describe the biological properties of new indolinone derivatives identified as a new, chiral class of ghrelin antagonists. Their synthesis as well as the structure-activity relationship will be discussed herein. The in vitro identified compound 14f was a potent GHSR1a antagonist (IC50 = 7 nM). When tested in vivo, on gastric emptying model, 14f showed an inhibitory intrinsic effect when given alone and it dose dependently inhibited ghrelin stimulation. Compound 14f also reduced food intake stimulated both by fasting condition (high level of endogenous ghrelin) and by icv ghrelin. Moreover this compound improved glucose tolerance in ipGTT test. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.018
• 作为产物：
  描述：

  在 palladium diacetate 、 对甲苯磺酸 、 水 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 6-chloro-3-(4-chlorophenyl)-3-hydroxyindolin-2-one
  参考文献：
  名称：

  Pd和Cu前驱体催化2-炔基芳基叠氮化物一锅法合成2-氨基二苯甲酮

  摘要：

  公开了一种从 2-炔基芳基叠氮化物制备 2-氨基二苯甲酮的新型一锅三步合成方法。该反应由钯催化形成 3-羟基-3-苯基吲哚-2-酮，随后酰胺键水解和铜催化脱羧生成 2-氨基二苯甲酮。在温和的反应条件下以中等至良好的产率得到所需产物。

  DOI：

  10.1002/ejoc.202100772

文献信息

• Oxindole derivatives
  申请人：Luk Kim-Chun

  公开号：US20060293319A1

  公开（公告）日：2006-12-28

  The invention describes compounds of the general formula I or the pharmaceutically acceptable salts thereof, wherein R 1 , R 2 , R 3 and X are herein described, a process for their manufacture, medicaments containing them as well as the use of these compounds as pharmaceutically active agents. The compounds show activity as antiproliferative agents and may be especially useful for the treatment of cancer.

  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。
• In Situ Generation of Electrophilic Trifluoromethylthio Reagents for Enantioselective Trifluoromethylthiolation of Oxindoles
  作者：Xing-Li Zhu、Jin-Hui Xu、Dao-Juan Cheng、Li-Jiao Zhao、Xin-Yuan Liu、Bin Tan

  DOI：10.1021/ol5006888

  日期：2014.4.18

  An organocatalytic asymmetric trifluoromethylthiolation reaction via in situ generation of active electrophilic trifluoromethylthio species involving trichloroisocyanuric acid and AgSCF3 as a practical and easily handled electrophilic SCF3 source for CSP3–SCF3 bond formation was developed. Reactions with this one-pot version strategy occurred in good yields and excellent stereoselectivities to access

  开发了一种有机催化不对称三氟甲硫基化反应，该反应通过原位产生活性亲电三氟甲硫基物质而涉及，其中三氯异氰尿酸和AgSCF 3是一种实用且易于处理的亲电SCF 3源，用于形成C SP 3 -SCF 3键。与这种一锅法策略的反应以高收率和优异的立体选择性发生，以接近带有SCF 3取代的季手性中心的对映体纯的吲哚。这里描述的简单方法使用简单的原料，并在温和的条件下进行，这将在药物化学和面向多样性的合成中有用。
• One-pot synthesis of 3-hydroxy-2-oxindoles <i>via</i> acyloin rearrangements of 2-hydroxy-indolin-3-ones generated <i>in situ</i> from 2-alkynyl arylazides
  作者：Zhiqiang Zhou、Yao Xu、Boyu Zhu、Ping Li、Guiwen Hu、Fan Yang、Shijie Xu、Xiaoxiang Zhang

  DOI：10.1039/d0nj04588h

  日期：——

  A novel one-pot method to prepare 3-hydroxy-2-oxindoles via acyloin rearrangements of 2-hydroxy-indolin-3-ones generated in situ from 2-alkynyl arylazides has been described. The reaction was accomplished to afford a variety of 3-hydroxy-2-oxindole derivatives in moderate to good yields under mild conditions.

  已经描述了一种新颖的一锅法，该方法通过由2-炔基芳基叠氮化物就地产生的2-羟基-吲哚-3-酮的酰基转移而制备3-羟基-2-氧吲哚。在温和的条件下完成反应，以中等至良好的产率得到各种3-羟基-2-氧吲哚衍生物。
• OXINDOLE DERIVATIVES
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1896412A2

  公开（公告）日：2008-03-12
• US7576082B2
  申请人：——

  公开号：US7576082B2

  公开（公告）日：2009-08-18