1-acetyl-4-methoxyindoline | 91132-99-9

• 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-acetyl-4-methoxyindoline
• 英文别名: 1-(4-methoxy-2,3-dihydroindol-1-yl)ethanone
• CAS: 91132-99-9
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: FAIUJBNBBDWUAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-acetyl-4-methoxyindoline 在 sodium nitrate 、 三氯化铝 、 高氯酸 、 thallium(I) nitrate 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 11.0h， 生成 methyl (1-acetyl-4-methoxy-5-nitroindolin-7-yl)acetate
  参考文献：
  名称：

  Effects of Aromatic Substituents on the Photocleavage of 1-Acyl-7-nitroindolines

  摘要：

  Photolysis of 1-acyl-7-nitroindolines in aqueous solution gives a carboxylic acid and a 7-nitrosoindole, These compounds are useful as photolabile precursors of carboxylic acids, particularly neuroactive amino acids. The effect of electron-donating substituents at the 4-position has been explored for its effect on photolysis efficiency. 4-Methoxy substitution improved the photolysis efficiency >2-fold but the 4-dimethylamino analogue was essentially inert. A 5-alkyl substituent, that blocks unwanted nitration at this position, reduced the beneficial effect of the 4-methoxy group. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00745-6
• 作为产物：
  描述：

  4-甲氧基吲哚 在 sodium cyanoborohydride 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 1-acetyl-4-methoxyindoline
  参考文献：
  名称：

  [EN] EGFR SMALL MOLECULE INHIBITOR, PHARMACEUTICAL COMPOSITION CONTAINING SAME, AND USE THEREOF
  [FR] INHIBITEUR À PETITES MOLÉCULES EGFR, COMPOSITION PHARMACEUTIQUE LE CONTENANT ET SON UTILISATION
  [ZH] EGFR小分子抑制剂、含其的药物组合物及其用途

  摘要：

  本发明公开了一种多靶点小分子抑制剂、含其的药物组合物及其用途。具体地，本发明化合物具有式(I)所示结构，本发明还公开了所述化合物的制备方法及其作为EGFR抑制剂的用途，其可以用于治疗EGFR、HER-2、c-MET等介导的相关疾病(如癌症)，尤其是针对由于EGFR二突变与三突变、HER-2扩增和exon20突变、c-MET扩增等中的一种或多种基因突变所导致的对早期相关药物的耐药性的疾病(如癌症)有特别效果。

  公开号：

  WO2024017258A1

文献信息

• Rhodium-catalyzed C7-alkylation of indolines with maleimides
  作者：Changduo Pan、Yun Wang、Chao Wu、Jin-Tao Yu

  DOI：10.1039/c7ob03039h

  日期：——

  A rhodium(III)-catalyzed direct cross-coupling reaction of indolines with maleimides via C–H bond activation was developed. This protocol displays good functional group tolerance, which offers a novel approach to access C7 modified indoline derivatives including maleimide analogues.

  开发了铑（III）催化的吲哚啉与马来酰亚胺通过C–H键活化的直接交叉偶联反应。该协议显示出良好的官能团耐受性，这为获得包括马来酰亚胺类似物的C7修饰的吲哚衍生物提供了一种新颖的方法。
• 1-Acyl-7-nitroindoline derivatives, their preparation and their use as photocleavable precursors
  申请人：Medical Research Council

  公开号：US06765014B1

  公开（公告）日：2004-07-20

  Photoreleasable compounds comprising a caging moiety linked to an effector moiety represented by structural formula (I) wherein R1 is hydrogen; C1-10 alkyl or substituted alkyl; O(CH2)n—Y; N(COZ)(CH2)mY; or N[(CH2)mY′[(CH2)NY]; R2 and R3 are independently selected from: hydrogen; C1-10 alkyl or substituted alkyl; or R2 and R3 together are cycloalkyl; R4 is hydrogen; C1-10 alkyl or substituted alkyl; phenyl or substituted phenyl; (CH2)nY; or (CH2)mO(CH2)nY; wherein m and n are independently between 1 and 10; Y and Y′ are independently selected from hydrogen, CO2H or salts thereof or OPO32−, Z is hydrogen or C1-10 alkyl or substituted alkyl; and, X is an effector moiety or a group capable of being coupled or converted to an effector moiety, which are capable of releasing the effector moiety on irradiation, typically by flash irradiation with UV light. The photoreleasable compounds can therefor be used to deliver biologically active effector moieties such as neuroactive amino acids or metal chelators to sites where their activity is required.

  含有一个与结构式（I）所代表的效应子结构式相连的光释放化合物，其中R1为氢；C1-10烷基或取代烷基；O(CH2)n—Y；N(COZ)(CH2)mY；或N[(CH2)mY′[(CH2)NY]; R2和R3分别选择自：氢；C1-10烷基或取代烷基；或R2和R3一起为环烷基；R4为氢；C1-10烷基或取代烷基；苯基或取代苯基；(CH2)nY；或(CH2)mO(CH2)nY；其中m和n分别在1和10之间；Y和Y′分别选择自氢、CO2H或其盐或OPO32−，Z为氢或C1-10烷基或取代烷基；X为效应子或能够与效应子偶联或转化的基团，能够在照射下释放效应子，通常通过紫外光的闪烁照射。因此，这些光释放化合物可用于将生物活性效应子，如神经活性氨基酸或金属螯合剂，输送到需要其活性的部位。
• Rhodium(III)-catalyzed direct C-7 sulfonamidation and amination of indolines with arylsulfonamides and trifluoroacetamide
  作者：Yaqun Dong、Song Sun、Jin-tao Yu、Jiang Cheng

  DOI：10.1016/j.tetlet.2019.03.069

  日期：2019.5

  A rhodium-catalyzed direct C–H sulfonamidation and amidation of C-7 position of indolines by simple and commercially available arylsulfonamides and trifluoroacetamide has been developed, affording a series of N-arylsulfonamides and N-aryltrifluoroacetamides in moderate to excellent yields, respectively. Notably, this catalytic system is highly convenient on mmol scale.

  已开发出铑可通过简单的市售芳基磺酰胺和三氟乙酰胺直接催化C–H磺酰胺化和吲哚的C-7位酰胺化，从而分别以中等至优异的收率提供了一系列N-芳基磺酰胺和N-芳基三氟乙酰胺。值得注意的是，该催化体系在毫摩尔规模上非常方便。
• Designed switch from covalent to non-covalent inhibitors of carboxylesterase Notum activity
  作者：Benjamin N. Atkinson、Nicky J. Willis、Yuguang Zhao、Chandni Patel、Sarah Frew、Kathryn Costelloe、Lorenza Magno、Fredrik Svensson、E. Yvonne Jones、Paul V. Fish

  DOI：10.1016/j.ejmech.2023.115132

  日期：2023.5

  palmiteolate pocket with key interactions being aromatic stacking and a water mediated hydrogen bond to the oxyanion hole. These N-acyl indolines 4 will be useful tools for use in vitro studies to investigate the role of Notum in disease models, especially when paired with a structurally related covalent inhibitor (e.g. 4w and 2a). Overall, this study highlights the designed switch from covalent to non-covalent

  N-酰基二氢吲哚4是有效的非共价 Notum 抑制剂，由共价虚拟筛选命中2a开发而成。先导化合物合成简单，在生化 Notum-OPTS 测定中实现了优异的效力，并在基于细胞的 TCF/LEF 报告基因测定中恢复了 Wnt 信号传导。多个高分辨率X射线结构建立了这些抑制剂的共同结合模式，二氢吲哚结合在棕榈醇酸袋的中心，关键相互作用是芳族堆积和水介导的与氧阴离子孔的氢键。这些N -酰基二氢吲哚4将成为体外研究的有用工具，用于研究 Notum 在疾病模型中的作用，特别是与结构相关的共价抑制剂（例如4w和2a）配对时。总的来说，这项研究强调了从共价到非共价 Notum 抑制剂的设计转换，因此说明了命中生成和目标抑制的补充方法。
• REGIOSELECTIVE NITRATION OF 1-ACYL-4-METHOXYINDOLINES LEADS TO EFFICIENT SYNTHESIS OF A PHOTOLABILE<scp>l</scp>-GLUTAMATE PRECURSOR
  作者：George Papageorgiou、John E. T. Corrie

  DOI：10.1081/scc-120004148

  日期：2002.1

  Different nitrating reagents give different ratios of 5- and 7-nitro isomers of the title indolines. The best ratio of the 7-nitro isomer was obtained with claycop-acetic anhydride, and these conditions were particularly useful for preparation of a photolabile L-glutamate derivative.