1-methyl-3-(thiophen-2-ylmethyl)indolin-2-one | 1033200-48-4

• 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-methyl-3-(thiophen-2-ylmethyl)indolin-2-one
• 英文别名: 1-Methyl-3-[(thiophen-2-YL)methyl]-2,3-dihydro-1H-indol-2-one；1-methyl-3-(thiophen-2-ylmethyl)-3H-indol-2-one
• CAS: 1033200-48-4
• 化学式: C₁₄H₁₃NOS
• 分子量: 243.329
• InChiKey: JPOBBUUVQQPACV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-3-(thiophen-2-ylmethyl)indolin-2-one 在 lithium aluminium tetrahydride 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 77.0h， 生成 1,9-dimethyl-4a-(thiophen-2-ylmethyl)-4,4a,9,9a-tetrahydro-1H-pyrido[2,3-b]indol-2(3H)-one
  参考文献：
  名称：

  A facile and efficient synthesis of hexahydro-1H-pyrido[2,3-b]indol-2-one scaffolds via a sequential Michael addition/amidation/reductive cyclization process

  摘要：

  A new methodology was developed for the synthesis of hexahydro-1H-pyrido[2,3-b]indol-2-one scaffolds via a sequential Michael addition/amidation/reductive cyclization process. A wide variety of products bearing a hexahydro-1H-pyrido[2,3-b]indol-2-one core with varying degrees of substitution around it, which is a key structural skeleton found in a large number of biologically active natural products and pharmaceutical compounds, were obtained smoothly with high efficiency (up to overall yield of 67%). Furthermore, their biological activities have been preliminarily demonstrated by in vitro evaluation against human prostate cancer cells PC-3, human lung cancer cells A549 and human leukemia cells k562 by the MU-based assays, using the commercially available standard drug Cisplatin as a positive control. These results suggested there is a trend that lipophilic groups improve the potency, and also suggested a carbonyl moiety located in the hexahydro-1H-pyrido[2,3-b]indol-2-one scaffolds is beneficial for the activity. The results also demonstrated that most of the compounds showed considerable cytotoxicities to these three cell lines K562, A549 and PC-3, and that hexahydro-1H-pyrido[2,3-b]indol-2-one scaffolds may be potential leads for further antitumor activity screenings. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.10.039
• 作为产物：
  描述：

  在 iron(II) triflate 、 t-butyldimethylsilane 、 过氧化苯甲酰 作用下， 反应 12.0h， 以69%的产率得到1-methyl-3-(thiophen-2-ylmethyl)indolin-2-one
  参考文献：
  名称：

  一种铁催化氧化吲哚类化合物合成2-吲哚酮类化合物的方法

  摘要：

  本发明公开了一种铁催化氧化吲哚类化合物合成2‑吲哚酮类化合物的方法，包括在有机溶剂、水或有机溶剂的水溶液中，以氢硅烷为促进剂，在氧化剂和铁催化剂作用下，由吲哚类化合物(I)制得2‑吲哚酮类化合物(II)。本发明方法具有催化剂来源广泛、廉价和环保的优势；氧化剂来源广泛、廉价和绿色环保的优势；反应条件温和、选择性高和产率高；底物来源广泛且稳定；底物官能团相容性好且底物的适用范围广；复杂小分子可兼容，能很好的转化成酮。

  公开号：

  CN110256327A

文献信息

• A highly efficient and eco-friendly method for the synthesis of 1,3-indandione ring-fused 3-oxindoles bearing two contiguous quaternary stereocenters via an aldol reaction in aqueous media
  作者：Xiong-Li Liu、Bo-Wen Pan、Wen-Hui Zhang、Chao Yang、Jun Yang、Yang Shi、Ting-Ting Feng、Ying Zhou、Wei-Cheng Yuan

  DOI：10.1039/c4ob02103g

  日期：——

  method for the synthesis of oxindoles featuring two contiguous quaternary carbon centers via an aldol reaction starting from various 3-substituted oxindoles has been established. A wide variety of such featured multi-substituted 1,3-indandione ring-fused 3-oxindole scaffolds were obtained smoothly in good yields (up to 98%) employing the most green of solvents, namely water, as reaction medium. Furthermore

  已经建立了一种高效且环境友好的方法，该方法通过从各种3-取代的羟吲哚开始的醛醇缩合反应合成具有两个连续的季碳中心的羟吲哚。使用最绿色的溶剂（即水）作为反应介质，可以高收率（高达98％）顺利获得各种各样的此类具有特征的多取代1，3-茚满二酮环稠合的3-氧吲哚骨架。此外，使用市售标准药物顺铂作为阳性试验，通过基于MTT的检测方法对人前列腺癌细胞PC-3，人肺癌细胞A549和人白血病细胞K562进行体外评估，初步证明了其生物学活性。控制。令人高兴的是，化合物3s，3u，3y和3c'对人白血病细胞K562表现出最佳的体外抑制活性水平，分别是阳性对照顺铂的2.0倍，2.8倍，2.5倍和2.2倍。化合物3y对PC-3癌细胞的阳性对照的活性为顺铂的2.7倍，而3s，3u和3c'的体外对PC-3癌细胞的抑制活性与顺铂相当。化合物3s，3u和3y对人肺癌细胞A549具有良好的抑制作用。结果表明，1，3-茚满
• Synthesis of 3-substituted 2-oxindoles from secondary α-bromo-propionanilides <i>via</i> palladium-catalyzed intramolecular cyclization
  作者：Hui Shen、Yu Du、Jian Kan、Weiping Su

  DOI：10.1039/d2ob00480a

  日期：——

  aromatic halides, coupling reactions involving oxidative addition of alkyl halides, especially secondary or tertiary halides, to transition metals tend to be more challenging. Herein a palladium-catalyzed intramolecular cyclization of α-bromo-propionanilides has been developed, delivering a series of 3-substituted 2-oxindoles in high yields. The method features easy to prepare starting materials, broad substrate

  与芳族卤化物相比，涉及将卤代烷，尤其是仲卤化物或叔卤化物氧化加成到过渡金属上的偶联反应往往更具挑战性。本文开发了一种钯催化的 α-溴代丙酰苯胺的分子内环化，以高产率提供了一系列 3-取代的 2-羟基吲哚。该方法具有起始原料容易制备、底物范围广、官能团耐受性好等特点。已经进行了详细的机械研究。
• A simple and eco-friendly method for the aminomethylation of 3-substituted oxindoles via three-component Mannich reaction in aqueous media
  作者：Xiong-Li Liu、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1016/j.tetlet.2010.12.060

  日期：2011.2

  A simple and eco-friendly method for the aminomethylation of various 3-substituted oxindoles via three-component Mannich reaction in aqueous media has been established. A variety of oxindoles containing a quaternary carbon center, which comprises an aminomethyl group were obtained smoothly in good yields (up to 93%) with this method. Particularly valuable features, such as employing cheap and readily available formalin as a useful aminomethylation Cl unit and using water as a reaction medium, are embodied in this method. (C) 2010 Elsevier Ltd. All rights reserved.
• 一种铁催化氧化吲哚类化合物合成2-吲哚酮类化合物的方法
  申请人：南京师范大学

  公开号：CN110256327A

  公开（公告）日：2019-09-20

  本发明公开了一种铁催化氧化吲哚类化合物合成2‑吲哚酮类化合物的方法，包括在有机溶剂、水或有机溶剂的水溶液中，以氢硅烷为促进剂，在氧化剂和铁催化剂作用下，由吲哚类化合物(I)制得2‑吲哚酮类化合物(II)。本发明方法具有催化剂来源广泛、廉价和环保的优势；氧化剂来源广泛、廉价和绿色环保的优势；反应条件温和、选择性高和产率高；底物来源广泛且稳定；底物官能团相容性好且底物的适用范围广；复杂小分子可兼容，能很好的转化成酮。
• A facile and efficient synthesis of hexahydro-1H-pyrido[2,3-b]indol-2-one scaffolds via a sequential Michael addition/amidation/reductive cyclization process
  作者：Xiong-Li Liu、Wen-Hui Zhang、Zhen Yao、Xiong-Wei Liu、Li-Jun Peng、Zhi Zhao、Yi Lu、Ying Zhou、Wei-Cheng Yuan

  DOI：10.1016/j.tet.2015.10.039

  日期：2015.12

  A new methodology was developed for the synthesis of hexahydro-1H-pyrido[2,3-b]indol-2-one scaffolds via a sequential Michael addition/amidation/reductive cyclization process. A wide variety of products bearing a hexahydro-1H-pyrido[2,3-b]indol-2-one core with varying degrees of substitution around it, which is a key structural skeleton found in a large number of biologically active natural products and pharmaceutical compounds, were obtained smoothly with high efficiency (up to overall yield of 67%). Furthermore, their biological activities have been preliminarily demonstrated by in vitro evaluation against human prostate cancer cells PC-3, human lung cancer cells A549 and human leukemia cells k562 by the MU-based assays, using the commercially available standard drug Cisplatin as a positive control. These results suggested there is a trend that lipophilic groups improve the potency, and also suggested a carbonyl moiety located in the hexahydro-1H-pyrido[2,3-b]indol-2-one scaffolds is beneficial for the activity. The results also demonstrated that most of the compounds showed considerable cytotoxicities to these three cell lines K562, A549 and PC-3, and that hexahydro-1H-pyrido[2,3-b]indol-2-one scaffolds may be potential leads for further antitumor activity screenings. (C) 2015 Elsevier Ltd. All rights reserved.