1-(4-bromobenzyl)-5-chloroindoline-2,3-dione | 1041534-00-2

• 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-(4-bromobenzyl)-5-chloroindoline-2,3-dione
• 英文别名: 1-[(4-bromophenyl)methyl]-5-chloroindole-2,3-dione
• CAS: 1041534-00-2
• 化学式: C₁₅H₉BrClNO₂
• 分子量: 350.599
• InChiKey: FBPBKOQLHLKLJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-bromobenzyl)-5-chloroindoline-2,3-dione 在 sodium azide 、 水 、 sodium hydride 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 0.33h， 生成 1'-(4-bromobenzyl)-5'-chloro-4,7-dihydrospiro[[1,2,3]triazolo[5,1-c][1,4]oxazine-6,3'-indolin]-2'-one
  参考文献：
  名称：

  Spirooxindole-derived morpholine-fused-1,2,3-triazoles: Design, synthesis, cytotoxicity and apoptosis inducing studies

  摘要：

  A series of new spirooxindole-derived morpholine-fused-1,2,3-triazole derivatives has been synthesized from isatin spiro-epoxides. The protocol involves regiospecific isatin-epoxide ring opening with azide nucleophile followed by sequential O-propargylation, and intramolecular 1,3-dipolar cycloaddition reaction. These compounds have been evaluated for their antiproliferative activity against selected human tumor cell lines of lung (A549), breast (MCF-7), cervical (HeLa), and prostate (DU-145). Among the tested compounds, 61, 6n and 6p showed potent growth inhibition against A549 cell line with IC50 values in the range of 1.87-436 mu M, which are comparable to reference standards doxorubicin and 5-flourouracil. The compounds 6i and 6p treated A549 cells displayed typical apoptotic morphological features such as cell shrinkage, nuclear condensation, fragmentation, and decreased migration potential. Flow-cytometry analysis revealed that the compounds arrested the cells in G2/M phase of cell cycle. Hoechst and acridine orange/ethidium bromide staining studies also showed that the cell proliferation was inhibited through induction of apoptosis. Moreover, the compounds treatment led to collapse of the mitochondrial membrane potential (WPM) and increased levels of reactive oxygen species (ROS) were noted in A549 cells. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.08.017
• 作为产物：
  描述：

  对氯苯胺 在 盐酸 、 盐酸羟胺 、 sodium hydride 、 sodium sulfate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-(4-bromobenzyl)-5-chloroindoline-2,3-dione
  参考文献：
  名称：

  Spirooxindole-derived morpholine-fused-1,2,3-triazoles: Design, synthesis, cytotoxicity and apoptosis inducing studies

  摘要：

  A series of new spirooxindole-derived morpholine-fused-1,2,3-triazole derivatives has been synthesized from isatin spiro-epoxides. The protocol involves regiospecific isatin-epoxide ring opening with azide nucleophile followed by sequential O-propargylation, and intramolecular 1,3-dipolar cycloaddition reaction. These compounds have been evaluated for their antiproliferative activity against selected human tumor cell lines of lung (A549), breast (MCF-7), cervical (HeLa), and prostate (DU-145). Among the tested compounds, 61, 6n and 6p showed potent growth inhibition against A549 cell line with IC50 values in the range of 1.87-436 mu M, which are comparable to reference standards doxorubicin and 5-flourouracil. The compounds 6i and 6p treated A549 cells displayed typical apoptotic morphological features such as cell shrinkage, nuclear condensation, fragmentation, and decreased migration potential. Flow-cytometry analysis revealed that the compounds arrested the cells in G2/M phase of cell cycle. Hoechst and acridine orange/ethidium bromide staining studies also showed that the cell proliferation was inhibited through induction of apoptosis. Moreover, the compounds treatment led to collapse of the mitochondrial membrane potential (WPM) and increased levels of reactive oxygen species (ROS) were noted in A549 cells. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.08.017

文献信息

• Synthesis of isatin based N1-alkylated 3-β-C-glycoconjugated-oxopropylidene oxindoles as potent antiplasmodial agents
  作者：Ravi Kumar Thakur、Prince Joshi、Kapil Upadhyaya、Kartikey Singh、Gaurav Sharma、Sanjeev K. Shukla、Renu Tripathi、Rama Pati Tripathi

  DOI：10.1016/j.ejmech.2018.11.008

  日期：2019.1

  In an attempt to develop new antimalarial drugs, we have synthesized a new class of N-alkylated 3-glycoconjugated-oxopropylidene oxindoles starting from substituted isatins and glucopyranosyl propanone via a well-known cross-aldol reaction followed by dehydration. The newly synthesized compounds were screened for their in vitro antiplasmodial activity, and among all the compounds 9g, 9f, 9b, 8d, 9d

  为了开发新的抗疟疾药物，我们已经合成了新的一类N-烷基化的3-糖基共轭-氧亚丙基氧吲哚，它是由取代的靛红和葡萄糖基吡喃糖基丙酮通过众所周知的交叉羟醛反应然后脱水而合成的。筛选了新合成的化合物的体外抗血浆活性，在所有化合物9g，9f，9b，8d，9d，9c和9e中显示出有效的活性，对氯喹的IC 50值在0.1–0.3μM范围内（CQ）敏感的Pf 3D7菌株，而化合物9d，9b，9e，8c，8f，9c和9a显示出对CQ耐药的Pf K1菌株的IC 50值在0.1-0.4μM范围内的有希望的活性，甚至比标准药物氯喹的IC 50值为0.5更好。微米
• 3-SUBSTITUTED-3-HYDROXY OXINDOLE DERIVATIVES AND PROCESS FOR PREPARATION THEREOF
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：US20130345438A1

  公开（公告）日：2013-12-26

  The present invention relates to expedient method for synthesis of 3-substituted-3-hydroxy-oxindole derivatives, which are useful as synthetic precursors to valuable pharmaceutical compounds. These are synthesized by reacting nitromethane with the corresponding isatins of formula (I). The reaction process of isatins was carried using water as a solvent at room temperature to form the corresponding 3-hydroxy-3-nitromethylindolin-2-ones of formula (II).

  本发明涉及一种合成3-取代-3-羟基-恩二酮衍生物的便捷方法，这些衍生物可用作有价值的药用化合物的合成前体。这些衍生物是通过将硝基甲烷与相应的式(I)的吲哚酮反应而合成的。吲哚酮的反应过程是在室温下使用水作为溶剂进行的，形成相应的式(II)的3-羟基-3-硝基甲基吲哚烷-2-酮。
• 3-substituted-3-hydroxy oxindole derivatives and process for preparation thereof
  申请人：Council of Scientific & Industrial Research

  公开号：US08933248B2

  公开（公告）日：2015-01-13

  The present invention relates to expedient method for synthesis of 3-substituted-3-hydroxy-oxindole derivatives, which are useful as synthetic precursors to valuable pharmaceutical compounds. These are synthesized by reacting nitromethane with the corresponding isatins of formula (I). The reaction process of isatins was carried using water as a solvent at room temperature to form the corresponding 3-hydroxy-3-nitromethylindolin-2-ones of formula (II).

  本发明涉及一种合成3-取代-3-羟基-氧化吲哚衍生物的便捷方法，这些衍生物可用作有价值的药物化合物的合成前体。它们是通过将硝基甲烷与式(I)的相应异色酮反应合成的。异色酮的反应过程在室温下使用水作溶剂进行，以形成相应的式(II)的3-羟基-3-硝基甲基吲哚啉-2-酮。
• “On water” expedient synthesis of 3-indolyl-3-hydroxy oxindole derivatives and their anticancer activity in vitro
  作者：Parvathaneni Sai Prathima、Pamanji Rajesh、Janapala Venkateswara Rao、Uppalapati Sai Kailash、Balasubramanian Sridhar、Mandapati Mohan Rao

  DOI：10.1016/j.ejmech.2014.07.004

  日期：2014.9

  A series of 3-indolyl-3-hydroxy oxindole derivatives (n = 41) were synthesized by the green aminocatalytic method with excellent yields under mild reaction conditions. All the newly synthesized derivatives were subjected to evaluate their cytotoxic properties against different human cancer cell lines. Results indicated that about 73% of the derivatives exhibited significant anti-proliferative activities against leukemia (U937, THP-1), lung (A549) and breast cancer (MCF7) cell lines. Among them a few of the derivatives exhibited the most potent and effective cytotoxic activities on U937 (34, 36, 38 and 41) and MCF7 (12, 35, 40 and 41) cell lines, and their anti-proliferation activities are better than the positive control, Etoposide.
• Spirooxindole-derived morpholine-fused-1,2,3-triazoles: Design, synthesis, cytotoxicity and apoptosis inducing studies
  作者：Kishna Ram Senwar、Pankaj Sharma、T. Srinivasa Reddy、Manish Kumar Jeengar、V. Lakshma Nayak、V.G.M. Naidu、Ahmed Kamal、Nagula Shankaraiah

  DOI：10.1016/j.ejmech.2015.08.017

  日期：2015.9

  A series of new spirooxindole-derived morpholine-fused-1,2,3-triazole derivatives has been synthesized from isatin spiro-epoxides. The protocol involves regiospecific isatin-epoxide ring opening with azide nucleophile followed by sequential O-propargylation, and intramolecular 1,3-dipolar cycloaddition reaction. These compounds have been evaluated for their antiproliferative activity against selected human tumor cell lines of lung (A549), breast (MCF-7), cervical (HeLa), and prostate (DU-145). Among the tested compounds, 61, 6n and 6p showed potent growth inhibition against A549 cell line with IC50 values in the range of 1.87-436 mu M, which are comparable to reference standards doxorubicin and 5-flourouracil. The compounds 6i and 6p treated A549 cells displayed typical apoptotic morphological features such as cell shrinkage, nuclear condensation, fragmentation, and decreased migration potential. Flow-cytometry analysis revealed that the compounds arrested the cells in G2/M phase of cell cycle. Hoechst and acridine orange/ethidium bromide staining studies also showed that the cell proliferation was inhibited through induction of apoptosis. Moreover, the compounds treatment led to collapse of the mitochondrial membrane potential (WPM) and increased levels of reactive oxygen species (ROS) were noted in A549 cells. (C) 2015 Elsevier Masson SAS. All rights reserved.