isoindolo[2,1-a]quinoxalin-6(5H)-one | 1018073-72-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: isoindolo[2,1-a]quinoxalin-6(5H)-one
• 英文别名: 5H-isoindolo[2,1-a]quinoxalin-6-one
• CAS: 1018073-72-7
• 化学式: C₁₅H₁₀N₂O
• 分子量: 234.257
• InChiKey: SCMIDKNBCPXKLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  isoindolo[2,1-a]quinoxalin-6(5H)-one 在 四(三苯基膦)钯 、 sodium cyanoborohydride 、 potassium carbonate 、 溶剂黄146 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 甲苯 为溶剂， 反应 33.0h， 生成 6-fluoro-2-{1-[4-(isoindolo[2,1-a]quinoxalin-6-yl)benzyl]piperidin-4-yl}-1H-benzimidazole
  参考文献：
  名称：

  Synthesis and evaluation of the antiproliferative activity of novel isoindolo[2,1-a]quinoxaline and indolo[1,2-a]quinoxaline derivatives

  摘要：

  A novel series of isoindolo[2,1-a]quinoxaline and indolo[1,2-a]quinoxaline derivatives was synthesized and evaluated in vitro against various human cancer cell lines for antiproliferative activity. These new compounds displayed activity against leukemia and breast cancer cell lines in the 3- to 18-mu M concentration range.

  DOI：

  10.3109/14756366.2010.548326
• 作为产物：
  描述：

  2H-异吲哚-1-羧酸甲酯 在 copper(l) iodide 、 氯化亚砜 、 caesium carbonate 、 L-proline 、 potassium hydroxide 作用下， 以 甲醇 、 乙醚 、 水 、 二甲基亚砜 为溶剂， 反应 11.0h， 生成 isoindolo[2,1-a]quinoxalin-6(5H)-one
  参考文献：
  名称：

  撤回：铜催化合成取代异吲哚并[2,1-a]喹喔啉和异吲哚并[2,1-a]喹喔啉-6(5H)-酮

  摘要：

  已经开发出一种操作简单且有效的级联策略，通过取代 2H-异吲哚-1-甲醛和取代 2-卤代苯胺之间的一步铜催化 C-N 偶联反应获得取代的异吲哚 [2,1-a] 喹喔啉。描述了另一种简单的方法来制备取代的异吲哚并 [2,1-a] 喹喔啉-6(5H)-酮，其中包括将取代的 2H-异吲哚-1-羧酸转化为酰氯，然后与取代的 2-碘苯胺和铜催化的 C-N 偶联反应。

  DOI：

  10.1002/ejoc.201300466

文献信息

• WO2008/41264
  申请人：——

  公开号：——

  公开（公告）日：——
• Isoindolo[2,1-<i>a</i>]quinoxaline Derivatives, Novel Potent Antitumor Agents with Dual Inhibition of Tubulin Polymerization and Topoisomerase I
  作者：Patrizia Diana、Annamaria Martorana、Paola Barraja、Alessandra Montalbano、Gaetano Dattolo、Girolamo Cirrincione、Francesco Dall’Acqua、Alessia Salvador、Daniela Vedaldi、Giuseppe Basso、Giampietro Viola

  DOI：10.1021/jm070834t

  日期：2008.4.1

  Isoindoloquinoxalines 4 and 5 were obtained by refluxing 2-(2'-aminoaryl)-1-cyanoisoindoles 3a-e in acetic or formic acid. All derivatives were screened by the National Cancer Institute (Bethesda, MD) for the in vitro one dose primary anticancer assay against a 3-cell line panel. Compounds 4a-e, screened against a panel of about 60 human tumor cell lines, showed remarkable antineoplastic activity; they had GI(50) values in the low micromolar or submicromolar range and reached, in the case of 4c, nanomolar concentrations on 88% of the 59 tested cell lines. Flow cytometric analysis of cell cycle after treatment with 4c demonstrated an arrest of the cell cycle in G2/M phase. This effect was accompanied with apoptosis of the cells, mitochondrial depolarization, generation of reactive oxygen species, and activation of caspase-3 and caspase-9. Moreover, 4c induced a clear increase in the mitotic index, inhibited microtubule assembly in vitro, and interestingly also acted as a topoisomerase I inhibitor.
• Synthesis and evaluation of the antiproliferative activity of novel isoindolo[2,1-<i>a</i>]quinoxaline and indolo[1,2-<i>a</i>]quinoxaline derivatives
  作者：Vanessa Desplat、Stéphane Moreau、Solene Belisle-Fabre、Denis Thiolat、Juliette Uranga、Romain Lucas、Laure de Moor、Stéphane Massip、Christian Jarry、Djavad M. Mossalayi、Pascal Sonnet、Gérard Déléris、Jean Guillon

  DOI：10.3109/14756366.2010.548326

  日期：2011.10.1

  A novel series of isoindolo[2,1-a]quinoxaline and indolo[1,2-a]quinoxaline derivatives was synthesized and evaluated in vitro against various human cancer cell lines for antiproliferative activity. These new compounds displayed activity against leukemia and breast cancer cell lines in the 3- to 18-mu M concentration range.
• Retracted: Copper-Catalyzed Synthesis of Substituted Isoindolo[2,1-<i>a</i>]quinoxalines and Isoindolo[2,1-<i>a</i>]quinoxalin-6(5<i>H</i>)-ones
  作者：Subhasish Biswas、Sanjay Batra

  DOI：10.1002/ejoc.201300466

  日期：2013.8

  An operationally simple and efficient cascade strategy has been developed to access substituted isoindolo[2,1-a]quinoxalines through a one-step copper-catalyzed C–N coupling reaction between substituted 2H-isoindole-1-carbaldehydes and substituted 2-halophenylamines. Another straightforward procedure is described to prepare substituted isoindolo[2,1-a]quinoxalin-6(5H)-ones, which involved the transformation

  已经开发出一种操作简单且有效的级联策略，通过取代 2H-异吲哚-1-甲醛和取代 2-卤代苯胺之间的一步铜催化 C-N 偶联反应获得取代的异吲哚 [2,1-a] 喹喔啉。描述了另一种简单的方法来制备取代的异吲哚并 [2,1-a] 喹喔啉-6(5H)-酮，其中包括将取代的 2H-异吲哚-1-羧酸转化为酰氯，然后与取代的 2-碘苯胺和铜催化的 C-N 偶联反应。