6-allyl-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione | 81721-77-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6-allyl-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione
• 英文别名: 6-Allyl-5H-indeno(1,2-c)isoquinoline-5,11(6H)-dione；6-prop-2-enylindeno[1,2-c]isoquinoline-5,11-dione
• CAS: 81721-77-9
• 化学式: C₁₉H₁₃NO₂
• 分子量: 287.318
• InChiKey: LKYGYLCYRUQUNK-UHFFFAOYSA-N

物化性质

• 熔点：
  165.6-167 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  508.9±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  6-allyl-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione 在 溴 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 30.0h， 生成 (2'RS)-5,6-dihydro-6-[(2',3'-dihydroxypropyl)]-5,11-dioxo-11H-indeno[1,2-c]isoquinoline
  参考文献：
  名称：

  Synthesis and cytotoxic evaluation of novel indenoisoquinoline-propan-2-ol hybrids

  摘要：

  The synthesis of N-substituted indenoisoquinolines was performed by applying a two-step condensation between 2-carboxybenzaldehyde and phthalide, followed by treatment with various primary amines. N-allylindenoisoquinoline was subsequently selected as a substrate for hydroxybromination, providing 6-(3-bromo-2-hydroxy)indenoisoquinoline as a key intermediate for derivatization in the lactam side chain. In this way, a series of 6-(2-hydroxypropyl)indenoisoquinolines bearing various functional groups at the 3'-position were prepared, which can be considered as novel indenoisoquinoline-propan-2-ol hybrid molecules. Subsequent cytotoxic evaluation of 28 indenoisoquinolines against two human cancer cell lines (Hep-G2 and KB) demonstrated a moderate to high antiproliferative activity displayed by 11 indenoisoquinolines thus synthesized. In particular, the introduction of the 2-hydroxypropyl side chain was shown to be beneficial for the overall cytotoxic activity, pointing to the potential relevance of these novel indenoisoquinoline-propan-2-ol hybrids. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.12.045
• 作为产物：
  描述：

  2-(2-Carboxyphenyl)-1,3-indandion 在 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 30.0h， 生成 6-allyl-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione
  参考文献：
  名称：

  Synthesis and cytotoxic evaluation of novel indenoisoquinoline-propan-2-ol hybrids

  摘要：

  The synthesis of N-substituted indenoisoquinolines was performed by applying a two-step condensation between 2-carboxybenzaldehyde and phthalide, followed by treatment with various primary amines. N-allylindenoisoquinoline was subsequently selected as a substrate for hydroxybromination, providing 6-(3-bromo-2-hydroxy)indenoisoquinoline as a key intermediate for derivatization in the lactam side chain. In this way, a series of 6-(2-hydroxypropyl)indenoisoquinolines bearing various functional groups at the 3'-position were prepared, which can be considered as novel indenoisoquinoline-propan-2-ol hybrid molecules. Subsequent cytotoxic evaluation of 28 indenoisoquinolines against two human cancer cell lines (Hep-G2 and KB) demonstrated a moderate to high antiproliferative activity displayed by 11 indenoisoquinolines thus synthesized. In particular, the introduction of the 2-hydroxypropyl side chain was shown to be beneficial for the overall cytotoxic activity, pointing to the potential relevance of these novel indenoisoquinoline-propan-2-ol hybrids. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.12.045

文献信息

• 茚并异喹啉衍生物的制备方法
  申请人：姚清发

  公开号：CN109748870B

  公开（公告）日：2021-02-12

  一种如下式(I)所示的茚并异喹啉衍生物的制备方法，包括下列步骤：(A)提供一如下式(II)所示的第一反应物及一如下式(III)所示的第二反应物：其中，R1、R3、A、X、Y、Z、m及n如说明书中所定义；以及(B)将式(II)所示的第一反应物及式(III)所示的第二反应物置于一溶剂中进行反应，并选择性的添加R2NH2进行反应，以得到如式(I)所示的茚并异喹啉衍生物。
• Synthesis of Biologically Active Indenoisoquinoline Derivatives via a One-Pot Copper(II)-Catalyzed Tandem Reaction
  作者：Chia-Yu Huang、Veerababurao Kavala、Chun-Wei Kuo、Ashok Konala、Tang-Hao Yang、Ching-Fa Yao

  DOI：10.1021/acs.joc.6b02814

  日期：2017.2.17

  A concise route for the synthesis of indenoisoquinoline derivatives from 2-iodobenzamide and 1,3-indanedione derivatives in the presence of copper(II) chloride and cesium carbonate in acetonitrile solvent is reported. A wide variety of 2-iodobenzamide derivatives and indandiones could be used to synthesize indenoisoquinoline derivatives and other fused indenoisoquinoline in moderate to good yields

  据报道，在氯化铜（II）和碳酸铯存在下，在乙腈溶剂中，由2-碘联苯甲酰胺和1,3-茚满二酮衍生物合成茚并异喹啉衍生物的简便方法。各种各样的2-碘代苯甲酰胺衍生物和茚满二酮可用于以中等至良好的产率合成茚并异喹啉衍生物和其他稠合的茚并异喹啉。该方法适用于一步合成一系列临床活性拓扑异构酶I抑制剂，例如NSC 314622，LMP-400，LMP-776。
• Method for preparing indenoisoquinoline derivatives
  申请人：NATIONAL TAIWAN NORMAL UNIVERSITY

  公开号：US10336704B2

  公开（公告）日：2019-07-02

  A method for preparing indenoisoquinoline derivatives represented by the following formula (I) is disclosed, which comprises the following steps: (A) providing a first reactant represented by the following formula (II) and a second reactant represented by the following formula (III): and (B) reacting the first reactant represented by the formula (II) and the second reactant represented by the formula (III) in a solvent and selectively adding R2NH2 therein, to obtain the indenoisoquinoline derivatives represented by the formula (I), wherein, R1, R2, R3, A, X, Y, Z, m and n are defined in the specification.

  本发明公开了一种制备下式（I）所代表的茚并异喹啉衍生物的方法，该方法包括以下步骤： (A) 提供下式（II）代表的第一反应物和下式（III）代表的第二反应物： 和 (B) 将式（II）代表的第一反应物和式（III）代表的第二反应物在溶剂中反应，并在其中选择性地加入 R2NH2，得到式（I）代表的茚并异喹啉衍生物，其中，R1、R2、R3、A、X、Y、Z、m 和 n 在说明书中定义。
• WAWZONEK, S., ORG. PREP. AND PROCED. INT., 1982, 14, N 3, 163-168
  作者：WAWZONEK, S.

  DOI：——

  日期：——
• Method for Preparing Indenoisoquinoline Derivatives
  申请人：NATIONAL TAIWAN NORMAL UNIVERSITY

  公开号：US20190127330A1

  公开（公告）日：2019-05-02

  A method for preparing indenoisoquinoline derivatives represented by the following formula (I) is disclosed, which comprises the following steps: (A) providing a first reactant represented by the following formula (II) and a second reactant represented by the following formula (III): and (B) reacting the first reactant represented by the formula (II) and the second reactant represented by the formula (III) in a solvent and selectively adding R 2 NH 2 therein, to obtain the indenoisoquinoline derivatives represented by the formula (I), wherein, R 1 , R 2 , R 3 , A, X, Y, Z, m and n are defined in the specification.