6-(3-methoxypropyl)-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione | 1426998-22-2

• 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-(3-methoxypropyl)-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione
• 英文别名: 6-(3-Methoxypropyl)indeno[1,2-c]isoquinoline-5,11-dione；6-(3-methoxypropyl)indeno[1,2-c]isoquinoline-5,11-dione
• CAS: 1426998-22-2
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: BKWQKKMXDYBDDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯并[d]茚并[1,2-b]吡喃-5,11-二酮 、 3-甲氧基丙胺 以 四氢呋喃 、 氯仿 为溶剂， 反应 2.0h， 以66%的产率得到6-(3-methoxypropyl)-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Indenoisoquinoline Rexinoids with Chemopreventive Potential

  摘要：

  Nuclear receptors, such as the retinoid X receptor (RXR), are proteins that regulate a myriad of cellular processes. Molecules that function as RXR agonists are of special interest for the prevention and control of carcinogenesis. The majority of these ligands possess an acidic moiety that is believed to be key for RXR activation. This communication presents the design, synthesis, and biological evaluation of both acidic and nonacidic indenoisoquinolines as new RXR ligands. In addition, a comprehensive structure-activity relationship study is presented that identifies the important features of the indenoisoquinoline rexinoids. The ease of modification of the indenoisoquinoline core and the lack of the necessity of a carboxyl group for activity make them an attractive and unusual family of RXR agonists. This work establishes a structural foundation for the design of new and novel rexinoid cancer chemopreventive agents.

  DOI：

  10.1021/jm400026k

文献信息

• METHOD FOR PREPARING INDENOISOQUINOLINE DERIVATIVES
  申请人：National Taiwan Normal University

  公开号：EP3480187A1

  公开（公告）日：2019-05-08

  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。
• 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。
• 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.
• Design, Synthesis, and Biological Evaluation of Indenoisoquinoline Rexinoids with Chemopreventive Potential
  作者：Martin Conda-Sheridan、Eun-Jung Park、Daniel E. Beck、P. V. Narasimha Reddy、Trung X. Nguyen、Bingjie Hu、Lian Chen、Jerry J. White、Richard B. van Breemen、John M. Pezzuto、Mark Cushman

  DOI：10.1021/jm400026k

  日期：2013.3.28

  Nuclear receptors, such as the retinoid X receptor (RXR), are proteins that regulate a myriad of cellular processes. Molecules that function as RXR agonists are of special interest for the prevention and control of carcinogenesis. The majority of these ligands possess an acidic moiety that is believed to be key for RXR activation. This communication presents the design, synthesis, and biological evaluation of both acidic and nonacidic indenoisoquinolines as new RXR ligands. In addition, a comprehensive structure-activity relationship study is presented that identifies the important features of the indenoisoquinoline rexinoids. The ease of modification of the indenoisoquinoline core and the lack of the necessity of a carboxyl group for activity make them an attractive and unusual family of RXR agonists. This work establishes a structural foundation for the design of new and novel rexinoid cancer chemopreventive agents.