3,6-Dimethylindeno[1,2-c]isoquinoline-5,11-dione | 1426997-99-0

• 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: 3,6-Dimethylindeno[1,2-c]isoquinoline-5,11-dione
• CAS: 1426997-99-0
• 化学式: C₁₈H₁₃NO₂
• 分子量: 275.307
• InChiKey: GCKGMJTXKYWKBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  3,6-Dimethylindeno[1,2-c]isoquinoline-5,11-dione 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 silver nitrate 作用下， 以 四氯化碳 、 1,4-二氧六环 、 水 为溶剂， 反应 11.0h， 以5%的产率得到6-Methyl-5,11-dioxoindeno[1,2-c]isoquinoline-3-carbaldehyde
  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
• 作为产物：
  描述：

  2,7-dimethyl-1-oxo-3-phenyl-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid 在 氯化亚砜 、 aluminum (III) chloride 作用下， 以 苯 、 硝基苯 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以14.3%的产率得到3,6-Dimethylindeno[1,2-c]isoquinoline-5,11-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