3-bromoindeno[1,2-c]isochromene-5,11-dione | 1426998-09-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 3-bromoindeno[1,2-c]isochromene-5,11-dione
• 英文别名: 3-Bromoindeno[1,2-c]isochromene-5,11-dione
• CAS: 1426998-09-5
• 化学式: C₁₆H₇BrO₃
• 分子量: 327.134
• InChiKey: GWVCXTIBWBGXQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromoindeno[1,2-c]isochromene-5,11-dione 在 四(三苯基膦)钯 、 氯化亚砜 、 水 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 氯仿 为溶剂， 反应 30.0h， 生成
  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：

  6-氨基四氯苯酞 在 N-溴代丁二酰亚胺(NBS) 、 氢溴酸 、 sodium methylate 、 potassium hydroxide 、 sodium nitrite 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 水 、 乙酸乙酯 为溶剂， 反应 109.46h， 生成 3-bromoindeno[1,2-c]isochromene-5,11-dione
  参考文献：
  名称：

  Discovery of Potent Indenoisoquinoline Topoisomerase I Poisons Lacking the 3-Nitro Toxicophore

  摘要：

  3-Nitroindenoisoquinoline human topoisomerase IB (Top1) poisons have potent antiproliferative effects on cancer cells. The undesirable nitro toxicophore could hypothetically be replaced by other functional groups that would retain the desired biological activities and minimize potential safety risks. Eleven series of indenoisoquinolines bearing 3-nitro bioisosteres were synthesized. The molecules were evaluated in the Top1-mediated DNA cleavage assay and in the National Cancer Institute's 60 cell line cytotoxicity assay. The data reveal that fluorine and chlorine may substitute for the 3-nitro group with minimal loss of Top1 poisoning activity. The new information gained from these efforts can be used to design novel indenoisoquinolines with improved safety.

  DOI：

  10.1021/acs.jmedchem.5b00303