8-bromo-6-chloro-2-(2-(1H-indol-3-yl)ethyl)chroman-4-on | 1138464-50-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 8-bromo-6-chloro-2-(2-(1H-indol-3-yl)ethyl)chroman-4-on
• 英文别名: 8-bromo-6-chloro-2-[2-(1H-indol-3-yl)ethyl]-2,3-dihydrochromen-4-one
• CAS: 1138464-50-2
• 化学式: C₁₉H₁₅BrClNO₂
• 分子量: 404.691
• InChiKey: UWRZUKJDAYEQIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3'-溴-5'-氯-2'-羟基苯乙酮 、 3-(1H-indol-3-yl)propanal 在 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以86%的产率得到8-bromo-6-chloro-2-(2-(1H-indol-3-yl)ethyl)chroman-4-on
  参考文献：
  名称：

  Synthesis and Evaluation of Substituted Chroman-4-one and Chromone Derivatives as Sirtuin 2-Selective Inhibitors

  摘要：

  A series of substituted chromone/chroman-4-one derivatives has been synthesized and evaluated as novel inhibitors of SIRT2, an enzyme involved in aging-related diseases, e.g., neurodegenerative disorders. The analogues were efficiently synthesized in a one-step procedure including a base-mediated aldol condensation using microwave irradiation. The most potent compounds, with inhibitory concentrations in the low micromolar range, were substituted in the 2-, 6-, and 8-positions. Larger, electron-withdrawing substituents in the 6- and 8-positions were favorable. The most potent inhibitor of SIRT2 was 6,8-dibromo-2-pentylchroman-4-one with an IC50 of 1.5 mu M. The synthesized compounds show high selectivity toward SIRT2 over SIRT1 and SIRT3 and represent an important starting point for the development of novel SIRT2 inhibitors.

  DOI：

  10.1021/jm3005288

文献信息

• Synthesis of 2-Alkyl-Substituted Chromone Derivatives Using Microwave Irradiation
  作者：Maria Fridén-Saxin、Nils Pemberton、Krystle da Silva Andersson、Christine Dyrager、Annika Friberg、Morten Grøtli、Kristina Luthman

  DOI：10.1021/jo802783z

  日期：2009.4.3

  A base-promoted condensation between 2-hydroxyacetophenones and aliphatic aldehydes has been studied. The reaction has been optimized to afford 2-alkyl-substituted 4-chromanones in an efficient manner using microwave heating. Performing the reaction using diisopropylamine in EtOH at 170 degrees C for 1 h gave moderate to high yields (43-88%). The 4-chromanones could be further converted into highly functionalized 2,3,6,8-tetrasubstituted chromones in which a 3-substituent (acetate, amine, or bromine) was introduced via straightforward chemical transformations.