6-ethyl-2-hydroxynaphthalene-1-carbaldehyde | 1597710-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-ethyl-2-hydroxynaphthalene-1-carbaldehyde
• 英文别名: 6-ethyl-2-hydroxy-1-naphthaldehyde
• CAS: 1597710-21-8
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: ZLTKSRJPWKDKAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-ethyl-2-hydroxynaphthalene-1-carbaldehyde 在 哌啶 、 吡啶 、 sodium tetrahydroborate 、 肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 4-[(6-ethyl-2-hydroxynaphthalen-1-yl)methyl]-5-(4-methylphenyl)-2,3-dihydro-1H-pyrazol-3-one
  参考文献：
  名称：

  Development of Pyrazolone and Isoxazol-5-one Cambinol Analogues as Sirtuin Inhibitors

  摘要：

  Sirtuins are a family of NAD+-dependent protein deacetylases that play critical roles in epigenetic regulation, stress responses, and cellular aging in eukaryotic cells. In an effort to identify small molecule inhibitors of sirtuins for potential use as chemotherapeutics as well as tools to modulate sirtuin activity, we previously identified a nonselective sirtuin inhibitor called cambinol (IC50 approximate to 50 mu M for SIRT1 and SIRT2) with in vitro and in vivo antilymphoma activity. In the current study, we used saturation transfer difference (STD) NMR experiments with recombinant SIRT1 and 20 to map parts of the inhibitor that interacted with the protein. Our ongoing efforts to optimize cambinol analogues for potency and selectivity have resulted in the identification of isoform selective analogues: 17 with >7.8-fold selectivity for SIRT1, 24 with >15.4-fold selectivity for SIRT2, and 8 with 6.8- and 5.3-fold selectivity for SIRT3 versus SIRT1 and SIRT2, respectively. In vitro cytotoxicity studies with these compounds as well as EX527, a potent and selective SIRT1 inhibitor, suggest that antilymphoma activity of this compound class. may be predominantly due to SIRT2 inhibition.

  DOI：

  10.1021/jm4018064
• 作为产物：
  描述：

  1,1-二氯甲醚 、 6-乙基-2-萘酚 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 6-ethyl-2-hydroxynaphthalene-1-carbaldehyde
  参考文献：
  名称：

  N-杂环卡宾有机催化阻转选择性合成1,2-二轴三芳基α-吡喃酮

  摘要：

  通过 NHC 有机催化完成了具有立体异构 1,2-二轴的三芳基 α-吡喃酮的单步阻转选择性构建。底物的结构和催化系统对该协议的成功起着至关重要的作用。进行 DFT 计算以合理化高立体选择性的起源。

  DOI：

  10.1002/anie.202212005

文献信息

• [EN] SMALL MOLECULE INHIBITORS OF A PROTEIN COMPLEX<br/>[FR] INHIBITEURS À PETITES MOLÉCULES D'UN COMPLEXE PROTÉIQUE
  申请人：UNIV CALIFORNIA

  公开号：WO2020247608A1

  公开（公告）日：2020-12-10

  Compositions and methods for treating thrombosis, inflammation, and atherosclerosis by administration of a compound that binds to KRIT1 to inhibit binding with HEG1.

  通过给予结合到KRIT1以抑制与HEG1结合的化合物的治疗血栓形成、炎症和动脉粥样硬化的组合物和方法。