9-methoxy-2,2-dimethyl-2H-naphtho<2,3-b>pyran-5,10-dione | 58785-62-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 9-methoxy-2,2-dimethyl-2H-naphtho<2,3-b>pyran-5,10-dione
• 英文别名: 9-methoxy-2,2-dimethyl-2H-benzo[g]chromene-5,10-dione；2H-Naphtho[2,3-b]pyran-5,10-dione, 9-methoxy-2,2-dimethyl-；9-methoxy-2,2-dimethylbenzo[g]chromene-5,10-dione
• CAS: 58785-62-9
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: LQAOFMNANKHBPH-UHFFFAOYSA-N

物化性质

• 沸点：
  458.1±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-methoxy-2,2-dimethyl-2H-naphtho<2,3-b>pyran-5,10-dione 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以99%的产率得到9-甲氧基-alpha-拉帕醌
  参考文献：
  名称：

  Tapia, Ricardo; Valderrama, Jaime A.; Quintanar, Carmina, Heterocycles, 1994, vol. 38, # 8, p. 1797 - 1804

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-dihydro-4-hydroxy-2,2-dimethyl-2H-1-benzopiran-5,8-dione 在 sodium hydride 、 magnesium sulfate 、 对甲苯磺酸 、 silver(l) oxide 作用下， 以 甲醇 、 xylene 为溶剂， 反应 4.25h， 生成 9-methoxy-2,2-dimethyl-2H-naphtho<2,3-b>pyran-5,10-dione
  参考文献：
  名称：

  Tapia, Ricardo; Valderrama, Jaime A.; Quintanar, Carmina, Heterocycles, 1994, vol. 38, # 8, p. 1797 - 1804

  摘要：

  DOI：

文献信息

• Indoleamine 2,3-Dioxygenase Is the Anticancer Target for a Novel Series of Potent Naphthoquinone-Based Inhibitors
  作者：Sanjeev Kumar、William P. Malachowski、James B. DuHadaway、Judith M. LaLonde、Patrick J. Carroll、Daniel Jaller、Richard Metz、George C. Prendergast、Alexander J. Muller

  DOI：10.1021/jm7014155

  日期：2008.3.1

  Indoleamine 2,3-dioxygenase (IDO) is emerging as an important new therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. While small molecule inhibitors of IDO exist, there remains a dearth of high-potency compounds offering in vivo efficacy and clinical translational potential. In this study, we address this gap by defining a new class of naphthoquinone-based IDO inhibitors exemplified by the natural product menadione, which is shown in mouse tumor models to have similar antitumor activity to previously characterized IDO inhibitors. Genetic validation that IDO is the critical in vivo target is demonstrated using IDO-null mice. Elaboration of menadione to a pyranonaphthoquinone has yielded low nanomolar potency inhibitors, including new compounds which are the most potent reported to date (K-i = 61-70 nM). Synthetic accessibility of this class will facilitate preclinical chemical-genetic studies as well as further optimization of pharmacological parameters for clinical translation.
• GILES R. G. F.; ROOS G. H. P., TETRAHEDRON LETT. <TELE-AY>, 1975, NO 47, 4159-4160
  作者：GILES R. G. F.、 ROOS G. H. P.

  DOI：——

  日期：——
• Tapia, Ricardo; Valderrama, Jaime A.; Quintanar, Carmina, Heterocycles, 1994, vol. 38, # 8, p. 1797 - 1804
  作者：Tapia, Ricardo、Valderrama, Jaime A.、Quintanar, Carmina

  DOI：——

  日期：——