4-(2-hydroxyethoxy)-1-naphthol | 83115-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(2-hydroxyethoxy)-1-naphthol
• 英文别名: 4-(2-hydroxyethoxy)naphthalen-1-ol
• CAS: 83115-56-4
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: PABAILNRYWRUQG-UHFFFAOYSA-N

物化性质

• 熔点：
  88-90 °C
• 沸点：
  436.2±20.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 4-(2-hydroxyethoxy)-1-naphthol 在 吡啶 作用下， 生成
  参考文献：
  名称：

  Conjugate addition of acylate-nickel complexes to quinone monoketals: formal synthesis of the naphthoquinone antibiotics nanaomycin A and deoxyfrenolicin

  摘要：

  DOI：

  10.1021/jo00350a027
• 作为产物：
  描述：

  4,4-etilendioxinaftalen-1-ona 在 正丁基锂 、 tetracarbonyl nickel 作用下， 以 四氢呋喃 为溶剂， 以12%的产率得到4-(2-hydroxyethoxy)-1-naphthol
  参考文献：
  名称：

  Synthesis of naphthoquinone antibiotics: conjugate addition/electrophile trapping with acylnickel carbonylate anions

  摘要：

  DOI：

  10.1021/jo00143a055

文献信息

• Rational Design of Indoleamine 2,3-Dioxygenase Inhibitors
  作者：Ute F. Röhrig、Loay Awad、Aurélien Grosdidier、Pierre Larrieu、Vincent Stroobant、Didier Colau、Vincenzo Cerundolo、Andrew J. G. Simpson、Pierre Vogel、Benoît J. Van den Eynde、Vincent Zoete、Olivier Michielin

  DOI：10.1021/jm9014718

  日期：2010.2.11

  design new inhibitors of this enzyme. First, we investigated the modes of binding of all known IDO inhibitors. On the basis of the observed docked conformations, we developed a pharmacophore model, which was then used to devise new compounds to be tested for IDO inhibition. We also used a fragment-based approach to design and to optimize small organic molecule inhibitors. Both approaches yielded several

  吲哚胺2,3-双加氧酶（IDO）是治疗癌症等涉及病理性免疫逃逸的疾病的重要治疗靶点。我们使用进化对接算法 EADock 来设计该酶的新抑制剂。首先，我们研究了所有已知 IDO 抑制剂的结合模式。根据观察到的对接构象，我们开发了药效团模型，然后用该模型设计新化合物以测试 IDO 抑制作用。我们还使用基于片段的方法来设计和优化小有机分子抑制剂。这两种方法都产生了几种新的低分子量抑制剂支架，其中最活跃的是酶测定中的纳摩尔效力。细胞测定证实了四种不同支架的潜在生物学相关性。
• IDO INHIBITORS AND THERAPEUTIC USES THEREOF
  申请人：Roehrig Ute

  公开号：US20110112282A1

  公开（公告）日：2011-05-12

  Compounds of formula (I), and pharmaceutically acceptable salts thereof, in which each compound is adapted to occupy the binding site of human IDO, which comprises a large hydrophobic pocket A and a second, proximal hydrophobic pocket B, the compound comprising at least one of the following elements: (i) a large hydrophobic fragment to substantially fill pocket A in the binding site of human IDO; (ii) an atom that can coordinate to the heme iron of human IDO, (iii) a positively charged group that can form a salt-bridge with the heme 7-propionate of the human IDO; (iv) a negatively charged group that can form a salt-bridge with Arg231 of the human IDO; (v) a hydrophobic group that can form van der Waals interactions with pocket B; and (vi) one or more substituents that can hydrogen bond to Ser167 and to Gly262, and as IDO inhibitors and their therapeutic use, eg in the treatment of cancer.
• US9353257B2
  申请人：——

  公开号：US9353257B2

  公开（公告）日：2016-05-31
• Conjugate addition of acylate-nickel complexes to quinone monoketals: formal synthesis of the naphthoquinone antibiotics nanaomycin A and deoxyfrenolicin
  作者：M. F. Semmelhack、L. Keller、T. Sato、E. J. Spiess、W. Wulff

  DOI：10.1021/jo00350a027

  日期：1985.12
• Synthesis of naphthoquinone antibiotics: conjugate addition/electrophile trapping with acylnickel carbonylate anions
  作者：M. F. Semmelhack、Leonard Keller、Tadahisa Sato、E. Spiess

  DOI：10.1021/jo00143a055

  日期：1982.10