N-(6-hydroxynaphthalen-1-yl)benzamide | 855262-78-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(6-hydroxynaphthalen-1-yl)benzamide
• 英文别名: N-(6-hydroxy-[1]naphthyl)-benzamide；N-(6-Hydroxy-[1]naphthyl)-benzamid；5-Benzamino-naphthol-(2)；N-(6-Hydroxy-naphthalen-1-yl)-benzamide
• CAS: 855262-78-1
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: MXBRJEQSGCBYIH-UHFFFAOYSA-N

物化性质

• 沸点：
  399.4±15.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-重氮基-1-[4-硝基苯基]-乙酮 、 N-(6-hydroxynaphthalen-1-yl)benzamide 在 1,4-二氧六环 、 copper dichloride 作用下， 生成 N-[6-(4-nitro-phenacyloxy)-[1]naphthyl]-benzamide
  参考文献：
  名称：

  Notes: The Use of Substituted α-Diazoacetophenones for the Preparation of Derivatives of Sulfonic Acids, NBenzoylated Aminocarboxylic and Aminosulfonic Acids, N-Benzoylated Aminophenols and an N-Benzoylated Amino Thiol

  摘要：

  DOI：

  10.1021/jo01094a601
• 作为产物：
  描述：

  sodium 2-naphtholate 在 sodium hydroxide 、 萘 、 sodium amide 作用下， 生成 N-(6-hydroxynaphthalen-1-yl)benzamide
  参考文献：
  名称：

  Sachs, Chemische Berichte, 1906, vol. 39, p. 3021

  摘要：

  DOI：

文献信息

• Compounds and methods of use
  申请人：Potashman Michele

  公开号：US20060241115A1

  公开（公告）日：2006-10-26

  Selected compounds are effective for prophylaxis and treatment of diseases, such as HGF mediated diseases. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving, cancer and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

  所选化合物对于预防和治疗HGF介导的疾病等具有有效性。本发明涵盖了新颖的化合物、类似物、前药和其药学上可接受的盐，以及用于预防和治疗涉及癌症等疾病和其他疾病或状况的药物组合物和方法。该发明还涉及制备此类化合物的过程，以及在此类过程中有用的中间体。
• Discovery of Potent and Selective Sirtuin 2 (SIRT2) Inhibitors Using a Fragment-Based Approach
  作者：Huaqing Cui、Zeeshan Kamal、Teng Ai、Yanli Xu、Swati S. More、Daniel J. Wilson、Liqiang Chen

  DOI：10.1021/jm500777s

  日期：2014.10.23

  Sirtuin 2 (SIRT2) is one of the sirtuins, a family of NAD(+)-dependent deacetylases that act on a variety of histone and non-histone substrates. Accumulating biological functions and potential therapeutic applications have drawn interest in the discovery and development of SIRT2 inhibitors. Herein we report our discovery of novel SIRT2 inhibitors using a fragment-based approach. Inspired by the purported close binding proximity of suramin and nicotinamide, we prepared two sets of fragments, namely, the naphthylamide sulfonic acids and the naphthalene-benzamides and -nicotinamides. Biochemical evaluation of these two series provided structure-activity relationship (SAR) information, which led to the design of (5-benzamidonaphthalen-1/2-yloxy)nicotinamide derivatives. Among these inhibitors, one compound exhibited high anti-SIRT2 activity (48 nM) and excellent selectivity for SIRT2 over SIRT1 and SIRT3. In vitro, it also increased the acetylation level of a-tubulin, a well-established SIRT2 substrate, in both concentration- and time-dependent manners. Further kinetic studies revealed that this compound behaves as a competitive inhibitor against the peptide substrate and most likely as a noncompetitive inhibitor against NAD(+). Taken together, these results indicate that we have discovered a potent and selective SIRT2 inhibitor whose novel structure merits further exploration.
• COMPOUNDS AND METHODS OF USE
  申请人：AMGEN INC.

  公开号：EP1713484A2

  公开（公告）日：2006-10-25
• US7435823B2
  申请人：——

  公开号：US7435823B2

  公开（公告）日：2008-10-14
• US8178557B2
  申请人：——

  公开号：US8178557B2

  公开（公告）日：2012-05-15