2-naphthylltropone | 93327-57-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-naphthylltropone
• 英文别名: 2-[2]naphthyl-cycloheptatrienone；2-[2]Naphthyl-cycloheptatrienon；2-Naphthyl-(2)-tropon；2-Naphthalen-2-ylcyclohepta-2,4,6-trien-1-one；2-naphthalen-2-ylcyclohepta-2,4,6-trien-1-one
• CAS: 93327-57-2
• 化学式: C₁₇H₁₂O
• 分子量: 232.282
• InChiKey: GPPRZOVVTDKYDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-naphthylltropone 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 生成 MO‐OH‐Nap
  参考文献：
  名称：

  Tropolones As Lead-Like Natural Products: The Development of Potent and Selective Histone Deacetylase Inhibitors

  摘要：

  Natural products have long been recognized as a rich source of potent therapeutics but further development is often limited by high structural complexity and high molecular weight. In contrast, at the core of the thujaplicins is a lead-like tropolone scaffold characterized by relatively low molecular weight, ample sites for diversification, and metal-binding functionality poised for targeting a range of metalloenzyme drug targets. Here, we describe the development of this underutilized scaffold for the discovery of tropolone derivatives that function as isozyme-selective inhibitors of the validated anticancer drug target, histone deacetylase (HDAC). Several monosubstituted tropolones display remarkable levels of selectivity for HDAC2 and potently inhibit the growth of T-cell lymphocyte cell lines. The tropolones represent a new chemotype of isozyme-selective HDAC inhibitors.

  DOI：

  10.1021/ml400158k
• 作为产物：
  描述：

  6-hydroxy-7-oxo-cyclohepta-1,3,5-trienecarbonitrile 在 硫酸 、 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 生成 2-naphthylltropone
  参考文献：
  名称：

  Synthesis and Reactions of Cyano- and Carboxytropones

  摘要：

  DOI：

  10.1246/bcsj.34.1610

文献信息

• Substituted Tropolone Derivatives and Methods of Use
  申请人：University of Connecticut

  公开号：US20150166448A1

  公开（公告）日：2015-06-18

  The compositions and methods described herein relate generally to substituted tropolone derivatives, which, among other features, are useful as histone deacetylase (HDAC) inhibitors.
• US9790158B2
  申请人：——

  公开号：US9790158B2

  公开（公告）日：2017-10-17
• Tropolones As Lead-Like Natural Products: The Development of Potent and Selective Histone Deacetylase Inhibitors
  作者：Sophia N. Ononye、Michael D. VanHeyst、E. Zachary Oblak、Wangda Zhou、Mohamed Ammar、Amy C. Anderson、Dennis L. Wright

  DOI：10.1021/ml400158k

  日期：2013.8.8

  Natural products have long been recognized as a rich source of potent therapeutics but further development is often limited by high structural complexity and high molecular weight. In contrast, at the core of the thujaplicins is a lead-like tropolone scaffold characterized by relatively low molecular weight, ample sites for diversification, and metal-binding functionality poised for targeting a range of metalloenzyme drug targets. Here, we describe the development of this underutilized scaffold for the discovery of tropolone derivatives that function as isozyme-selective inhibitors of the validated anticancer drug target, histone deacetylase (HDAC). Several monosubstituted tropolones display remarkable levels of selectivity for HDAC2 and potently inhibit the growth of T-cell lymphocyte cell lines. The tropolones represent a new chemotype of isozyme-selective HDAC inhibitors.
• Synthesis and Reactions of Cyano- and Carboxytropones
  作者：Katsuo Kikuchi

  DOI：10.1246/bcsj.34.1610

  日期：1961.11