MO‐OH‐Nap | 1442653-70-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: MO‐OH‐Nap
• 英文别名: MO-OH-Nap；2-hydroxy-3-naphthalen-2-ylcyclohepta-2,4,6-trien-1-one
• CAS: 1442653-70-4
• 化学式: C₁₇H₁₂O₂
• 分子量: 248.281
• InChiKey: ZAJVVUCLCLFUFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  MO‐OH‐Nap 在 吡啶 作用下， 以 氘代氯仿 、 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  通过形式 C(sp3)−C(sp2) 偶联反应对肌钙蛋白进行电化学位点选择性烷基化

  摘要：

  托酮的第一个位点选择性电化学烷基化是通过 2-乙酰氧基托酮和氧化还原活性酯的反应实现的。电还原方案能够以高收率（高达 71%）和非常温和的条件制备各种（27 个示例）单取代和二取代托酮。专用伏安测量用于鉴定 2-乙酰氧基托酮作为一类有价值的亲核自由基捕获剂，并揭示整个机理。对传统官能团的广泛耐受性（27 个示例）以及对生物活性化合物后期功能化的应用，强调了本方法的合成影响

  DOI：

  10.1002/adsc.202400050
• 作为产物：
  描述：

  2-氯-2,4,6-环庚三烯-1-酮 在 bis-triphenylphosphine-palladium(II) chloride 、 caesium carbonate 、 一水合肼 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 32.0h， 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

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.
• Electrochemical Site‐Selective Alkylation of Tropones via Formal C(<i>sp</i>³)−C(<i>sp</i>²) Coupling Reaction
  作者：Andrea Brunetti、Mauro Garbini、Nico Gino Kub、Magda Monari、Riccardo Pedrazzani、Chiara Zanardi、Giulio Bertuzzi、Marco Bandini

  DOI：10.1002/adsc.202400050

  日期：——

  The first site‐selective electrochemical alkylation of tropones is realized by reacting 2‐acetoxytropones and redox‐active‐esters. The electroreductive protocol enables the preparation of a wide range (27 examples) of mono‐ and disubstituted tropones in high yields (up to 71%) and very mild conditions. Dedicated voltammetric measurements served for the identification of 2‐acetoxytropones as a class

  托酮的第一个位点选择性电化学烷基化是通过 2-乙酰氧基托酮和氧化还原活性酯的反应实现的。电还原方案能够以高收率（高达 71%）和非常温和的条件制备各种（27 个示例）单取代和二取代托酮。专用伏安测量用于鉴定 2-乙酰氧基托酮作为一类有价值的亲核自由基捕获剂，并揭示整个机理。对传统官能团的广泛耐受性（27 个示例）以及对生物活性化合物后期功能化的应用，强调了本方法的合成影响