4-tertbutyltropolone

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 4-tertbutyltropolone
• 英文别名: 6-tert-butyl-2-hydroxycyclohepta-2,4,6-trien-1-one
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: YCJXIOAKVCHNQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  4-tertbutyltropolone 以 乙腈 为溶剂， 反应 4.0h， 生成 2-(5-tert-Butyl-2-hydroxy-3-oxo-cyclohepta-1,4,6-trienyl)-[1,3]dithiol-1-ylium
  参考文献：
  名称：

  SYNTHESIS AND PROPERTIES OF 7-(1,3-DITHIOL-2-YLIDENE)-3,5-CYCLOHEPTADIENE-1,2-DIONE (OR 7,10-DITHIASESQUIFULVALENE-1,2-QUINONE) DERIVATIVES

  摘要：

  合成了三种稳定的 7,10-二硫代酶基奎福缬烯-1,2-醌（或邻丙醌二硫醚）的 4-叔丁基、5-溴和 3,5- 二溴衍生物，并根据它们的光谱数据和前沿电子密度分布讨论了它们的物理和化学特性，密度分布充分显示了硫原子对这些化合物的稳定（降低反应性）作用。

  DOI：

  10.1246/cl.1981.805
• 作为产物：
  描述：

  在 samarium diiodide 、 potassium hydroxide 作用下， 生成 4-tertbutyltropolone
  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

• The furan route to tropolones: probing the antiproliferative effects of β-thujaplicin analogs
  作者：E. Zachary Oblak、Erin S. D. Bolstad、Sophia N. Ononye、Nigel D. Priestley、M. Kyle Hadden、Dennis L. Wright

  DOI：10.1039/c2ob26553b

  日期：——

  A direct route to analogs of the naturally occurring tropolone β-thujaplicin has been developed in just four steps from furan. Using this method, a series of derivatives were synthesized and evaluated. Several of these compounds demonstrated very high levels of potency against bacterial and fungal pathogens with good selectivity over mammalian cells.

  距离天然托洛酮β-thujaplicin类似物的直接途径仅需四个步骤即可完成 呋喃。使用这种方法，合成并评估了一系列衍生物。这些化合物中的几种显示出对细菌和真菌病原体非常高的效力，并且对哺乳动物细胞具有良好的选择性。
• Reactions of Alkyltropylium Ions with a Base
  作者：Tetsuo Nozoe、Kazuko Takahashi、Hiroshi Yamamoto

  DOI：10.1246/bcsj.42.3277

  日期：1969.11

  On the reaction with a base (e.g., aqueous sodium hydroxide), isopropyl- and methyl-tropylium ions afforded cycloheptatrienyl polymers with an alkylene bridge, such as IIIa and IIIb, while the t-butyltropylium ion gave a mixture of 3- and 4-t-butyltropone, which was then transformed to 4-and 5-t-butyltropolone (VIIIa and IX). The bromination of VIIIa with 3 mol of bromine in methanol gave 3,7-dibromo-4-t-butyl-2-methoxy-2,3-dihydrotropolone (XIIa). On the heating of the adduct (XIIa) at 130°C, 7-bromo-4-t-butyltropolone (XIa) was formed.

  与碱（例如水合氢氧化钠）的反应中，异丙基和甲基托比里昂离子产生了具有烷基桥的环戊三烯聚合物，例如 IIIa 和 IIIb，而叔丁基托比里昂离子则产生了3-和4-叔丁基托烯的混合物，随后转化为4-和5-叔丁基托烯醇（VIIIa 和 IX）。用3摩尔溴在甲醇中溴化 VIIIa 得到3,7-二溴-4-叔丁基-2-甲氧基-2,3-二氢托烯醇（XIIa）。在130°C加热产物（XIIa）时，形成了7-溴-4-叔丁基托烯醇（XIa）。
• Substituted tropolone compounds, oral care compositions containing the same and methods of using the same
  申请人：——

  公开号：US20040018216A1

  公开（公告）日：2004-01-29

  The present invention relates to novel tropolone compounds of the present invention and to oral care compositions suitable for preventing or treating diseases or conditions of the oral cavity in warm-blooded animals including humans, comprising an oral care effective amount of at least one novel tropolone compounds, and a pharmaceutically acceptable oral carrier. This invention further relates to a method for preventing or treating diseases or conditions of the oral cavity in warm-blooded animals including humans, by applying an oral care effective amount of the oral care composition to the oral cavity.

  本发明涉及本发明的新型环己酮化合物以及适用于预防或治疗温血动物包括人类口腔疾病或状况的口腔护理组合物，包括口腔护理有效量的至少一种新型环己酮化合物和药用可接受的口腔载体。本发明还涉及一种方法，通过将口腔护理组合物的口腔护理有效量应用于口腔，预防或治疗温血动物包括人类口腔疾病或状况。
• ORAL CARE COMPOSITIONS COMPRISING TROPOLONE COMPOUNDS AND ESSENTIAL OILS AND METHODS OF USING THE SAME
  申请人：——

  公开号：US20040018154A1

  公开（公告）日：2004-01-29

  The present invention relates to oral care compositions suitable for preventing or treating diseases or conditions of the oral cavity in warm-blooded animals including humans, comprising an oral care effective amount of at least one tropolone compound in combination with at least one essential oil, and a pharmaceutically acceptable oral carrier. This invention further relates to a method for preventing or treating diseases or conditions of the oral cavity in warm-blooded animals including humans, by applying an oral care effective amount of the oral care composition to the oral cavity.

  本发明涉及适用于预防或治疗温血动物，包括人类口腔腔内疾病或病症的口腔护理组合物，包括至少一种茚三酮化合物和至少一种精油的口腔护理有效量，以及药学上可接受的口腔载体。本发明还涉及一种方法，通过将口腔护理组合物的口腔护理有效量应用于口腔，预防或治疗温血动物，包括人类口腔腔内疾病或病症。
• Oral care compositions comprising tropolone compounds and essential oils and methods of using the same
  申请人：——

  公开号：US20040185010A1

  公开（公告）日：2004-09-23

  The present invention relates to oral care compositions suitable for preventing or treating diseases or conditions of the oral cavity in warm-blooded animals including humans, comprising an oral care effective amount of at least one tropolone compound in combination with at least one essential oil, and a pharmaceutically acceptable oral carrier. This invention further relates to a method for preventing or treating diseases or conditions of the oral cavity in warm-blooded animals including humans, by applying an oral care effective amount of the oral care composition to the oral cavity.

  本发明涉及适用于预防或治疗包括人类在内的温血动物口腔疾病或病症的口腔护理组合物，该组合物包含口腔护理有效量的至少一种tropolone化合物与至少一种精油，以及药学上可接受的口腔载体。本发明进一步涉及一种预防或治疗包括人类在内的温血动物口腔疾病或病症的方法，方法是将口腔护理有效量的口腔护理组合物涂抹于口腔。