neotheaflavin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: neotheaflavin
• 英文别名: Neotheaflavin；3,4,6-trihydroxy-8-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]-1-[(2R,3S)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]benzo[7]annulen-5-one
• 化学式: C₂₉H₂₄O₁₂
• 分子量: 564.502
• InChiKey: IPMYMEWFZKHGAX-WCQFOESSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  41
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  218
• 氢给体数：
  9
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  (2R,3R)-5,7,5,7-tetra-O-(2-nitrobenzenesulfonyl)neotheaflavin 在 caesium carbonate 、 苯硫酚 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.0h， 以55%的产率得到neotheaflavin
  参考文献：
  名称：

  通过仿生氧化偶联反应合成茶黄素

  摘要：

  从儿茶素仿生合成茶黄素是通过使用 2-硝基苯磺酰基 (Ns) 作为苯酚的保护基团来实现的，以最大限度地减少富电子芳环的不良副反应。这使得能够在一步氧化偶联反应中构建复杂的苯并托酚酮核心。

  DOI：

  10.1055/s-0032-1318131

文献信息

• Benzotropolone derivatives and modulation of inflammatory response
  申请人：Ho Chi-Tang

  公开号：US20050049284A1

  公开（公告）日：2005-03-03

  The present invention provides novel benzotropolone derivatives represented by the general formula: including neotheaflavate B and EGCGCa. The benzotropolone derivatives of the present invention are effective antioxidant and anti-inflammatory agents. The present invention also provides novel method of synthesizing benzotropolone compounds in high yields and method of treating inflammatory conditions using benzotropolone containing compounds.

  本发明提供了一种由通式表示的新型苯并三酮衍生物： 包括新茶黄素B和EGCGCa。本发明的苯并三酮衍生物是有效的抗氧化剂和抗炎药物。本发明还提供了一种高产率合成苯并三酮化合物的新方法，以及使用含有苯并三酮的化合物治疗炎症症状的方法。
• Nonenzymatic Biomimetic Synthesis of Black Tea Pigment Theaflavins
  作者：Yosuke Matsuo、Takashi Tanaka、Ryosuke Oowatashi、Yoshinori Saito

  DOI：10.1055/s-0036-1588529

  日期：2017.11

  Theaflavins are reddish-orange black tea pigments with a benzotropolone chromophore, and their various biological activities have been reported. Theaflavins are produced by oxidative coupling between catechol-type and pyrogallol-type catechins via bicyclo[3.2.1]octane-type intermediates. In this study, a new method for nonenzymatic biomimetic synthesis of theaflavins was developed using the DPPH radical as an oxidizing agent.

  茶黄素是一种带有苯并噻吩色团的红橙色黑茶色素，已报道其多种生物活性。茶黄素是由儿茶素型和儿茶酚型儿茶素通过双环[3.2.1]辛烷型中间体之间的氧化偶联产生的。在这项研究中，开发了一种利用DPPH自由基作为氧化剂的非酶仿生合成茶黄素的新方法。
• Enzymatic synthesis of tea theaflavin derivatives and their anti-inflammatory and cytotoxic activities
  作者：Shengmin Sang、Joshua D Lambert、Shiying Tian、Jungil Hong、Zhe Hou、Jae-He Ryu、Ruth E Stark、Robert T Rosen、Mou-Tuan Huang、Chung S Yang、Chi-Tang Ho

  DOI：10.1016/j.bmc.2003.10.024

  日期：2004.1

  Derivatives based on a benzotropolone skeleton (9-26) have been prepared by the enzymatic coupling (horseradish peroxidase/H2O2) of selected pairs of compounds (1-8), one with a vic-trihydroxyphenyl moiety, and the other with an ortho-dihydroxyphenyl structure. Some of these compounds have been found to inhibit TPA-induced mice ear edema, nitric oxide (NO) synthesis, and arachidonic acid release by LPS-stimulated RAW 264.7 cells. Their cytotoxic activites against KYSE 150 and 510 human esophageal squamous cell carcinoma and HT 29 human colon cancer cells were also evaluated. (C) 2003 Elsevier Ltd. All rights reserved.
• BENZOTROPOLONE DERIVATIVES AND MODULATION OF INFLAMMATORY RESPONSE
  申请人：Wellgen, Inc.

  公开号：EP1663931B1

  公开（公告）日：2013-04-10
• Identification of Small Molecule Inhibitors of Jumonji AT-Rich Interactive Domain 1A (JARID1A) and 1B (JARID1B) Histone Demethylase
  申请人：Yale University

  公开号：US20150272939A1

  公开（公告）日：2015-10-01

  The present invention includes a novel high-throughput screen capable of identifying compounds that inhibit JARID1B demethylase activity or JARID1A demethylase activity. The present invention further includes novel inhibitors of JARID1B demethylase activity and/or JARID1A demethylase activity, and methods using the same.