3,8-dihydroxy-9-methoxy-6H-benzo[c]chromen-6-one | 1006683-96-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3,8-dihydroxy-9-methoxy-6H-benzo[c]chromen-6-one
• 英文别名: 3,8-Dihydroxy-9-methoxy-6H-dibenzo[b,d]pyran-6-one；3,8-dihydroxy-9-methoxybenzo[c]chromen-6-one
• CAS: 1006683-96-0
• 化学式: C₁₄H₁₀O₅
• 分子量: 258.23
• InChiKey: QLSVBZAFSSELCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-溴-5-羟基-4-甲氧基苯甲醛 在 4-二甲氨基吡啶 、 potassium permanganate 、 三乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 24.0h， 生成 3,8-dihydroxy-9-methoxy-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  Exploration of Novel Urolithin C Derivatives as Non-Competitive Inhibitors of Liver Pyruvate Kinase

  摘要：

  肝脏丙酮酸激酶是一种脂肪在肝脏中逐渐积累并最终导致肝硬化的疾病，抑制肝脏丙酮酸激酶有助于阻止或逆转非酒精性脂肪肝。最近，有报道称尿石素 C 是开发肝丙酮酸激酶（PKL）异位抑制剂的新支架。本研究对尿石素 C 进行了全面的结构-活性分析。我们合成了 50 多种类似物，并测试了这些类似物所具有的化学特征。这些数据可为开发更强效、更具选择性的 PKL 异位抑制剂铺平道路。

  DOI：

  10.3390/ph16050668

文献信息

• Copper(II) Salt Catalyzed Coupling Strategy Towards Synthesis of Substituted Dibenzopyranones
  作者：Avidha Kulshrestha、Ruchi Rupanwal、Nidhi Singh、Shridhar Satpute、Deepa Panhekar、Jaya Pandey

  DOI：10.14233/ajchem.2017.20640

  日期：——

  dibenzopyranones but by using Pd(II) and Cu(II) dual catalytic system. Shi’s group has also enlisted several other ways of synthesizing this scafold. In present work, we used a substrate that does not require in ligand yet extremely effective in coupling reaction towards the synthesis of dibenzopyranones. The dibenzopyranone is found in many natural products Copper(II) Salt Catalyzed Coupling Strategy Towards Synthesis

  特别是由过渡金属催化的偶联反应因其适用性而受到广泛关注 [1-6]。在 150 年前，Glaser [7] 开发了第一个铜介导的偶联反应之一，其特征是末端乙炔的二聚化。Ullmann 和 Bielecki [8] 大约在 1901 年为从芳基溴化物开始铜介导合成联芳烃铺平了道路。 人们发现用于各种偶联反应的铜基催化剂更具吸引力，因为成本较低且与之相关的环境因素 [9] -12]。事实上，乙炔和卤化物在 Sonogashira 反应 [13] 中作为伙伴使用催化量的 Pd(0) 和 Cu(I)。Buchwald 等人将催化作为一门科学推进。通过合并螯合配体对铜催化的交叉偶联反应做出贡献 [14-16]。从机制上讲，在此类过程中使用配体可降低金属催化剂的活化能并以更快的速度缓和偶联反应。最近有报道称，在光和铜（I）催化剂的存在下，氮亲核试剂在温和条件下与卤代烷发生 C-N 偶联。此外，还确定光诱导的铜催化烷基化也可以应用于
• Identification of Urinary and Intestinal Bacterial Metabolites of Ellagitannin Geraniin in Rats
  作者：Hideyuki Ito、Ayumu Iguchi、Tsutomu Hatano

  DOI：10.1021/jf0726942

  日期：2008.1.1

  Hydrolyzable tannins, including ellagitannins, occur in foods such as berries and nuts. Various biological activities, including antioxidant, antiviral, and antitumor activities, have been noted and reported for ellagitannins, but the absorption and metabolism of purified ellagitannins are poorly understood. We describe herein the characterization of urinary and intestinal microbial metabolites in rats after the ingestion of ellagitannins. Urine samples were collected after oral administration of ellagitannins such as geraniin (1), corilagin (2), and their related polyphenols. The suspension of rat intestinal microflora. was anaerobically incubated with ellagitannins. Each sample was separated by column chromatography and/or preparative HPLC to give seven metabolites, M1-M7. The structures of these metabolites were determined on the basis of spectroscopic data and chemical evidence. These compounds, except for M1, were characterized as ellagitannin metabolites for the first time. Furthermore, among four major metabolites (M1-M4) in urine, M2 showed an antioxidant activity comparable to intact geraniin and related polyphenols.
• METHOD FOR PRODUCING UROLITHINS
  申请人：DAICEL CORPORATION

  公开号：US20190323045A1

  公开（公告）日：2019-10-24

  An object of the present invention is to provide a method for eliminating the hydroxyl group at the 9-position of a urolithin to produce another kind of urolithin. This object is achieved by a method for producing a second urolithin, including Step (a): allowing, in a solution containing a first urolithin, a microorganism having an ability to produce the second urolithin from the first urolithin to produce the second urolithin from the first urolithin.
• Exploration of Novel Urolithin C Derivatives as Non-Competitive Inhibitors of Liver Pyruvate Kinase
  作者：Umberto Maria Battisti、Leticia Monjas、Fady Akladios、Josipa Matic、Eric Andresen、Carolin H. Nagel、Malin Hagkvist、Liliana Håversen、Woonghee Kim、Mathias Uhlen、Jan Borén、Adil Mardinoğlu、Morten Grøtli

  DOI：10.3390/ph16050668

  日期：——

  The inhibition of liver pyruvate kinase could be beneficial to halt or reverse non-alcoholic fatty liver disease (NAFLD), a progressive accumulation of fat in the liver that can lead eventually to cirrhosis. Recently, urolithin C has been reported as a new scaffold for the development of allosteric inhibitors of liver pyruvate kinase (PKL). In this work, a comprehensive structure–activity analysis of urolithin C was carried out. More than 50 analogues were synthesized and tested regarding the chemical features responsible for the desired activity. These data could pave the way to the development of more potent and selective PKL allosteric inhibitors.

  肝脏丙酮酸激酶是一种脂肪在肝脏中逐渐积累并最终导致肝硬化的疾病，抑制肝脏丙酮酸激酶有助于阻止或逆转非酒精性脂肪肝。最近，有报道称尿石素 C 是开发肝丙酮酸激酶（PKL）异位抑制剂的新支架。本研究对尿石素 C 进行了全面的结构-活性分析。我们合成了 50 多种类似物，并测试了这些类似物所具有的化学特征。这些数据可为开发更强效、更具选择性的 PKL 异位抑制剂铺平道路。