异尿石素A | 174023-48-4

• 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
• 中文名称: 异尿石素A
• 英文名称: 3,9-dihydroxy-6H-dibenzo[b,d]pyran-6-one
• 英文别名: 3,9-dihydroxy-dibenzo[b,d]pyran-6-one；3,9-dihydroxydibenzo[b,d]pyran-6-one；3,9-dihydroxyurolithin；iso-urolithin A；isourolithin A；3,9-dihydroxy-6H-benzo[c]chromen-6-one；3,9-dihydroxybenzo[c]chromen-6-one
• CAS: 174023-48-4
• 化学式: C₁₃H₈O₄
• 分子量: 228.204
• InChiKey: WDGSXHQNUPZEHA-UHFFFAOYSA-N

物化性质

• 熔点：
  >228°C (dec.)
• 沸点：
  526.3±43.0 °C(Predicted)
• 密度：
  1.516±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷（少许）、DMSO（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-二乙基氯甲酰胺 、 异尿石素A 在 吡啶 作用下， 以79%的产率得到3,9-bis(diethylcarbamoyl)dibenzo[b,d]pyran-6-one
  参考文献：
  名称：

  一些新的二苯并吡喃酮和二苯并吡喃的合成和生物学活性：寻找潜在的雌激素受体激动剂和拮抗剂。

  摘要：

  在继续寻找新的雌激素激动剂或拮抗剂并扩展对苯并吡喃相关化合物的探索方面，已经合成了在3,4-二芳基苯并二氢吡喃和2,3-二芳基苯并吡喃的活性分子之间架桥的一些新的三环分子。已经进行了在不同位置用已知的赋予激动剂或拮抗剂活性的元素进行结构修饰以制备所需的分子。筛选目标化合物的抗骨质疏松（激动剂）和抗子宫营养（拮抗剂）活性，发现它们具有中等活性。

  DOI：

  10.1016/j.bmc.2004.02.018
• 作为产物：
  描述：

  3,9-Dimethoxy-6H-dibenzopyran-6-one 在 氢碘酸 、 乙酸酐 作用下， 反应 18.0h， 以93%的产率得到异尿石素A
  参考文献：
  名称：

  （杂）芳基取代的苯基的可扩展多组分合成：专注于无金属的卤代联芳基，3-Arylindoles和异鸟氨酸A的合成

  摘要：

  在压力金属容器中完成了（杂）亚芳基丙酮的简单，可扩展且无金属的多组分烯醇乙酰化反应，然后与丙酸甲酯进行了Diels-Alder热反应。环加合物中间体的芳构化得到相应的官能化的（杂）联芳基。

  DOI：

  10.1002/ejoc.201901551

文献信息

• Compositions comprising urolithins and uses thereof for the stimulation of insulin secretion
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：EP2862568A1

  公开（公告）日：2015-04-22

  The present invention relates to a composition comprising an effective amount of urolithin A, urolithin B, urolithin C, urolithin D, or a combination thereof, for the stimulation of insulin secretion, and to the use of a compound chosen among urolithin A, urolithin B, urolithin C, urolithin D, or a combination thereof, for the stimulation of insulin secretion. The present invention also relates to a composition comprising an effective amount of urolithin B, urolithin C, urolithin D, or a combination thereof, for the treatment or the prevention of diabetes mellitus, and to the use of a compound chosen among urolithin B, urolithin C, urolithin D, and a combination thereof, for the treatment or the prevention of diabetes mellitus.

  本发明涉及一种组合物，包括有效量的尿石素A、尿石素B、尿石素C、尿石素D或其组合，用于刺激胰岛素分泌，并且涉及从尿石素A、尿石素B、尿石素C、尿石素D或其组合中选择一种化合物，用于刺激胰岛素分泌的用途。 本发明还涉及一种组合物，包括有效量的尿石素B、尿石素C、尿石素D或其组合，用于治疗或预防糖尿病，并且涉及从尿石素B、尿石素C、尿石素D或其组合中选择一种化合物，用于治疗或预防糖尿病的用途。
• 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。
• 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.
• UROLITHIN A AND A COMPOSITION CONTAINING SAME FOR EXTERNAL USE IN INFLAMMATIONS OF VARIOUS ETIOLOGIES
  申请人：WARSZAWSKI UNIWERSYTET MEDYCZNY

  公开号：US20220062226A1

  公开（公告）日：2022-03-03

  The invention relates to the compound urolithin A and its compositions for topical use in inflammatory skin conditions of various etiologies. Anti-inflammatory activity has been demonstrated in vivo in a model of inflammation of the ear caused by infiltration with dinitrochlorobenzene in rats. Topical application of an ointment containing 0.2 and 1.0% urolithin A resulted in a decrease in ear edema and scratching frequency, which was associated with a decrease in the number of immune cells responsible for the progression of inflammation. The results obtained indicate the possibility of using a composition containing urolithin A in local therapy of skin inflammations, in treatment of which hydrocortisone or other steroids are currently used.
• [EN] DIRECT AMPK ACTIVATOR COMPOUNDS COMBINED WITH INDIRECT AMPK ACTIVATOR COMPOUNDS, COMPOSITIONS, METHODS AND USES THEREOF<br/>[FR] COMPOSÉS ACTIVATEURS DIRECTS D'AMPK COMBINÉS À DES COMPOSÉS ACTIVATEURS INDIRECTS D'AMPK , COMPOSITIONS, PROCÉDÉS ET UTILISATIONS DE CEUX-CI
  申请人：NESTLE SA

  公开号：WO2021105074A1

  公开（公告）日：2021-06-03

  The present invention relates to a combinations of direct AMPK activators with indirect AMPK activators for use in activating AMPK. In particular, combinations of benzocoumarins of formula I which are direct AMPK activators with urolithins of formula VII which are indirect AMPK activators.