2,2-dimethyl-2H-chromen-4-yl trifluoromethanesulfonate | 1251910-86-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,2-dimethyl-2H-chromen-4-yl trifluoromethanesulfonate
• 英文别名: (2,2-dimethylchromen-4-yl) trifluoromethanesulfonate
• CAS: 1251910-86-7
• 化学式: C₁₂H₁₁F₃O₄S
• 分子量: 308.278
• InChiKey: PGSUMRXAPAVUCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙烯基硼酸二丁酯 、 2,2-dimethyl-2H-chromen-4-yl trifluoromethanesulfonate 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 10.0h， 生成 2,2-dimethyl-4-vinyl-2H-chromene
  参考文献：
  名称：

  Antidiabetic and Antiobesity Effects of Ampkinone (6f), a Novel Small Molecule Activator of AMP-Activated Protein Kinase

  摘要：

  Adenosine 5'-monophosphate (AMP) activated protein kinase (AMPK) has emerged as an attractive target molecule for the treatment of metabolic disorders, including obesity and type 2 diabetes. In this study, we identified a novel small molecule, ampkinone (6f), as an indirect AMPK activator, which was derived from the small molecule library constructed by diversity-oriented synthesis. Ampkinone stimulated the phosphorylation of AMPK via the indirect activation of AMPK in various cell lines. Ampkinone-mediated activation of AMPK required the activity of LKB1 and resulted in increased glucose uptake in muscle cells. In addition, ampkinone-treated DIO mice significantly reduced total body weight and overall fat mass. Histological examination and measurement of lipid parameters showed that ampkinone effectively improved metabolic abnormalities in the DIO mice model. Our results demonstrate that ampkinone, a small molecule with a privileged benzopyran substructure, has a potential as a new class of therapeutic agent for antidiabetic and antiobesity treatment via the indirect stimulation of AMPK.

  DOI：

  10.1021/jm100565d
• 作为产物：
  描述：

  2,2-二甲基-苯并二氢吡喃-4-酮 、 三氟甲磺酸酐 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 2,2-dimethyl-2H-chromen-4-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Antidiabetic and Antiobesity Effects of Ampkinone (6f), a Novel Small Molecule Activator of AMP-Activated Protein Kinase

  摘要：

  Adenosine 5'-monophosphate (AMP) activated protein kinase (AMPK) has emerged as an attractive target molecule for the treatment of metabolic disorders, including obesity and type 2 diabetes. In this study, we identified a novel small molecule, ampkinone (6f), as an indirect AMPK activator, which was derived from the small molecule library constructed by diversity-oriented synthesis. Ampkinone stimulated the phosphorylation of AMPK via the indirect activation of AMPK in various cell lines. Ampkinone-mediated activation of AMPK required the activity of LKB1 and resulted in increased glucose uptake in muscle cells. In addition, ampkinone-treated DIO mice significantly reduced total body weight and overall fat mass. Histological examination and measurement of lipid parameters showed that ampkinone effectively improved metabolic abnormalities in the DIO mice model. Our results demonstrate that ampkinone, a small molecule with a privileged benzopyran substructure, has a potential as a new class of therapeutic agent for antidiabetic and antiobesity treatment via the indirect stimulation of AMPK.

  DOI：

  10.1021/jm100565d

文献信息

• [EN] CHROMANE AND CHROMENE DERIVATIVES AND THEIR USE AS CRAC MODULATORS<br/>[FR] DÉRIVÉS DE CHROMANE ET DE CHROMÈNE ET LEUR UTILISATION EN TANT QUE MODULATEURS DE CRAC
  申请人：LUPIN LTD

  公开号：WO2014207648A1

  公开（公告）日：2014-12-31

  The invention relates to compounds of Formula (I) and their pharmaceutically acceptable salts, wherein the substituents are as described herein, and their use in medicine for the treatment of diseases, disorders associated with the modulation of calcium release-activated calcium (CRAC) channel. The invention also relates to pharmaceutical compositions containing such compounds in treating diseases disorders associated with calcium release- activated calcium (CRAC) channel modulators.

  这项发明涉及到式（I）化合物及其药用可接受的盐，其中取代基如本文所述，并且它们在医学上用于治疗与调节钙释放激活钙（CRAC）通道相关的疾病、紊乱。该发明还涉及含有这种化合物的药物组合物，用于治疗与钙释放激活钙（CRAC）通道调节剂相关的疾病、紊乱。
• CHROMANE AND CHROMENE DERIVATIVES AND THEIR USE AS CRAC MODULATORS
  申请人：LUPIN LIMITED

  公开号：US20160137659A1

  公开（公告）日：2016-05-19

  The invention relates to compounds of Formula (I) and their pharmaceutically acceptable salts, wherein the substituents are as described herein, and their use in medicine for the treatment of diseases, disorders associated with the modulation of calcium release-activated calcium (CRAC) channel. The invention also relates to pharmaceutical compositions containing such compounds in treating diseases disorders associated with calcium release-activated calcium (CRAC) channel modulators.

  本发明涉及公式（I）化合物及其药学上可接受的盐，其中取代基如本文所述，并且在医学上用于治疗与调节钙释放激活钙（CRAC）通道相关的疾病和紊乱。本发明还涉及包含这些化合物的药物组合物，用于治疗与钙释放激活钙（CRAC）通道调节剂相关的疾病和紊乱。
• US9790231B2
  申请人：——

  公开号：US9790231B2

  公开（公告）日：2017-10-17
• [EN] COMPOUNDS WITH EMBEDDED BENZOPYRAN MOTIF FOR CORE STRUCTURES AND PREPARATION METHOD THEREOF<br/>[FR] COMPOSÉS INCLUANT UN MOTIF BENZOPYRANE POUR STRUCTURES DE NOYAU, ET MÉTHODE DE PRÉPARATION DES COMPOSÉS
  申请人：SEOUL NAT UNIV IND FOUNDATION

  公开号：WO2008072801A1

  公开（公告）日：2008-06-19

  [EN] The present invention relates to a compound having benzopyran core, a preparation method of the derivatives by liquid phase synthesis and solid phase synthesis through diversity-oriented synthesis, and an anticancer agent comprising the compound that exhibit excellent cytotoxicity against cancer cells.
  [FR] La présente invention concerne un composé présentant un noyau benzopyrane; une méthode de préparation des dérivés par synthèse en phase liquide et synthèse en phase solide, au moyen d'une synthèse orientée vers la diversité; et un agent anticancéreux comprenant le composé, qui présente une excellente toxicité contre les cellules cancéreuses.