(E)-白皮杉醇葡萄糖苷 | 29884-49-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: (E)-白皮杉醇葡萄糖苷
• 中文别名: 白皮杉醇葡萄糖苷
• 英文名称: (E)-astringin
• 英文别名: astringin；trans-astringin；trans-3,5,3’,4’-tetrahydroxystilbene-3-O-β-D-glucopyranoside；(2S,3R,4S,5S,6R)-2-[3-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 29884-49-9
• 化学式: C₂₀H₂₂O₉
• 分子量: 406.389
• InChiKey: PERPNFLGJXUDDW-CUYWLFDKSA-N

物化性质

• 熔点：
  218-220℃
• 沸点：
  756.1±60.0 °C(Predicted)
• 密度：
  1.593±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO：150 mg/mL（369.11 mM；需要超声波）

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  160
• 氢给体数：
  7
• 氢受体数：
  9

安全信息

• WGK Germany：
  3
• 储存条件：
  2-8°C，存于密封且干燥的环境中。

制备方法与用途

生物活性方面，Astringin（trans-Astringin）是一种天然糖苷，存在于云杉（Picea sitchensis）、挪威云杉（Picea abies）、葡萄细胞培养物以及葡萄酒中。它具有强大的抗氧化能力，并展现出显著的癌症化学预防活性。

反应信息

• 作为反应物：
  描述：

  (E)-白皮杉醇葡萄糖苷 生成 白皮杉醇
  参考文献：
  名称：

  Comparative study of radical scavenger and antioxidant properties of phenolic compounds from Vitis vinifera cell cultures using in vitro tests

  摘要：

  Vitis vinifera cell suspensions were used to isolate and characterize the flavonoids (anthocyanins, catechins) and non-flavonoids (stilbenes) found in red wine. Furthermore, we showed that astringin is produced although this stilbene has not previously been reported to be a constituent of V. vinifera or wine. The ability of these compounds to act as radical scavengers was investigated using 1,1-diphenyl-2-picryl-hydrazyl (DPPH), a stable free radical. Antioxidant activities were assessed by their capacity to prevent Fe2+-induced lipid peroxidation in microsomes and their action on Cu2+-induced lipid peroxidation in low-density lipoproteins. The results showed that astringin has an important antioxidant effect similar to that of trans-resveratrol, and a higher radical scavenger activity than the latter. Astringinin appeared to be more active. These data indicate that phenolic compounds (stilbenes, catechins, anthocyanins) exhibit interesting properties which may account in part for the so-called ''French paradox,'' i.e. that moderate drinking of red wine over a long period of time can protect against coronary heart disease.

  DOI：

  10.1016/s0024-3205(97)00883-7
• 作为产物：
  描述：

  虎杖甙 在 4-二甲氨基吡啶 、 sodium dithionite 、 sodium hydroxide 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 31.0h， 生成 (E)-白皮杉醇葡萄糖苷
  参考文献：
  名称：

  Short-step syntheses of naturally occurring polyoxygenated aromatics based on site-selective transformation

  摘要：

  摘要：Wogonin和astringin是从廉价的芹菜素和白藜芦醇中经过简短步骤合成的。这些合成的关键特点是位点选择性转化。从起始材料中，目标分子分别以27%和62%的产率获得。

  DOI：

  10.1080/09168451.2017.1303362

文献信息

• [EN] SUBSTITUTED IMIDAZO-QUINOLINES AS NLRP3 MODULATORS<br/>[FR] IMIDAZO-QUINOLÉINES SUBSTITUÉES UTILISÉES EN TANT QUE MODULATEURS DE NLRP3
  申请人：INNATE TUMOR IMMUNITY INC

  公开号：WO2018152396A1

  公开（公告）日：2018-08-23

  This disclosure features chemical entities (e.g., a compound or a pharmaceutically acceptable salt, and/or hydrate, and/or cocrystal, and/or drug combination of the compound) that modulate (e.g., agonizes or partially agonizes) NLRP3 that are useful, e.g., for treating a condition, disease or disorder in which an increase in NLRP3 signaling may correct a deficiency in innate immune activity (e.g., a condition, disease or disorder associated with an insufficient immune response) that contributes to the pathology and/or symptoms and/ or progression of the condition, disease or disorder (e.g., cancer) in a subject (e.g., a human). This disclosure also features compositions as well as other methods of using and making the same.

  本公开涉及化学实体（例如，化合物或药用可接受盐，和/或水合物，和/或共晶体，和/或该化合物的药物组合），其调节（例如，激动或部分激动）对NLRP3有用，例如，用于治疗增加NLRP3信号可能纠正先天免疫活性缺陷的情况，疾病或紊乱（例如，与免疫反应不足有关的情况，疾病或紊乱），这些情况，疾病或紊乱的病理学和/或症状和/或进展（例如，癌症）的贡献者（例如，人类）中。本公开还涉及组合物以及使用和制备相同的其他方法。
• [EN] COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH STING ACTIVITY<br/>[FR] COMPOSÉS ET COMPOSITIONS POUR TRAITER DES ÉTATS ASSOCIÉS À UNE ACTIVITÉ DE STING
  申请人：IFM DUE INC

  公开号：WO2020252240A1

  公开（公告）日：2020-12-17

  This disclosure features chemical entities (e.g., a compound or a pharmaceutically acceptable salt, and/or hydrate, and/or cocrystal, and/or drug combination of the compound) that inhibit (e.g., antagonize) Stimulator of Interferon Genes (STING). Said chemical entities are useful, e.g., for treating a condition, disease or disorder in which increased (e.g., excessive) STING activation (e.g., STING signaling) contributes to the pathology and/or symptoms and/or progression of the condition, disease or disorder (e.g., cancer) in a subject (e.g., a human). This disclosure also features compositions containing the same as well as methods of using and making the same.

  本公开涉及抑制（例如，拮抗）干扰素基因激活因子（STING）的化学实体（例如，化合物或药用可接受的盐，和/或水合物，和/或共晶，和/或化合物的药物组合）。所述化学实体是有用的，例如，用于治疗在受试者（例如，人）中增加（例如，过量）STING激活（例如，STING信号传导）有助于病理和/或症状和/或进展的状况、疾病或失调（例如，癌症）。本公开还涉及含有相同成分的药物组合物以及使用和制备相同成分的方法。
• [EN] NOVEL SULFONAMIDE CARBOXAMIDE COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS DE SULFONAMIDE CARBOXAMIDE
  申请人：INFLAZOME LTD

  公开号：WO2019008025A1

  公开（公告）日：2019-01-10

  The present invention relates to compounds of formula (I) wherein Q is selected from O or S; R1 is a non-aromatic heterocyclic group comprising at least one ring nitrogen atom, wherein R1 is attached to the sulfur atom of the sulfonylurea group by a ring carbon atom, and wherein R1 may optionally be substituted; and R2 is a cyclic group substituted at the α-position, wherein R2 may optionally be further substituted. The present invention further relates to salts, solvates and prodrugs of such compounds, to pharmaceutical compositions comprising such compounds, and to the use of such compounds in the treatment and prevention of medical disorders and diseases, most especially by the inhibition of NLRP3.

  本发明涉及式（I）的化合物，其中Q从O或S中选择；R1是一个非芳香杂环基团，包括至少一个环氮原子，其中R1通过一个环碳原子连接到磺酰脲基团的硫原子，并且R1可以选择性地被取代；R2是在α位被取代的环基团，其中R2也可以选择性地被进一步取代。本发明还涉及这些化合物的盐、溶剂合物和前药，包括这些化合物的药物组合物，以及利用这些化合物治疗和预防医学疾病和疾病的用途，尤其是通过抑制NLRP3。
• [EN] NOVEL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：INFLAZOME LTD

  公开号：WO2019068772A1

  公开（公告）日：2019-04-11

  The present invention relates to compounds of formula (I): wherein Q is selected from O or S; R1 is a saturated or unsaturated hydrocarbyl group, wherein the hydrocarbyl group may be straight-chained or branched, or be or include cyclic groups, wherein the hydrocarbyl group may optionally be substituted, and wherein the hydrocarbyl group may optionally include one or more heteroatoms N, O or S in its carbon skeleton; and R2 is a cyclic group substituted at the a-position, wherein R2 may optionally be further substituted. The present invention further relates to salts, solvates and prodrugs of such compounds, to pharmaceutical compositions comprising such compounds, and to the use of such compounds in the treatment and prevention of medical disorders and diseases, most especially by the inhibition of NLRP3.

  本发明涉及以下式(I)的化合物：其中Q从O或S中选择；R1是饱和或不饱和的烃基团，其中烃基团可以是直链或支链的，或者包括环状基团，其中烃基团可以选择性地被取代，并且其中烃基团的碳骨架中可以选择性地包含一个或多个杂原子N、O或S；以及R2是在α位取代的环状基团，其中R2可以选择性地进一步取代。本发明还涉及这些化合物的盐、溶剂合物和前药，包括这些化合物的药物组合物，以及利用这些化合物治疗和预防医学疾病和疾病的用途，尤其是通过抑制NLRP3。
• [EN] MACROCYCLIC SULFONYLUREA DERIVATIVES USEFUL AS NLRP3 INHIBITORS<br/>[FR] DÉRIVÉS DE SULFONYLURÉE MACROCYCLIQUES UTILES EN TANT QU'INHIBITEURS DE NLRP3
  申请人：INFLAZOME LTD

  公开号：WO2021032591A1

  公开（公告）日：2021-02-25

  The present invention relates to macrocyclic compounds, such as macrocyclic sulfonyl ureas. The present invention further relates to associated salts, solvates, prodrugs and pharmaceutical compositions and to the use of such compounds in the treatment and prevention of medical disorders and diseases, most especially by NLRP 3 inhibition.

  本发明涉及大环化合物，如大环磺酰脲。本发明还涉及相关的盐、溶剂合物、前药和药物组合物，以及利用这些化合物在治疗和预防医学障碍和疾病中的应用，尤其是通过NLRP 3抑制。