4-(3,4-methylenedioxyphenoxy)butyric acid | 127556-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4-(3,4-methylenedioxyphenoxy)butyric acid
• 英文别名: 4-(Benzo[1,3]dioxol-5-yloxy)-butyric acid；4-(1,3-benzodioxol-5-yloxy)butanoic acid
• CAS: 127556-98-3
• 化学式: C₁₁H₁₂O₅
• mdl: MFCD07403058
• 分子量: 224.213
• InChiKey: TUKIMVAQBCKDGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3,4-methylenedioxyphenoxy)butyric acid 在 三氟乙酸酐 作用下， 以 三氟乙酸 为溶剂， 以18%的产率得到7H,8H-1,3-dioxolo[4,5-h]benzoxepin-9(6H)-one
  参考文献：
  名称：

  Freedman, Jules; Stewart, Kenneth T., Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1547 - 1554

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 4-(3-methylenedioxyphenoxy)butyrate 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 以44.94%的产率得到4-(3,4-methylenedioxyphenoxy)butyric acid
  参考文献：
  名称：

  1,3-苯并二氧杂环戊烯基贝特衍生物作为潜在的降血脂和保肝剂

  摘要：

  设计并合成了一系列目标化合物1,3-苯并二氧戊环基贝特衍生物。所有目标化合物均通过Triton WR-1339诱导的高脂血症小鼠进行初步评估，其中化合物12显示出比其他化合物以及阳性药物非诺贝特（FF）更大的抗高脂血症活性。图 12显示高脂肪饮食 (HFD) 诱导的高脂血症小鼠的血脂显着降低，例如甘油三酯 (TG)、总胆固醇 (TC) 和低密度脂蛋白胆固醇 (LDL-C)。此外，肝转氨酶（AST 和 ALT）在给药12后改善，尤其是 AST，组织病理学检查显示12改善肝脏脂质蓄积。参与脂质代谢的PPAR-α在12治疗组的肝组织中表达上调。其他显着活性，如抗氧化和抗炎作用得到证实，并加强了12作为潜在低血脂和保肝剂的作用。

  DOI：

  10.1016/j.bmcl.2021.127898

文献信息

• Identification of Small Molecules Blocking the Pseudomonas aeruginosa Type III Secretion System Protein PcrV
  作者：Charlotta Sundin、Michael Saleeb、Sara Spjut、Liena Qin、Mikael Elofsson

  DOI：10.3390/biom11010055

  日期：——

  Pseudomonas aeruginosa is an opportunistic bacterial pathogen that employs its type III secretion system (T3SS) during the acute phase of infection to translocate cytotoxins into the host cell cytoplasm to evade the immune system. The PcrV protein is located at the tip of the T3SS, facilitates the integration of pore-forming proteins into the eukaryotic cell membrane, and is required for translocation of cytotoxins into the host cell. In this study, we used surface plasmon resonance screening to identify small molecule binders of PcrV. A follow-up structure-activity relationship analysis resulted in PcrV binders that protect macrophages in a P. aeruginosa cell-based infection assay. Treatment of P. aeruginosa infections is challenging due to acquired, intrinsic, and adaptive resistance in addition to a broad arsenal of virulence systems such as the T3SS. Virulence blocking molecules targeting PcrV constitute valuable starting points for development of next generation antibacterials to treat infections caused by P. aeruginosa.

  铜绿假单胞菌是一种机会性细菌病原体，它在感染的急性阶段利用其III型分泌系统（T3SS）将细胞毒素转运到宿主细胞胞质中，以逃避免疫系统。PcrV蛋白位于T3SS的顶端，促进孔形成蛋白与真核细胞膜的整合，并且需要将细胞毒素转运到宿主细胞中。在这项研究中，我们使用表面等离子共振筛选识别PcrV的小分子结合物。随后进行的结构-活性关系分析得出了能在基于P. aeruginosa细胞的感染实验中保护巨噬细胞的PcrV结合物。治疗P. aeruginosa感染具有挑战性，因为除了广泛的毒力系统（如T3SS）外，还存在获得性、固有性和适应性抗性。针对PcrV的毒力阻断分子为开发下一代抗菌剂治疗由铜绿假单胞菌引起的感染提供了宝贵的起点。
• Pharmaceutical use of substituted amides
  申请人：Andersen Sune Henrik

  公开号：US20060111366A1

  公开（公告）日：2006-05-25

  The use of substituted amides for modulating the activity of 11β-hydroxysteroid dehydrogenase type 1 (11βHSD1) and the use of these compounds as pharmaceutical compositions, are described. Also a novel class of substituted amides, their use in therapy, pharmaceutical compositions comprising the compounds, as well as their use in the manufacture of medicaments are described. The present compounds are modulators and more specifically inhibitors of the activity of 11βHSD1 and may be useful in the treatment, prevention and/or prophylaxis of a range of medical disorders where a decreased intracellular concentration of active glucocorticoid is desirable.

  本文介绍了使用取代酰胺来调节11β-羟化甾体脱氢酶1型（11βHSD1）的活性以及将这些化合物用作制药组合物的方法。还介绍了一类新型的取代酰胺，它们在治疗中的应用、包含这些化合物的制药组合物以及它们在药物制剂制造中的应用。这些化合物是11βHSD1的调节剂，更具体地说是抑制剂，可用于治疗、预防和/或预防一系列需要降低活性糖皮质激素细胞内浓度的医学疾病。
• Amide Derivatives and Pharmaceutical Use Thereof
  申请人：Andersen Henrik Sune

  公开号：US20090264414A1

  公开（公告）日：2009-10-22

  The use of substituted amides for modulating the activity of 11β-hydroxysteroid dehydrogenase type 1 (11βHSD1) and the use of these compounds as pharmaceutical compositions, are described. Also a novel class of substituted amides, their use in therapy, pharmaceutical compositions comprising the compounds, as well as their use in the manufacture of medicaments are described. The present compounds are modulators and more specifically inhibitors of the activity of 11βHSD1 and may be useful in the treatment, prevention and/or prophylaxis of a range of medical disorders where a decreased intracellular concentration of active glucocorticoid is desirable.

  本文描述了使用取代酰胺来调节11β-羟化类固醇脱氢酶1型（11βHSD1）活性以及这些化合物作为药物组分的用途。还描述了一类新型的取代酰胺，它们在治疗中的用途，包括含有这些化合物的药物组分以及它们在制造药物中的用途。这些化合物是调节剂，更具体地说是11βHSD1活性的抑制剂，可用于治疗、预防和/或预防一系列医学疾病，其中降低细胞内活性糖皮质激素的浓度是可取的。
• FREEDMAN, JULES;STEWART, KENNETH T., J. HETEROCYCL. CHEM., 26,(1989) N, C. 1547-1554
  作者：FREEDMAN, JULES、STEWART, KENNETH T.

  DOI：——

  日期：——
• EP1615698A2
  申请人：——

  公开号：EP1615698A2

  公开（公告）日：2006-01-18