4-[(甲基磺酰基)氧基]-苯乙酸 | 64369-79-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[(甲基磺酰基)氧基]-苯乙酸
• 中文别名: 4 - [(甲基磺酰基)氧基]苯乙酸
• 英文名称: 2-(4-methylsulfonyloxyphenyl)acetic acid
• 英文别名: methyl 2-(4-methylsulfonyloxyphenyl)acetic acid；(4-methanesulfonyloxy-phenyl)-acetic acid；2-[4-(Methanesulfonyloxy)phenyl]acetic acid
• CAS: 64369-79-5
• 化学式: C₉H₁₀O₅S
• mdl: MFCD09800580
• 分子量: 230.241
• InChiKey: QTOQTPBCDMNMCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  89
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  C
• 海关编码：
  2916399090
• 储存条件：
  存放在2-8°C的环境中，需密封并保持干燥。

反应信息

• 作为反应物：
  描述：

  4-[(甲基磺酰基)氧基]-苯乙酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 C₉H₉ClO₄S
  参考文献：
  名称：

  Pd II-催化与苯并恶唑和苯并噻唑相邻的C（sp 3）–H键的甲氧基化

  摘要：

  Pd（OAc）2 / PhI（OAc）2催化剂体系促进与苯并恶唑和苯并噻唑环相邻的C（sp 3）–H键的高区域选择性脱氢甲氧基化。标题转换构成了Pd催化的C（sp 3）-H在定向辅助剂的近端选择性α位置上激活甲氧基化的第一个例子，并提供了方便的途径来访问重要的一类由唑修饰的甲基醚（高达90％的分离产率）。通过消除苯并恶唑助剂获得α-甲氧基乙酸，并获得O-甲基化Breslow中间体的前体，证明了该方法的合成实用性。

  DOI：

  10.1039/c9ob00337a
• 作为产物：
  描述：

  4-[(methoxycarbonyl)methyl]phenyl mesylate 在 水 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以61.4%的产率得到4-[(甲基磺酰基)氧基]-苯乙酸
  参考文献：
  名称：

  Compounds and their use in medicine, process for their preparation and pharmaceutical compositions containing them

  摘要：

  本发明涉及具有化学式（I）的新型抗糖尿病、降血脂、抗肥胖和降胆固醇化合物，其衍生物、类似物、互变异构体、立体异构体、多晶形态、药学上可接受的盐、药学上可接受的溶剂化物以及含有它们的药学上可接受的组合物。

  公开号：

  US20030229083A1

文献信息

• COMPOUNDS AND THEIR USE IN MEDICINE, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：Debnath Bhuniya

  公开号：US20070142470A1

  公开（公告）日：2007-06-21

  The present invention relates to novel antidiabetic, hypolipidemic, antiobesity and hypocholesterolemic compounds of formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them.

  本发明涉及一种新型抗糖尿病、降脂、抗肥胖和降胆固醇的化合物，其化学式为(I)，其衍生物、类似物、互变异构体、立体异构体、多晶形态、药学上可接受的盐、药学上可接受的溶剂和含有它们的药学上可接受的组合物。
• 2-Substituted-3-Phenylpropionic Acid Derivatives and Their Use in the Treatment of Inflammatory Bowel Disease
  申请人：Broo Anders

  公开号：US20110166157A1

  公开（公告）日：2011-07-07

  The present invention relates to 2-(substituted sulphur, sulphone or sulphoxide)-3-(substituted phenyl)propionic acid derivatives, 2-(substituted oxygen)-3-(substituted phenyl)propionic acid derivatives, benzoic acid derivatives, and derivatives of 2-methyl-2-(phenoxy or phenylthio)propanoic acid and 2-(methyl or ethyl)-2-(phenoxy or phenylthio)butanoic acid, to processes for preparing such compounds, to their use in the treatment of inflammatory conditions, and to pharmaceutical compositions containing them.

  本发明涉及2-(取代硫、磺酰或亚磺酸基)-3-(取代苯基)丙酸衍生物、2-(取代氧)-3-(取代苯基)丙酸衍生物、苯甲酸衍生物以及2-甲基-2-(苯氧基或苯硫基)丙酸和2-(甲基或乙基)-2-(苯氧基或苯硫基)丁酸的衍生物，以及制备这些化合物的方法，它们在治疗炎症病症中的应用，以及含有它们的制药组合物。
• 2-substituted-3-phenylpropionic acid derivatives and their use in the treatment of inflammatory bowel disease
  申请人：Broo Anders

  公开号：US08785681B2

  公开（公告）日：2014-07-22

  The present invention relates to 2-(substituted sulphur, sulphone or sulphoxide)-3-(substituted phenyl)propionic acid derivatives, 2-(substituted oxygen)-3-(substituted phenyl)propionic acid derivatives, benzoic acid derivatives, and derivatives of 2-methyl-2-(phenoxy or phenylthio)propanoic acid and 2-(methyl or ethyl)-2-(phenoxy or phenylthio)butanoic acid, to processes for preparing such compounds, to their use in the treatment of inflammatory conditions, and to pharmaceutical compositions containing them.

  本发明涉及2-(取代硫、磺酰或亚磺酰基)-3-(取代苯基)丙酸衍生物，2-(取代氧)-3-(取代苯基)丙酸衍生物，苯甲酸衍生物，以及2-甲基-2-(苯氧基或苯硫基)丙酸和2-(甲基或乙基)-2-(苯氧基或苯硫基)丁酸衍生物，以及制备这些化合物的方法，它们在治疗炎症状况中的应用以及含有它们的药物组合物。
• 2 -SUBSTITUTED- 3 -PHENYLPROPIONIC ACID DERIVATIVES AND THEIR USE IN THE TREATMENT OF INFLAMMATORY BOWEL DISEASE
  申请人：Broo Anders

  公开号：US20110021534A1

  公开（公告）日：2011-01-27

  The present invention relates to 2-(substituted sulphur, sulphone or sulphoxide)-3-(substituted phenyl) propionic acid derivatives, 2-(substituted oxygen)-3-(substituted phenyl) propionic acid derivatives, benzoic acid derivatives, and derivatives of 2-methyl-2-(phenoxy or phenylthio)propanoic acid and 2-(methylor ethyl)-2-(phenoxy or phenylthio)butanoic acid, to processes for preparing such compounds, to their use in the treatment of inflammatory conditions, and to pharmaceutical compositions containing them.

  本发明涉及2-(取代硫、砜或亚砜)-3-(取代苯基)丙酸衍生物、2-(取代氧)-3-(取代苯基)丙酸衍生物、苯甲酸衍生物、2-甲基-2-(苯氧基或苯硫基)丙酸和2-(甲基或乙基)-2-(苯氧基或苯硫基)丁酸衍生物，制备这些化合物的过程，它们在治疗炎症疾病中的应用以及含有它们的制药组合物。
• A privileged dual action Alzheimer's disease therapeutic platform targeting immunopathic and proteopathic mechanisms: (<i>E</i>)-3-styrylindoles as inhibitors of indoleamine 2,3-dioxygenase-mediated tryptophan metabolism and β-amyloid aggregation
  作者：Brendan J. Kelly、Elena Diez-Cecilia、Luzhe Pan、Braden Sweeting、Laura Villar、Alexander Kreft、Mayuri Gupta、Shea L. Johnson、Donald F. Weaver

  DOI：10.1139/cjc-2021-0324

  日期：2022.9.1

  The design of potent indoleamine 2,3-dioxygenase 1 (IDO1) enzyme inhibitors targeting immunopathic neuroinflammation has emerged as an area of interest for the treatment of Alzheimer's disease (AD); additionally, recent findings on the clinical benefits of antibodies preventing β-amyloid (Aβ) aggregation have renewed efforts to discover small molecule anti-aggregants targeting proteopathic protein misfolding. Exploiting an endogenous tryptophan-like scaffold, we describe the design and synthesis of small-molecule inhibitors of both immunopathic and proteopathic processes, thus presenting the possibility of single therapeutics acting simultaneously on multiple AD pathogeneses. Specifically, investigations on compounds that inhibit both IDO1 (in human recombinant enzyme, transfected HEK293 cells, and interferon-γ stimulated human microglia assays) and Aβ aggregation (in thioflavin-T and biotinylated-Aβ oligomeric assays) are presented. Five compounds have been identified with high potency against both targets, identifying ( E)-3-styryl indoles as useful tool compounds for developing Alzheimer's therapeutics. Brain penetration of these compounds via passive diffusion or active transport was predicted using Blood-Brain Barrier Score and Brain Exposure Efficiency Score calculations, respectively; the effects of efflux (pgp, BCRP), and influx (OCT1, OCT2) transporters were similarly predicted. Structure–activity relationships were rationalised with molecular docking and molecular dynamics simulations, which also provide insights for future lead compound optimisation.

  针对免疫病理性神经炎症，设计强效吲哚酮 2,3-双加氧酶 1 (IDO1) 酶抑制剂，已成为治疗阿尔茨海默病 (AD) 的研究兴趣领域；此外，最近关于抗体预防β-淀粉样蛋白 (Aβ) 聚集的临床益处的发现，重新激发了发现小分子抗聚集物质靶向蛋白质异常折叠的努力。利用内源性色氨酸样支架，我们描述了小分子抑制剂的设计和合成，可同时作用于免疫病理和蛋白质病理进程，从而提供了单一治疗同时作用于多种AD病因学的可能性。具体而言，介绍了抑制IDO1 (在人重组酶、转染HEK293细胞和干扰素-γ刺激的人类小胶质细胞实验中) 和Aβ聚集 (在硫酸亚油酰胺-T和生物素化-Aβ寡聚物实验中) 的化合物的研究。已经确定了五种对两种靶点具有高效抑制作用的化合物，确定了(E)-3-苯乙烯基吲哚作为开发阿尔茨海默病治疗药物的有用工具化合物。预测了这些化合物通过被动扩散或主动转运的血脑屏障分数和脑暴露效率分数计算的脑穿透性，类似地预测了外流 (pgp、BCRP) 和内流 (OCT1、OCT2) 转运体的影响。通过分子对接和分子动力学模拟对结构活性关系进行了合理化解释，同时为未来的前导化合物优化提供了见解。