(2-phenylthiophen-3-yl)acetic acid methyl ester | 875271-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-phenylthiophen-3-yl)acetic acid methyl ester
• 英文别名: (2-Phenylthiophene-3-yl)acetic acid methyl ester；methyl 2-(2-phenylthiophen-3-yl)acetate
• CAS: 875271-79-7
• 化学式: C₁₃H₁₂O₂S
• 分子量: 232.303
• InChiKey: UGIZZTDNAKPZOX-UHFFFAOYSA-N

物化性质

• 熔点：
  29-31 °C
• 沸点：
  349.3±30.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-phenylthiophen-3-yl)acetic acid methyl ester 在 二(氰基苯)二氯化钯 、 四(三苯基膦)钯 sodium hydroxide 、 copper(l) iodide 、 三氯化铝 、 1-羟基苯并三唑 、 溶剂黄146 、 二乙胺 、 N,N-二异丙基乙胺 、 cesium fluoride 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 tin(ll) chloride 作用下， 以 甲醇 、 二氯甲烷 、 2,2,2-三氟乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 104.0h， 生成 2-{5-[1-(4-N-Boc-aminobutyl)-2-phenyl-1H-indol-6-carbonyl]-2-phenylthiophen-3-yl}-N-hydroxyacetamide
  参考文献：
  名称：

  Serotype-selective, small-molecule inhibitors of the zinc endopeptidase of botulinum neurotoxin serotype A

  摘要：

  Botulinum neurotoxin serotype A (BoNTA) is one of the most toxic substances known. Currently, there is no antidote to BoNTA. Small molecules identified from high-throughput screening reportedly inhibit the endopeptidase-the zinc-bound, catalytic domain of BoNTA-at a drug concentration of 20 mu M. However, optimization of these inhibitors is hampered by challenges including the computational evaluation of the ability of a zinc ligand to compete for coordination with nearby residues in the active site of BoNTA. No improved inhibitor of the endopeptidase has been reported. This article reports the development of a serotype-selective, small-molecule inhibitor of BoNTA with a K-i of 12 mu M. This inhibitor was designed to coordinate the zinc ion embedded in the active site of the enzyme for affinity and to interact with a species-specific residue in the active site for selectivity. It is the most potent small-molecule inhibitor of BoNTA reported to date. The results suggest that multiple molecular dynamics simulations using the cationic dummy atom approach are useful to structure-based design of zinc protease inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.018
• 作为产物：
  描述：

  Ethyl 4-chloro-3-formyl-4-phenylbut-3-enoate 在 盐酸 、 氢氧化钾 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 30.0h， 生成 (2-phenylthiophen-3-yl)acetic acid methyl ester
  参考文献：
  名称：

  Serotype-selective, small-molecule inhibitors of the zinc endopeptidase of botulinum neurotoxin serotype A

  摘要：

  Botulinum neurotoxin serotype A (BoNTA) is one of the most toxic substances known. Currently, there is no antidote to BoNTA. Small molecules identified from high-throughput screening reportedly inhibit the endopeptidase-the zinc-bound, catalytic domain of BoNTA-at a drug concentration of 20 mu M. However, optimization of these inhibitors is hampered by challenges including the computational evaluation of the ability of a zinc ligand to compete for coordination with nearby residues in the active site of BoNTA. No improved inhibitor of the endopeptidase has been reported. This article reports the development of a serotype-selective, small-molecule inhibitor of BoNTA with a K-i of 12 mu M. This inhibitor was designed to coordinate the zinc ion embedded in the active site of the enzyme for affinity and to interact with a species-specific residue in the active site for selectivity. It is the most potent small-molecule inhibitor of BoNTA reported to date. The results suggest that multiple molecular dynamics simulations using the cationic dummy atom approach are useful to structure-based design of zinc protease inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.018

文献信息

• Palladium-catalyzed Direct Monoarylation of Thiophene-, Benzothiophene-, and Indoleacetic Acids through Regioselective C–H Bond Cleavage
  作者：Daisuke Takeda、Mana Yamashita、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1246/cl.2011.1015

  日期：2011.9.5

  Regioselective monoarylation of thiophene-3-acetic acid with aryl bromides proceeds efficiently under palladium catalysis to selectively give the corresponding C2-arylated thiophene derivatives. The procedure is also applicable to the C2-arylations of benzothiophene-3- and indole-3-acetic acids.

  在钯催化下，噻吩-3-乙酸与芳基溴化物的 regioselective 单芳基化反应高效进行，能够选择性地生成相应的 C2-芳基化噻吩衍生物。该过程同样适用于苯噻吩-3-和吲哚-3-乙酸的 C2-芳基化反应。
• SMALL-MOLECULE BOTULINUM TOXIN INHIBITORS
  申请人：Pang Yuan-Ping

  公开号：US20100260778A1

  公开（公告）日：2010-10-14

  Small-molecule inhibitors of Botulinum toxin, including BoNTA, BoNTD and BoNTE are provided, as well as methods of using the inhibitors.

  本发明提供了肉毒毒素的小分子抑制剂，包括BoNTA、BoNTD和BoNTE，以及使用这些抑制剂的方法。
• Small-molecule botulinum toxin inhibitors
  申请人：Pang Yuan-Ping

  公开号：US08492428B2

  公开（公告）日：2013-07-23

  Small-molecule inhibitors of Botulinum toxin, including BoNTA, BoNTD and BoNTE are provided, as well as methods of using the inhibitors.

  本发明提供了肉毒毒素的小分子抑制剂，包括BoNTA、BoNTD和BoNTE，以及使用这些抑制剂的方法。
• US8492428B2
  申请人：——

  公开号：US8492428B2

  公开（公告）日：2013-07-23
• [EN] SMALL-MOLECULE BOTULINUM TOXIN INHIBITORS<br/>[FR] INHIBITEURS DE TOXINE BOTULINIQUE DE TYPE PETITES MOLÉCULES
  申请人：MAYO FOUNDATION

  公开号：WO2008051197A2

  公开（公告）日：2008-05-02

  [EN] Small-molecule inhibitors of Botulinum toxin, including BoNTA, BoNTD and BoNTE are provided, as well as methods of using the inhibitors.
  [FR] L'invention concerne des inhibiteurs de type petites molécules de toxine botulinique, notamment BoNTA, BoNTD et BoNTE, ainsi que des procédés d'utilisation des inhibiteurs.