(2-苯基噻吩-3-基)乙酸乙酯 | 875271-86-6

• 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: (2-苯基噻吩-3-基)乙酸乙酯
• 英文名称: (2-phenylthiophen-3-yl)acetic acid ethyl ester
• 英文别名: (2-phenylthiophene-3-yl)acetic acid ethyl ester；Ethyl 2-(2-phenylthiophen-3-yl)acetate
• CAS: 875271-86-6
• 化学式: C₁₄H₁₄O₂S
• 分子量: 246.33
• InChiKey: CIKBVTPZQABLRV-UHFFFAOYSA-N

物化性质

• 沸点：
  363.0±30.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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-苯基噻吩-3-基)乙酸乙酯 在 二(氰基苯)二氯化钯 、 四(三苯基膦)钯 盐酸 、 氢氧化钾 、 sodium hydroxide 、 copper(l) iodide 、 三氯化铝 、 1-羟基苯并三唑 、 二乙胺 、 N,N-二异丙基乙胺 、 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 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 2-[2-Phenyl-5-(2-phenyl-1H-indole-6-carbonyl)-thiophen-3-yl]-N-trityloxy-acetamide
  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：

  4-氧代-4-苯基丁酸乙酯 在 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 38.0h， 生成 (2-苯基噻吩-3-基)乙酸乙酯
  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

• Regioselective Oxidative Coupling Reactions of 3-Substituted Thiophenes with Arylboronic Acids
  作者：Ingo Schnapperelle、Stefan Breitenlechner、Thorsten Bach

  DOI：10.1021/ol201292v

  日期：2011.7.15

  Under optimized conditions, 3-substituted thiophenes (EWG = COOEt, PO(OEt)2) undergo a facile and regioselective oxidative coupling reaction at carbon atom C4. The reactions were performed with various aryl boronic acids as nucleophiles in the presence of silver oxide (2.0 equiv), cesium trifluoroacetate (tfa) (1.0 equiv), benzoquinone (BQ) (0.5 equiv), and catalytic amounts of Pd(tfa)2 (10 mol %)

  在优化的条件下，3-取代的噻吩（EWG = COOEt，PO（OEt）2）在碳原子C4处进行便捷的区域选择性氧化偶联反应。反应是在氧化银（2.0当量），三氟乙酸铯（tfa）（1.0当量），苯醌（BQ）（0.5当量）和催化量的Pd（tfa）2存在下，以各种芳基硼酸作为亲核试剂进行的。使用三氟乙酸（TFA）作为溶剂的（10mol％）。
• 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。
• SHVEDOV, V. I.;FEDOROVA, I. N.;SAVITSKAYA, N. V.;SHVARTS, G. YA.;SYUBAEV,+
  作者：SHVEDOV, V. I.、FEDOROVA, I. N.、SAVITSKAYA, N. V.、SHVARTS, G. YA.、SYUBAEV,+

  DOI：——

  日期：——
• 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.