methyl 6-(bromomethyl)benzo[b]thiophene-2-carboxylate | 82787-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: methyl 6-(bromomethyl)benzo[b]thiophene-2-carboxylate
• 英文别名: Methyl 6-(bromomethyl)-1-benzothiophene-2-carboxylate
• CAS: 82787-74-4
• 化学式: C₁₁H₉BrO₂S
• 分子量: 285.161
• InChiKey: GDRKRAZPZNBNDQ-UHFFFAOYSA-N

物化性质

• 熔点：
  103.5-106 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  382.2±27.0 °C(Predicted)
• 密度：
  1.580±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  methyl 6-(bromomethyl)benzo[b]thiophene-2-carboxylate 在 sodium azide 、 palladium on activated charcoal 、 氢气 作用下， 以 N,N-二甲基甲酰胺 、 四氢呋喃 为溶剂， 生成 Methyl 6-(aminomethyl)-1-benzothiophene-2-carboxylate
  参考文献：
  名称：

  Benzofused hydroxamic acids: Useful fragments for the preparation of histone deacetylase inhibitors. Part 1: Hit identification

  摘要：

  In the search for a new class of histone deacetylase inhibitors, we prepared a series of simple benzofused hydroxamic acids to find an anchoring fragment of minimal molecular weight. These initial hits, all belonging to the benzothiophene class, showed very good ligand efficiencies. Following these findings, a classical fragment growing approach was performed to increase binding affinity and cytotoxicity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.053
• 作为产物：
  描述：

  甲基6-甲基-1-苯并噻吩-2-羧酸酯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 生成 methyl 6-(bromomethyl)benzo[b]thiophene-2-carboxylate
  参考文献：
  名称：

  Benzofused hydroxamic acids: Useful fragments for the preparation of histone deacetylase inhibitors. Part 1: Hit identification

  摘要：

  In the search for a new class of histone deacetylase inhibitors, we prepared a series of simple benzofused hydroxamic acids to find an anchoring fragment of minimal molecular weight. These initial hits, all belonging to the benzothiophene class, showed very good ligand efficiencies. Following these findings, a classical fragment growing approach was performed to increase binding affinity and cytotoxicity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.053

文献信息

• Arylmethoxy Isoindoline Derivatives and Compositions Comprising and Methods of Using the Same
  申请人：Man Hon-Wah

  公开号：US20110196150A1

  公开（公告）日：2011-08-11

  Provided are 4′-arylmethoxy isoindoline compounds, and pharmaceutically acceptable salts, solvates, clathrates, stereoisomers, and prodrugs thereof. Methods of use, and pharmaceutical compositions of these compounds are disclosed.

  提供了4'-芳基甲氧基异吲哚啉化合物，以及其药用盐、溶剂合物、包合物、立体异构体和前药。公开了这些化合物的使用方法和药物组合物。
• ARYLMETHOXY ISOINDOLINE DERIVATIVES AND COMPOSITIONS COMPRISING AND METHODS OF USING THE SAME
  申请人：Celgene Corporation

  公开号：US20180037567A1

  公开（公告）日：2018-02-08

  Provided are 4′-arylmethoxy isoindoline compounds, and pharmaceutically acceptable salts, solvates, clathrates, stereoisomers, and prodrugs thereof. Methods of use, and pharmaceutical compositions of these compounds are disclosed.

  提供了4'-芳基甲氧基异吲哚啉化合物及其药学上可接受的盐、溶剂合物、笼合物、立体异构体和前药。公开了这些化合物的使用方法和药物组合物。
• Arylmethoxy isoindoline derivatives and compositions comprising and methods of using the same
  申请人：Celgene Corporation

  公开号：US10189814B2

  公开（公告）日：2019-01-29

  Provided are 4′-arylmethoxy isoindoline compounds, and pharmaceutically acceptable salts, solvates, clathrates, stereoisomers, and prodrugs thereof. Methods of use, and pharmaceutical compositions of these compounds are disclosed.

  本发明提供了 4′-芳基甲氧基异吲哚啉化合物及其药学上可接受的盐、溶液剂、凝胶体、立体异构体和原药。还公开了这些化合物的使用方法和药物组合物。
• Selective thromboxane synthetase inhibitors. 3. 1H-Imidazol-1-yl-substituted benzo[b]furan-, benzo[b]thiophene- and indole-2- and 3-carboxylic acids
  作者：Peter E. Cross、Roger P. Dickinson、M. John Parry、Michael J. Randall

  DOI：10.1021/jm00159a012

  日期：1986.9

  The preparation of a series of 1H-imidazol-1-yl-substituted benzo[b]furan-, benzo[b]thiophene-, and indolecarboxylic acids is described. Most of the compounds were potent inhibitors of TxA2 synthetase in vitro, and the distance between the imidazole and carboxylic acid groups was found to be important for optimal potency. The most potent compound in vivo was 6-(1H-imidazol-1-ylmethyl)-3-methylbenzo[b]thiophene-2-carboxylic acid (71), which, in conscious dogs, showed a similar profile of activity to that of dazoxiben (1).
• CROSS P. E.; DICKINSON R. P.; PARRY M. J.; RANDALL M. J., J. MED. CHEM., 1986, 29, N 9, 1637-1643
  作者：CROSS P. E.、 DICKINSON R. P.、 PARRY M. J.、 RANDALL M. J.

  DOI：——

  日期：——