2-(5-硝基-1-苯并噻吩-6-基)乙醇 | 159730-75-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 2-(5-硝基-1-苯并噻吩-6-基)乙醇
• 英文名称: 2-(5-nitro-6-benzothienyl)ethanol
• 英文别名: Benzo[b]thiophene-6-ethanol, 5-nitro-；2-(5-nitro-1-benzothiophen-6-yl)ethanol
• CAS: 159730-75-3
• 化学式: C₁₀H₉NO₃S
• 分子量: 223.252
• InChiKey: CKPYKTBJJJYBKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  94.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(5-硝基-1-苯并噻吩-6-基)乙醇 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 25.0~50.0 ℃ 、101.33 kPa 条件下， 反应 2.5h， 生成 6,7-dihydro-5H-thieno[2,3-f]indole
  参考文献：
  名称：

  Synthesis, Biological Activity, and Molecular Modeling Studies of Selective 5-HT_2C/2B Receptor Antagonists

  摘要：

  The synthesis and biological activity are reported for a series of analogues of the previously published indole urea 2 (SB-206553), designed to probe the 5-HT2C receptor binding site. Small molecule modeling studies have been used to define a region in space which is allowed at the 5-HT2C receptor but disallowed at the 5-HT2A receptor. In a complementary approach, docking of 2 into our model of the 5-HT2C receptor has allowed us to propose a novel primary binding interaction for this series of diaryl ureas, involving a potential double hydrogen-bonding interaction between the urea carbonyl oxygen of the ligand and two serine residues in the receptor. The difference of two valine residues in the 5-HT2C receptor for leucine residues in the 5-HT2A receptor is believed to account for the observed 5-HT2C/5-HT2A selectivity with 2.

  DOI：

  10.1021/jm960571v
• 作为产物：
  描述：

  2-溴-4-甲基苯甲醛 在 四氢吡咯 、 喹啉 、 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 硫酸 、 硝酸 、 sodium ethanolate 、 铜 作用下， 以 乙醇 为溶剂， 反应 14.16h， 生成 2-(5-硝基-1-苯并噻吩-6-基)乙醇
  参考文献：
  名称：

  Synthesis, Biological Activity, and Molecular Modeling Studies of Selective 5-HT_2C/2B Receptor Antagonists

  摘要：

  The synthesis and biological activity are reported for a series of analogues of the previously published indole urea 2 (SB-206553), designed to probe the 5-HT2C receptor binding site. Small molecule modeling studies have been used to define a region in space which is allowed at the 5-HT2C receptor but disallowed at the 5-HT2A receptor. In a complementary approach, docking of 2 into our model of the 5-HT2C receptor has allowed us to propose a novel primary binding interaction for this series of diaryl ureas, involving a potential double hydrogen-bonding interaction between the urea carbonyl oxygen of the ligand and two serine residues in the receptor. The difference of two valine residues in the 5-HT2C receptor for leucine residues in the 5-HT2A receptor is believed to account for the observed 5-HT2C/5-HT2A selectivity with 2.

  DOI：

  10.1021/jm960571v

文献信息

• THIENO-INDOLE DERIVATIVES AS 5HT2c AND 5HT2b ANTAGONISTS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0691973A1

  公开（公告）日：1996-01-17
• [EN] THIENO-INDOLE DERIVATIVES AS 5HT2c AND 5HT2b ANTAGONISTS<br/>[FR] DERIVES THIENO-INDOLIQUES UTILISES COMME ANTAGONISTES DE 5HT2c ET DE 5HT2b
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO1994022871A1

  公开（公告）日：1994-10-13

  (EN) Novel thieno-indole compounds being 5HT2c and 5HT2b antagonists, processes for their preparation, compositions containing them and their use in the treatment of mammals.(FR) Nouveaux composés thiéno-indoliques utilisables comme antagonistes de 5HT2c et 5HT2b, leurs procédés de préparation, compositions les renfermant, et leur utilisation dans le traitement des mammifères.
• Synthesis, Biological Activity, and Molecular Modeling Studies of Selective 5-HT_2C/2B Receptor Antagonists
  作者：Ian T. Forbes、Steven Dabbs、D. Malcolm Duckworth、Peter Ham、Graham E. Jones、Frank D. King、Damian V. Saunders、Frank E. Blaney、Christopher B. Naylor、Gordon S. Baxter、Thomas P. Blackburn、Guy A. Kennett、Martyn D. Wood

  DOI：10.1021/jm960571v

  日期：1996.1.1

  The synthesis and biological activity are reported for a series of analogues of the previously published indole urea 2 (SB-206553), designed to probe the 5-HT2C receptor binding site. Small molecule modeling studies have been used to define a region in space which is allowed at the 5-HT2C receptor but disallowed at the 5-HT2A receptor. In a complementary approach, docking of 2 into our model of the 5-HT2C receptor has allowed us to propose a novel primary binding interaction for this series of diaryl ureas, involving a potential double hydrogen-bonding interaction between the urea carbonyl oxygen of the ligand and two serine residues in the receptor. The difference of two valine residues in the 5-HT2C receptor for leucine residues in the 5-HT2A receptor is believed to account for the observed 5-HT2C/5-HT2A selectivity with 2.