[3-(羟基甲基)-2-噻吩基]硼酸 | 222840-73-5

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: [3-(羟基甲基)-2-噻吩基]硼酸
• 中文别名: 脲,N-甲氧基-N-甲基-N'-(3-甲基-1,2,4-噻二唑-5-基)-
• 英文名称: [3-(hydroxymethyl)-2-thienyl]boronic acid
• 英文别名: 3-hydroxymethylthiophene-2-boronic acid；(3-(Hydroxymethyl)thiophen-2-yl)boronic acid；[3-(hydroxymethyl)thiophen-2-yl]boronic acid
• CAS: 222840-73-5
• 化学式: C₅H₇BO₃S
• mdl: MFCD09952072
• 分子量: 157.986
• InChiKey: HUUVNOIORZPHNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  88.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氟溴苄 、 [3-(羟基甲基)-2-噻吩基]硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 12.75h， 生成 [2-(3-fluorobenzyl)-3-thienyl]methanol
  参考文献：
  名称：

  The Discovery of 4-{1-[({2,5-Dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]cyclopropyl}benzoic Acid (MK-2894), A Potent and Selective Prostaglandin E₂ Subtype 4 Receptor Antagonist

  摘要：

  The discovery of highly potent and selective second generation EP4 antagonist MK-2894 (34d) is discussed. This compound exhibits favorable pharmacokinetic profile in a number of preclinical species and potent anti-inflammatory activity in several animal models of pain/inflammation. It also shows favorable GI tolerability profile in rats when compared to traditional NSAID indomethacin.

  DOI：

  10.1021/jm901771h
• 作为产物：
  描述：

  3-甲酸基噻吩-2-硼酸 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 3-噻吩甲醇 、 [3-(羟基甲基)-2-噻吩基]硼酸
  参考文献：
  名称：

  The Discovery of 4-{1-[({2,5-Dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]cyclopropyl}benzoic Acid (MK-2894), A Potent and Selective Prostaglandin E₂ Subtype 4 Receptor Antagonist

  摘要：

  The discovery of highly potent and selective second generation EP4 antagonist MK-2894 (34d) is discussed. This compound exhibits favorable pharmacokinetic profile in a number of preclinical species and potent anti-inflammatory activity in several animal models of pain/inflammation. It also shows favorable GI tolerability profile in rats when compared to traditional NSAID indomethacin.

  DOI：

  10.1021/jm901771h

文献信息

• Aryl thiophene derivatives as PDE IV inhibitors
  申请人：Merck & Co., Inc.

  公开号：US06034089A1

  公开（公告）日：2000-03-07

  The invention encompasses the novel compound of Formula I useful in the treatment of diseases, including asthma, by raising the level of cyclic adenosine-3',5'-monophosphate (cAMP) through the inhibition of phosphodiesterase IV (PDE IV). ##STR1## The invention also encompasses certain pharmaceutical compositions and methods for treatment of diseases by inhibition of PDE IV, resulting in an elevation of cAMP, comprising the use of compounds of Formula I.

  该发明涵盖了一种新型化合物，其化学式为I，可用于治疗包括哮喘在内的疾病，通过通过抑制磷酸二酯酶IV（PDE IV）提高环状腺苷-3'，5'-单磷酸（cAMP）的水平。 该发明还涵盖了通过抑制PDE IV治疗疾病的某些药物组合物和方法，导致cAMP升高，包括使用化合物I的用途。
• Solid phase parallel synthesis of highly substituted thiophene derivatives and identification of novel phosphodiesterase-4 (PDE-4) inhibitors
  作者：Yongxin Han、André Giroux、Carole Lépine、France Laliberté、Zheng Huang、Hélène Perrier、Christopher I Bayly、Robert N Young

  DOI：10.1016/s0040-4020(99)00686-9

  日期：1999.9

  A versatile protocol for solid phase synthesis of highly substituted thiophene derivatives and their activity against the PDE-4 enzyme are discussed. This protocol employs 3-hydroxymethylthiophene-2-boronic acid (5) as the scaffold and sequential palladium catalyzed cross-coupling reactions as the C-C bond forming step. This methodology allows convenient modification of the thiophene core from three directions, giving rise to structurally diverse derivatives with overall high chemical purity and yield. A novel series of potent PDE-4 inhibitors have been identified from these compounds. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• The Discovery of 4-{1-[({2,5-Dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]cyclopropyl}benzoic Acid (MK-2894), A Potent and Selective Prostaglandin E₂ Subtype 4 Receptor Antagonist
  作者：Marc Blouin、Yongxin Han、Jason Burch、Julie Farand、Christophe Mellon、Mireille Gaudreault、Mark Wrona、Jean-François Lévesque、Danielle Denis、Marie-Claude Mathieu、Rino Stocco、Erika Vigneault、Alex Therien、Patsy Clark、Steve Rowland、Daigen Xu、Gary O’Neill、Yves Ducharme、Rick Friesen

  DOI：10.1021/jm901771h

  日期：2010.3.11

  The discovery of highly potent and selective second generation EP4 antagonist MK-2894 (34d) is discussed. This compound exhibits favorable pharmacokinetic profile in a number of preclinical species and potent anti-inflammatory activity in several animal models of pain/inflammation. It also shows favorable GI tolerability profile in rats when compared to traditional NSAID indomethacin.