(2,4-dibromo-thiophen-3-yl)-acetic acid methyl ester | 905838-65-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: (2,4-dibromo-thiophen-3-yl)-acetic acid methyl ester
• 英文别名: methyl (2,4-dibromothien-3-yl)acetate；Methyl (2,4-dibromothien-3-yl)acetate；methyl 2-(2,4-dibromothiophen-3-yl)acetate
• CAS: 905838-65-5
• 化学式: C₇H₆Br₂O₂S
• 分子量: 313.997
• InChiKey: VCKGWFPWDUKUCC-UHFFFAOYSA-N

物化性质

• 沸点：
  310.2±37.0 °C(Predicted)
• 密度：
  1.913±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  (2,4-dibromo-thiophen-3-yl)-acetic acid methyl ester 、 4-正丙氧基-3-甲基苯硼酸 在 palladium bis[bis(diphenylphosphino)ferrocene] dichloride potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 生成
  参考文献：
  名称：

  Thiophene substituted acylguanidines as BACE1 inhibitors

  摘要：

  A series of thiophene-substituted acylguanidines were designed from a pyrrole substituted acylguanidine HTS lead. This template allowed a greater flexibility, through differential Suzuki couplings, to explore the binding site of BACE1 and to enhance the inhibitory potencies. This exploration provided a 25-fold enhancement in potency to yield compound 10a, which was 150 nM in a BACE1 FRET assay.

  DOI：

  10.1016/j.bmcl.2007.08.010
• 作为产物：
  描述：

  甲醇 、 (2,4-dibromothiophen-3-yl)-acetonitrile 在 硫酸 作用下， 反应 14.0h， 以88%的产率得到(2,4-dibromo-thiophen-3-yl)-acetic acid methyl ester
  参考文献：
  名称：

  Substituted thienyl and furyl acylguanidines and methods of their use as beta-secretase modulators

  摘要：

  本发明提供了一种式I的取代噻吩或呋喃酰基胍化合物。 本发明还提供了用于抑制β-分泌酶（BACE）和治疗β-淀粉样沉积物和神经原纤维缠结的方法。

  公开号：

  US20060183792A1

文献信息

• Substituted thienyl and furyl acylguanidines and methods of their use as beta-secretase modulators
  申请人：Fobare Floyd William

  公开号：US20060183792A1

  公开（公告）日：2006-08-17

  The present invention provides a substituted thienyl or furyl acylguanidine compound of formula I The present invention also provides methods for the inhibition of β-secretase (BACE) and for the treatment of β-amyloid deposits and neurofibrillary tangles.

  本发明提供了一种式I的取代噻吩或呋喃酰基胍化合物。 本发明还提供了用于抑制β-分泌酶（BACE）和治疗β-淀粉样沉积物和神经原纤维缠结的方法。
• Thiophene substituted acylguanidines as BACE1 inhibitors
  作者：William F. Fobare、William R. Solvibile、Albert J. Robichaud、Michael S. Malamas、Eric Manas、Jim Turner、Yun Hu、Erik Wagner、Rajiv Chopra、Rebecca Cowling、Guixan Jin、Jonathan Bard

  DOI：10.1016/j.bmcl.2007.08.010

  日期：2007.10

  A series of thiophene-substituted acylguanidines were designed from a pyrrole substituted acylguanidine HTS lead. This template allowed a greater flexibility, through differential Suzuki couplings, to explore the binding site of BACE1 and to enhance the inhibitory potencies. This exploration provided a 25-fold enhancement in potency to yield compound 10a, which was 150 nM in a BACE1 FRET assay.