5-{5-[(Benzyl-tert-butoxycarbonyl-amino)-methyl]-pyridin-2-yl}-thiophene-2-carboxylic acid | 928260-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 5-{5-[(Benzyl-tert-butoxycarbonyl-amino)-methyl]-pyridin-2-yl}-thiophene-2-carboxylic acid
• CAS: 928260-54-2
• 化学式: C₂₃H₂₄N₂O₄S
• 分子量: 424.521
• InChiKey: ZNOXWOHMZBJWEA-UHFFFAOYSA-N

物化性质

• 沸点：
  614.8±55.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  79.73
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-{5-[(Benzyl-tert-butoxycarbonyl-amino)-methyl]-pyridin-2-yl}-thiophene-2-carboxylic acid 在 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 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-(5-((benzylamino)methyl)pyridin-2-yl)-N-hydroxythiophene-2-carboxamide
  参考文献：
  名称：

  Identification and optimisation of a series of substituted 5-pyridin-2-yl-thiophene-2-hydroxamic acids as potent histone deacetylase (HDAC) inhibitors

  摘要：

  Further investigation of a series of thienyl-based hydroxamic acids that included ADS 100380 and ADS 102550 led to the identification of the 5-pyridin-2-yl-thiophene-2-hydroxamic acid 3c, which possessed modest HDAC inhibitory activity. Substitution at the 5- and 6-positions of the pyridyl ring of compound 3c provided compounds 5a-g, 7a, b, 9, and 13a. Compound 5b demonstrated improved potency, in vitro DMPK profile, and rat oral bioavailability, compared to ADS 102550. Functionalisation of the pendent phenyl group of compounds 5b, 5e and 13a provided analogues that possessed excellent enzyme inhibition and anti-proliferative activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.045
• 作为产物：
  描述：

  2-溴-5-醛基吡啶 在 四(三苯基膦)钯 、 三乙酰氧基硼氢化钠 、 sodium carbonate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 21.0h， 生成 5-{5-[(Benzyl-tert-butoxycarbonyl-amino)-methyl]-pyridin-2-yl}-thiophene-2-carboxylic acid
  参考文献：
  名称：

  Identification and optimisation of a series of substituted 5-pyridin-2-yl-thiophene-2-hydroxamic acids as potent histone deacetylase (HDAC) inhibitors

  摘要：

  Further investigation of a series of thienyl-based hydroxamic acids that included ADS 100380 and ADS 102550 led to the identification of the 5-pyridin-2-yl-thiophene-2-hydroxamic acid 3c, which possessed modest HDAC inhibitory activity. Substitution at the 5- and 6-positions of the pyridyl ring of compound 3c provided compounds 5a-g, 7a, b, 9, and 13a. Compound 5b demonstrated improved potency, in vitro DMPK profile, and rat oral bioavailability, compared to ADS 102550. Functionalisation of the pendent phenyl group of compounds 5b, 5e and 13a provided analogues that possessed excellent enzyme inhibition and anti-proliferative activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.045