5-[1-(2,2-Dimethoxy-ethyl)-1H-pyrazol-3-yl]-thiophene-2-carboxylic acid methyl ester | 929102-03-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 5-[1-(2,2-Dimethoxy-ethyl)-1H-pyrazol-3-yl]-thiophene-2-carboxylic acid methyl ester
• CAS: 929102-03-4
• 化学式: C₁₃H₁₆N₂O₄S
• 分子量: 296.347
• InChiKey: AZFNREFSGVOKEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.58
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-[1-(2,2-Dimethoxy-ethyl)-1H-pyrazol-3-yl]-thiophene-2-carboxylic acid methyl ester 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.03h， 以80%的产率得到5-[1-(2-Oxo-ethyl)-1H-pyrazol-3-yl]-thiophene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Identification and optimisation of a series of substituted 5-(1H-pyrazol-3-yl)-thiophene-2-hydroxamic acids as potent histone deacetylase (HDAC) inhibitors

  摘要：

  Optimisation of ADS100380, a sub-micromolar HDAC inhibitor identified using a virtual screening approach, led to a series of substituted 5-(1H-pyrazol-3-yl)-thiophene-2-hydroxamic acids (6a-i), that possessed significant HDAC inhibitory activity. Subsequent functionalisation of the pendent phenyl group of compounds 6f and 6g provided analogues 6j-w with further enhanced enzyme and anti-proliferative activity. Compound 6j demonstrated efficacy in a mouse xenograft experiment. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.048
• 作为产物：
  描述：

  5-(1H-pyrazol-3-yl)-thiophene-2-carbonitrile 在 盐酸 、 sodium hydroxide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 5-[1-(2,2-Dimethoxy-ethyl)-1H-pyrazol-3-yl]-thiophene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Identification and optimisation of a series of substituted 5-(1H-pyrazol-3-yl)-thiophene-2-hydroxamic acids as potent histone deacetylase (HDAC) inhibitors

  摘要：

  Optimisation of ADS100380, a sub-micromolar HDAC inhibitor identified using a virtual screening approach, led to a series of substituted 5-(1H-pyrazol-3-yl)-thiophene-2-hydroxamic acids (6a-i), that possessed significant HDAC inhibitory activity. Subsequent functionalisation of the pendent phenyl group of compounds 6f and 6g provided analogues 6j-w with further enhanced enzyme and anti-proliferative activity. Compound 6j demonstrated efficacy in a mouse xenograft experiment. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.048