5-(1-Phenylcarbamoylmethyl-1H-pyrazol-3-yl)-thiophene-2-carboxylic acid | 945930-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(1-Phenylcarbamoylmethyl-1H-pyrazol-3-yl)-thiophene-2-carboxylic acid
• 英文别名: 5-[1-(2-anilino-2-oxoethyl)pyrazol-3-yl]thiophene-2-carboxylic acid
• CAS: 945930-70-1
• 化学式: C₁₆H₁₃N₃O₃S
• 分子量: 327.364
• InChiKey: UBROLUCBSGCBDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(1-Phenylcarbamoylmethyl-1H-pyrazol-3-yl)-thiophene-2-carboxylic acid 在 对甲苯磺酸 、 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 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-(1-phenylcarbamoylmethyl-1H-pyrazol-3-yl)thiophene-2-carboxylic acid hydroxamide
  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：

  2-[3-(5-Cyano-thiophen-2-yl)-pyrazol-1-yl]-N-phenyl-acetamide 在 sodium hydroxide 作用下， 反应 2.0h， 生成 5-(1-Phenylcarbamoylmethyl-1H-pyrazol-3-yl)-thiophene-2-carboxylic acid
  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