5-[(4-oxo-3H-phthalazin-1-yl)methyl]thiophene-3-carboxylic acid | 1622867-34-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5-[(4-oxo-3H-phthalazin-1-yl)methyl]thiophene-3-carboxylic acid
• CAS: 1622867-34-8
• 化学式: C₁₄H₁₀N₂O₃S
• 分子量: 286.311
• InChiKey: HUNBIKZWAGQJGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[(4-oxo-3H-phthalazin-1-yl)methyl]thiophene-3-carboxylic acid 、 (4-硝基苯基)哌嗪-1-基-甲酮 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 水 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 49.0h， 生成 4-[[4-[4-(4-nitrobenzoyl)piperazine-1-carbonyl]thiophen-2-yl]methyl]-2H-phthalazin-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of substituted 4-(thiophen-2-ylmethyl)-2H-phthalazin-1-ones as potent PARP-1 inhibitors

  摘要：

  We have developed a series of substituted 4-(thiophen-2-ylmethyl)-2H-phthalazin-1-ones as potent PARP-1 inhibitors. Preliminary biological evaluation indicated that most compounds possessed inhibitory potencies comparable to, or higher than AZD-2281. Among these compounds, 18q appeared to be the most notable one, which displayed an 8-fold improvement in enzymatic activity compared to AZD-2281. These efforts lay the foundation for our further investigation.

  DOI：

  10.1016/j.bmcl.2014.07.001
• 作为产物：
  描述：

  5-甲酰基-3-噻吩甲腈 在 水 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 34.5h， 生成 5-[(4-oxo-3H-phthalazin-1-yl)methyl]thiophene-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of substituted 4-(thiophen-2-ylmethyl)-2H-phthalazin-1-ones as potent PARP-1 inhibitors

  摘要：

  We have developed a series of substituted 4-(thiophen-2-ylmethyl)-2H-phthalazin-1-ones as potent PARP-1 inhibitors. Preliminary biological evaluation indicated that most compounds possessed inhibitory potencies comparable to, or higher than AZD-2281. Among these compounds, 18q appeared to be the most notable one, which displayed an 8-fold improvement in enzymatic activity compared to AZD-2281. These efforts lay the foundation for our further investigation.

  DOI：

  10.1016/j.bmcl.2014.07.001