1-[(2-methylthiazol-4-yl)methyl]-7-nitro-1H-indazole | 1229662-01-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 1-[(2-methylthiazol-4-yl)methyl]-7-nitro-1H-indazole
• 英文别名: 2-Methyl-4-[(7-nitroindazol-1-yl)methyl]-1,3-thiazole
• CAS: 1229662-01-4
• 化学式: C₁₂H₁₀N₄O₂S
• 分子量: 274.303
• InChiKey: LQLYOHJKCPOSGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[(2-methylthiazol-4-yl)methyl]-7-nitro-1H-indazole 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 ammonium hydroxide 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 以91%的产率得到7-amino-1-[(2-methylthiazol-4-yl)methyl]-1H-indazole
  参考文献：
  名称：

  Synthesis and modulation properties of imidazo[4,5-b]pyridin-7-one and indazole-4,7-dione derivatives towards the Cryptosporidium parvum CpABC3 transporter

  摘要：

  The syntheses of new N-polysubstituted imidazo[4,5-b]pyridine-7-one (IF, 5 and 8a-8f) and indazole-4,7-dione (ID, 9 and 10) derivatives are described. The binding affinity of IP and ID towards the recombinant Nucleotide Binding Domain NBD1 of Cryptosporidium parvum CpABC3 was evaluated by intrinsic fluorescence quenching. IP induced a moderate quenching of the intrinsic fluorescence of H6-NBD1 whereas IDs 9 and 10 showed a binding affinity comparable to the ATP analogue TNP-ATP. In addition, 8d, Se and 10 were shown to be competitive inhibitors of the ATPase activity, but with low affinity. These compounds could thus act like some flavonoid derivatives, which can partly overlap both the nucleotide-binding site and the adjacent hydrophobic steroid-binding region of mammalian P-glycoproteins.

  DOI：

  10.1016/j.ejmech.2010.02.033
• 作为产物：
  描述：

  4-(氯甲基)-2-甲基-1,3-噻唑 、 7-硝基吲唑 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 15.08h， 以30%的产率得到1-[(2-methylthiazol-4-yl)methyl]-7-nitro-1H-indazole
  参考文献：
  名称：

  Synthesis and modulation properties of imidazo[4,5-b]pyridin-7-one and indazole-4,7-dione derivatives towards the Cryptosporidium parvum CpABC3 transporter

  摘要：

  The syntheses of new N-polysubstituted imidazo[4,5-b]pyridine-7-one (IF, 5 and 8a-8f) and indazole-4,7-dione (ID, 9 and 10) derivatives are described. The binding affinity of IP and ID towards the recombinant Nucleotide Binding Domain NBD1 of Cryptosporidium parvum CpABC3 was evaluated by intrinsic fluorescence quenching. IP induced a moderate quenching of the intrinsic fluorescence of H6-NBD1 whereas IDs 9 and 10 showed a binding affinity comparable to the ATP analogue TNP-ATP. In addition, 8d, Se and 10 were shown to be competitive inhibitors of the ATPase activity, but with low affinity. These compounds could thus act like some flavonoid derivatives, which can partly overlap both the nucleotide-binding site and the adjacent hydrophobic steroid-binding region of mammalian P-glycoproteins.

  DOI：

  10.1016/j.ejmech.2010.02.033

文献信息

• Synthesis and modulation properties of imidazo[4,5-b]pyridin-7-one and indazole-4,7-dione derivatives towards the Cryptosporidium parvum CpABC3 transporter
  作者：Waël Zeinyeh、Hexue Xia、Philippe Lawton、Sylvie Radix、Christelle Marminon、Pascal Nebois、Nadia Walchshofer

  DOI：10.1016/j.ejmech.2010.02.033

  日期：2010.6

  The syntheses of new N-polysubstituted imidazo[4,5-b]pyridine-7-one (IF, 5 and 8a-8f) and indazole-4,7-dione (ID, 9 and 10) derivatives are described. The binding affinity of IP and ID towards the recombinant Nucleotide Binding Domain NBD1 of Cryptosporidium parvum CpABC3 was evaluated by intrinsic fluorescence quenching. IP induced a moderate quenching of the intrinsic fluorescence of H6-NBD1 whereas IDs 9 and 10 showed a binding affinity comparable to the ATP analogue TNP-ATP. In addition, 8d, Se and 10 were shown to be competitive inhibitors of the ATPase activity, but with low affinity. These compounds could thus act like some flavonoid derivatives, which can partly overlap both the nucleotide-binding site and the adjacent hydrophobic steroid-binding region of mammalian P-glycoproteins.