(1-乙酰基吲唑-5-基)乙酸酯 | 36174-07-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: (1-乙酰基吲唑-5-基)乙酸酯
• 中文别名: 1-乙酰基-1H-吲唑-5-基乙酸酯
• 英文名称: N,O-diacetyl-5-hydroxy-1H-indazole
• 英文别名: N,O-diacetyl-1H-indazolol；1-Acetyl-5-acetoxyindazol；5-acetoxy-1-acetyl-1H-indazole；1-Acetyl-1h-indazol-5-yl acetate；(1-acetylindazol-5-yl) acetate
• CAS: 36174-07-9
• 化学式: C₁₁H₁₀N₂O₃
• 分子量: 218.212
• InChiKey: STKYXVXUUPIMSU-UHFFFAOYSA-N

物化性质

• 熔点：
  98 °C
• 沸点：
  385.3±34.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (1-乙酰基吲唑-5-基)乙酸酯 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以7.99 g的产率得到1H-吲唑-5-醇
  参考文献：
  名称：

  Design and synthesis of Rho kinase inhibitors (II)

  摘要：

  In a previous study, we identified several structurally unrelated scaffolds of the Rho kinase inhibitor using pharmacophore information obtained from the results of a high-throughput screening and structural information from a homology model of Rho kinase. 1H-Indazole is one of the candidate scaffolds on which a new series of potent Rho kinase inhibitors could be developed. In this study, the detailed structure-activity relationship of 1H-indazole analogues was studied. During this study, we found that the cell-free enzyme inhibitory potential of Rho kinase inhibitors having the 1H-indazole scaffold did not necessarily correlate with their inhibitory potential toward the chemotaxis of cultured cells. The choice of the linker substructure was shown to be an important factor for the 1H-indazole analogues to inhibit the chemotaxis of cells. Optimization of the 1H-indazole inhibitors with respect to the in vitro inhibition of monocyte chemotaxis induced by MCP-1 was carried out. The inhibitory potential was improved both in the cell-free enzyme assay and in the chemotaxis assay. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.052
• 作为产物：
  描述：

  4-氨基-3-甲基苯酚 、 乙酸酐 在 potassium acetate 、 亚硝酸异戊酯 作用下， 以 苯 为溶剂， 反应 20.0h， 以55%的产率得到(1-乙酰基吲唑-5-基)乙酸酯
  参考文献：
  名称：

  Ruechardt, Christoph; Hassmann, Volker, Liebigs Annalen der Chemie, 1980, # 6, p. 908 - 927

  摘要：

  DOI：

文献信息

• Ruechardt, Christoph; Hassmann, Volker, Liebigs Annalen der Chemie, 1980, # 6, p. 908 - 927
  作者：Ruechardt, Christoph、Hassmann, Volker

  DOI：——

  日期：——
• RUECHARDT C.; HASSMANN V., LIEBIGS ANN. CHEM., 1980, NO 6, 908-927
  作者：RUECHARDT C.、 HASSMANN V.

  DOI：——

  日期：——
• US7217722B2
  申请人：——

  公开号：US7217722B2

  公开（公告）日：2007-05-15
• Design and synthesis of Rho kinase inhibitors (II)
  作者：Masayuki Iwakubo、Atsuya Takami、Yuji Okada、Takehisa Kawata、Yoshimichi Tagami、Hiroshi Ohashi、Motoko Sato、Terumi Sugiyama、Kayoko Fukushima、Hiroshi Iijima

  DOI：10.1016/j.bmc.2006.09.052

  日期：2007.1.1

  In a previous study, we identified several structurally unrelated scaffolds of the Rho kinase inhibitor using pharmacophore information obtained from the results of a high-throughput screening and structural information from a homology model of Rho kinase. 1H-Indazole is one of the candidate scaffolds on which a new series of potent Rho kinase inhibitors could be developed. In this study, the detailed structure-activity relationship of 1H-indazole analogues was studied. During this study, we found that the cell-free enzyme inhibitory potential of Rho kinase inhibitors having the 1H-indazole scaffold did not necessarily correlate with their inhibitory potential toward the chemotaxis of cultured cells. The choice of the linker substructure was shown to be an important factor for the 1H-indazole analogues to inhibit the chemotaxis of cells. Optimization of the 1H-indazole inhibitors with respect to the in vitro inhibition of monocyte chemotaxis induced by MCP-1 was carried out. The inhibitory potential was improved both in the cell-free enzyme assay and in the chemotaxis assay. (c) 2006 Elsevier Ltd. All rights reserved.