2-(3-hydroxypropyl)-1,2-dihydro-3H-indazol-3-one | 89438-61-9

• 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: 2-(3-hydroxypropyl)-1,2-dihydro-3H-indazol-3-one
• 英文别名: 2-(3-Hydroxypropyl)-1H-indazol-3(2H)-one；2-(3-hydroxypropyl)-1H-indazol-3-one
• CAS: 89438-61-9
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: HEFDTDAUQOACPX-UHFFFAOYSA-N

物化性质

• 沸点：
  374.5±44.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-羟基-1H-吲唑 在 吡啶 、 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 2-(3-hydroxypropyl)-1,2-dihydro-3H-indazol-3-one
  参考文献：
  名称：

  Hypolipidemic activity of phthalimide derivatives. 7. Structure-activity studies of indazolone analogs

  摘要：

  The apparent benefit of limiting serum cholesterol and triglyceride levels either by dietary restriction or drug therapy has prompted work in our laboratories toward development of a suitable antihyperlipidemic agent. We have demonstrated the antihyperlipidemic activity of a series of phthalimide derivatives in rodents to be significantly greater than that of clofibrate at a dose of 20 mg/(kg day), intraperitoneally. Here we report the synthesis and biological evaluation of a series of indazolone derivatives, which are heterocycles that are structurally related to the phthalimides . In general, structure-activity relationships within the phthalimide series may be extended to the indazolones . While indazolone itself is only moderately active, N1-carbethoxy substitution produced a more active compound. Substitution of the N2 position with an n-butyl group afforded the most active compound, as also seen in the phthalimide series. Aromatic substitution with electron-releasing and -withdrawing groups lessened the antihyperlipidemic activity.

  DOI：

  10.1021/jm00372a011

文献信息

• Inhibition of myeloperoxidase: Evaluation of 2H-indazoles and 1H-indazolones
  作者：Aaron Roth、Sean Ott、Kelli M. Farber、Teresa A. Palazzo、Wayne E. Conrad、Makhluf J. Haddadin、Dean J. Tantillo、Carroll E. Cross、Jason P. Eiserich、Mark J. Kurth

  DOI：10.1016/j.bmc.2014.09.044

  日期：2014.11

  Myeloperoxidase (MPO) produces hypohalous acids as a key component of the innate immune response; however, release of these acids extracellularly results in inflammatory cell and tissue damage. The twostep, one-pot Davis-Beirut reaction was used to synthesize a library of 2H-indazoles and 1H-indazolones as putative inhibitors of MPO. A structure-activity relationship study was undertaken wherein compounds were evaluated utilizing taurine-chloramine and MPO-mediated H2O2 consumption assays. Docking studies as well as toxicophore and Lipinski analyses were performed. Fourteen compounds were found to be potent inhibitors with IC50 values < 1 mu M, suggesting these compounds could be considered as potential modulators of pro-oxidative tissue injury pertubated by the inflammatory MPO/H2O2/HOCl/HOBr system. (C) 2014 Elsevier Ltd. All rights reserved.
• Hypolipidemic activity of phthalimide derivatives. 7. Structure-activity studies of indazolone analogs
  作者：Steven D. Wyrick、P. Josee Voorstad、George Cocolas、Iris H. Hall

  DOI：10.1021/jm00372a011

  日期：1984.6

  The apparent benefit of limiting serum cholesterol and triglyceride levels either by dietary restriction or drug therapy has prompted work in our laboratories toward development of a suitable antihyperlipidemic agent. We have demonstrated the antihyperlipidemic activity of a series of phthalimide derivatives in rodents to be significantly greater than that of clofibrate at a dose of 20 mg/(kg day), intraperitoneally. Here we report the synthesis and biological evaluation of a series of indazolone derivatives, which are heterocycles that are structurally related to the phthalimides . In general, structure-activity relationships within the phthalimide series may be extended to the indazolones . While indazolone itself is only moderately active, N1-carbethoxy substitution produced a more active compound. Substitution of the N2 position with an n-butyl group afforded the most active compound, as also seen in the phthalimide series. Aromatic substitution with electron-releasing and -withdrawing groups lessened the antihyperlipidemic activity.