6-ethoxy-5-(2-(4-nitrophenyl)hydrazono)-6-oxohexanoic acid | 1360616-79-0

• 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: 6-ethoxy-5-(2-(4-nitrophenyl)hydrazono)-6-oxohexanoic acid
• 英文别名: Hexanedioic acid, 2-[2-(4-nitrophenyl)hydrazinylidene]-, 1-ethyl ester；6-ethoxy-5-[(4-nitrophenyl)hydrazinylidene]-6-oxohexanoic acid
• CAS: 1360616-79-0
• 化学式: C₁₄H₁₇N₃O₆
• 分子量: 323.305
• InChiKey: KATNVRLLTXPDPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  23.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  131.13
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6-ethoxy-5-(2-(4-nitrophenyl)hydrazono)-6-oxohexanoic acid 在 硫酸 、 水 、 对甲苯磺酸 、 sodium hydroxide 作用下， 以 乙醇 、 苯 为溶剂， 反应 48.0h， 生成 3-(2-carboxyethyl)-5-nitro-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Design and synthesis of novel inhibitors of human kynurenine aminotransferase-I

  摘要：

  Herein we report 6-ethoxy-6-oxo-5-(2-phenylhydrazono) hexanoic acid and 3-(2-carboxyethyl)-1H-indole- 2-carboxylic acid derivatives as synthetically accessible leads for human kynurenine aminotransferase-I (KAT-I) inhibitors. In total, 12 compounds were synthesized and their biological activities were determined using the HPLC-UV based KAT-I inhibition assay. Of the 12 compounds synthesized, 10 were found to inhibit human KAT-I and the most active compound was found to be 5-(2-(4-chlorophenyl) hydrazono)-6-ethoxy-6-oxohexanoic acid (9a) with an IC50 of 19.8 mu M. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.138
• 作为产物：
  描述：

  2-氧代环戊羧酸乙酯 、 4-硝基苯胺 在 盐酸 、 sodium nitrite 、 sodium acetate 、 三乙胺 作用下， 以 水 为溶剂， 反应 1.75h， 以83%的产率得到6-ethoxy-5-(2-(4-nitrophenyl)hydrazono)-6-oxohexanoic acid
  参考文献：
  名称：

  Discovery of novel indole derivatives as allosteric inhibitors of fructose-1,6-bisphosphatase

  摘要：

  A series of novel indole derivatives was designed and synthesized as inhibitors of fructose-1,6-bisphosphatase (FBPase). The most potent compound 14c was identified with an IC50 value of 0.10 mu M by testing the inhibitory activity against recombinant human FBPase. The structure-activity relationships were investigated on the substitution at 4- and 5-position of the indole scaffold. The binding interactions of the title compounds at AMP binding site of FBPase were predicted using CDOCKER algorithm. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.049

文献信息

• Discovery of novel indole derivatives as allosteric inhibitors of fructose-1,6-bisphosphatase
  作者：Jianbo Bie、Shuainan Liu、Zhanmei Li、Yongzhao Mu、Bailing Xu、Zhufang Shen

  DOI：10.1016/j.ejmech.2014.11.049

  日期：2015.1

  A series of novel indole derivatives was designed and synthesized as inhibitors of fructose-1,6-bisphosphatase (FBPase). The most potent compound 14c was identified with an IC50 value of 0.10 mu M by testing the inhibitory activity against recombinant human FBPase. The structure-activity relationships were investigated on the substitution at 4- and 5-position of the indole scaffold. The binding interactions of the title compounds at AMP binding site of FBPase were predicted using CDOCKER algorithm. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Design and synthesis of novel inhibitors of human kynurenine aminotransferase-I
  作者：Fady N. Akladios、Naveed A. Nadvi、Joohong Park、Jane R. Hanrahan、Vimal Kapoor、Mark D. Gorrell、W. Bret Church

  DOI：10.1016/j.bmcl.2011.12.138

  日期：2012.2

  Herein we report 6-ethoxy-6-oxo-5-(2-phenylhydrazono) hexanoic acid and 3-(2-carboxyethyl)-1H-indole- 2-carboxylic acid derivatives as synthetically accessible leads for human kynurenine aminotransferase-I (KAT-I) inhibitors. In total, 12 compounds were synthesized and their biological activities were determined using the HPLC-UV based KAT-I inhibition assay. Of the 12 compounds synthesized, 10 were found to inhibit human KAT-I and the most active compound was found to be 5-(2-(4-chlorophenyl) hydrazono)-6-ethoxy-6-oxohexanoic acid (9a) with an IC50 of 19.8 mu M. (C) 2012 Elsevier Ltd. All rights reserved.