4-hydroxy-3-(3-nitrobenzoyl)-2H-isoquinolin-1-one | 1372790-48-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-3-(3-nitrobenzoyl)-2H-isoquinolin-1-one
• CAS: 1372790-48-1
• 化学式: C₁₆H₁₀N₂O₅
• 分子量: 310.266
• InChiKey: UANDSAOFZIWKHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-(3-nitrobenzoyl)-2H-isoquinolin-1-one 在 氢气 、 钯 作用下， 以 乙醇 为溶剂， 生成 3-(3-aminobenzoyl)-4-hydroxy-2H-isoquinolin-1-one
  参考文献：
  名称：

  Identification of benzoylisoquinolines as potential anti-Chagas agents

  摘要：

  A set of three 3-benzoyl substituted isoquinolones was synthesized in good yields and assayed for in vitro trypanocidal activity against Trypanosoma cruzi, the protozoan parasite that causes Chagas' disease. Depending on the concentration evaluated, a greater or equivalent reduction in the number of blood-borne trypomastigotes compared to that observed with benznidazole, a drug currently used to attack the parasite, was observed for two of the samples. In order to assess the potential of the 3-benzoylisoquinolone nucleus as a possible scaffold in the design of novel anti-trypanosomal lead structures, a computational analysis was performed using structural and inhibition information from both functional and target assays archived in the online database, ChEMBL. Chemical space projection of the synthesized compounds along with 3067 structures with known activities against T. cruzi shows that the isoquinolones occupy a sparsely-populated region of chemical space, indicating their potential for development as a novel class of trypanocidals. In addition, 2D and 3D structural similarity analyses revealed micromolar and submicromolar inhibitors of T. cruzi in ChEMBL with high similarity to the synthesized structures. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.046
• 作为产物：
  描述：

  2-(1-苯基乙酮-2-基)异吲哚啉-1,3-二酮 在 硫酸 、 硝酸 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 4-hydroxy-3-(3-nitrobenzoyl)-2H-isoquinolin-1-one
  参考文献：
  名称：

  Identification of benzoylisoquinolines as potential anti-Chagas agents

  摘要：

  A set of three 3-benzoyl substituted isoquinolones was synthesized in good yields and assayed for in vitro trypanocidal activity against Trypanosoma cruzi, the protozoan parasite that causes Chagas' disease. Depending on the concentration evaluated, a greater or equivalent reduction in the number of blood-borne trypomastigotes compared to that observed with benznidazole, a drug currently used to attack the parasite, was observed for two of the samples. In order to assess the potential of the 3-benzoylisoquinolone nucleus as a possible scaffold in the design of novel anti-trypanosomal lead structures, a computational analysis was performed using structural and inhibition information from both functional and target assays archived in the online database, ChEMBL. Chemical space projection of the synthesized compounds along with 3067 structures with known activities against T. cruzi shows that the isoquinolones occupy a sparsely-populated region of chemical space, indicating their potential for development as a novel class of trypanocidals. In addition, 2D and 3D structural similarity analyses revealed micromolar and submicromolar inhibitors of T. cruzi in ChEMBL with high similarity to the synthesized structures. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.046

文献信息

• Identification of benzoylisoquinolines as potential anti-Chagas agents
  作者：Kendall G. Byler、Marco Brito-Arias、Adrian Marquez-Navarro、Benjamin Nogueda-Torres、Luis G. Torres-Bustillos、Karina Martínez-Mayorga

  DOI：10.1016/j.bmc.2012.02.046

  日期：2012.4

  A set of three 3-benzoyl substituted isoquinolones was synthesized in good yields and assayed for in vitro trypanocidal activity against Trypanosoma cruzi, the protozoan parasite that causes Chagas' disease. Depending on the concentration evaluated, a greater or equivalent reduction in the number of blood-borne trypomastigotes compared to that observed with benznidazole, a drug currently used to attack the parasite, was observed for two of the samples. In order to assess the potential of the 3-benzoylisoquinolone nucleus as a possible scaffold in the design of novel anti-trypanosomal lead structures, a computational analysis was performed using structural and inhibition information from both functional and target assays archived in the online database, ChEMBL. Chemical space projection of the synthesized compounds along with 3067 structures with known activities against T. cruzi shows that the isoquinolones occupy a sparsely-populated region of chemical space, indicating their potential for development as a novel class of trypanocidals. In addition, 2D and 3D structural similarity analyses revealed micromolar and submicromolar inhibitors of T. cruzi in ChEMBL with high similarity to the synthesized structures. (C) 2012 Elsevier Ltd. All rights reserved.