5-Isopropyl-9-nitro-5H-phenanthridin-6-one | 596821-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-Isopropyl-9-nitro-5H-phenanthridin-6-one
• CAS: 596821-90-8
• 化学式: C₁₆H₁₄N₂O₃
• 分子量: 282.299
• InChiKey: FRBNFLJSBKCYDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  65.14
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-Isopropyl-9-nitro-5H-phenanthridin-6-one 在 palladium on activated charcoal 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 2-dimethylamino-N-(5-isopropyl-6-oxo-5,6-dihydro-phenanthridin-9-yl)-acetamide
  参考文献：
  名称：

  Structure–activity relationships in a series of NPY Y5 antagonists: 3-amido-9-ethylcarbazoles, core-modified analogues and amide isosteres

  摘要：

  Beginning with carbazole la, the amide and alkyl substituents were optimized to maintain potency while adding solubilizing groups. Efforts to replace the 3-amino-9-ethylcarbazole core, a known carcinogen, used the SAR generated in the carbazole series for guidance and led to the synthesis of a number of core-modified analogues. In addition, an isosteric series, in which the amide was replaced with an imidazole, was prepared. Two potent new series lacking the putative toxicophore were identified from these endeavors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00329-9
• 作为产物：
  描述：

  2-iodo-4-nitrobenzoyl chloride 在 4-二甲氨基吡啶 、 palladium diacetate 、 三乙胺 、 三苯基膦 、 silver carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 5-Isopropyl-9-nitro-5H-phenanthridin-6-one
  参考文献：
  名称：

  Structure–activity relationships in a series of NPY Y5 antagonists: 3-amido-9-ethylcarbazoles, core-modified analogues and amide isosteres

  摘要：

  Beginning with carbazole la, the amide and alkyl substituents were optimized to maintain potency while adding solubilizing groups. Efforts to replace the 3-amino-9-ethylcarbazole core, a known carcinogen, used the SAR generated in the carbazole series for guidance and led to the synthesis of a number of core-modified analogues. In addition, an isosteric series, in which the amide was replaced with an imidazole, was prepared. Two potent new series lacking the putative toxicophore were identified from these endeavors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00329-9