3-(2-Dimethylamino-ethylamino)-5-phenylamino-benzo[c]isoxazole-4,7-dione | 137058-47-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-Dimethylamino-ethylamino)-5-phenylamino-benzo[c]isoxazole-4,7-dione
• 英文别名: 5-Anilino-3-[2-(dimethylamino)ethylamino]-2,1-benzoxazole-4,7-dione
• CAS: 137058-47-0
• 化学式: C₁₇H₁₈N₄O₃
• 分子量: 326.355
• InChiKey: CALUSVARSAUTBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  87.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,5-bisanilino-3-carboethoxy-1,4-benzoquinone 在 lead(IV) acetate 、 氨 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 氯仿 为溶剂， 反应 22.5h， 生成 3-(2-Dimethylamino-ethylamino)-5-phenylamino-benzo[c]isoxazole-4,7-dione
  参考文献：
  名称：

  Synthesis and evaluation of a series of 3,5-disubstituted benzisoxazole-4,7-diones. Potent radiosensitizers in vitro

  摘要：

  A series of 3,5-disubstituted-2,1-benzisoxazole-4,7-diones was synthesized and evaluated as radiosensitizers both in vitro and in vivo. These compounds were designed as non-nitro electron-affinic agents in an effort to alleviate some of the toxicities seen with the 2-nitroimidazole radiosensitizers evaluated in the clinic. Several compounds in this series were potent radiosensitizers in vitro, with sensitizer enhancement ratios of 2.0-2.3 at concentrations < 0.5 mM. Compounds with potent in vitro activity were also evaluated in vivo. However, none of these compounds showed radiosensitizing activity in vivo. The reduction potentials of these compounds were determined by cyclic voltammetry and compared to other electron-affinic radiosensitizers. In general, the reduction potentials of this series of compounds was slightly more positive than the 2-nitroimidazoles, but they fell within the range postulated as acceptable to yield in vivo activity. The results suggest that factors other than reduction potential may be responsible for the lack of in vivo radiosensitizing activity observed for this class of radiosensitizers.

  DOI：

  10.1021/jm00115a019

文献信息

• Synthesis and evaluation of a series of 3,5-disubstituted benzisoxazole-4,7-diones. Potent radiosensitizers in vitro
  作者：Mark J. Suto、Michael A. Stier、R. Thomas Winters、William R. Turner、Cheryl D. Pinter、William E. Elliott、Judith S. Sebolt-Leopold

  DOI：10.1021/jm00115a019

  日期：1991.11

  A series of 3,5-disubstituted-2,1-benzisoxazole-4,7-diones was synthesized and evaluated as radiosensitizers both in vitro and in vivo. These compounds were designed as non-nitro electron-affinic agents in an effort to alleviate some of the toxicities seen with the 2-nitroimidazole radiosensitizers evaluated in the clinic. Several compounds in this series were potent radiosensitizers in vitro, with sensitizer enhancement ratios of 2.0-2.3 at concentrations < 0.5 mM. Compounds with potent in vitro activity were also evaluated in vivo. However, none of these compounds showed radiosensitizing activity in vivo. The reduction potentials of these compounds were determined by cyclic voltammetry and compared to other electron-affinic radiosensitizers. In general, the reduction potentials of this series of compounds was slightly more positive than the 2-nitroimidazoles, but they fell within the range postulated as acceptable to yield in vivo activity. The results suggest that factors other than reduction potential may be responsible for the lack of in vivo radiosensitizing activity observed for this class of radiosensitizers.