2,5-Bis-(4-chloro-phenylamino)-3,6-dioxo-cyclohexa-1,4-dienecarboxylic acid ethyl ester | 137058-32-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-Bis-(4-chloro-phenylamino)-3,6-dioxo-cyclohexa-1,4-dienecarboxylic acid ethyl ester
• 英文别名: ethyl 2,5-bis(4-chloroanilino)-3,6-dioxocyclohexa-1,4-diene-1-carboxylate
• CAS: 137058-32-3
• 化学式: C₂₁H₁₆Cl₂N₂O₄
• 分子量: 431.275
• InChiKey: JWXGKLDWBIMSHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-Bis-(4-chloro-phenylamino)-3,6-dioxo-cyclohexa-1,4-dienecarboxylic acid ethyl ester 在 palladium(II) acetate 、 氨 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 19.5h， 生成 5-(4-Chloroanilino)-3-ethoxy-2,1-benzoxazole-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
• 作为产物：
  描述：

  二羟基苯甲酸乙酯 、 对氯苯胺 在 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 反应 19.0h， 以91%的产率得到2,5-Bis-(4-chloro-phenylamino)-3,6-dioxo-cyclohexa-1,4-dienecarboxylic acid ethyl ester
  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