2-[(4-{4-[bis(2-hydroxyethyl)amino]phenylthio}phenyl)(2-hydroxyethyl)amino]ethan-1-ol | 189639-06-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-[(4-{4-[bis(2-hydroxyethyl)amino]phenylthio}phenyl)(2-hydroxyethyl)amino]ethan-1-ol
• 英文别名: bis-{4-[bis-(2-hydroxy-ethyl)-amino]-phenyl}-sulfide；Tetrakis-N-(2-hydroxy-aethyl)-4,4'-sulfandiyl-di-anilin；Bis-{4-[bis-(2-hydroxy-aethyl)-amino]-phenyl}-sulfid；2-[4-[4-[bis(2-hydroxyethyl)amino]phenyl]sulfanyl-N-(2-hydroxyethyl)anilino]ethanol
• CAS: 189639-06-3
• 化学式: C₂₀H₂₈N₂O₄S
• 分子量: 392.519
• InChiKey: GOXHNVGTUWPAEF-UHFFFAOYSA-N

物化性质

• 熔点：
  135-136 °C(Solv: ethanol (64-17-5); ligroine (8032-32-4))
• 沸点：
  662.8±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  113
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(4-{4-[bis(2-hydroxyethyl)amino]phenylthio}phenyl)(2-hydroxyethyl)amino]ethan-1-ol 在 三氟乙酸 、 三氯氧磷 作用下， 反应 3.17h， 生成 4-[4-[bis(2-chloroethyl)amino]phenyl]sulfinyl-N,N-bis(2-chloroethyl)aniline
  参考文献：
  名称：

  Sulfoxide-Containing Aromatic Nitrogen Mustards as Hypoxia-Directed Bioreductive Cytotoxins

  摘要：

  A series of diaryl and alkylaryl sulfoxide-containing nitrogen mustards were synthesized and evaluated for their hypoxia-selective cytotoxicity against V-79 cells in vitro as well as for their metabolism profiles with the rat S-9 fractions. In general, the diaryl sulfoxides (4, 5, and 7-9) showed much greater hypoxia selectivity (11-27-fold) than the alkylaryl sulfoxides (similar to3-fold) (1 and 3). The fused diphenyl sulfoxides (10 and 11), on the other hand, showed very low hypoxia selectivity (1.3-3-fold). Compound 10 was highly cytotoxic under both aerobic and anaerobic conditions, while 11 showed low cytotoxicity under both conditions. The bioreduction of 8 by the rat S-9 fraction under anaerobic conditions was inhibited by menadione and enhanced by benzaldehyde, acetaldehyde, or 2-hydroxypyrimidine suggesting the involvement of aldehyde oxidase in the reduction of the sulfoxides. Bioreductive metabolism studies of selected model sulfoxides suggested that diaryl sulfoxides are better substrates for aldehyde oxidase than alkylaryl sulfoxides.

  DOI：

  10.1021/jm9904957
• 作为产物：
  描述：

  4,4-二氨基二苯硫醚 、 2-氯乙醇 在 calcium carbonate 作用下， 以 水 为溶剂， 反应 72.0h， 以26.8%的产率得到2-[(4-{4-[bis(2-hydroxyethyl)amino]phenylthio}phenyl)(2-hydroxyethyl)amino]ethan-1-ol
  参考文献：
  名称：

  Sulfoxide-Containing Aromatic Nitrogen Mustards as Hypoxia-Directed Bioreductive Cytotoxins

  摘要：

  A series of diaryl and alkylaryl sulfoxide-containing nitrogen mustards were synthesized and evaluated for their hypoxia-selective cytotoxicity against V-79 cells in vitro as well as for their metabolism profiles with the rat S-9 fractions. In general, the diaryl sulfoxides (4, 5, and 7-9) showed much greater hypoxia selectivity (11-27-fold) than the alkylaryl sulfoxides (similar to3-fold) (1 and 3). The fused diphenyl sulfoxides (10 and 11), on the other hand, showed very low hypoxia selectivity (1.3-3-fold). Compound 10 was highly cytotoxic under both aerobic and anaerobic conditions, while 11 showed low cytotoxicity under both conditions. The bioreduction of 8 by the rat S-9 fraction under anaerobic conditions was inhibited by menadione and enhanced by benzaldehyde, acetaldehyde, or 2-hydroxypyrimidine suggesting the involvement of aldehyde oxidase in the reduction of the sulfoxides. Bioreductive metabolism studies of selected model sulfoxides suggested that diaryl sulfoxides are better substrates for aldehyde oxidase than alkylaryl sulfoxides.

  DOI：

  10.1021/jm9904957

文献信息

• Lecocq, Bulletin de la Societe Chimique de France, 1950, p. 188,190
  作者：Lecocq

  DOI：——

  日期：——