N'-[2-(4-chloro-phenylsulfanyl)-phenyl]-N,N-dimethyl-propanediyldiamine | 108975-28-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N'-[2-(4-chloro-phenylsulfanyl)-phenyl]-N,N-dimethyl-propanediyldiamine
• 英文别名: N'-[2-(4-Chlor-phenylmercapto)-phenyl]-N,N-dimethyl-propandiyldiamin；N-[2-(4-chlorophenyl)sulfanylphenyl]-N',N'-dimethylpropane-1,3-diamine
• CAS: 108975-28-6
• 化学式: C₁₇H₂₁ClN₂S
• 分子量: 320.886
• InChiKey: NRNVZYGBAHHCDV-UHFFFAOYSA-N

物化性质

• 沸点：
  198-199.5 °C(Press: 1.5 Torr)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-硝基-4'-氯二苯硫醚 在 锌 作用下， 以 溶剂黄146 为溶剂， 生成 N'-[2-(4-chloro-phenylsulfanyl)-phenyl]-N,N-dimethyl-propanediyldiamine
  参考文献：
  名称：

  Mechanism of inhibition of tumor necrosis factor production by chlorpromazine and its derivatives in mice

  摘要：

  In previous work, we reported that chlorpromazine inhibits tumor necrosis factor (TNF) production in endotoxin lipopolysaccharide-treated mice, and protects against lipopolysaccharide toxicity. Chlorpromazine is used as an antipsychotic and has several effects on the central nervous system. It acts on different neurotransmitter receptors and has other biochemical activities some of which, like inhibition of phospholipase A(2), might be responsible for the inhibitory effect on TNF production. To investigate the role of these actions in the inhibition of TNF production by chlorpromazine, we have synthesized some chlorpromazine derivatives that do not have central activities. Some of these analogs have lost their affinity for various receptors and their phospholipase A(2) inhibitory activity, but still inhibit TNF production. No correlation was found between TNF inhibition and the ability to inhibit nitric oxide (NO) synthase, whereas a good correlation was evident between TNF inhibition and antioxidant activity.

  DOI：

  10.1016/s0014-2999(96)00728-5

文献信息

• Chlorinated <i>o</i>-Dimethylaminopropylaminodiphenyl Sulfide Derivatives
  作者：ALFRED. BURGER、JOSEPH L. STANMYER

  DOI：10.1021/jo01118a013

  日期：1956.12.1
• Mechanism of inhibition of tumor necrosis factor production by chlorpromazine and its derivatives in mice
  作者：Pietro Ghezzi、Silvio Garattini、Tiziana Mennini、Riccardo Bertini、René Delgado Hernandez、Fabio Benigni、Silvano Sacco、Malgorzata Skorupska、Manuela Mengozzi、Roberto Latini、Mami Kurosaki、Alain Lombet、Arnel Fradin、Jacqueline Bonnet、Yves Rolland、Jean-Daniel Brion

  DOI：10.1016/s0014-2999(96)00728-5

  日期：1996.12

  In previous work, we reported that chlorpromazine inhibits tumor necrosis factor (TNF) production in endotoxin lipopolysaccharide-treated mice, and protects against lipopolysaccharide toxicity. Chlorpromazine is used as an antipsychotic and has several effects on the central nervous system. It acts on different neurotransmitter receptors and has other biochemical activities some of which, like inhibition of phospholipase A(2), might be responsible for the inhibitory effect on TNF production. To investigate the role of these actions in the inhibition of TNF production by chlorpromazine, we have synthesized some chlorpromazine derivatives that do not have central activities. Some of these analogs have lost their affinity for various receptors and their phospholipase A(2) inhibitory activity, but still inhibit TNF production. No correlation was found between TNF inhibition and the ability to inhibit nitric oxide (NO) synthase, whereas a good correlation was evident between TNF inhibition and antioxidant activity.