2,4-dinitro-1-fluoro-5-[N-methyl-(p-methoxyphenyl)amino]benzene | 377090-11-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4-dinitro-1-fluoro-5-[N-methyl-(p-methoxyphenyl)amino]benzene
• 英文别名: JS-25-119；Benzenamine, 5-fluoro-N-(4-methoxyphenyl)-N-methyl-2,4-dinitro-；5-fluoro-N-(4-methoxyphenyl)-N-methyl-2,4-dinitroaniline
• CAS: 377090-11-4
• 化学式: C₁₄H₁₂FN₃O₅
• 分子量: 321.265
• InChiKey: AFLLNFJBMBHXMR-UHFFFAOYSA-N

物化性质

• 熔点：
  138-140 °C(Solv: ethanol (64-17-5))
• 沸点：
  504.5±50.0 °C(Predicted)
• 密度：
  1.422±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-hydroxy-3,3-dimethyltriaz-1-ene 2-oxide sodium salt 、 2,4-dinitro-1-fluoro-5-[N-methyl-(p-methoxyphenyl)amino]benzene 在 碳酸氢钠 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 48.0h， 以1.44 g的产率得到(Z)-dimethylamino-[5-(4-methoxy-N-methylanilino)-2,4-dinitrophenoxy]imino-oxidoazanium
  参考文献：
  名称：

  Antitumor Activity of JS-K [O²-(2,4-Dinitrophenyl) 1-[(4-Ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate] and Related O²-Aryl Diazeniumdiolates in Vitro and in Vivo

  摘要：

  The literature provides evidence that metabolic nitric oxide ( NO) release mediates the cytotoxic activities ( against human leukemia and prostate cancer xenografts in mice) of JS-K, a compound of structure R2N-(O)=NO-Ar for which R2N is 4-(ethoxycarbonyl) piperazin-1-yl and Ar is 2,4-dinitrophenyl. Here we present comparative data on the potencies of JS-K and 41 other O-2-arylated diazeniumdiolates as inhibitors of HL-60 human leukemia cell proliferation, as well as in the NCI 51-cell-line screen for six of them. The data show JS-K to be the most potent of the 42 in both screens and suggest that other features of its structure and metabolism besides NO release may contribute importantly to its activity. Results with control compounds implicate JS-K's arylating ability, and the surprisingly low IC50 value of the N-(ethoxycarbonyl) piperazine byproduct of NO release suggests a role for the R2N moiety. In addition to the above-mentioned in vivo activities, JS-K is shown here to be carcinostatic in a rat liver cancer model.

  DOI：

  10.1021/jm060022h
• 作为产物：
  描述：

  1,5-二氟-2,4-二硝基苯 、 N-甲基-P-氨基苯甲醚 在 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 2,4-dinitro-1-fluoro-5-[N-methyl-(p-methoxyphenyl)amino]benzene
  参考文献：
  名称：

  Antitumor Activity of JS-K [O²-(2,4-Dinitrophenyl) 1-[(4-Ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate] and Related O²-Aryl Diazeniumdiolates in Vitro and in Vivo

  摘要：

  The literature provides evidence that metabolic nitric oxide ( NO) release mediates the cytotoxic activities ( against human leukemia and prostate cancer xenografts in mice) of JS-K, a compound of structure R2N-(O)=NO-Ar for which R2N is 4-(ethoxycarbonyl) piperazin-1-yl and Ar is 2,4-dinitrophenyl. Here we present comparative data on the potencies of JS-K and 41 other O-2-arylated diazeniumdiolates as inhibitors of HL-60 human leukemia cell proliferation, as well as in the NCI 51-cell-line screen for six of them. The data show JS-K to be the most potent of the 42 in both screens and suggest that other features of its structure and metabolism besides NO release may contribute importantly to its activity. Results with control compounds implicate JS-K's arylating ability, and the surprisingly low IC50 value of the N-(ethoxycarbonyl) piperazine byproduct of NO release suggests a role for the R2N moiety. In addition to the above-mentioned in vivo activities, JS-K is shown here to be carcinostatic in a rat liver cancer model.

  DOI：

  10.1021/jm060022h