1-nitroso-4-[(4',4''-difluorodiphenyl)methyl]piperazine | 141528-78-1

• 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: 1-nitroso-4-[(4',4''-difluorodiphenyl)methyl]piperazine
• 英文别名: 1-[bis(4-fluorophenyl)methyl]-4-nitrosopiperazine
• CAS: 141528-78-1
• 化学式: C₁₇H₁₇F₂N₃O
• 分子量: 317.338
• InChiKey: QBDIFKVUQDIEGO-UHFFFAOYSA-N

物化性质

• 熔点：
  126-129 °C
• 沸点：
  432.6±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  35.91
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-nitroso-4-[(4',4''-difluorodiphenyl)methyl]piperazine 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 甲醇 、 乙醚 、 水 、 苯 为溶剂， 反应 9.0h， 生成 1-N-[(4'''-methoxyphenyl)aminomethylamino]-4-[(4',4''-difluorodiphenyl)methyl]piperazine
  参考文献：
  名称：

  Savaliya; Dobariya; Kathiriya, Indian Journal of Heterocyclic Chemistry, 2011, vol. 20, # 3, p. 249 - 252

  摘要：

  DOI：
• 作为产物：
  描述：

  4,4'-二氟苯甲哌嗪 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 以80%的产率得到1-nitroso-4-[(4',4''-difluorodiphenyl)methyl]piperazine
  参考文献：
  名称：

  Savaliya; Dobariya; Kathiriya, Indian Journal of Heterocyclic Chemistry, 2011, vol. 20, # 3, p. 249 - 252

  摘要：

  DOI：

文献信息

• New triazine derivatives as potent modulators of multidrug resistance
  作者：Alain Dhainaut、Gilbert Regnier、Ghanem Atassi、Alain Pierre、Stephane Leonce、Laurence Kraus-Berthier、Jean Francois Prost

  DOI：10.1021/jm00091a017

  日期：1992.6

  A series of 70 triazine derivatives have been synthesized and tested for their capacity to modulate multidrug resistance (MDR) in DC-3F/AD and KB-A1 tumor cells in vitro, in comparison with verapamil (VRP), a calcium channel antagonist currently used in therapy as an antihypertensive drug, which also shows MDR modulating activity. Among the 12 selected compounds, 16 (S9788) showed high MDR reversing properties in vitro (300- and 6-fold VRP at 5-mu-M in DC-3F/AD and KB-A1 cells, respectively) and induced a strong accumulation of adriamycin. The relationship between the increase of ADR accumulation and the fold reversal induced by these compounds and their lack of effects on the sensitive DC-3F cells suggest that they act mainly by inhibiting the P-glycoprotein (Pgp) catalyzed efflux of cytotoxic agents, as already described for a majority of MDR modulators. In vivo, in association with the antitumor drug vincristine (0.25 mg/kg), 16 (100 mg/kg) increased the TIC by 39% in mice bearing the resistant tumor cell line P388/VCR. According to these interesting properties, 16 was selected for a clinical development because it was more bioavailable than 34, even though it was less active.