4-[5-(4-甲脒基-2-硝基苯氧基)戊氧基]-3-硝基苯甲脒 | 125901-98-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[5-(4-甲脒基-2-硝基苯氧基)戊氧基]-3-硝基苯甲脒
• 中文别名: 肉豆蔻酸异辛酯
• 英文名称: 1,5-bis(3-nitrobenzamidine-4-oxy)pentane
• 英文别名: 3,3'-dinitro-4,4'-pentanediyldioxy-bis-benzamidine；1.5-Bis-(2-nitro-4-carbamimidoyl-phenoxy)-pentan；3,3'-Dinitro-4,4'-pentandiyldioxy-bis-benzamidin；4,4'-(1,5-Pentanediylbis(oxy))bis(3-nitrobenzenecarboximidamide)；4-[5-(4-carbamimidoyl-2-nitrophenoxy)pentoxy]-3-nitrobenzenecarboximidamide
• CAS: 125901-98-6
• 化学式: C₁₉H₂₂N₆O₆
• 分子量: 430.42
• InChiKey: QGYJOIDDJBUEBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  210
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1,5-二(4-氰基苯氧基)戊烷 在 盐酸 、 氨 、 硝酸 、 三氟乙酸 作用下， 以 氯仿 、 乙酸酐 为溶剂， 反应 48.0h， 生成 4-[5-(4-甲脒基-2-硝基苯氧基)戊氧基]-3-硝基苯甲脒
  参考文献：
  名称：

  Analogs of 1,5-bis(4-amidinophenoxy)pentane (pentamidine) in the treatment of experimental Pneumocystis carinii pneumonia

  摘要：

  A series of 33 analogues of the anti-Pneumocystis carinii drug 1,5-bis(4-amidinophenoxy)pentane (pentamidine) was synthesized for screening against a rat model of P. carinii pneumonia (PCP). Twenty-five of the compounds showed efficacy against PCP when compared to a saline-treated control group. Two compounds, 1,4-bis(4-amidinophenoxy)butane (butamidine, 6) and 1,3-bis(4-amidino-2-methoxyphenoxy)propane (DAMP, 16), were statistically more effective than the parent drug in treating PCP in the rat model of infection. In addition to their activity against PCP, the compounds were also evaluated for antitrypsin activity, ability to inhibit thymidylate synthetase, affinity for DNA, and toxicity. No correlation was observed between the tested molecular interactions of the diamidines and their effectiveness against PCP.

  DOI：

  10.1021/jm00166a026

文献信息

• 138. The search for chemotherapeutic amidines. Part X. Substituted 4 : 4′-diamidino-αω-diphenoxyalkanes and -diphenyl ethers
  作者：S. S. Berg、G. Newbery

  DOI：10.1039/jr9490000642

  日期：——
• Analogs of 1,5-bis(4-amidinophenoxy)pentane (pentamidine) in the treatment of experimental Pneumocystis carinii pneumonia
  作者：Richard R. Tidwell、Susan Kilgore Jones、J. Dieter Geratz、Kwasi A. Ohemeng、Michael Cory、James Edwin Hall

  DOI：10.1021/jm00166a026

  日期：1990.4

  A series of 33 analogues of the anti-Pneumocystis carinii drug 1,5-bis(4-amidinophenoxy)pentane (pentamidine) was synthesized for screening against a rat model of P. carinii pneumonia (PCP). Twenty-five of the compounds showed efficacy against PCP when compared to a saline-treated control group. Two compounds, 1,4-bis(4-amidinophenoxy)butane (butamidine, 6) and 1,3-bis(4-amidino-2-methoxyphenoxy)propane (DAMP, 16), were statistically more effective than the parent drug in treating PCP in the rat model of infection. In addition to their activity against PCP, the compounds were also evaluated for antitrypsin activity, ability to inhibit thymidylate synthetase, affinity for DNA, and toxicity. No correlation was observed between the tested molecular interactions of the diamidines and their effectiveness against PCP.