3,3′-(pentane-1,5-diylbis(oxy))dibenzimidamide | 35872-76-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,3′-(pentane-1,5-diylbis(oxy))dibenzimidamide
• 英文别名: m-Pentamidine；1,5-bis(benzamidine-3-oxy)pentane；3,3'-pentanediyldioxy-bis-benzamidine；1.5-Bis-(3-carbamimidoyl-phenoxy)-pentan；3,3'-Pentandiyldioxy-bis-benzamidin；Benzenecarboximidamide, 3,3'-(1,5-pentanediylbis(oxy))bis-；3-[5-(3-carbamimidoylphenoxy)pentoxy]benzenecarboximidamide
• CAS: 35872-76-5
• 化学式: C₁₉H₂₄N₄O₂
• 分子量: 340.425
• InChiKey: PASMXCHSIJZQBM-UHFFFAOYSA-N

物化性质

• 沸点：
  545.2±60.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 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：
  118
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氰基苯酚 在 盐酸 、 氨 、 sodium ethanolate 作用下， 以 苯 为溶剂， 反应 126.0h， 生成 3,3′-(pentane-1,5-diylbis(oxy))dibenzimidamide
  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

• Structure–Activity Studies with Bis-Amidines That Potentiate Gram-Positive Specific Antibiotics against Gram-Negative Pathogens
  作者：Charlotte M. J. Wesseling、Cornelis J. Slingerland、Shanice Veraar、Samantha Lok、Nathaniel I. Martin

  DOI：10.1021/acsinfecdis.1c00466

  日期：2021.12.10

  observed synergistic activity reported for pentamidine, while further assessing the capacity for structurally similar bis-amidines to also potentiate Gram-positive specific antibiotics against Gram-negative pathogens. Among the bis-amidines prepared, a number of them were found to exhibit synergistic activity greater than pentamidine. These synergists were shown to effectively potentiate the activity of

  喷他脒是一种 FDA 批准的抗寄生虫药，最近被鉴定为一种外膜破坏增效剂，可增强红霉素、利福平和新生霉素对革兰氏阴性菌的作用。同一项研究还描述了使用市售喷他脒类似物的初步构效关系。我们在这里报告了受喷他脒启发的更广泛的双脒组的设计、合成和评估。本研究既验证了先前观察到的喷他脒的协同活性，同时进一步评估了结构相似的双脒增强革兰氏阳性特异性抗生素对抗革兰氏阴性病原体的能力。在制备的双脒中，发现其中一些表现出比喷他脒更大的协同活性。鲍曼不动杆菌、肺炎克雷伯菌、铜绿假单胞菌和大肠杆菌，包括耐多粘菌素和碳青霉烯的菌株。
• Amidine derivatives for treating amyloidosis
  申请人：Chalifour J. Robert

  公开号：US20070021483A1

  公开（公告）日：2007-01-25

  The present invention relates to the use of amidine compounds in the treatment of amyloid-related diseases. In particular, the invention relates to a method of treating or preventing an amyloid-related disease in a subject comprising administering to the subject a therapeutic amount of an amidine compound. Among the compounds for use according to the invention are those according to the following Formula, such that, when administered, amyloid fibril formation, neurodegeneration, or cellular toxicity is reduced or inhibited:

  本发明涉及在治疗与淀粉样相关疾病中使用氨基脲类化合物。特别地，本发明涉及一种治疗或预防受试者淀粉样相关疾病的方法，包括向受试者施用治疗剂量的氨基脲类化合物。根据本发明使用的化合物包括以下化学式的化合物，当施用时，可减少或抑制淀粉样纤维形成、神经退行性或细胞毒性：
• USES OF PENTAMIDINE AND RELATED COMPOUNDS
  申请人：Berglund John Andrew

  公开号：US20100323993A1

  公开（公告）日：2010-12-23

  Methods are provided herein for treatment of myotonic dystrophy and other toxic RNA diseases in a subject. In some examples, the method comprises administration of a compound that binds a nucleotide repeat expansion in a ribonucleic acid molecule, thereby treating the disease. In additional examples, the method comprises administration of a compound that disrupts binding of muscleblind-like proteins to an RNA nucleotide repeat expansion. Compounds for use in the disclosed method include pentamidine or heptamidine or derivatives thereof. Representative compounds are described herein.

  本文提供了一种治疗肌无力萎缩症和其他毒性RNA疾病的方法。在某些例子中，该方法包括给受体注射一种化合物，该化合物能够结合核糖核酸分子中的核苷酸重复扩展，从而治疗该疾病。在其他例子中，该方法包括给受体注射一种化合物，该化合物能够破坏肌肉盲样蛋白与RNA核苷酸重复扩展的结合。用于该方法的化合物包括戊二酸二甲胺或庚二酸二甲胺或其衍生物。本文描述了代表性化合物。
• US8436049B2
  申请人：——

  公开号：US8436049B2

  公开（公告）日：2013-05-07
• 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.