3-(hexadecylamino)-4-((2-(dimethylamino)ethyl)amino)cyclobut-3-ene-1,2-dione | 1541171-07-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(hexadecylamino)-4-((2-(dimethylamino)ethyl)amino)cyclobut-3-ene-1,2-dione
• 英文别名: 3-[2-(Dimethylamino)ethylamino]-4-(hexadecylamino)cyclobut-3-ene-1,2-dione；3-[2-(dimethylamino)ethylamino]-4-(hexadecylamino)cyclobut-3-ene-1,2-dione
• CAS: 1541171-07-6
• 化学式: C₂₄H₄₅N₃O₂
• 分子量: 407.64
• InChiKey: YPTTVHATSJIIKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  29
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  61.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(hexadecylamino)-4-((2-(dimethylamino)ethyl)amino)cyclobut-3-ene-1,2-dione 、 碘甲烷 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 12.0h， 以90%的产率得到2-((2-hexadecylamino)-3,4-dioxocyclobut-1-en-1-yl)amino-N,N,N,-trimethylammonium iodide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of N,N′-Squaramides with High in Vivo Efficacy and Low Toxicity: Toward a Low-Cost Drug against Chagas Disease

  摘要：

  Access to basic drugs is a major issue in developing countries. Chagas disease caused by Trypanosorna cruzi is a paradigmatic example of a chronic disease without an effective treatment. Current treatments based on benznidazole and nifurtimox are expensive, ineffective, and toxic. N,N'-Squaramides are amide-type compounds that feature both hydrogen bond donor and acceptor groups and are capable of multiple interactions with complementary sites. When combined with amine and carboxylic groups, squaramide compounds have increased solubility and therefore make suitable therapeutic agents. In this work, we introduce a group of Lipiriski's rule of five compliant squararnides as candidates for treating Chagas disease. The in vivo studies confirmed the positive expectations arising from the preliminary in vitro studies, revealing compound 17 to be the most effective for both acute and chronic phases. The activity, stability, low cost of starting materials, and straightforward synthesis make amino squaramides appropriate molecules for the development of an affordable anti-Chagasic agent.

  DOI：

  10.1021/jm4017015
• 作为产物：
  描述：

  十六胺 以 乙醚 、 乙醇 为溶剂， 反应 24.0h， 生成 3-(hexadecylamino)-4-((2-(dimethylamino)ethyl)amino)cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Synthesis and Biological Evaluation of N,N′-Squaramides with High in Vivo Efficacy and Low Toxicity: Toward a Low-Cost Drug against Chagas Disease

  摘要：

  Access to basic drugs is a major issue in developing countries. Chagas disease caused by Trypanosorna cruzi is a paradigmatic example of a chronic disease without an effective treatment. Current treatments based on benznidazole and nifurtimox are expensive, ineffective, and toxic. N,N'-Squaramides are amide-type compounds that feature both hydrogen bond donor and acceptor groups and are capable of multiple interactions with complementary sites. When combined with amine and carboxylic groups, squaramide compounds have increased solubility and therefore make suitable therapeutic agents. In this work, we introduce a group of Lipiriski's rule of five compliant squararnides as candidates for treating Chagas disease. The in vivo studies confirmed the positive expectations arising from the preliminary in vitro studies, revealing compound 17 to be the most effective for both acute and chronic phases. The activity, stability, low cost of starting materials, and straightforward synthesis make amino squaramides appropriate molecules for the development of an affordable anti-Chagasic agent.

  DOI：

  10.1021/jm4017015

文献信息

• Synthesis and Biological Evaluation of <i>N</i>,<i>N</i>′-Squaramides with High in Vivo Efficacy and Low Toxicity: Toward a Low-Cost Drug against Chagas Disease
  作者：Francisco Olmo、Carmen Rotger、Inmaculada Ramírez-Macías、Luis Martínez、Clotilde Marín、Lucas Carreras、Kristína Urbanová、Manel Vega、Guillermo Chaves-Lemaur、Angel Sampedro、María Jose Rosales、Manuel Sánchez-Moreno、Antonio Costa

  DOI：10.1021/jm4017015

  日期：2014.2.13

  Access to basic drugs is a major issue in developing countries. Chagas disease caused by Trypanosorna cruzi is a paradigmatic example of a chronic disease without an effective treatment. Current treatments based on benznidazole and nifurtimox are expensive, ineffective, and toxic. N,N'-Squaramides are amide-type compounds that feature both hydrogen bond donor and acceptor groups and are capable of multiple interactions with complementary sites. When combined with amine and carboxylic groups, squaramide compounds have increased solubility and therefore make suitable therapeutic agents. In this work, we introduce a group of Lipiriski's rule of five compliant squararnides as candidates for treating Chagas disease. The in vivo studies confirmed the positive expectations arising from the preliminary in vitro studies, revealing compound 17 to be the most effective for both acute and chronic phases. The activity, stability, low cost of starting materials, and straightforward synthesis make amino squaramides appropriate molecules for the development of an affordable anti-Chagasic agent.