3-(butylamino)-4-((2-(dimethylamino)ethyl)amino)cyclobut-3-ene-1,2-dione | 1541171-06-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(butylamino)-4-((2-(dimethylamino)ethyl)amino)cyclobut-3-ene-1,2-dione
• 英文别名: 3-(Butylamino)-4-[2-(dimethylamino)ethylamino]cyclobut-3-ene-1,2-dione；3-(butylamino)-4-[2-(dimethylamino)ethylamino]cyclobut-3-ene-1,2-dione
• CAS: 1541171-06-5
• 化学式: C₁₂H₂₁N₃O₂
• 分子量: 239.318
• InChiKey: WJRVPSWFZNKKCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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-(butylamino)-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， 生成 2-[[2-(Butylamino)-3,4-dioxocyclobuten-1-yl]amino]ethyl-trimethylazanium;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：

  N,N-二甲基乙二胺 、 3-butylamino-4-ethoxycyclobut-3-ene-1,2-dione 以 乙醇 为溶剂， 反应 12.0h， 以84%的产率得到3-(butylamino)-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

• [EN] MRNAS ENCODING IMMUNE MODULATING POLYPEPTIDES AND USES THEREOF<br/>[FR] ARNM CODANT DES POLYPEPTIDES DE MODULATION IMMUNITAIRE ET LEURS UTILISATIONS
  申请人：MODERNA TX INC

  公开号：WO2021076805A1

  公开（公告）日：2021-04-22

  The disclosure features lipid nanoparticle (LNP) compositions comprising immune modulating polypeptides and uses thereof. The LNP compositions of the present disclosure comprise mRNA therapeutics encoding immune modulating polypeptides, e.g., interleukin 2 (IL- 2) and/or granulocyte macrophage colony stimulating factor (GM-CSF). The LNP compositions of the present disclosure can stimulate T regulatory cells, e.g., increase the level and/or activity of T regulatory cells in vivo or ex vivo.

  披露了包含免疫调节多肽的脂质纳米粒子（LNP）组合物及其用途。本公开的LNP组合物包括编码免疫调节多肽的mRNA治疗药物，例如白细胞介素2（IL-2）和/或粒细胞巨噬细胞集落刺激因子（GM-CSF）。本公开的LNP组合物可以刺激T调节细胞，例如在体内或体外增加T调节细胞的水平和/或活性。
• COMPOUNDS AND COMPOSITIONS FOR INTRACELLULAR DELIVERY OF THERAPEUTIC AGENTS
  申请人：ModernaTX, Inc.

  公开号：US20220409536A1

  公开（公告）日：2022-12-29

  The disclosure features novel lipids and compositions involving the same. Nanoparticle compositions include a novel lipid as well as additional lipids such as phospholipids, structural lipids, and PEG lipids. Nanoparticle compositions further including therapeutic and/or prophylactics such as RNA are useful in the delivery of therapeutic and/or prophylactics to mammalian cells or organs to, for example, regulate polypeptide, protein, or gene expression.

  该披露涉及新型脂质和相关组合物。纳米粒子组合物包括一种新型脂质以及其他脂质，例如磷脂、结构脂质和PEG脂质。纳米粒子组合物进一步包括治疗和/或预防剂，例如RNA，可用于将治疗和/或预防剂传递到哺乳动物细胞或器官中，例如调节多肽、蛋白质或基因表达。
• [EN] ANTIPARASITIC ACTIVITY OF SQUARAMIDE<br/>[ES] ACTIVIDAD ANTIPARASITARIA DE ESCUARAMIDAS<br/>[FR] ACTIVITÉ ANTIPARASITAIRE DES SQUARAMIDES
  申请人：UNIV GRANADA

  公开号：WO2014184416A1

  公开（公告）日：2014-11-20

  La presente invención se refiere a la síntesis y uso de compuestos de base escuaramida para el tratamiento de enfermedades de origen parasitario como son la Tripanosomiasis americana también conocida como enfermedad de Chagas o la Leishmaniasis.
• [EN] COMPOUNDS AND COMPOSITIONS FOR INTRACELLULAR DELIVERY OF THERAPEUTIC AGENTS<br/>[FR] COMPOSÉS ET COMPOSITIONS POUR L'ADMINISTRATION INTRACELLULAIRE D'AGENTS THÉRAPEUTIQUES
  申请人：MODERNATX INC

  公开号：WO2020061367A1

  公开（公告）日：2020-03-26

  The disclosure features novel lipids and compositions involving the same. Nanoparticle compositions include a novel lipid as well as additional lipids such as phospholipids, structural lipids, and PEG lipids. Nanoparticle compositions further including therapeutic and/or prophylactics such as RNA are useful in the delivery of therapeutic and/or prophylactics to mammalian cells or organs to, for example, regulate polypeptide, protein, or gene expression.
• 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.