3-(butylamino)-4-((3-(dimetilamino)propyl)(methyl)amino)cyclobut-3-en-1,2-dione | 1541171-10-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(butylamino)-4-((3-(dimetilamino)propyl)(methyl)amino)cyclobut-3-en-1,2-dione
• 英文别名: 3-(butylamino)-4-((3-(dimethylamino)propyl)(methyl)amino)cyclobut-3-ene-1,2-dione；3-(Butylamino)-4-[3-(dimethylamino)propyl-methylamino]cyclobut-3-ene-1,2-dione；3-(butylamino)-4-[3-(dimethylamino)propyl-methylamino]cyclobut-3-ene-1,2-dione
• CAS: 1541171-10-1
• 化学式: C₁₄H₂₅N₃O₂
• 分子量: 267.371
• InChiKey: VUQKBHWXTBNFPC-UHFFFAOYSA-N

物化性质

• 沸点：
  356.9±52.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  三甲基-1,3-丙二胺 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 3-(butylamino)-4-((3-(dimetilamino)propyl)(methyl)amino)cyclobut-3-en-1,2-dione
  参考文献：
  名称：

  方酸酰胺和方酸水解的动力学分析及机理

  摘要：

  方胺和方酸的水解降解，是方酰胺部分水解的产物，已通过紫外光谱在37°C和3-10的pH范围内进行了评估。在这些条件下，这些化合物在很长一段时间（> 100天）内都具有动力学稳定性。在pH> 10，在两个squaramate的squaramate阴离子所示的一阶依赖性和OH的水解- 。在相同的温度和[OH - ]，squaramides的水解通常显示与地层squaramates作为检测反应中间体的双相光谱变化（A→B→C动力学模型）。所测得的速率的第一步骤（ķ 1 ≈10 -4中号-1小号-1）是2-3个数量级比用于第二步骤（更快ķ 2 ≈10 -6中号-1小号-1）。在不同温度下的实验提供激活参数与Δ的值ħ ⧧听，说：9-18千卡摩尔-1和Δ小号⧧听，说：-5至-30 CALķ -1摩尔-1。DFT计算表明，方酸的碱性水解机理与酰胺十分相似。

  DOI：

  10.1021/acs.joc.6b02963

文献信息

• [EN] ONE-POT SYNTHESIS OF SQUARAMIDES<br/>[FR] SYNTHÈSE MONOTOPE DE SQUARAMIDES
  申请人：UNIV ZARAGOZA

  公开号：WO2016005407A1

  公开（公告）日：2016-01-14

  The present invention refers to the first one-pot synthesis of squaramides. The one-pot synthesis of squaramides described herein is an easy and straightforward procedure to obtain squaramide derivatives which saves energy, avoids time consuming purification steps, reduces costs and provides better yields as compared with those squaramides obtained through the traditional "stop-and-go" approach. Moreover, the authors of the present invention herein demonstrate the efficiency of this one-pot process with the synthesis of three biologically active structures, improving in most of the cases the results of the previous stepwise syntheses.

  本发明涉及对方酰胺的首次一锅合成。本文描述的方酰胺一锅合成是一种简单直接的程序，可获得方酰胺衍生物，节省能源，避免耗时的纯化步骤，降低成本，并提供比通过传统的“停-继续”方法获得的方酰胺更好的产率。此外，本发明的作者在这里展示了这种一锅过程的效率，通过合成三种具有生物活性的结构，在大多数情况下改善了以前逐步合成的结果。
• 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.
• [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.
• Kinetic Analysis and Mechanism of the Hydrolytic Degradation of Squaramides and Squaramic Acids
  作者：Marta Ximenis、Emilio Bustelo、Andrés G. Algarra、Manel Vega、Carmen Rotger、Manuel G. Basallote、Antonio Costa

  DOI：10.1021/acs.joc.6b02963

  日期：2017.2.17

  squaramic acids, the product of partial hydrolysis of squaramides, has been evaluated by UV spectroscopy at 37 °C in the pH range 3–10. Under these conditions, the compounds are kinetically stable over long time periods (>100 days). At pH >10, the hydrolysis of the squaramate anions shows first-order dependence on both squaramate and OH–. At the same temperature and [OH–], the hydrolysis of squaramides

  方胺和方酸的水解降解，是方酰胺部分水解的产物，已通过紫外光谱在37°C和3-10的pH范围内进行了评估。在这些条件下，这些化合物在很长一段时间（> 100天）内都具有动力学稳定性。在pH> 10，在两个squaramate的squaramate阴离子所示的一阶依赖性和OH的水解- 。在相同的温度和[OH - ]，squaramides的水解通常显示与地层squaramates作为检测反应中间体的双相光谱变化（A→B→C动力学模型）。所测得的速率的第一步骤（ķ 1 ≈10 -4中号-1小号-1）是2-3个数量级比用于第二步骤（更快ķ 2 ≈10 -6中号-1小号-1）。在不同温度下的实验提供激活参数与Δ的值ħ ⧧听，说：9-18千卡摩尔-1和Δ小号⧧听，说：-5至-30 CALķ -1摩尔-1。DFT计算表明，方酸的碱性水解机理与酰胺十分相似。