2-cyano-N-(2,3-dihydroxypropyl)acetamide | 71586-36-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-cyano-N-(2,3-dihydroxypropyl)acetamide
• 英文别名: cyanoacetamide propanediol
• CAS: 71586-36-2
• 化学式: C₆H₁₀N₂O₃
• 分子量: 158.157
• InChiKey: TVRYNOHOKJTCOG-UHFFFAOYSA-N

物化性质

• 熔点：
  139-143 °C
• 沸点：
  550.8±50.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  93.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-cyano-N-(2,3-dihydroxypropyl)acetamide 在 哌啶 、 盐酸 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 24.0h， 生成 2-cyano-N-(2,3-dihydroxypropyl)-3-(6-(piperidin-1-yl)naphthalen-2-yl)acrylamide
  参考文献：
  名称：

  [EN] IN VITRO COMPOSITIONS COMPRISING HUMAN SAMPLE AND AMYLOID TARGETING AGENT
  [FR] COMPOSITIONS IN VITRO COMPRENANT UN ÉCHANTILLON HUMAIN ET UN AGENT CIBLANT LES SUBSTANCES AMYLOÏDES

  摘要：

  公开号：

  WO2016040891A3
• 作为产物：
  描述：

  3-氨基-1,2-丙二醇 、 氰乙酸甲酯 以 乙醇 为溶剂， 生成 2-cyano-N-(2,3-dihydroxypropyl)acetamide
  参考文献：
  名称：

  可逆共轭加成的研究

  摘要：

  Benzalcyanoacetamides 被设计和合成为可逆硫醇共轭加成受体。这些硫杂结合物的添加可以在中性 pH 值的水性条件下快速且可逆地达到平衡。动力学研究表明，苯并氰基乙酰胺苯环 4 位的吸电子基团促进了平衡时的共轭加成。这些共轭受体的动态硫醇交换比单独激活的 α,β-不饱和羰基化合物更快。这些硫杂结合物可以组装成动态组合化学中潜在有用的成分。

  DOI：

  10.1002/ejoc.201300358

文献信息

• Synthesis of resveratrol acrylamides derivatives and biological evaluation of their anti-proliferative effect on cancer cell lines
  作者：Ban-Feng Ruan、Si-Qi Wang、Xiao-Lin Ge、Ri-Sheng Yao

  DOI：10.2174/15701808113109990057

  日期：2013.11

  A new series of resveratrol acrylamides amine derivatives was designed, synthesized, and evaluated for their anti-proliferative activity against three cancer cell lines including human chronic myelocytic leukemia cell K562, human hepatoma HuH-7 and human lung carcinoma A549. Most of the compounds showed superior activity against three cell lines when compared to parent resveratrol. C13 had the best anti-tumor activity against the HuH-7 cell line and its IC50 was 4.5 μmol/L; C16 had the best anti-tumor activity against the K562 cell line and its IC50 was 2.9 μmol/L; C18 had the best anti-tumor activity against the A549 cell line and its IC50 was 3.8 μmol/L. It could be seen that the activity of the aromatic amine derivatives was better than the fatty amine derivatives by analyzing the experimental data.

  设计、合成并评价了一系列白藜芦醇丙烯酰胺胺衍生物对三种癌细胞株的抗增殖活性，包括人慢性髓细胞白血病细胞K562、人肝癌HuH-7和人肺癌A549。与母体白藜芦醇相比，大多数化合物对三种细胞株表现出更强的活性。C13对HuH-7细胞株具有最佳的抗肿瘤活性，其IC50为4.5 μmol/L; C16对K562细胞株具有最佳的抗肿瘤活性，其IC50为2.9 μmol/L；C18对A549细胞株具有最佳的抗肿瘤活性，其IC50为3.8 μmol/L。通过分析实验数据可以发现，芳香胺衍生物的活性优于脂肪胺衍生物。
• [EN] AMYLOID TARGETING AGENTS AND METHODS OF USING THE SAME<br/>[FR] AGENTS CIBLANT LES AMYLOÏDES ET PROCÉDÉS DE LEUR UTILISATION
  申请人：AMYDIS DIAGNOSTICS

  公开号：WO2015143185A1

  公开（公告）日：2015-09-24

  Provided herein is the design and synthesis of novel molecular rotor fluorophores useful for detection of amyloid or amyloid like proteins. The fluorophores are designed to exhibit enhanced fluorescence emission upon associating with amyloid or amyloid like proteins as compared to unbound compound. Also disclosed herein are the methods for treating of diseases associated with an amyloid or amyloid like proteins.

  本文提供了用于检测淀粉样蛋白或类淀粉样蛋白的新型分子转子荧光团的设计和合成。这些荧光团被设计为与淀粉样蛋白或类淀粉样蛋白结合时，与未结合化合物相比表现出增强的荧光发射。本文还披露了用于治疗与淀粉样蛋白或类淀粉样蛋白相关疾病的方法。
• AMYLOID TARGETING AGENTS AND METHODS OF USING THE SAME
  申请人：The Regents of the University of California

  公开号：US20180327373A1

  公开（公告）日：2018-11-15

  Provided herein is the design and synthesis of novel molecular rotor fluorophores useful for detection of amyloid or amyloid like proteins. The fluorophores are designed to exhibit enhanced fluorescence emission upon associating with amyloid or amyloid like proteins as compared to unbound compound. Also disclosed herein are methods for treating diseases associated with amyloid or amyloid like proteins.

  本文提供了用于检测淀粉样或类淀粉蛋白的新型分子转子荧光团的设计和合成。这些荧光团被设计为与淀粉样或类淀粉蛋白结合时，与未结合化合物相比表现出增强的荧光发射。本文还披露了治疗与淀粉样或类淀粉蛋白相关疾病的方法。
• Designing, synthesis, and characterization of some novel coumarin derivatives as probable anticancer drugs
  作者：Darla Mark Manidhar、Rajesh Kumar Kesharwani、N. Bakthavatchala Reddy、C. Suresh Reddy、Krishna Misra

  DOI：10.1007/s00044-012-0299-0

  日期：2013.9

  activity. The chemical syntheses of 4-methyl-7-hydroxycoumarin and its 8-formyl derivative were carried out using Pechmann’s condensation followed by Duffs reaction. Treatment of the 8-formyl derivative with nine different N,N-di substituted cyanoacetamides in the presence of piperidine afforded the corresponding nine new 8-substituted-4-methyl-7-hydroxycoumarin derivatives. These compounds were characterized

  香豆素是具有多种医学性质的天然存在的氧杂环，因此用作设计新的有效类似物的先导化合物。基于含有香豆素核的抑制剂与人NAD（P）H：醌氧化还原酶-1和人磷酸二酯酶4B酶的复合物的X射线晶体结构，某些新型香豆素衍生物已被设计为专门用于胰腺癌的抑制剂。这两种酶在各种肿瘤中过表达，前者特别在胰腺癌中表达。通过电子药效团和对接研究进行的计算分析表明，4-甲基-7-羟基香豆素第8位的特定基团具有抗小鼠皮肤癌的抗癌活性，并可以增强抗肿瘤活性。使用Pechmann缩合然后进行Duffs反应进行4-甲基-7-羟基香豆素及其8-甲酰基衍生物的化学合成。用九种不同的方法处理8-甲酰基衍生物在哌啶存在下，N，N-二取代的氰基乙酰胺提供了相应的九种新的8-取代的-4-甲基-7-羟基香豆素衍生物。这些化合物的特征在于IR，1 H，1313 C NMR，质谱和元素分析。有趣的是，分子对接表明九种香豆素衍生物相对于香豆素本
• Amyloid targeting agents and methods of using the same
  申请人：Amydis Diagnostics, Inc.

  公开号：US10005745B2

  公开（公告）日：2018-06-26

  Provided herein is the design and synthesis of novel molecular rotor fluorophores useful for detection of amyloid or amyloid like proteins. The fluorophores are designed to exhibit enhanced fluorescence emission upon associating with amyloid or amyloid like proteins as compared to unbound compound. Also disclosed herein are the methods for treating of diseases associated with an amyloid or amyloid like proteins.

  本文提供了可用于检测淀粉样蛋白或类似淀粉样蛋白的新型分子转子荧光团的设计与合成。与未结合的化合物相比，这些荧光团在与淀粉样蛋白或类似淀粉样蛋白结合时会表现出更强的荧光发射。本文还公开了治疗与淀粉样蛋白或类似淀粉样蛋白相关疾病的方法。