3-diethylaminopropyl cyanoacetamide | 15029-14-8

• 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: 3-diethylaminopropyl cyanoacetamide
• 英文别名: N-(3-Diethylamino-propyl)-cyanacetamid；2-cyano-N-[3-(diethylamino)propyl]acetamide
• CAS: 15029-14-8
• 化学式: C₁₀H₁₉N₃O
• 分子量: 197.28
• InChiKey: GMAXPLZAXLQROQ-UHFFFAOYSA-N

物化性质

• 沸点：
  376.9±27.0 °C(Predicted)
• 密度：
  0.985±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  56.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-diethylaminopropyl cyanoacetamide 、 2-氨基-5-氯苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以76%的产率得到2-Amino-6-chloro-N-(3-(diethylamino)propyl)quinoline-3-carboxamide
  参考文献：
  名称：

  Cyanoacetamides (IV): Versatile One-Pot Route to 2-Quinoline-3-carboxamides

  摘要：

  Cyanoacetic acid derivatives are the starting materials for a plethora of multicomponent reaction (MCR) scaffolds. Herein, we describe scope of a valuable general protocol for the synthesis of arrays of 2-aminoquinoline-3-carboxamides from cyanoacetamides and 2-aminobenzaldehydes or heterocyclic derivatives via a Friedlander reaction variation. In many cases, the reactions involve a very convenient work up by simple precipitation and filtration. More than 40 new products are described. We foresee our protocol and the resulting derivatives becoming very valuable to greatly expanding the scaffold space of cyanoacetamide derivatives.

  DOI：

  10.1021/co3000133
• 作为产物：
  描述：

  3-二乙胺基丙胺 、 氰乙酸甲酯 以33.3 g的产率得到3-diethylaminopropyl cyanoacetamide
  参考文献：
  名称：

  [EN] ISOINDOLINE DERIVATIVES
  [FR] DÉRIVÉS D'ISOINDOLINE

  摘要：

  公式（I）的异吲哚啉衍生物，其中变量的定义如权利要求1所述，并提供含有该衍生物的组合物。该异吲哚啉衍生物和颜料组合物适用于着色高分子质量有机材料，特别是涂料、印刷油墨、用于彩色滤光片应用的抗性配方、电子摄影色调剂、化妆品、塑料、薄膜或纤维。

  公开号：

  WO2021063999A1

文献信息

• ISOINDOLINE DERIVATIVES
  申请人：BASF Colors & Effects GmbH

  公开号：EP3798271A1

  公开（公告）日：2021-03-31

  An isoindoline derivative of formula wherein the variables are defined as in claim 1, and compositions containing the same are provided. The isoindoline derivative and the pigment composition are suitable, for example, for coloring high molecular mass organic material, especially paints, printing inks, resist formulations for color filter applications, electrophotographic toners, cosmetics, plastics, films or fibers.

  式中的异吲哚啉衍生物 其中变量的定义如权利要求 1 所述，并提供了含有该衍生物的组合物。例如，异吲哚啉衍生物和颜料组合物适用于高分子有机材料的着色，特别是涂料、印刷油墨、彩色滤光片用抗蚀剂配方、电子照相调色剂、化妆品、塑料、薄膜或纤维。
• Pteridinecarboxamide Diuretics. II. Reaction of 4,6-Diamino-5-nitrosopyrimidines with N-Substituted Cyanoacetamides
  作者：T. S. Osdene、Arthur A. Santilli、Lee E. McCardle、Marvin E. Rosenthale

  DOI：10.1021/jm00314a008

  日期：1967.3
• Discovery of chromenes as inhibitors of macrophage migration inhibitory factor
  作者：Tjie Kok、Hannah Wapenaar、Kan Wang、Constantinos G. Neochoritis、Tryfon Zarganes-Tzitzikas、Giordano Proietti、Nikolaos Eleftheriadis、Katarzyna Kurpiewska、Justyna Kalinowska-Tłuścik、Robbert H. Cool、Gerrit J. Poelarends、Alexander Dömling、Frank J. Dekker

  DOI：10.1016/j.bmc.2017.12.032

  日期：2018.3

  Macrophage migration inhibitory factor (MIF) is an essential signaling cytokine with a key role in the immune system. Binding of MIF to its molecular targets such as, among others, the cluster of differentiation 74 (CD74) receptor plays a key role in inflammatory diseases and cancer. Therefore, the identification of MIF binding compounds gained importance in drug discovery. In this study, we aim to discover novel MIF binding compounds by screening of a focused compound collection for inhibition of its tautomerase enzyme activity. Inspired by the known chromen-4-one inhibitor Orita-13, a focused collection of compounds with a chromene scaffold was screened for MIF binding. The library was synthesized using versatile cyanoacetamide chemistry to provide diversely substituted chromenes. The screening provided inhibitors with IC50's in the low micromolar range. Kinetic evaluation suggested that the inhibitors were reversible and did not bind in the binding pocket of the substrate. Thus, we discovered novel inhibitors of the MIF tautomerase activity, which may ultimately support the development of novel therapeutic agents against diseases in which MIF is involved. (C) 2017 Elsevier Ltd. All rights reserved.
• US3985763A
  申请人：——

  公开号：US3985763A

  公开（公告）日：1976-10-12