N-(2-aminoethyl)formamide | 69219-13-2

• 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: N-(2-aminoethyl)formamide
• 英文别名: N-Formylethylendiamin；2-aminoethylformamide；N-(2-Amino-aethyl)-formamid；N-formylethylenediamine
• CAS: 69219-13-2
• 化学式: C₃H₈N₂O
• 分子量: 88.1093
• InChiKey: VAFIWTIWOOZYCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-aminoethyl)formamide 在 sulfur 作用下， 生成 亚乙基硫脲
  参考文献：
  名称：

  环状硫脲。

  摘要：

  DOI：

  10.1021/ja01211a509
• 作为产物：
  描述：

  乙二胺 生成 N-(2-aminoethyl)formamide
  参考文献：
  名称：

  DURANLEAU, R. G.;KNIFTON, J. F.;SPERANZA, G. P.

  摘要：

  DOI：

文献信息

• Solvatochromic Reagents for Multicomponent Reactions and their Utility in the Development of Cell-Permeable Macrocyclic Peptide Vectors
  作者：Benjamin H. Rotstein、Rida Mourtada、Shana O. Kelley、Andrei K. Yudin

  DOI：10.1002/chem.201102096

  日期：2011.10.24

  scaffolds: An isocyanide equipped with an environment‐sensitive fluorophore was used to synthesize peptide macrocycles. The photophysical properties of the product macrocycles are sensitive to both peptide sequence and configuration. A mitochondria‐penetrating peptide was constrained within a cyclic peptide framework and showed increased uptake and localization relative to a linear control (see scheme)

  敏感支架：配有对环境敏感的荧光团的异氰酸酯可用于合成肽大环化合物。产物大环化合物的光物理性质对肽序列和构型均敏感。线粒体穿透肽被限制在环状肽框架内，并且相对于线性对照显示出增加的摄取和定位（参见方案）。
• [EN] PHYTOSPHINGOSINE DERIVATIVES AS ADJUVANTS IN IMMUNE STIMULATION<br/>[FR] DÉRIVÉS DE PHYTOSPHINGOSINE SERVANT D'ADJUVANTS DANS LA STIMULATION IMMUNITAIRE
  申请人：HELMHOLTZ ZENTRUM INFEKTIONSFORSCHUNG GMBH

  公开号：WO2021255287A1

  公开（公告）日：2021-12-23

  The invention relates to phytosphingosine derivatives, suitable as adjuvants in immune stimulation. The invention further relates to pharmaceutical compositions comprising such compounds and the medical use of said compounds and/or compositions in therapeutic or prophylactic methods of immune stimulation in a subject, and for use in the treatment of a disease, for which stimulation of an immune response in a subject produces a therapeutic benefit. The invention further relates to the phytosphingosine derivative as described herein for use as an adjuvant in a method of vaccinating a subject. The invention further relates to the phytosphingosine derivative as described herein for use in stimulating antibody production, stimulating an immune response against infection, stimulating an immune response against a cancer, or preventing and/or treating septic shock. The invention further relates to a method for the manufacture of said derivatives comprising an Ugi-4-component reaction (Ugi-4CR).

  该发明涉及植物鞘氨醇衍生物，适用于免疫刺激的辅助剂。该发明还涉及包含这些化合物的药物组合物，以及所述化合物和/或组合物在治疗或预防免疫刺激方法中的医疗用途，用于治疗疾病，对于在受试者中刺激免疫反应产生治疗益处的用途。该发明还涉及所述植物鞘氨醇衍生物用作接种受试者的辅助剂的方法。该发明还涉及所述植物鞘氨醇衍生物用于刺激抗体产生，刺激抗感染免疫反应，刺激抗癌免疫反应，或预防和/或治疗感染性休克的方法。该发明还涉及一种制备所述衍生物的方法，包括Ugi-4组分反应（Ugi-4CR）。
• A Reversible Liquid Organic Hydrogen Carrier System Based on Methanol‐Ethylenediamine and Ethylene Urea
  作者：Yinjun Xie、Peng Hu、Yehoshoa Ben‐David、David Milstein

  DOI：10.1002/anie.201901695

  日期：2019.4

  liquid organic hydrogen carrier (LOHC) system, with a high theoretical hydrogen capacity, based on the unpresented hydrogenation of ethylene urea to ethylenediamine and methanol, and its reverse dehydrogenative coupling, was established. For the dehydrogenation only a small amount of solvent is required. This system is rechargeable, as the H2‐rich compounds could be regenerated by hydrogenation of the resulting

  建立了一种新型的液态有机氢载体（LOHC）系统，该系统具有较高的理论氢容量，其基于乙烯脲未加氢为乙二胺和甲醇及其反向脱氢偶合反应。对于脱氢，仅需要少量溶剂。该系统是可充电的，因为富H 2的化合物可通过所得脱氢混合物的氢化而再生。使用相同的催化剂，在相对温和的条件下，实现了氢气装载和卸载的两个方向。机理研究揭示了H 2贫化化合物形成的可能途径。
• Pyridyl substituted aminoalkyl-thioureas and ureas
  申请人：Smith Kline & French Laboratories, Inc.

  公开号：US03932427A1

  公开（公告）日：1976-01-13

  The compounds are pyridyl substituted aminoalkylthioureas and ureas which are inhibitors of H-2 histamine receptors. A compound of this invention is N-methyl-N'-[2-(2-pyridylmethylamino)ethyl]thiourea.

  这些化合物是取代吡啶基的氨基烷基硫脲和脲，它们是H-2组胺受体的抑制剂。本发明的一种化合物是N-甲基-N'-[2-(2-吡啶甲基氨基)乙基]硫脲。
• Diversification of a Novel α‐Galactosyl Ceramide Hotspot Boosts the Adjuvant Properties in Parenteral and Mucosal Vaccines
  作者：Yanira Méndez、Aldrin V. Vasco、Thomas Ebensen、Kai Schulze、Mohammad Yousefi、Mehdi D. Davari、Ludger A. Wessjohann、Carlos A. Guzmán、Daniel G. Rivera、Bernhard Westermann

  DOI：10.1002/anie.202310983

  日期：2024.1.2

  The development of potent adjuvants is an important step for improving the performance of subunit vaccines. CD1d agonists, such as the prototypical α‐galactosyl ceramide (α‐GalCer), are of special interest due to their ability to activate iNKT cells and trigger rapid dendritic cell maturation and B‐cell activation. Herein, we introduce a novel derivatization hotspot at the α‐GalCer skeleton, namely the N‐substituent at the amide bond. The multicomponent diversification of this previously unexplored glycolipid chemotype space permitted the introduction of a variety of extra functionalities that can either potentiate the adjuvant properties or serve as handles for further conjugation to antigens toward the development of self‐adjuvanting vaccines. This strategy led to the discovery of compounds eliciting enhanced antigen‐specific T cell stimulation and a higher antibody response when delivered by either the parenteral or the mucosal route, as compared to a known potent CD1d agonist. Notably, various functionalized α‐GalCer analogues showed a more potent adjuvant effect after intranasal immunization than a PEGylated α‐GalCer analogue previously optimized for this purpose. Ultimately, this work could open multiple avenues of opportunity for the use of mucosal vaccines against microbial infections.

  摘要开发强效佐剂是提高亚单位疫苗性能的重要一步。CD1d激动剂，如典型的α-半乳糖基神经酰胺（α-GalCer），因其能激活iNKT细胞并引发树突状细胞快速成熟和B细胞活化而备受关注。在这里，我们介绍了α-GalCer 骨架上的一个新型衍生热点，即酰胺键上的 N-取代基。这种以前未曾探索过的糖脂化学型空间的多组分多样化允许引入各种额外的官能团，这些官能团既可以增强佐剂特性，也可以作为进一步与抗原共轭的处理剂，以开发自佐剂疫苗。通过这一策略，我们发现了一些化合物，与已知的强效 CD1d 激动剂相比，这些化合物在通过肠外或粘膜途径给药时能增强对抗原特异性 T 细胞的刺激并提高抗体反应。值得注意的是，在鼻内免疫后，各种官能化的α-GalCer类似物比以前为此目的优化过的PEG化α-GalCer类似物显示出更强的佐剂效应。最终，这项工作将为使用粘膜疫苗预防微生物感染开辟多种途径。