propynoylaminoacetic acid ethyl ester | 18352-59-5

• 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: propynoylaminoacetic acid ethyl ester
• 英文别名: N-Propioloylglycinethylester；Ethyl 2-(prop-2-ynoylamino)acetate
• CAS: 18352-59-5
• 化学式: C₇H₉NO₃
• 分子量: 155.153
• InChiKey: FGDHUFLJPLSFPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  propynoylaminoacetic acid ethyl ester 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以84%的产率得到Ethyl 2-[[6-[(2-ethoxy-2-oxoethyl)amino]-6-oxohexa-2,4-diynoyl]amino]acetate
  参考文献：
  名称：

  A mild copper-mediated Glaser-type coupling reaction under the novel CuI/NBS/DIPEA promoting system

  摘要：

  A simple copper promoting system CuI/NBS/DIPEA was first found to efficiently promote Glaser coupling reaction under ambient temperature. The alkynes with sensitive groups such as acetal and ketal, TBDMS, ester and amide could react smoothly to afford the functionalized 1,3-diynes under the CuI/NBS/DIPEA promoting system in good yields. And the successful application of the Cul/NBS/DIPEA promoting system in sugar and amino acid-building blocks indicated the potential of this method in the construction of designed sugar and peptide biomolecules. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.04.065
• 作为产物：
  描述：

  2-胺基乙酸乙酯 、 丙炔酸 在 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 2.25h， 生成 propynoylaminoacetic acid ethyl ester
  参考文献：
  名称：

  Structure-activity relationships for binding of 4-substituted triazole-phenols to macrophage migration inhibitory factor (MIF)

  摘要：

  Macrophage migration inhibitory factor (MIF) is a versatile protein that plays a role in inflammation, autoimmune diseases and cancers. Development of novel inhibitors will enable further exploration of MIF as a drug target. In this study, we investigated structure-activity relationships of MIF inhibitors using a MIF tautomerase activity assay to measure binding. Importantly, we notified that transition metals such as copper (II) and zinc (II) interfere with the MIF tautomerase activity under the assay conditions applied. EDTA was added to the assay buffer to avoid interference of residual heavy metals with tautomerase activity measurements. Using these assay conditions the structure-activity relationships for MIF binding of a series of triazole-phenols was explored. The most potent inhibitors in this series provided activities in the low micromolar range. Enzyme kinetic analysis indicates competitive binding that proved reversible. Binding to the enzyme was confirmed using a microscale thermophoresis (MST) assay. Molecular modelling was used to rationalize the observed structure-activity relationships. The most potent inhibitor 2d inhibited proliferation of A549 cells in a clonogenic assay. In addition, 2d attenuated MIF induced ERK phosphorylation in A549 cells. Altogether, this study provides insights in the structure-activity relationships for MIF binding of triazole-phenols and further validates this class of compounds as MIF binding agents in cell-based studies. (C) 2019 The Author(s). Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2019.111849

文献信息

• Copper-Catalyzed Amine-Alkyne-Alkyne Addition Reaction: An Efficient Method For the Synthesis of γ,δ-Alkynyl-β-amino Acid Derivatives
  作者：Lei Zhou、Qi Shuai、Huan-feng Jiang、Chao-Jun Li

  DOI：10.1002/chem.200901416

  日期：2009.11.2

  A simple and efficient method for the synthesis of γ,δ‐alkynyl‐β‐amino acid derivatives by a copper‐catalyzed three‐component amine–alkyne–alkyne addition reaction was developed. Various γ,δ‐alkynyl‐β‐amino acid derivatives were synthesized in moderate to good yields in one step. With chiral prolinol derivatives employed as the amine component, excellent diastereoselectivities (up to >99:1 diastereomeric

  开发了一种通过铜催化的三组分胺-炔烃-炔烃加成反应合成γ，δ-炔基-β-氨基酸衍生物的简单有效的方法。一步合成中，高产率的各种γ，δ-炔基-β-氨基酸衍生物。将手性脯氨醇衍生物用作胺组分，可获得优异的非对映选择性（高达> 99：1的非对映异构体比率（dr））。还描述了反应的范围和所得氨基酸衍生物的进一步转化，例如脱保护和环化。
• Potential Carcinolytic Agents.^1,2 V. Enamine Mustards
  作者：Zinon B. Papanastassiou、Robert J. Bruni、Edward V. White V

  DOI：10.1021/jm00316a040

  日期：1967.7