ethyl 2-(propylamino)-2-oxoacetate | 20943-65-1

• 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: ethyl 2-(propylamino)-2-oxoacetate
• 英文别名: ethyl 2-oxo-2-(propylamino)acetate；Oxalsaeure-n-propylamidethylester；ethyl N-n-propyloxamate；propyloxalamic acid ethyl ester；Propyl-oxalamidsaeure-aethylester；Acetic acid, 2-oxo-2-(propylamino)-, ethyl ester
• CAS: 20943-65-1
• 化学式: C₇H₁₃NO₃
• 分子量: 159.185
• InChiKey: FAHKAKRNEJWVNP-UHFFFAOYSA-N

物化性质

• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  ethyl 2-(propylamino)-2-oxoacetate 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 0.5h， 生成 氧代(丙基氨基)乙酸
  参考文献：
  名称：

  Oxamic acid analogues as LDH-C4-specific competitive inhibitors

  摘要：

  We performed kinetic studies to determine whether oxamate analogues are selective inhibitors of LDH-C4, owing to their potential usefulness in fertility control and treatment of some cancers. These substances were shown to be competitive inhibitors of LDH isozymes and are able to discriminate among subtle differences that differentiate the active sites of LDH-A4, LDH-B4 and LDH-C4. N-Ethyl oxamate was the most potent inhibitor showing the highest affinity for LDH-C4. However, N-propyl oxamate was the most selective inhibitor showing a high degree of selectivity towards LDH-C4. Non-polar four carbon atoms chains, linear or branched, dramatically diminished the affinity and selectivity towards LDH-C4. N-Propyl oxamate significantly reduced ATP levels, capacitation and mouse sperm motility, in line with results shown by others, suggesting that LDH-C4 plays an essential role in mouse fertility.

  DOI：

  10.3109/14756366.2011.566221
• 作为产物：
  描述：

  正丙胺 、 草酰氯单乙酯 反应 24.0h， 生成 ethyl 2-(propylamino)-2-oxoacetate
  参考文献：
  名称：

  高选择性和有效的G蛋白偶联受体激酶2（GRK2）抑制剂的设计，合成和评估，可用于治疗心力衰竭

  摘要：

  用于心力衰竭的一类新型治疗药物，高效和选择性的GRK2抑制剂，在体外研究中表现出增强的β-肾上腺素信号传导能力。HTS将衍生物5和1,2,4-三唑衍生物24a鉴定为命中化合物。新一代的脚手架和所有部分的SAR研究都产生了带有N-苄基羧酰胺部分的4-甲基-1,2,4-三唑衍生物，对GRK2的活性很高，对其他激酶的选择性更高。在亚型选择性方面，这些化合物对GRK1、5、6和7表现出足够的选择性，并且对GRK3具有几乎相同的抑制作用。我们的药物化学努力导致发现了115h（GRK2 IC 50= 18 nM），获得了与人GRK2和GRK2抑制剂的共晶体结构，该抑制剂增强了β-肾上腺素能受体（βAR）介导的cAMP积累，并防止了用异丙肾上腺素处理过的表达β2AR的HEK293细胞中βAR的内在化。因此，115h似乎是心力衰竭治疗的一种新型疗法。

  DOI：

  10.1021/acs.jmedchem.7b00443

文献信息

• Environmentally friendly transesterification and transacylation reactions under LiBr catalysis
  作者：M. Saeed Abaee、Elahe Akbarzadeh、Roholah Sharifi、Mohammad M. Mojtahedi

  DOI：10.1007/s00706-010-0325-1

  日期：2010.7

  AbstractA room-temperature, convenient transesterification of various esters, induced by catalytic amounts of lithium bromide and diethylamine in a solvent-free environment, is described. Products are obtained in good purity by simple filtration to remove the catalyst and evaporation of the volatile portion. The procedure has also been successfully applied to transacetylation and aminolysis of esters

  摘要描述了在无溶剂环境中由催化量的溴化锂和二乙胺引发的各种酯的室温便捷酯交换反应。通过简单的过滤除去催化剂和蒸发挥发性部分而获得高纯度的产物。该方法也已成功地用于酯的转乙酰和氨解。 图形概要
• Synthesis, Crystal Structure, and Insecticidal Activity of Novel <i>N</i>-Alkyloxyoxalyl Derivatives of 2-Arylpyrrole
  作者：Yu Zhao、Chunhui Mao、Yongqiang Li、Pengxiang Zhang、Zhiqiang Huang、Fuchun Bi、Runqiu Huang、Qingmin Wang

  DOI：10.1021/jf801311h

  日期：2008.8.1

  Two series of novel N-alkyloxyoxalyl derivatives of 2-arylpyrrole were synthesized, and their structures were characterized by (1)H NMR spectroscopy, elemental analysis, and single-crystal X-ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities, and their insecticidal activities against oriental armyworm, mosquito, and spider mite are comparable to those of the commercialized Chlorfenapyr.
• Hydrogen bond patterns in solid state carboxylic acids. Vibrational behaviour of the catamer pattern as exhibited by the N-alkyloxamic acids
  作者：Ilse Wolfs、Herman O. Desseyn

  DOI：10.1016/0584-8539(96)01689-3

  日期：1996.10

  The vibrational study presented in this publication shows that the N-alkyloxamic acids are hydrogen bonded through a catamer hydrogen bond pattern in the solid state. Two different hydrogen bond patterns are possible for these products, and these patterns can be very clearly distinguished by their vibrational behaviour. Deuteration and low temperature spectra make the assignment and characterisation more obvious.
• Synthesis and properties of 3-substituted 2h-1,2,4-benzothiadiazine 1,1-dioxides
  作者：V. P. Chernykh、V. I. Gridasov、P. A. Petyunin

  DOI：10.1007/bf00480424

  日期：1976.4
• [EN] GRK2 INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE GRK2 ET LEURS UTILISATIONS
  申请人：CYGNAL THERAPEUTICS INC

  公开号：WO2021242844A8

  公开（公告）日：2022-01-06