diethyl 2-butyramidomalonate | 88744-18-7

• 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: diethyl 2-butyramidomalonate
• 英文别名: Butyrylaminomalonsaeure-diaethylester；Butylamino-malonester；Diethyl butanamidopropanedioate；diethyl 2-(butanoylamino)propanedioate
• CAS: 88744-18-7
• 化学式: C₁₁H₁₉NO₅
• mdl: MFCD12488730
• 分子量: 245.276
• InChiKey: SGJVLZNBFKVSMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.727
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-butyramidomalonate 在 lithium aluminium tetrahydride 、 caesium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 17.0h， 生成 2-(butylamino)-2-hexadecylpropane-1,3-diol
  参考文献：
  名称：

  Synthesis of new ligands for targeting the S1P1 receptor

  摘要：

  Sphingosine-1-phosphate (S1P) influences various fundamental biological processes by interacting with a family of five G protein-coupled receptors (S1P(1-5)). FTY720, a sphingosine analogue, which was approved for treatment of relapsing forms of multiple sclerosis, is phosphorylated in vivo and acts as an agonist of four of the five S1P receptor subtypes. Starting from these lead structures we developed new agonists for the S1P(1) receptor. The biological activity was tested in vivo and promising ligands were fluorinated at different positions to identify candidates for positron emission tomography (PET) imaging after [F-18]-labelling. The radioligands shall enable the imaging of S1P(1) receptor expression in vivo and thus may serve as novel imaging markers of S1P-related diseases. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.014
• 作为产物：
  描述：

  氨基丙二酸二乙酯盐酸盐 、 丁酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.25h， 以99%的产率得到diethyl 2-butyramidomalonate
  参考文献：
  名称：

  Synthesis of new ligands for targeting the S1P1 receptor

  摘要：

  Sphingosine-1-phosphate (S1P) influences various fundamental biological processes by interacting with a family of five G protein-coupled receptors (S1P(1-5)). FTY720, a sphingosine analogue, which was approved for treatment of relapsing forms of multiple sclerosis, is phosphorylated in vivo and acts as an agonist of four of the five S1P receptor subtypes. Starting from these lead structures we developed new agonists for the S1P(1) receptor. The biological activity was tested in vivo and promising ligands were fluorinated at different positions to identify candidates for positron emission tomography (PET) imaging after [F-18]-labelling. The radioligands shall enable the imaging of S1P(1) receptor expression in vivo and thus may serve as novel imaging markers of S1P-related diseases. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.014

文献信息

• Inhibition of nNOS Activity in Rat Brain by Synthetic Kynurenines:  Structure−Activity Dependence
  作者：Encarnación Camacho、Josefa León、Adoración Carrión、Antonio Entrena、Germaine Escames、Huda Khaldy、Darío Acuña-Castroviejo、Miguel A. Gallo、Antonio Espinosa

  DOI：10.1021/jm010916w

  日期：2002.1.1

  The overstimulation of the N-methyl-D-aspartate (NMDA) subtype of glutamate receptors is involved in excitotoxicity, a process participating in neurodegeneration that characterizes some neurological disorders and acute cerebral insults. In looking for compounds with neuroprotective properties, a series of kynurenine derivatives were synthesized, and their effects on both the NMDA and nNOS activity in rat striatum were evaluated. Two compounds, 15a (2-acetamido-4-(2-amino-5-methoxyphenyl)-4-oxobutyric acid) and 15c (2-butyramido-4-(2-amino-5-methoxyphenyl)-4-oxobutyric acid), displayed more potent activities than the other synthetic compounds tested for the inhibition of NMDA excitability and nNOS activity. Two other compounds, 18a (2-acetamido-4-(3-methoxyphenyl)-4-oxobutyric acid) and 18c (2-butyramido-4-(3-methoxyphenyl)-4-oxobutyric acid), that have the same structure as 15a and 15c, except the amino group in R-1, showed different effects. Whereas compound 18a showed lower electrophysiological potency than compounds 15a and 15c in the inhibition of the NMDA-dependent excitability, compound 18c showed the opposite effect. Moreover, compounds 18a and 18c were unable to modify nNOS activity. The remaining kynurenines tested behave like compound 18a. These results suggest that a structure-related activity of these synthetic kynurenines and a N-H bond in a specific direction is necessary for some kynurenine analogues to inhibit nNOS activity.
• 4-Hydroxy-2-quinolones. 31. 3-Amino-ir-2-oxo-4-hydroxyquinolines and their acyl derivatives
  作者：I. V. Ukrainets、S. G. Taran、L. V. Sidorenko、O. V. Gorokhova、A. A. Ogirenko、A. V. Turov、N. I. Filimonova

  DOI：10.1007/bf01176974

  日期：1996.8
• Ginzburg,O.F.; Ryaboi,V.I., Journal of general chemistry of the USSR, 1964, vol. 34, p. 1175 - 1176
  作者：Ginzburg,O.F.、Ryaboi,V.I.

  DOI：——

  日期：——
• 4-HETEROARYL PIPERIDINE INTERMEDIATES AND THEIR PREPARATION
  申请人：NOVO NORDISK A/S

  公开号：EP0502024B1

  公开（公告）日：1996-07-10
• ARCT, B.;KOSSOWSKA, B.;LORENZ, M.;PRELICZ, D.;SEDZIK-HIBNER, D.;OSTROWSKI+, J. ENVIRON. SCI. AND HEALTH, 1983, 18, N 4-5, 559-568
  作者：ARCT, B.、KOSSOWSKA, B.、LORENZ, M.、PRELICZ, D.、SEDZIK-HIBNER, D.、OSTROWSKI+

  DOI：——

  日期：——