propionylamino-malonic acid diethyl ester | 88744-16-5

• 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: propionylamino-malonic acid diethyl ester
• 英文别名: Propionylamino-malonsaeure-diaethylester；Propionylaminomalonsaeure-diaethylester；Propionylamino-malonester；Diethyl propanamidopropanedioate；diethyl 2-(propanoylamino)propanedioate
• CAS: 88744-16-5
• 化学式: C₁₀H₁₇NO₅
• mdl: MFCD02668058
• 分子量: 231.249
• InChiKey: FDEDTSWJULBKKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  propionylamino-malonic acid diethyl ester 在 platinum(IV) oxide sodium hydroxide 、 氢气 、 sodium ethanolate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 1.16h， 生成 N-(2,3,6,7-tetrahydro-3-oxo-1H,5H-benzoquinolizin-2-yl)propanamide
  参考文献：
  名称：

  Dopaminergic and serotonergic activities of imidazoquinolinones and related compounds

  摘要：

  The synthesis of 5-(dipropylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (5), a potent dopamine D2 agonist showing high dopamine/serotonin (5HT1A) selectivity, is described. Dopaminergic activity is associated with the (R)-enantiomer of 5; the (S)-enantiomer shows no dopaminergic activity. A series of analogues where the imidazolone ring was modified to various 5- or 6-membered heterocyclic rings were prepared. Some of these compounds showed a combination of dopaminergic and serotonergic activity, while one compound, 6-(dipropylamino)-1,2,6,7-tetrahydro-3H,5H-pyrido[3,2,1-ij]quinazolin-3-one (24), was a selective serotonergic agonist. Various analogues of 5 where the dipropylamine substituent was modified were prepared. Most of these showed reduced dopaminergic activity, while several were as potent as 5 at the serotonin 5HT1A receptor. Orientations for the new compounds at dopamine and serotonin receptors are proposed and compared with those of other tricyclic ligands known to have high affinity at these receptors.

  DOI：

  10.1021/jm00084a013
• 作为产物：
  描述：

  氨基丙二酸二乙酯盐酸盐 、 丙酸酐 在 三乙胺 作用下， 反应 0.75h， 以72%的产率得到propionylamino-malonic acid diethyl ester
  参考文献：
  名称：

  Dopaminergic and serotonergic activities of imidazoquinolinones and related compounds

  摘要：

  The synthesis of 5-(dipropylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (5), a potent dopamine D2 agonist showing high dopamine/serotonin (5HT1A) selectivity, is described. Dopaminergic activity is associated with the (R)-enantiomer of 5; the (S)-enantiomer shows no dopaminergic activity. A series of analogues where the imidazolone ring was modified to various 5- or 6-membered heterocyclic rings were prepared. Some of these compounds showed a combination of dopaminergic and serotonergic activity, while one compound, 6-(dipropylamino)-1,2,6,7-tetrahydro-3H,5H-pyrido[3,2,1-ij]quinazolin-3-one (24), was a selective serotonergic agonist. Various analogues of 5 where the dipropylamine substituent was modified were prepared. Most of these showed reduced dopaminergic activity, while several were as potent as 5 at the serotonin 5HT1A receptor. Orientations for the new compounds at dopamine and serotonin receptors are proposed and compared with those of other tricyclic ligands known to have high affinity at these receptors.

  DOI：

  10.1021/jm00084a013

文献信息

• Reaction of Tetramethyl Ethynyldiphosphonate with Diethyl 2-Amidomalonates
  作者：D. M. Egorov、A. A. Petrosyan、Yu. L. Piterskaya、N. I. Svintsitskaya、A. V. Dogadina

  DOI：10.1134/s1070363218110294

  日期：2018.11

  Stereoselective reaction of tetramethyl ethynyldiphosphonate with diethyl 2-amidomalonates yielded Z-vinyldiphosphonates, namely Z-2-[1,2-bis(dimethoxyphosphoryl)-2-alkyl(aryl)amidovinyl]malonic acid diethyl esters. A possibility of cyclization of the amidomalonate fragment of the obtained alkenes with the formation of an oxazole-substituted Z-vinyldiphosphonate was shown.

  乙炔基二膦酸四甲酯与2-氨基苯甲酸二乙酯的立体选择反应产生Z-乙烯基二膦酸酯，即Z -2- [1,2-双（二甲氧基磷酰基）-2-烷基（芳基）氨基乙烯基]丙二酸二乙酯。显示了形成的恶唑取代的Z-乙烯基二膦酸酯可能环化所获得的烯烃的酰胺基丙二酸酯片段。
• Structure-based de novo design, synthesis, and biological evaluation of the indole-based PPARγ ligands (I)
  作者：Xiaochun Dong、Zhenshan Zhang、Ren Wen、Jianhua Shen、Xu Shen、Hualiang Jiang

  DOI：10.1016/j.bmcl.2006.06.093

  日期：2006.11

  MCSS and LeapFrog, two de novo drug design programs, were used for the novel indole-based PPARgamma ligands' study. The designed compounds were synthesized and tested for the PPARgamma protein binding activities in vitro. Out of the compounds that were synthesized, two molecules (compounds 14d and 7d) possessed potent PPARgamma protein binding activity close to rosiglitazone in vitro.

  MCSS和LeapFrog是两个从头设计的药物设计程序，用于基于吲哚的新型PPARgamma配体的研究。合成了设计的化合物，并测试了其在体外的PPARgamma蛋白结合活性。在合成的化合物中，两个分子（化合物14d和7d）在体外具有接近罗格列酮的有效PPARgamma蛋白结合活性。
• 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：——