ethyl N-(3,4-dimethoxyphenyl)ethyl-3-(aminocarbonyl)propionate | 108163-97-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl N-(3,4-dimethoxyphenyl)ethyl-3-(aminocarbonyl)propionate
• 英文别名: ethyl [β-(3,4-dimethoxy)phenethylamino]-oxobutanoate；Ethyl 4-[2-(3,4-dimethoxyphenyl)ethylamino]-4-oxobutanoate
• CAS: 108163-97-9
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: CDEHXZNOUDWOHA-UHFFFAOYSA-N

物化性质

• 熔点：
  106-108 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  497.1±45.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl N-(3,4-dimethoxyphenyl)ethyl-3-(aminocarbonyl)propionate 在 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 ethyl 3-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)propionate
  参考文献：
  名称：

  Synthesis of new antimicrobial pyrrolo[2,1-a]isoquinolin-3-ones

  摘要：

  The attractive structure of the pyrroloisoquinoline moiety, together with its potential antimicrobial activity, encouraged us to prepare six 8-substituted and seven 8,9-disubstituted-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinolin-3-ones in a few steps with good yields. We applied a convenient methodology via double intramolecular cyclization conducted by a Bischler-Napieralski cyclodehydration-imine reduction sequence, which is widely employed in the synthesis of isoquinoline alkaloids. Therefore, we synthesized three series of these pyrrolo[2,1-a]isoquinolin-3-ones characterized by the substituent at the 8-position or 8,9-positions of the aromatic ring: (a) different side chains are attached to an 8-OH group (series 1); (b) a chlorine atom is attached to the 8-position (series 2); and (c) 8- and 9-carbons are bearing an identical group (series 3). The compounds bearing a benzylic moiety at the 8-position, for example, 8-benzyloxy-pyrrolo[2,1-a]isoquinolin-3-one (1a) and 8-(4-fluorobenzyloxy)-pyrrolo[2,1-a]isoquinolin-3-one (1e), as well as, a 8-chloro-9-methoxy moiety including the 8-chloro-9-methoxy-pyrrolo[2,1-a]isoquinolin-3-one (2a), provided the most fungicide and bactericide agents, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.033
• 作为产物：
  描述：

  丁二酸单乙酯酰氯 、 3,4-二甲氧基苯乙胺 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 ethyl N-(3,4-dimethoxyphenyl)ethyl-3-(aminocarbonyl)propionate
  参考文献：
  名称：

  取代的吡咯并[2,1-a]异喹啉酮衍生物的设计，合成，生物学评估和分子建模：AChE和BChE的有效抑制剂的发现

  摘要：

  我们在这里报告了一系列新的取代吡咯并[2,1- a]的设计，合成和生物学评估。]异喹啉-3-酮衍生物，其中一些对AChE和BChE酶都具有很强的抑制活性。这些新抑制剂的设计以利凡斯的明为起始结构。因此，在使用组合技术（对接，动态分子模拟和QTAIM计算）进行的详尽的分子建模研究的基础上，我们获得了比参考化合物rivastigmine具有更强抑制作用的新配体。QTAIM分析为我们提供了有关稳定不同配体-酶复合物的分子相互作用的详细信息。这些计算表明与CAS酯位点相互作用对于这些化合物的抑制作用的重要性。尽管如此，

  DOI：

  10.1039/d1nj00345c

文献信息

• BLASKO G.; KARDOS J.; BAITZ-GACS E.; SIMONYI M.; SZANTAY C., HETEROCYCLES, 24,(1986) N 10, 2887-2900
  作者：BLASKO G.、 KARDOS J.、 BAITZ-GACS E.、 SIMONYI M.、 SZANTAY C.

  DOI：——

  日期：——
• Blasko, Gabor; Kardos, Julianna; Baitz-Gacs, Eszter, Heterocycles, 1986, vol. 24, # 10, p. 2887 - 2900
  作者：Blasko, Gabor、Kardos, Julianna、Baitz-Gacs, Eszter、Simonyi, Miklos、Szantay, Csaba

  DOI：——

  日期：——
• Synthesis of new antimicrobial pyrrolo[2,1-a]isoquinolin-3-ones
  作者：Laura Moreno、Javier Párraga、Abraham Galán、Nuria Cabedo、Jaime Primo、Diego Cortes

  DOI：10.1016/j.bmc.2012.09.033

  日期：2012.11

  The attractive structure of the pyrroloisoquinoline moiety, together with its potential antimicrobial activity, encouraged us to prepare six 8-substituted and seven 8,9-disubstituted-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinolin-3-ones in a few steps with good yields. We applied a convenient methodology via double intramolecular cyclization conducted by a Bischler-Napieralski cyclodehydration-imine reduction sequence, which is widely employed in the synthesis of isoquinoline alkaloids. Therefore, we synthesized three series of these pyrrolo[2,1-a]isoquinolin-3-ones characterized by the substituent at the 8-position or 8,9-positions of the aromatic ring: (a) different side chains are attached to an 8-OH group (series 1); (b) a chlorine atom is attached to the 8-position (series 2); and (c) 8- and 9-carbons are bearing an identical group (series 3). The compounds bearing a benzylic moiety at the 8-position, for example, 8-benzyloxy-pyrrolo[2,1-a]isoquinolin-3-one (1a) and 8-(4-fluorobenzyloxy)-pyrrolo[2,1-a]isoquinolin-3-one (1e), as well as, a 8-chloro-9-methoxy moiety including the 8-chloro-9-methoxy-pyrrolo[2,1-a]isoquinolin-3-one (2a), provided the most fungicide and bactericide agents, respectively. (C) 2012 Elsevier Ltd. All rights reserved.
• Design, synthesis, biological evaluation and molecular modelling of substituted pyrrolo[2,1-<i>a</i>]isoquinolinone derivatives: discovery of potent inhibitors of AChE and BChE
  作者：Oscar Parravicini、Emilio Angelina、Roque Spinelli、Francisco Garibotto、Álvaro S. Siano、Laura Vila、Nuria Cabedo、Diego Cortes、Ricardo D. Enriz

  DOI：10.1039/d1nj00345c

  日期：——

  We report here the design, synthesis and biological evaluation of a new series of substituted pyrrolo[2,1-a]isoquinolin-3-one derivatives, some of which have strong inhibitory activity against both AChE and BChE enzymes. The design of these new inhibitors was carried out taking rivastigmine as the starting structure. Thus, on the basis of an exhausting molecular modeling study using combined techniques

  我们在这里报告了一系列新的取代吡咯并[2,1- a]的设计，合成和生物学评估。]异喹啉-3-酮衍生物，其中一些对AChE和BChE酶都具有很强的抑制活性。这些新抑制剂的设计以利凡斯的明为起始结构。因此，在使用组合技术（对接，动态分子模拟和QTAIM计算）进行的详尽的分子建模研究的基础上，我们获得了比参考化合物rivastigmine具有更强抑制作用的新配体。QTAIM分析为我们提供了有关稳定不同配体-酶复合物的分子相互作用的详细信息。这些计算表明与CAS酯位点相互作用对于这些化合物的抑制作用的重要性。尽管如此，