3-(4-Methoxy-phenyl)-propionimidic acid ethyl ester | 683200-28-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-Methoxy-phenyl)-propionimidic acid ethyl ester
• 英文别名: Ethyl 3-(4-methoxyphenyl)propanimidate
• CAS: 683200-28-4
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: OJSGYWFHMCCHRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  42.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-Methoxy-phenyl)-propionimidic acid ethyl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 3-(4-Methoxy-phenyl)-propionamidine
  参考文献：
  名称：

  Substituted benzylamino-6-(trifluoromethyl)pyrimidin-4(1H)-ones: a novel class of selective human A-FABP inhibitors

  摘要：

  The synthesis and biological evaluation of novel human A-FABP inhibitors based on the 6-(trifluoromethyl)pyrimidine-4(1H)-one scaffold is described. Two series of compounds, bearing either an amino or carbon substituent in the 2-position of the pyrimidine ring were investigated. Modification of substituents and chain length optimization led to novel compounds with low micromolar activity and good selectivity for human A-FABP. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.058
• 作为产物：
  描述：

  乙醇 、 3-(4-甲氧基苯基)-丙腈 在 盐酸 、 碳酸氢钠 作用下， 以 乙醚 、 水 为溶剂， 反应 0.17h， 以80%的产率得到3-(4-Methoxy-phenyl)-propionimidic acid ethyl ester
  参考文献：
  名称：

  含氨基的3,5-二取代的1,2,4-三唑的合成

  摘要：

  通过将亚氨基酯与羧酸酰肼缩合制备的N ′-（1-亚氨基烷基）酰肼进行热环化，已经合成了含有直链和环状胺片段的3，5-二取代的1,2,4-三唑。通过Pinner反应以及在催化量的甲醇钠存在下腈与甲醇的反应已合成了起始的亚氨基酯。已经开发出一种合成5-取代的3-（3-硝基苯基）-1，2，4-三唑的方法，这些化合物通过在阮内镍上用水合肼还原而转化为3-氨基苯基衍生物。

  DOI：

  10.1134/s1070428016100195

文献信息

• 4,5-Dihydro-1-phenyl-1H-2,4-benzodiazepines: Novel antiarrhythmic agents
  作者：Robert E. Johnson、Eugene R. Baizman、Carolyn Becker、Eric A. Bohnet、Rebecca H. Bell、Nancy C. Birsner、Carl A. Busacca、Philip M. Carabateas、Christopher C. Chadwick

  DOI：10.1021/jm00074a017

  日期：1993.10

  A series of 4,5-dihydro-1-phenyl-1H-2,4-benzodiazepines has been identified as potential antiarrhythmic agents that interact with sodium and potassium channels and prolong the ventricular effective refractory period (ERP) in anesthetized guinea pigs. Concomitant displacement of radiolabeled bactrachotoxin from site II in Na+ channels and of radiolabeled dofetilide from delayed rectifier K+ channels was evident with all members of this chemical series at a concentration of 10 muM. Structure-activity relationship (SAR) studies using a paced guinea pig model to assess prolongation of the ERP indicated that methyl or ethyl at the 1-position had little effect on activity, while larger groups caused a diminution of activity. Compounds with substituents at either the 3- or 4-position that increased lipophilicity generally were more potent; however, too many lipophilic substituents simultaneously at positions 1, 3, and 4 resulted in less active compounds. Substituents on either aromatic ring had little influence on activity, and phenyl at the 5-position resulted in a significant reduction in antiarrhythmic activity. When two sets of enantiomerically pure compounds were tested in the guinea pig, chirality was shown to be important for activity of 8, where the (R)-enantiomer was the more active, but not in the case of 15, where the enantiomers were equiactive. Several compounds in this series increased the threshold for vertricular fibrillation and refractoriness in myocardially-infarcted anesthetized cata and delayed the onset of aconitine-induced arrhythmias in anesthetized guinea pigs following intravenous dosing. Moreover, these compounds possessed oral antiarrhythmic activity in conscious myocardially-infarcted dogs. Compound R-15 has been advanced for further biological and toxicological evaluations.
• Synthesis of 3,5-disubstituted 1,2,4-triazoles containing an amino group
  作者：N. Yu. Khromova、M. M. Fedorov、S. I. Malekin、A. V. Kutkin

  DOI：10.1134/s1070428016100195

  日期：2016.10

  cyclic amine fragments have been synthesized by thermal cyclization of N′-(1-iminoalkyl) hydrazides prepared by condensation of imido esters with carboxylic acid hydrazides. The initial imido esters have been synthesized by the Pinner reaction, as well as by reaction of nitriles with methanol in the presence of a catalytic amount of sodium methoxide. A procedure has been developed for the synthesis

  通过将亚氨基酯与羧酸酰肼缩合制备的N ′-（1-亚氨基烷基）酰肼进行热环化，已经合成了含有直链和环状胺片段的3，5-二取代的1,2,4-三唑。通过Pinner反应以及在催化量的甲醇钠存在下腈与甲醇的反应已合成了起始的亚氨基酯。已经开发出一种合成5-取代的3-（3-硝基苯基）-1，2，4-三唑的方法，这些化合物通过在阮内镍上用水合肼还原而转化为3-氨基苯基衍生物。
• Substituted benzylamino-6-(trifluoromethyl)pyrimidin-4(1H)-ones: a novel class of selective human A-FABP inhibitors
  作者：Rune Ringom、Eva Axen、Jonas Uppenberg、Thomas Lundbäck、Lena Rondahl、Tjeerd Barf

  DOI：10.1016/j.bmcl.2004.06.058

  日期：2004.9

  The synthesis and biological evaluation of novel human A-FABP inhibitors based on the 6-(trifluoromethyl)pyrimidine-4(1H)-one scaffold is described. Two series of compounds, bearing either an amino or carbon substituent in the 2-position of the pyrimidine ring were investigated. Modification of substituents and chain length optimization led to novel compounds with low micromolar activity and good selectivity for human A-FABP. (C) 2004 Elsevier Ltd. All rights reserved.