ethyl 3-(4-(dimethylamino)phenyl)-3-hydroxypropanoate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ethyl 3-(4-(dimethylamino)phenyl)-3-hydroxypropanoate
• 英文别名: Ethyl 3-[4-(dimethylamino)phenyl]-3-hydroxypropanoate；ethyl 3-[4-(dimethylamino)phenyl]-3-hydroxypropanoate
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: BZEVRRLTTIOYBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-(4-(dimethylamino)phenyl)-3-hydroxypropanoate 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 为溶剂， 以65%的产率得到3-hydroxy-3-[(4-N,N-dimethylamino)phenyl]propionylhydroxamic acid
  参考文献：
  名称：

  β-羟基-β-苯基丙酰基-异羟肟酸作为幽门螺杆菌脲酶抑制剂的合成，分子对接和动力学性质

  摘要：

  尿素酶的抑制导致幽门螺杆菌在胃中的生长停滞，从而促进尿素酶成为胃肠道溃疡治疗的有希望的靶标。因此，合成了黄酮类支架和异羟肟酸的二十种杂合衍生物，β-羟基-β-苯基丙酰基异羟肟酸，并针对幽门螺杆菌脲酶进行了评估。这些化合物的生物学评估表明，尿素酶抑制作用得到改善，表现出微摩尔至中纳摩尔级的IC 50值。最重要的是，3-（3-氯苯基）-3-羟基丙酰基-异羟肟酸（6g）表现出高效能，IC 50为0.083±0.004μM，K i为0.014±0.003μM，表明6g是开发新型抗溃疡药的优秀候选者。为了首次了解晶体学和动力学研究之间的矛盾，提出了一种竞争机制和非竞争机制的混合物，这是我们的分子对接研究所支持的。

  DOI：

  10.1016/j.ejmech.2013.07.047
• 作为产物：
  描述：

  (三甲基硅基)乙酸乙酯 、 对二甲氨基苯甲醛 在 potassium trimethylsilonate 、 四丁基氯化铵 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以61%的产率得到ethyl 3-(4-(dimethylamino)phenyl)-3-hydroxypropanoate
  参考文献：
  名称：

  Bu₄N⁺ Alkoxide-Initiated/Autocatalytic Addition Reactions with Organotrimethylsilanes

  摘要：

  The use of Me3SiO(-)/Bu4N(+) as a general activator of organotrimethylsilanes for addition reactions has been established. The broad scope of the method offers trimethylsilanes (including acetate, allyl, propargyl, benzyl, dithiane, heteroaryl, and aryl derivatives) as bench-stable organometallics that can be readily utilized as carbanion equivalents for synthesis. Reactions are achieved at rt without the requirement of specialized precautions that are commonplace for other organometallics.

  DOI：

  10.1021/jo5007637

文献信息

• 3-Arylpropionylhydroxamic acid derivatives as Helicobacter pylori urease inhibitors: Synthesis, molecular docking and biological evaluation
  作者：Wei-Kang Shi、Rui-Cheng Deng、Peng-Fei Wang、Qin-Qin Yue、Qi Liu、Kun-Ling Ding、Mei-Hui Yang、Hong-Yu Zhang、Si-Hua Gong、Min Deng、Wen-Run Liu、Qiu-Ju Feng、Zhu-Ping Xiao、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2016.07.052

  日期：2016.10

  Helicobacter pylori urease is involved in several physiologic responses such as stomach and duodenal ulcers, adenocarcinomas and stomach lymphomas. Thus, inhibition of urease is taken for a good chance to treat H. pylori-caused infections, we have therefore focused our efforts on seeking novel urease inhibitors. Here, a series of arylpropionylhydroxamic acids were synthesized and evaluated for urease inhibition. Out of these compounds, 3-(2-benzyloxy-5-chlorophenyl)-3-hydroxypropionylhydroxamic acid (d24) was the most active inhibitor with IC50 of 0.15 +/- 0.05 mu M, showing a mixed inhibition with both competitive and uncompetitive aspects. Non-linear fitting of kinetic data gives kinetics parameters of 0.13 and 0.12 mu g.mL(-1) for K-i and K-i', respectively. The plasma protein binding assays suggested that d24 exhibited moderate binding to human and rabbit plasma proteins. (C) 2016 Elsevier Ltd. All rights reserved.