N-1'-(1'-methoxycarbonyl-2'-phenylethyl)-4-hydroxybenzamide | 94168-82-8

• 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: N-1'-(1'-methoxycarbonyl-2'-phenylethyl)-4-hydroxybenzamide
• 英文别名: methyl (4-hydroxybenzoyl)phenylalaninate；methyl (2S)-2-[(4-hydroxybenzoyl)amino]-3-phenylpropanoate
• CAS: 94168-82-8
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: NOOQBXZAIPEBSY-HNNXBMFYSA-N

物化性质

• 沸点：
  534.7±50.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-1'-(1'-methoxycarbonyl-2'-phenylethyl)-4-hydroxybenzamide 在 N-甲基吗啉 、 potassium carbonate 、 sodium hydroxide 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 N-(N-4-(2-(dimethylamino)ethoxy)benzoyl-L-phenylalanyl)-L-phenylalanol
  参考文献：
  名称：

  Synthesis and biological evaluation of Matijing-Su derivatives as potent anti-HBV agents

  摘要：

  A series of Matijing-Su (MTS, N-(N-benzoyl-L-phenylalanyl)-O-acetyl-L-phenylalanol) derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activity in 2.2.15 cells. The IC50 of compounds 14a (0.71 mu M), 13c (2.85 mu M), 13b (4.37 mu M), etc. and the selective index of 13g (161.01), 13c (90.45), 13a (85.09) etc. of the inhibition on the replication of HBV DNA were better than those of the positive control lamivudine (IC50: 82.42 mu M, SI: 41.59). Compounds 13o, 13p, and 16a also exhibited significant anti-HBV activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.001
• 作为产物：
  描述：

  (1S,1'S + 1R,1'S)-N-1'-(1'-methoxycarbonyl 2'-phenylethyl)-1-hydroxy-4-oxo-2-cyclohexene-1-carbonamide 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 叔丁醇 为溶剂， 反应 50.0h， 生成 N-1'-(1'-methoxycarbonyl-2'-phenylethyl)-4-hydroxybenzamide
  参考文献：
  名称：

  细胞松弛素B中全氢异吲哚体系的研究

  摘要：

  使用以下反应序列描述全氢异吲哚体系17a，b，22和23的合成。甲硅烷基氧二烯4与丙烯酸甲酯的Diels-Alder环加成反应在甲醇分解后导致环己烯酮羧酸酯6，随后将α，β-不饱和酯7缩醛化和环氧化，生成环氧酯8和9。这些酯成酰基氯的转化率11，经由钠盐10以及随后与胺组分治疗（苯丙氨酸甲酯，氨基丙二酸二乙酯和2-氨基苯甲酰基乙酸酯）产生的环氧碳酰胺12，15和18分别。这些环氧酰胺经受酸催化的水解，得到cyclohexenonecarbonamides 13，16和19分别。随后酰胺16和19与碱的闭环分别导致全氢异吲哚衍生物17a，b和22。形成22个前进通过伴随的苯甲酰基转移反应。酰胺13未能闭环。酸处理18的副产物是21，其与碱经历苯甲酰基转移至全氢异吲哚23。通过X射线分析确定产物9a，22和23的结构。

  DOI：

  10.1016/0040-4020(84)85020-6

文献信息

• Highly efficient heterogeneous V ₂ O ₅ @TiO ₂ catalyzed the rapid transformation of boronic acids to phenols
  作者：Rahul Upadhyay、Deepak Singh、Sushil K. Maurya

  DOI：10.1002/ejoc.202100614

  日期：2021.7.26

  The hydroxylation of boronic acid into phenol using heterogeneous V2O5@TiO2 catalystis described. The methodology was successfully applied to transform a varied range of (hetero)aryl, pharmaceutical-derived and natural product-derived boronic acid into their corresponding phenols in good to excellent yields.

  描述了使用非均相 V 2 O 5 @TiO 2催化剂将硼酸羟基化成苯酚。该方法已成功应用于将各种（杂）芳基、药物衍生的和天然产物衍生的硼酸转化为相应的酚类，产率很高。
• Synthesis and anti-tumor activity evaluation of Matijin-Su derivatives
  作者：Bixue Xu、Ning Wang、Weidong Pan、Jingying Qiu、Peixue Cao、Meifen Zhu、Yibin Feng、Guangyi Liang

  DOI：10.1016/j.bioorg.2014.05.009

  日期：2014.10

  A series of Matijin-Su (MTS, N-(N-benzoyl-l-phenylalanyl)-O-acetyl-l-phenylalanol) derivatives was synthesized and evaluated for their anti-tumor activities in hepatocellular carcinoma cells. The IC50 of compounds 1, 3, 4, 11, 13 were less than 20μM, and compound 1 and 3 showed an IC50 value of less than 9μM. Expansion inhibition could be found significantly in compound 1 and 3-treated human hepatoma cell HepG2 and PLC/PRF/5, while both compounds exhibit lower toxicity to human hepatocyte cell line L-02. Compound 1 and 3 could induce cell cycle arrest at G1/S phase. This may be attributed to increase level of intracellular reactive oxygen species (ROS). Up-regulation of p38 MAPK activity in responding the ROS stabilize p53 and activate p21 transcription, the critical regulatory in G1/S checkpoint. Observations in this study shed light on the potential of MTS derivatives compound 1 and 3 as novel suppressors to human liver cancer.
• Synthesis and biological evaluation of Matijing-Su derivatives as potent anti-HBV agents
  作者：Jingying Qiu、Bixue Xu、Zhengming Huang、Weidong Pan、Peixue Cao、Changxiao Liu、Xiaojiang Hao、Baoan Song、Guangyi Liang

  DOI：10.1016/j.bmc.2011.08.001

  日期：2011.9

  A series of Matijing-Su (MTS, N-(N-benzoyl-L-phenylalanyl)-O-acetyl-L-phenylalanol) derivatives were synthesized and evaluated for their anti-hepatitis B virus (HBV) activity in 2.2.15 cells. The IC50 of compounds 14a (0.71 mu M), 13c (2.85 mu M), 13b (4.37 mu M), etc. and the selective index of 13g (161.01), 13c (90.45), 13a (85.09) etc. of the inhibition on the replication of HBV DNA were better than those of the positive control lamivudine (IC50: 82.42 mu M, SI: 41.59). Compounds 13o, 13p, and 16a also exhibited significant anti-HBV activity. (C) 2011 Elsevier Ltd. All rights reserved.
• Approach to the perhydroisoindole system in cytochalasin B
  作者：J.M. Lemmens、L. Thijs、B. Zwanenburg

  DOI：10.1016/0040-4020(84)85020-6

  日期：1984.1

  The synthesis of the perhydroisoindole systems 17a, b, 22 and 23 is described using the following sequence of reactions. Diels-Alder cycloaddition of silyloxydienes 4 with methyl acrylate leads, after methanolysis, to cyclohexenonecarboxylates 6, subsequent acetalization and epoxidation of the α,β-unsaturated esters 7 yields the epoxy esters 8 and 9. Conversion of these esters into acyl chlorides 11

  使用以下反应序列描述全氢异吲哚体系17a，b，22和23的合成。甲硅烷基氧二烯4与丙烯酸甲酯的Diels-Alder环加成反应在甲醇分解后导致环己烯酮羧酸酯6，随后将α，β-不饱和酯7缩醛化和环氧化，生成环氧酯8和9。这些酯成酰基氯的转化率11，经由钠盐10以及随后与胺组分治疗（苯丙氨酸甲酯，氨基丙二酸二乙酯和2-氨基苯甲酰基乙酸酯）产生的环氧碳酰胺12，15和18分别。这些环氧酰胺经受酸催化的水解，得到cyclohexenonecarbonamides 13，16和19分别。随后酰胺16和19与碱的闭环分别导致全氢异吲哚衍生物17a，b和22。形成22个前进通过伴随的苯甲酰基转移反应。酰胺13未能闭环。酸处理18的副产物是21，其与碱经历苯甲酰基转移至全氢异吲哚23。通过X射线分析确定产物9a，22和23的结构。