(S)-methyl 2-amino-3-(4-phenethoxyphenyl)propanoate | 163108-62-1

• 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: (S)-methyl 2-amino-3-(4-phenethoxyphenyl)propanoate
• 英文别名: methyl (2S)-2-amino-3-[4-(2-phenylethoxy)phenyl]propanoate
• CAS: 163108-62-1
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: DMCUIAZGZJMMEI-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-amino-3-(4-phenethoxyphenyl)propanoate 在 sodium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 (2S)-2-[(4-methylbenzoyl)amino]-3-[4-(2-phenylethoxy)phenyl]propanoic acid
  参考文献：
  名称：

  Design, synthesis and evaluation of novel metalloproteinase inhibitors based on l-tyrosine scaffold

  摘要：

  A series of novel L-tyrosine derivatives were designed, synthesized and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and histone deacetylase 8 (HDAC-8). The results showed that these L-tyrosine derivatives exhibited inhibitory profiles against MMP-2 and HDAC-8. The compounds 6h (IC50 = 0.013 +/- 0.001 mu M) and 6j (IC50 = 0.017 +/- 0.001 mu M) were equal potent MMP-2 inhibitors to the positive control NNGH (IC50 = 0.014 +/- 0.001 mu M). As for HDAC-8 inhibition, some of the hydroxamate compounds, such as 6d (IC50 = 3.6 +/- 0.2 mu M) and 6c (IC50 = 5.8 +/- 0.5 mu M), were equal potent to the positive control SAHA (IC50 = 1.6 +/- 0.1 mu M). Structure-activity relationships were also briefly discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.014
• 作为产物：
  描述：

  (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-phenethoxyphenyl)propanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以93.6%的产率得到(S)-methyl 2-amino-3-(4-phenethoxyphenyl)propanoate
  参考文献：
  名称：

  Design, synthesis and evaluation of novel metalloproteinase inhibitors based on l-tyrosine scaffold

  摘要：

  A series of novel L-tyrosine derivatives were designed, synthesized and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and histone deacetylase 8 (HDAC-8). The results showed that these L-tyrosine derivatives exhibited inhibitory profiles against MMP-2 and HDAC-8. The compounds 6h (IC50 = 0.013 +/- 0.001 mu M) and 6j (IC50 = 0.017 +/- 0.001 mu M) were equal potent MMP-2 inhibitors to the positive control NNGH (IC50 = 0.014 +/- 0.001 mu M). As for HDAC-8 inhibition, some of the hydroxamate compounds, such as 6d (IC50 = 3.6 +/- 0.2 mu M) and 6c (IC50 = 5.8 +/- 0.5 mu M), were equal potent to the positive control SAHA (IC50 = 1.6 +/- 0.1 mu M). Structure-activity relationships were also briefly discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.014