N-p-propoxybenzyl-L-Phe-OMe | 1342305-87-6

• 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-p-propoxybenzyl-L-Phe-OMe
• 英文别名: methyl (2S)-3-phenyl-2-[(4-propoxyphenyl)methylamino]propanoate
• CAS: 1342305-87-6
• 化学式: C₂₀H₂₅NO₃
• 分子量: 327.423
• InChiKey: UHDLPCZDDUJDRU-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-p-propoxybenzyl-L-Phe-OMe 在 三氯乙腈 、 三苯基膦 、 (叔丁基亚氨基)三(吡咯烷)膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.0h， 生成 (3S,4S)-4-benzyl-4-methoxycarbonyl-3-methyl-1-p-propoxybenzyl-2-azetidinone
  参考文献：
  名称：

  Optically active 1,3,4,4-tetrasubstituted β-lactams: Synthesis and evaluation as tumor cell growth inhibitors

  摘要：

  The in vitro cytotoxicity assays of several enantiopure (3S,4S)- and (3R,4R)-1,3,4,4-tetrasubstituted beta-lactams derived from amino acids have shown that the (3S,4S)-4-benzyl-1-p-methoxybenzyl-3-methyl-4-methoxycarbonyl derivative 2a, obtained from Phe, displays significant activity, which is comparable to that of the anticancer drug Doxorubicin against HT29 cell lines. Modifications at positions 1 and 4 of the beta-lactam ring led to identify the Tyr(2,6-ClBz) analogu 26d with similar activity data to those of 2a. The synthesis and SAR of all these tetrasubstituted beta-lactams are reported here. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.025
• 作为产物：
  描述：

  L-苯丙氨酸甲酯盐酸盐 、 4-丙氧基苯甲醛 在 三乙胺 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以78%的产率得到N-p-propoxybenzyl-L-Phe-OMe
  参考文献：
  名称：

  Optically active 1,3,4,4-tetrasubstituted β-lactams: Synthesis and evaluation as tumor cell growth inhibitors

  摘要：

  The in vitro cytotoxicity assays of several enantiopure (3S,4S)- and (3R,4R)-1,3,4,4-tetrasubstituted beta-lactams derived from amino acids have shown that the (3S,4S)-4-benzyl-1-p-methoxybenzyl-3-methyl-4-methoxycarbonyl derivative 2a, obtained from Phe, displays significant activity, which is comparable to that of the anticancer drug Doxorubicin against HT29 cell lines. Modifications at positions 1 and 4 of the beta-lactam ring led to identify the Tyr(2,6-ClBz) analogu 26d with similar activity data to those of 2a. The synthesis and SAR of all these tetrasubstituted beta-lactams are reported here. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.025

文献信息

• Optically active 1,3,4,4-tetrasubstituted β-lactams: Synthesis and evaluation as tumor cell growth inhibitors
  作者：Paula Pérez-Faginas、M. Teresa Aranda、M. Teresa García-López、Andrés Francesch、Carmen Cuevas、Rosario González-Muñiz

  DOI：10.1016/j.ejmech.2011.08.025

  日期：2011.10

  The in vitro cytotoxicity assays of several enantiopure (3S,4S)- and (3R,4R)-1,3,4,4-tetrasubstituted beta-lactams derived from amino acids have shown that the (3S,4S)-4-benzyl-1-p-methoxybenzyl-3-methyl-4-methoxycarbonyl derivative 2a, obtained from Phe, displays significant activity, which is comparable to that of the anticancer drug Doxorubicin against HT29 cell lines. Modifications at positions 1 and 4 of the beta-lactam ring led to identify the Tyr(2,6-ClBz) analogu 26d with similar activity data to those of 2a. The synthesis and SAR of all these tetrasubstituted beta-lactams are reported here. (C) 2011 Elsevier Masson SAS. All rights reserved.