methyl (2S)-2-[(4-methoxyphenyl)methylamino]-3-(4-phenylmethoxyphenyl)propanoate | 1342305-93-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: methyl (2S)-2-[(4-methoxyphenyl)methylamino]-3-(4-phenylmethoxyphenyl)propanoate
• CAS: 1342305-93-4
• 化学式: C₂₅H₂₇NO₄
• 分子量: 405.494
• InChiKey: HTGTUWMRMPUESM-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[(4-methoxyphenyl)methylamino]-3-(4-phenylmethoxyphenyl)propanoate 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-p-benzyloxybenzyl-1-p-methoxybenzyl-4-methoxycarbonyl-3-methyl-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：

  2-氨基-3-(4-苯基甲氧基苯基)丙酸甲酯 、 4-甲氧基苯甲醛 在 三乙胺 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以66%的产率得到methyl (2S)-2-[(4-methoxyphenyl)methylamino]-3-(4-phenylmethoxyphenyl)propanoate
  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.