(3S,4S)-4-p-benzyloxybenzyl-1-p-methoxybenzyl-4-methoxycarbonyl-3-methyl-2-azetidinone | 1342305-96-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3S,4S)-4-p-benzyloxybenzyl-1-p-methoxybenzyl-4-methoxycarbonyl-3-methyl-2-azetidinone
• 英文别名: methyl (2S,3S)-1-[(4-methoxyphenyl)methyl]-3-methyl-4-oxo-2-[(4-phenylmethoxyphenyl)methyl]azetidine-2-carboxylate
• CAS: 1342305-96-7
• 化学式: C₂₈H₂₉NO₅
• 分子量: 459.542
• InChiKey: JQYSDFRDDHOUQL-NGOKVRLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-p-benzyloxybenzyl-1-p-methoxybenzyl-4-methoxycarbonyl-3-methyl-2-azetidinone 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、206.85 kPa 条件下， 反应 4.0h， 以98%的产率得到(3S,4S)-4-p-hydroxybenzyl-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 在 三乙胺 、 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 、 甲醇 、 乙腈 为溶剂， 反应 3.0h， 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