3,5-Bis-benzyloxy-benzoic acid (R)-1-{(S)-2-[1-ethoxycarbonyl-meth-(Z)-ylidene]-4-oxo-azetidin-3-yl}-ethyl ester | 868083-12-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-Bis-benzyloxy-benzoic acid (R)-1-{(S)-2-[1-ethoxycarbonyl-meth-(Z)-ylidene]-4-oxo-azetidin-3-yl}-ethyl ester
• CAS: 868083-12-9
• 化学式: C₃₀H₂₉NO₇
• 分子量: 515.563
• InChiKey: MOYUBPQUVYTWOU-KXBBSBDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  100.16
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3,5-Bis-benzyloxy-benzoic acid (R)-1-{(S)-2-[1-ethoxycarbonyl-meth-(Z)-ylidene]-4-oxo-azetidin-3-yl}-ethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以100%的产率得到3,5-Dihydroxy-benzoic acid (R)-1-{(S)-2-[1-ethoxycarbonyl-meth-(Z)-ylidene]-4-oxo-azetidin-3-yl}-ethyl ester
  参考文献：
  名称：

  4-Alkyliden-β-lactams conjugated to polyphenols: Synthesis and inhibitory activity

  摘要：

  A series of compounds combining the beta-lactain and polyphenol scaffold have been prepared and evaluated for inhibition of human leukocyte elastase and matrix metallo-proteases MMP-2 and MMP-9. The design of these compounds has been based on the 'overlapping-type' strategy where two pharmacophores are linked in a single molecule. The most powerful compound against elastase was an N-galloyl-4-alkyliden beta-lactam, [3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-1-(3,4,5-tris-benzyloxy-benzoyl)-azetidin-2-ylidene]-acetic acid ethylester, with an IC50 of 0.5 mu M; while the most powerful against MMP-2 was a 4-alkyliden beta-lactam arylated on the C-3 hydroxy side chain (3,5-bis-benzyloxy-4-hydroxy-benzoic acid 1-(2-benzyloxycarbonylmethylene4-oxo-azetidin-3-yl)-ethyl ester) with an IC50 of 4 mu M. Of the total 35 compounds tested, high levels of inhibition of elastase and of MMPs were separately exerted by distinct molecules. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.041
• 作为产物：
  描述：

  ethyl {(2Z,3S)-3-[(1R)-(tert-butyldimethylsilanyloxy)ethyl]-4-oxoazetidin-2-ylidene}acetate 在 盐酸 、 四氯化锡 作用下， 以 乙腈 、 苯 为溶剂， 反应 4.0h， 生成 3,5-Bis-benzyloxy-benzoic acid (R)-1-{(S)-2-[1-ethoxycarbonyl-meth-(Z)-ylidene]-4-oxo-azetidin-3-yl}-ethyl ester
  参考文献：
  名称：

  4-Alkyliden-β-lactams conjugated to polyphenols: Synthesis and inhibitory activity

  摘要：

  A series of compounds combining the beta-lactain and polyphenol scaffold have been prepared and evaluated for inhibition of human leukocyte elastase and matrix metallo-proteases MMP-2 and MMP-9. The design of these compounds has been based on the 'overlapping-type' strategy where two pharmacophores are linked in a single molecule. The most powerful compound against elastase was an N-galloyl-4-alkyliden beta-lactam, [3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-1-(3,4,5-tris-benzyloxy-benzoyl)-azetidin-2-ylidene]-acetic acid ethylester, with an IC50 of 0.5 mu M; while the most powerful against MMP-2 was a 4-alkyliden beta-lactam arylated on the C-3 hydroxy side chain (3,5-bis-benzyloxy-4-hydroxy-benzoic acid 1-(2-benzyloxycarbonylmethylene4-oxo-azetidin-3-yl)-ethyl ester) with an IC50 of 4 mu M. Of the total 35 compounds tested, high levels of inhibition of elastase and of MMPs were separately exerted by distinct molecules. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.041