3-{[(3-phenyloxybenzyl)oxyacetyl]amino}propionic acid | 303780-48-5

• 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-{[(3-phenyloxybenzyl)oxyacetyl]amino}propionic acid
• 英文别名: 3-[[2-[(3-Phenoxyphenyl)methoxy]acetyl]amino]propanoic acid；3-[[2-[(3-phenoxyphenyl)methoxy]acetyl]amino]propanoic acid
• CAS: 303780-48-5
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: BXJABEXEMZRAJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-amino-N-(2,3-dimethyl-phenyl)benzenesulphonamide 、 3-{[(3-phenyloxybenzyl)oxyacetyl]amino}propionic acid 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以30%的产率得到N-[3-[(2,3-dimethylphenyl)sulfamoyl]phenyl]-3-[[2-[(3-phenoxyphenyl)methoxy]acetyl]amino]propanamide
  参考文献：
  名称：

  Design, synthesis and early structure–activity relationship of farnesyltransferase inhibitors which mimic both the peptidic and the prenylic substrate

  摘要：

  Inhibition of the farnesylation of ras proteins has been identified as a promising target in tumor therapy. Only a few farnesyltransferase inhibitors are bisubstrate analogues displaying features of both substrates, the farnesylpyrophosphate and the C-terminal CAAX-tetrapeptide sequence of the res protein. These known bisubstrate analogues consist of an AAX-tripeptide and a farnesyl residue connected through various linkers. We have developed a class of novel compounds that mimic a bisubstrate inhibitor structure and that differ from the known ones by lacking peptidic or farnesylic substructures. Long chain fatty acids and aryl-substituted carboxylic acids were used as farnesyl surrogates. These structures were linked to isoleucine amide, benzoic acid amide, N-substituted aminobenzenesulfonamides and N-alpha-aryl-substituted methionine derivatives, respectively, which function as AA- or AAX-mimetics. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00138-3
• 作为产物：
  描述：

  3-苯氧基苄醇 在 氯化亚砜 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 丙酮 、 甲苯 为溶剂， 反应 16.0h， 生成 3-{[(3-phenyloxybenzyl)oxyacetyl]amino}propionic acid
  参考文献：
  名称：

  Design, synthesis and early structure–activity relationship of farnesyltransferase inhibitors which mimic both the peptidic and the prenylic substrate

  摘要：

  Inhibition of the farnesylation of ras proteins has been identified as a promising target in tumor therapy. Only a few farnesyltransferase inhibitors are bisubstrate analogues displaying features of both substrates, the farnesylpyrophosphate and the C-terminal CAAX-tetrapeptide sequence of the res protein. These known bisubstrate analogues consist of an AAX-tripeptide and a farnesyl residue connected through various linkers. We have developed a class of novel compounds that mimic a bisubstrate inhibitor structure and that differ from the known ones by lacking peptidic or farnesylic substructures. Long chain fatty acids and aryl-substituted carboxylic acids were used as farnesyl surrogates. These structures were linked to isoleucine amide, benzoic acid amide, N-substituted aminobenzenesulfonamides and N-alpha-aryl-substituted methionine derivatives, respectively, which function as AA- or AAX-mimetics. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00138-3