(S)-(2-carboxy-4-oxoazetidine-1-carboxamido)phenylmethanaminium 2,2,2-trifluoroacetate | 1620568-08-2

• 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: (S)-(2-carboxy-4-oxoazetidine-1-carboxamido)phenylmethanaminium 2,2,2-trifluoroacetate
• 英文别名: (2S)-1-[[4-(aminomethyl)phenyl]carbamoyl]-4-oxoazetidine-2-carboxylic acid;2,2,2-trifluoroacetic acid
• CAS: 1620568-08-2
• 化学式: C₂HF₃O₂*C₁₂H₁₃N₃O₄
• 分子量: 377.277
• InChiKey: MNDNLZYZPARUJP-FVGYRXGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.06
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  155
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  tert-butyl 4-isocyanatobenzylcarbamate 在 palladium 10% on activated carbon 、 氢气 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 27.0h， 生成 (S)-(2-carboxy-4-oxoazetidine-1-carboxamido)phenylmethanaminium 2,2,2-trifluoroacetate
  参考文献：
  名称：

  Targeting integrins αvβ3 and α5β1 with new β-lactam derivatives

  摘要：

  The αvβ3 and α5β1 integrins are widely expressed in different cancer types and recognize the tripeptide Arg-Gly-Asp (RGD) motif present in several extracellular matrix proteins. We report here the design, synthesis and biological activity of some new β-lactam derivatives specifically designed to target integrins. The new molecules contain the azetidinone as the only cyclic framework armed with carboxylic acid and amine terminals spaced from 9 to 14 atoms to switch on recognition by integrins. All tested molecules showed a concentration-dependent enhancement in fibronectin-mediated adhesion of K562 and SK-MEL-24 cells; in particular 1, expressed a higher affinity towards α5β1 integrin (EC50 of 12 nM) and 2 was more selective for integrin αvβ3 (EC50 of 11 nM).

  DOI：

  10.1016/j.ejmech.2014.06.041

文献信息

• Targeting integrins αvβ3 and α5β1 with new β-lactam derivatives
  作者：Paola Galletti、Roberto Soldati、Matteo Pori、Margherita Durso、Alessandra Tolomelli、Luca Gentilucci、Samantha Deianira Dattoli、Monica Baiula、Santi Spampinato、Daria Giacomini

  DOI：10.1016/j.ejmech.2014.06.041

  日期：2014.8

  The αvβ3 and α5β1 integrins are widely expressed in different cancer types and recognize the tripeptide Arg-Gly-Asp (RGD) motif present in several extracellular matrix proteins. We report here the design, synthesis and biological activity of some new β-lactam derivatives specifically designed to target integrins. The new molecules contain the azetidinone as the only cyclic framework armed with carboxylic acid and amine terminals spaced from 9 to 14 atoms to switch on recognition by integrins. All tested molecules showed a concentration-dependent enhancement in fibronectin-mediated adhesion of K562 and SK-MEL-24 cells; in particular 1, expressed a higher affinity towards α5β1 integrin (EC50 of 12 nM) and 2 was more selective for integrin αvβ3 (EC50 of 11 nM).