tert-butyl 2-(2-(4'-(2-chloroacetamido)biphenyl-4-ylsulfonyl)phenyl)acetate | 1427565-63-6

• 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: tert-butyl 2-(2-(4'-(2-chloroacetamido)biphenyl-4-ylsulfonyl)phenyl)acetate
• 英文别名: Tert-butyl 2-[2-[4-[4-[(2-chloroacetyl)amino]phenyl]phenyl]sulfonylphenyl]acetate；tert-butyl 2-[2-[4-[4-[(2-chloroacetyl)amino]phenyl]phenyl]sulfonylphenyl]acetate
• CAS: 1427565-63-6
• 化学式: C₂₆H₂₆ClNO₅S
• 分子量: 500.015
• InChiKey: UTZADVZEWMISER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(2-(4'-(2-chloroacetamido)biphenyl-4-ylsulfonyl)phenyl)acetate 在 2-(2-(4-bromophenylthio)phenyl)acetic acid 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 0.37h， 生成 [¹⁸F]-2-(2-(4'-(2-fluoroacetamido)biphenyl-4-ylsulfonyl)phenyl)acetic acid
  参考文献：
  名称：

  Synthesis and Preliminary Evaluation in Tumor Bearing Mice of New ¹⁸F-Labeled Arylsulfone Matrix Metalloproteinase Inhibitors as Tracers for Positron Emission Tomography

  摘要：

  New fluorinated, arylsulfone-based matrix metalloproteinase (MMP) inhibitors containing carboxylate as the zinc binding group were synthesized as radiotracers for positron emission tomography. Inhibitors were characterized by K-i for MMP-2 in the nanomolar range and by a fair selectivity for MMP-2/9/12/13 over MMP-1/3/14. Two of these compounds were obtained in the F-18-radiolabeled form, with radiochemical purity and yield suitable for preliminary studies in mice xenografted with a human U-87 MG glioblastoma. Target density in xenografts was assessed by Western blot, yielding B-max/K-d = 14. The biodistribution of the tracer was dominated by liver uptake and hepatobiliary clearance. Tumor uptake of F-18-labeled MMP inhibitors was about 30% that of [F-18]fluorodeoxyglucose. Accumulation of radioactivity within the tumor periphery colocalized with MMP-2 activity (evaluated by in situ zimography). However, specific tumor uptake accounted for only 18% of total uptake. The aspecific uptake was ascribed to the high binding affinity between the radiotracer and serum albumin.

  DOI：

  10.1021/jm4001743
• 作为产物：
  描述：

  2-碘苯乙酸 在 potassium phosphate 、 四(三苯基膦)钯 、 oxone||potassium monopersulfate triple salt 、 铜 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0~140.0 ℃ 、689.49 kPa 条件下， 反应 28.2h， 生成 tert-butyl 2-(2-(4'-(2-chloroacetamido)biphenyl-4-ylsulfonyl)phenyl)acetate
  参考文献：
  名称：

  Synthesis and Preliminary Evaluation in Tumor Bearing Mice of New ¹⁸F-Labeled Arylsulfone Matrix Metalloproteinase Inhibitors as Tracers for Positron Emission Tomography

  摘要：

  New fluorinated, arylsulfone-based matrix metalloproteinase (MMP) inhibitors containing carboxylate as the zinc binding group were synthesized as radiotracers for positron emission tomography. Inhibitors were characterized by K-i for MMP-2 in the nanomolar range and by a fair selectivity for MMP-2/9/12/13 over MMP-1/3/14. Two of these compounds were obtained in the F-18-radiolabeled form, with radiochemical purity and yield suitable for preliminary studies in mice xenografted with a human U-87 MG glioblastoma. Target density in xenografts was assessed by Western blot, yielding B-max/K-d = 14. The biodistribution of the tracer was dominated by liver uptake and hepatobiliary clearance. Tumor uptake of F-18-labeled MMP inhibitors was about 30% that of [F-18]fluorodeoxyglucose. Accumulation of radioactivity within the tumor periphery colocalized with MMP-2 activity (evaluated by in situ zimography). However, specific tumor uptake accounted for only 18% of total uptake. The aspecific uptake was ascribed to the high binding affinity between the radiotracer and serum albumin.

  DOI：

  10.1021/jm4001743