N-(2-hydroxypropyl)-4-methyl-N-(4-methylphenyl)benzenesulfonamide | 1616490-60-8

• 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: N-(2-hydroxypropyl)-4-methyl-N-(4-methylphenyl)benzenesulfonamide
• CAS: 1616490-60-8
• 化学式: C₁₇H₂₁NO₃S
• 分子量: 319.425
• InChiKey: PJPOZBIKUPZAPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.61
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxypropyl)-4-methyl-N-(4-methylphenyl)benzenesulfonamide 在 [18F]-tetrabutylammonium fluoride 、 三甲胺盐酸盐 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 C₁₇H₂₀⁽¹⁸⁾FNO₂S
  参考文献：
  名称：

  Synthesis and evaluation of 18F-labeled tertiary benzenesulfonamides for imaging carbonic anhydrase IX expression in tumours with positron emission tomography

  摘要：

  Three tertiary benzenesulfonamide inhibitors 4a-c were radiolabeled with F-18 and evaluated for imaging carbonic anhydrase IX (CA IX) expression with positron emission tomography. All three inhibitors exhibit <10 nM affinity for CA IX with no measurable affinity for CA II. Despite good affinity/selectivity to CA IX and excellent stability in plasma, uptake of [F-18]4a-c in CA IX-expressing HT-29 tumours was low without significant contrast. [F-18]4a,b were excreted rapidly, while [F-18]4c exhibited significant in vivo defluorination leading to high bone uptake. Due to minimal uptake in HT-29 tumours compared to normal organs/tissues, F-18-labeled benzenesulfonamides [F-18]4a-c are not suitable as CA IX imaging agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.021
• 作为产物：
  描述：

  N-对甲苯基-对甲苯磺胺 、 methyloxirane 以 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到N-(2-hydroxypropyl)-4-methyl-N-(4-methylphenyl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis and evaluation of 18F-labeled tertiary benzenesulfonamides for imaging carbonic anhydrase IX expression in tumours with positron emission tomography

  摘要：

  Three tertiary benzenesulfonamide inhibitors 4a-c were radiolabeled with F-18 and evaluated for imaging carbonic anhydrase IX (CA IX) expression with positron emission tomography. All three inhibitors exhibit <10 nM affinity for CA IX with no measurable affinity for CA II. Despite good affinity/selectivity to CA IX and excellent stability in plasma, uptake of [F-18]4a-c in CA IX-expressing HT-29 tumours was low without significant contrast. [F-18]4a,b were excreted rapidly, while [F-18]4c exhibited significant in vivo defluorination leading to high bone uptake. Due to minimal uptake in HT-29 tumours compared to normal organs/tissues, F-18-labeled benzenesulfonamides [F-18]4a-c are not suitable as CA IX imaging agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.021