5-iodo-2-(4'-methyl-2'-nitrophenylthio)benzoic acid | 1005412-84-9

• 分子结构分类: 有机化合物
• 英文名称: 5-iodo-2-(4'-methyl-2'-nitrophenylthio)benzoic acid
• 英文别名: 5-Iodo-2-(4-methyl-2-nitrophenyl)sulfanylbenzoic acid
• CAS: 1005412-84-9
• 化学式: C₁₄H₁₀INO₄S
• 分子量: 415.208
• InChiKey: ZSAUMDDHVJNONM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-iodo-2-(4'-methyl-2'-nitrophenylthio)benzoic acid 在 N,N-二甲基甲酰胺 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 5-Iodo-2-(4-methyl-2-nitrophenyl)sulfanylbenzoyl chloride
  参考文献：
  名称：

  Synthesis and In Vivo Evaluation of Halogenated N,N-Dimethyl-2-(2′-amino-4′-hydroxymethylphenylthio)benzylamine Derivatives as PET Serotonin Transporter Ligands

  摘要：

  N,N-Dimethyl-2-(2'-amino-4'-hydroxymethylphenylthio)benylamine (38), substituted on ring A, was reported to display high binding affinity and selectivity to the human brain serotonin transporter (SERT). In an attempt to explore the potential of compounds substituted on ring B of the phenylthiophenyl core structure, three derivatives of 38 were synthesized: N,N-dimethyl-2-(2'-amino-4'-hydroxymethyl-phenylthio)-5-fluorobenzylamine (35), N,N-dimethyl-2-(2'-amino-4'-hydroxymethyl-phenylthio)-5-bromobenzylamine (36), and N,N-dimethyl-2-(2'-amino-4'-hydroxymethyl-phenylthio)-5-iodobenzylamine (37). The in vitro binding studies in cells transfected with human SERT, norepinephrine transporter (NET), and dopamine transporter (DAT) showed that 35, 36, and 37 exhibited high SERT affinity with K(i)s (SERT) = 1.26, 0.29, and 0.31 nM (vs [H-3]citalopram), respectively. [C-11-(35), [C-11-(36), and [C-11-(37) were prepared by methylation of their monomethyl precursors 16, 17, and 18, with [C-11]iodomethane in 28, 11, and 14% radiochemical yields, respectively. The microPET images of [C-11-(35), [C-11-(36), and [C-11-(37) showed high uptake in the monkey brain regions rich in SERT with peak midbrain to cerebellum ratios of 3.41, 3.24, and 3.00 at 85 min post-injection, respectively. In vivo bindings of [C-11-(35), [C-11-(36), and [C-11-(37) were shown to be specific to the SERT as displacement with citalopram (a potent SERT ligand) reduced radioactivity in SERT-rich regions to the cerebellum level. These results suggest that [C-11-(35), [C-11-(36), and [C-11-(37) could be potential agents for mapping human SERT by PET and radiolabeling 37 with iodine-123, which could afford the first SPECT SERT imaging agent exhibiting fast kinetics.

  DOI：

  10.1021/jm0707929
• 作为产物：
  描述：

  5-iodo-2-mercaptobenzoic acid 、 4-溴-3-硝基甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以62%的产率得到5-iodo-2-(4'-methyl-2'-nitrophenylthio)benzoic acid
  参考文献：
  名称：

  Synthesis and In Vivo Evaluation of Halogenated N,N-Dimethyl-2-(2′-amino-4′-hydroxymethylphenylthio)benzylamine Derivatives as PET Serotonin Transporter Ligands

  摘要：

  N,N-Dimethyl-2-(2'-amino-4'-hydroxymethylphenylthio)benylamine (38), substituted on ring A, was reported to display high binding affinity and selectivity to the human brain serotonin transporter (SERT). In an attempt to explore the potential of compounds substituted on ring B of the phenylthiophenyl core structure, three derivatives of 38 were synthesized: N,N-dimethyl-2-(2'-amino-4'-hydroxymethyl-phenylthio)-5-fluorobenzylamine (35), N,N-dimethyl-2-(2'-amino-4'-hydroxymethyl-phenylthio)-5-bromobenzylamine (36), and N,N-dimethyl-2-(2'-amino-4'-hydroxymethyl-phenylthio)-5-iodobenzylamine (37). The in vitro binding studies in cells transfected with human SERT, norepinephrine transporter (NET), and dopamine transporter (DAT) showed that 35, 36, and 37 exhibited high SERT affinity with K(i)s (SERT) = 1.26, 0.29, and 0.31 nM (vs [H-3]citalopram), respectively. [C-11-(35), [C-11-(36), and [C-11-(37) were prepared by methylation of their monomethyl precursors 16, 17, and 18, with [C-11]iodomethane in 28, 11, and 14% radiochemical yields, respectively. The microPET images of [C-11-(35), [C-11-(36), and [C-11-(37) showed high uptake in the monkey brain regions rich in SERT with peak midbrain to cerebellum ratios of 3.41, 3.24, and 3.00 at 85 min post-injection, respectively. In vivo bindings of [C-11-(35), [C-11-(36), and [C-11-(37) were shown to be specific to the SERT as displacement with citalopram (a potent SERT ligand) reduced radioactivity in SERT-rich regions to the cerebellum level. These results suggest that [C-11-(35), [C-11-(36), and [C-11-(37) could be potential agents for mapping human SERT by PET and radiolabeling 37 with iodine-123, which could afford the first SPECT SERT imaging agent exhibiting fast kinetics.

  DOI：

  10.1021/jm0707929