5-氨基-2-(苯基硫基)苯甲酸甲酯 | 361336-73-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 5-氨基-2-(苯基硫基)苯甲酸甲酯
• 英文名称: methyl 5-amino-2-(phenylthio)benzoate
• 英文别名: 5-Amino-2-phenylsulfanyl-benzoic acid methyl ester；methyl 5-amino-2-phenylsulfanylbenzoate
• CAS: 361336-73-4
• 化学式: C₁₄H₁₃NO₂S
• mdl: MFCD06658472
• 分子量: 259.329
• InChiKey: KXTIPIDMAUQQJF-UHFFFAOYSA-N

物化性质

• 沸点：
  429.8±35.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  5-氨基-2-(苯基硫基)苯甲酸甲酯 、 苄磺酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以49%的产率得到methyl 5-[bis(benzylsulfonyl)amino]-2-(phenylthio)benzoate
  参考文献：
  名称：

  Synthesis and Crystal Structures of Substituted Benzenes and Benzoquinones as Tissue Factor VIIa Inhibitors

  摘要：

  Several multistep syntheses of substituted benzenes are reported. The benzene analogues were designed such that their substitution pattern would occupy and interact with the S-1, S-2, and S-3 pockets of the tissue Factor VIIa enzyme. A variety of chemical transformations including nucleophilic additions, reductive aminations, Stille couplings, and polymer-assisted solution-phase (PASP) techniques were used to prepare key intermediates and final products. The initial analogues identified some weakly active compounds which ultimately led to a 340 nM (IC50) tissue Factor VIIa inhibitor with selectivity over other related enzymes. The structure-activity relationship of these inhibitors and the synthetic progression from the discovery of the lead compound to the development of potent analogues will be discussed. The X-ray crystal structures of fluorobenzene 50c and benzoquinone 54 inhibitors complexed with the TF/VIIa enzyme will also be described.

  DOI：

  10.1021/jm030233b
• 作为产物：
  描述：

  methyl 5-nitro-2-(phenylthio)benzoate 在 铁粉 、 溶剂黄146 作用下， 以75%的产率得到5-氨基-2-(苯基硫基)苯甲酸甲酯
  参考文献：
  名称：

  Synthesis and Crystal Structures of Substituted Benzenes and Benzoquinones as Tissue Factor VIIa Inhibitors

  摘要：

  Several multistep syntheses of substituted benzenes are reported. The benzene analogues were designed such that their substitution pattern would occupy and interact with the S-1, S-2, and S-3 pockets of the tissue Factor VIIa enzyme. A variety of chemical transformations including nucleophilic additions, reductive aminations, Stille couplings, and polymer-assisted solution-phase (PASP) techniques were used to prepare key intermediates and final products. The initial analogues identified some weakly active compounds which ultimately led to a 340 nM (IC50) tissue Factor VIIa inhibitor with selectivity over other related enzymes. The structure-activity relationship of these inhibitors and the synthetic progression from the discovery of the lead compound to the development of potent analogues will be discussed. The X-ray crystal structures of fluorobenzene 50c and benzoquinone 54 inhibitors complexed with the TF/VIIa enzyme will also be described.

  DOI：

  10.1021/jm030233b