3-hydroxy-4-{{1-[2-(benzyloxy)naphthalen-1-yl]methanoyl}amino}naphthalene-1-sulfonic acid | 374924-82-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-hydroxy-4-{{1-[2-(benzyloxy)naphthalen-1-yl]methanoyl}amino}naphthalene-1-sulfonic acid
• 英文别名: 3-Hydroxy-4-[(2-phenylmethoxynaphthalene-1-carbonyl)amino]naphthalene-1-sulfonic acid
• CAS: 374924-82-0
• 化学式: C₂₈H₂₁NO₆S
• 分子量: 499.544
• InChiKey: HXTVYDRRBAJRAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-hydroxy-4-{{1-[2-(benzyloxy)naphthalen-1-yl]methanoyl}amino}naphthalene-1-sulfonic acid 在 10percent Pd/C 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 3.0h， 以53%的产率得到3-Hydroxy-4-[(2-hydroxynaphthalene-1-carbonyl)amino]naphthalene-1-sulfonic acid
  参考文献：
  名称：

  Hydrazinonaphthalene and Azonaphthalene Thrombopoietin Mimics Are Nonpeptidyl Promoters of Megakaryocytopoiesis

  摘要：

  High-throughput screening for the induction of a luciferase reporter gene in a thrombopoietin (TPO)-responsive cell line resulted in the identification of 4-diazo-3-hydroxy-1-naphthalene-sulfonic acids as TPO mimics. Modification of the core structure and adjustment of unwanted functionality resulted in the development of (5-oxo-1,5-dihydropyrazol-4-ylidene)hydrazines which exhibited efficacies equivalent to those of TPO in several cell-based assays designed to measure thrombopoietic activity. Furthermore, these compounds elicited biochemical responses in TPO-receptor-expressing cells similar to those in TPO itself, including kinase activation and protein phosphorylation. Potencies for the best compounds were high for such low molecular weight compounds (MW < 500) with EC50 values in the region of 1-20 nM.

  DOI：

  10.1021/jm010283l
• 作为产物：
  描述：

  2-苄氧基-1-萘醛 在 吡啶 、 4-二甲氨基吡啶 、 sodium chlorite 、 草酰氯 、 氨基磺酸 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 25.02h， 生成 3-hydroxy-4-{{1-[2-(benzyloxy)naphthalen-1-yl]methanoyl}amino}naphthalene-1-sulfonic acid
  参考文献：
  名称：

  Hydrazinonaphthalene and Azonaphthalene Thrombopoietin Mimics Are Nonpeptidyl Promoters of Megakaryocytopoiesis

  摘要：

  High-throughput screening for the induction of a luciferase reporter gene in a thrombopoietin (TPO)-responsive cell line resulted in the identification of 4-diazo-3-hydroxy-1-naphthalene-sulfonic acids as TPO mimics. Modification of the core structure and adjustment of unwanted functionality resulted in the development of (5-oxo-1,5-dihydropyrazol-4-ylidene)hydrazines which exhibited efficacies equivalent to those of TPO in several cell-based assays designed to measure thrombopoietic activity. Furthermore, these compounds elicited biochemical responses in TPO-receptor-expressing cells similar to those in TPO itself, including kinase activation and protein phosphorylation. Potencies for the best compounds were high for such low molecular weight compounds (MW < 500) with EC50 values in the region of 1-20 nM.

  DOI：

  10.1021/jm010283l