methyl 4-(4-nitrophenoxy)thieno[2,3-c]pyridine-2-carboxylate | 402582-11-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-(4-nitrophenoxy)thieno[2,3-c]pyridine-2-carboxylate
• CAS: 402582-11-0
• 化学式: C₁₅H₁₀N₂O₅S
• 分子量: 330.321
• InChiKey: OIPQNQGUMVKMBO-UHFFFAOYSA-N

物化性质

• 沸点：
  503.8±45.0 °C(Predicted)
• 密度：
  1.457±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4-(4-nitrophenoxy)thieno[2,3-c]pyridine-2-carboxylate 在 10percent Pd/C 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 42.0h， 以75%的产率得到methyl 4-(4-aminophenoxy)thieno[2,3-c]pyridine-2-carboxylate
  参考文献：
  名称：

  Synthesis and Mode of Action of ¹²⁵I- and ³H-Labeled Thieno[2,3-c]pyridine Antagonists of Cell Adhesion Molecule Expression

  摘要：

  A series of thieno[2,3-c]pyridine antagonists of cell adhesion molecule (CAM) expression, such as A-205804 (1) and A-249377 (2), selectively suppressed the induced expression of E-selectin and ICAM-1 over VCAM-1. In an effort to explore the biological mechanism of action of these inhibitors, we synthesized I-125- and H-3-labeled thieno[2,3-c]pyridines 5 and 6. An isolated diazonium tetrafluoroborate salt efficiently trapped (NaI)-I-125 on very small scale (7.5 mug of (NaI)-I-125), providing the corresponding I-125-labeled thieno[2,3-c]pyridine in modest yield. Preliminary mechanistic investigations using these radiolabeled compounds revealed that, upon incubation with human umbilical vein endothelial cells (HUVECs), these inhibitors of CAM expression translocated to the cell nucleus and were noncovalently associated with macromolecules of molecular weight greater than 650 kDa.

  DOI：

  10.1021/jo016171j
• 作为产物：
  描述：

  3,5-二氯吡啶-4-甲醛 在 硫酸 、 potassium tert-butylate 、 caesium carbonate 、 potassium nitrate 作用下， 以 四氢呋喃 为溶剂， 反应 3.58h， 生成 methyl 4-(4-nitrophenoxy)thieno[2,3-c]pyridine-2-carboxylate
  参考文献：
  名称：

  Synthesis and Mode of Action of ¹²⁵I- and ³H-Labeled Thieno[2,3-c]pyridine Antagonists of Cell Adhesion Molecule Expression

  摘要：

  A series of thieno[2,3-c]pyridine antagonists of cell adhesion molecule (CAM) expression, such as A-205804 (1) and A-249377 (2), selectively suppressed the induced expression of E-selectin and ICAM-1 over VCAM-1. In an effort to explore the biological mechanism of action of these inhibitors, we synthesized I-125- and H-3-labeled thieno[2,3-c]pyridines 5 and 6. An isolated diazonium tetrafluoroborate salt efficiently trapped (NaI)-I-125 on very small scale (7.5 mug of (NaI)-I-125), providing the corresponding I-125-labeled thieno[2,3-c]pyridine in modest yield. Preliminary mechanistic investigations using these radiolabeled compounds revealed that, upon incubation with human umbilical vein endothelial cells (HUVECs), these inhibitors of CAM expression translocated to the cell nucleus and were noncovalently associated with macromolecules of molecular weight greater than 650 kDa.

  DOI：

  10.1021/jo016171j

文献信息

• Synthesis and Mode of Action of ¹²⁵I- and ³H-Labeled Thieno[2,3-<i>c</i>]pyridine Antagonists of Cell Adhesion Molecule Expression
  作者：Gui-Dong Zhu、Verlyn Schaefer、Steven A. Boyd、Gregory F. Okasinski

  DOI：10.1021/jo016171j

  日期：2002.2.1

  A series of thieno[2,3-c]pyridine antagonists of cell adhesion molecule (CAM) expression, such as A-205804 (1) and A-249377 (2), selectively suppressed the induced expression of E-selectin and ICAM-1 over VCAM-1. In an effort to explore the biological mechanism of action of these inhibitors, we synthesized I-125- and H-3-labeled thieno[2,3-c]pyridines 5 and 6. An isolated diazonium tetrafluoroborate salt efficiently trapped (NaI)-I-125 on very small scale (7.5 mug of (NaI)-I-125), providing the corresponding I-125-labeled thieno[2,3-c]pyridine in modest yield. Preliminary mechanistic investigations using these radiolabeled compounds revealed that, upon incubation with human umbilical vein endothelial cells (HUVECs), these inhibitors of CAM expression translocated to the cell nucleus and were noncovalently associated with macromolecules of molecular weight greater than 650 kDa.