ethyl 2-(2-phenylacetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate | 1351512-20-3

• 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: ethyl 2-(2-phenylacetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate
• 英文别名: Ethyl 2-[(2-phenylacetyl)amino]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate
• CAS: 1351512-20-3
• 化学式: C₁₈H₂₀N₂O₃S
• 分子量: 344.434
• InChiKey: DZPINZGHIYALDE-UHFFFAOYSA-N

物化性质

• 沸点：
  604.3±55.0 °C(predicted)
• 密度：
  1.275±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-phenylacetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate 、 异氰酸乙酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以7%的产率得到ethyl 6-(ethylcarbamoyl)-2-(2-phenylacetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate
  参考文献：
  名称：

  Thiophene inhibitors of PDE4: Crystal structures show a second binding mode at the catalytic domain of PDE4D2

  摘要：

  PDE4 inhibitors have been identified as therapeutic targets for a variety of conditions, particularly inflammatory diseases. We have serendipitously identified a novel class of phosphodiesterase 4 (PDE4) inhibitor during a study to discover antagonists of the parathyroid hormone receptor. X-ray crystallographic studies of PDE4D2 complexed to four potent inhibitors reveal the atomic details of how they inhibit the enzyme and a notable contrast to another recently reported thiophene-based inhibitor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.109
• 作为产物：
  描述：

  氰乙酸乙酯 在 吗啉 、 sulfur 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 48.5h， 生成 ethyl 2-(2-phenylacetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate
  参考文献：
  名称：

  Thiophene inhibitors of PDE4: Crystal structures show a second binding mode at the catalytic domain of PDE4D2

  摘要：

  PDE4 inhibitors have been identified as therapeutic targets for a variety of conditions, particularly inflammatory diseases. We have serendipitously identified a novel class of phosphodiesterase 4 (PDE4) inhibitor during a study to discover antagonists of the parathyroid hormone receptor. X-ray crystallographic studies of PDE4D2 complexed to four potent inhibitors reveal the atomic details of how they inhibit the enzyme and a notable contrast to another recently reported thiophene-based inhibitor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.109

文献信息

• Thiophene inhibitors of PDE4: Crystal structures show a second binding mode at the catalytic domain of PDE4D2
  作者：Jacob L. Nankervis、Susanne C. Feil、Nancy C. Hancock、Zhaohua Zheng、Hooi-Ling Ng、Craig J. Morton、Jessica K. Holien、Patricia W.M. Ho、Mark M. Frazzetto、Ian G. Jennings、David T. Manallack、T. John Martin、Philip E. Thompson、Michael W. Parker

  DOI：10.1016/j.bmcl.2011.09.109

  日期：2011.12

  PDE4 inhibitors have been identified as therapeutic targets for a variety of conditions, particularly inflammatory diseases. We have serendipitously identified a novel class of phosphodiesterase 4 (PDE4) inhibitor during a study to discover antagonists of the parathyroid hormone receptor. X-ray crystallographic studies of PDE4D2 complexed to four potent inhibitors reveal the atomic details of how they inhibit the enzyme and a notable contrast to another recently reported thiophene-based inhibitor. (C) 2011 Elsevier Ltd. All rights reserved.