cyclopentyl 2-(2-(thiophen-2-yl)acetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate trifluoroacetic acid | 1360058-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: cyclopentyl 2-(2-(thiophen-2-yl)acetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate trifluoroacetic acid
• CAS: 1360058-94-1
• 化学式: C₂HF₃O₂*C₁₉H₂₂N₂O₃S₂
• 分子量: 504.551
• InChiKey: HXFBDKWDYWXCHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  104.73
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  cyclopentyl 2-(2-(thiophen-2-yl)acetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate trifluoroacetic acid 、 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29%的产率得到cyclopentyl 6-(ethylcarbamoyl)-2-(2-(thiophen-2-yl)acetamido)-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：

  2-噻吩乙酸 在 2,4,6-三甲基吡啶 、 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 cyclopentyl 2-(2-(thiophen-2-yl)acetamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate trifluoroacetic acid
  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