ethyl 2-benzoyl-1-(4-(hex-1-yn-1-yl)phenyl)-5-phenyl-1H-pyrrole-3-carboxylate | 1396396-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 2-benzoyl-1-(4-(hex-1-yn-1-yl)phenyl)-5-phenyl-1H-pyrrole-3-carboxylate
• 英文别名: Ethyl 2-benzoyl-1-(4-hex-1-ynylphenyl)-5-phenylpyrrole-3-carboxylate；ethyl 2-benzoyl-1-(4-hex-1-ynylphenyl)-5-phenylpyrrole-3-carboxylate
• CAS: 1396396-25-0
• 化学式: C₃₂H₂₉NO₃
• 分子量: 475.587
• InChiKey: MCWOPCHVPYMKPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴苯乙酮 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 ethyl 2-benzoyl-1-(4-(hex-1-yn-1-yl)phenyl)-5-phenyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Pd-mediated functionalization of polysubstituted pyrroles: Their evaluation as potential inhibitors of PDE4

  摘要：

  Novel polysubstituted pyrroles have been designed and accessed via a one-pot multicomponent reaction followed by Pd-mediated C-C bond forming reactions. All the compounds synthesized were tested for their PDE4B inhibitory properties in vitro and two of them obtained via Heck reaction showed significant inhibition. The docking results suggested that these alkenyl derivatives containing ester moiety interact well with the PDE4B protein in silico where the ester carbonyl oxygen played a key role. The pyrrole framework presented here could be a new template for the identification of small molecule based novel inhibitors of PDE4. The single crystal X-ray data of a representative compound is presented. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.100

文献信息

• Pd-mediated functionalization of polysubstituted pyrroles: Their evaluation as potential inhibitors of PDE4
  作者：T. Bhaskar Kumar、Ch. Sumanth、S. Vaishaly、M. Srinivasa Rao、K.B. Chandra Sekhar、Chandana Lakshmi T. Meda、Ajit Kandale、D. Rambabu、G. Rama Krishna、C. Malla Reddy、K. Shiva Kumar、Kishore V.L. Parsa、Manojit Pal

  DOI：10.1016/j.bmcl.2012.06.100

  日期：2012.9

  Novel polysubstituted pyrroles have been designed and accessed via a one-pot multicomponent reaction followed by Pd-mediated C-C bond forming reactions. All the compounds synthesized were tested for their PDE4B inhibitory properties in vitro and two of them obtained via Heck reaction showed significant inhibition. The docking results suggested that these alkenyl derivatives containing ester moiety interact well with the PDE4B protein in silico where the ester carbonyl oxygen played a key role. The pyrrole framework presented here could be a new template for the identification of small molecule based novel inhibitors of PDE4. The single crystal X-ray data of a representative compound is presented. (C) 2012 Elsevier Ltd. All rights reserved.