4-bromo-N-(3-bromo-4-(3-(dimethylamino)propoxy)phenethyl)-1H-pyrrole-2-carboxamide hydrochloride | 1069472-65-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-bromo-N-(3-bromo-4-(3-(dimethylamino)propoxy)phenethyl)-1H-pyrrole-2-carboxamide hydrochloride
• 英文别名: dispyrin-HCl；4-bromo-N-[2-[3-bromo-4-[3-(dimethylamino)propoxy]phenyl]ethyl]-1H-pyrrole-2-carboxamide;hydrochloride
• CAS: 1069472-65-6
• 化学式: C₁₈H₂₃Br₂N₃O₂*ClH
• 分子量: 509.668
• InChiKey: BOOGVFFLOLCQJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  57.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Dispyrin 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以98%的产率得到4-bromo-N-(3-bromo-4-(3-(dimethylamino)propoxy)phenethyl)-1H-pyrrole-2-carboxamide hydrochloride
  参考文献：
  名称：

  Total Synthesis and Biological Evaluation of the Marine Bromopyrrole Alkaloid Dispyrin: Elucidation of Discrete Molecular Targets with Therapeutic Potential

  摘要：

  The first total synthesis of dispyrin, a recently reported bromopyrrole alkaloid from Agelas dispar with an unprecedented bromopyrrole tyramine motif, was achieved in three steps on a gram scale (69.4% overall). No biological activity was reported for dispyrin, so we evaluated synthetic dispyrin against > 200 discrete molecular targets in radioligand binding and functional assays. Unlike most marine natural products, dispyrin (1) possesses no antibacterial or anticancer activity, but was found to be it potent ligand and antagonist of several therapeutically relevant GPCRs, the alpha(1D) and alpha(2A) adrenergic receptors and the H2 and H3 histamine receptors.

  DOI：

  10.1021/np800339e

文献信息

• Total Synthesis and Biological Evaluation of the Marine Bromopyrrole Alkaloid Dispyrin: Elucidation of Discrete Molecular Targets with Therapeutic Potential
  作者：J. Phillip Kennedy、John T. Brogan、Craig W. Lindsley

  DOI：10.1021/np800339e

  日期：2008.10.24

  The first total synthesis of dispyrin, a recently reported bromopyrrole alkaloid from Agelas dispar with an unprecedented bromopyrrole tyramine motif, was achieved in three steps on a gram scale (69.4% overall). No biological activity was reported for dispyrin, so we evaluated synthetic dispyrin against > 200 discrete molecular targets in radioligand binding and functional assays. Unlike most marine natural products, dispyrin (1) possesses no antibacterial or anticancer activity, but was found to be it potent ligand and antagonist of several therapeutically relevant GPCRs, the alpha(1D) and alpha(2A) adrenergic receptors and the H2 and H3 histamine receptors.