Dispyrin | 934995-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Dispyrin
• 英文别名: 4-bromo-N-(3-bromo-4-(3-(dimethylamino)propoxy)phenethyl)-1H-pyrrole-2-carboxamide；4-bromo-N-[2-[3-bromo-4-[3-(dimethylamino)propoxy]phenyl]ethyl]-1H-pyrrole-2-carboxamide
• CAS: 934995-58-1
• 化学式: C₁₈H₂₃Br₂N₃O₂
• 分子量: 473.208
• InChiKey: MOWCGUQGNSAZSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 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：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-(3-溴-4-甲氧基苯基)乙胺 在 三溴化硼 、 1-羟基苯并三唑 、 caesium carbonate 、 N,N-二异丙基乙胺 、 potassium iodide 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -78.0~160.0 ℃ 、101.33 kPa 条件下， 反应 13.83h， 生成 Dispyrin
  参考文献：
  名称：

  [EN] UNNATURAL DISPYRIN ANALOGUES, PREPARATION AND USES THEREOF
  [FR] ANALOGUES DE DYSPYRINE NON NATURELS, LEURS PRÉPARATIONS ET LEURS UTILISATIONS

  摘要：

  本公开揭示了作为H3受体活性调节剂有用的dispyrin类似化合物，制备方法，包含同样化合物的药物组合物，以及使用同样化合物治疗与组胺H3受体活性相关的神经和精神障碍的方法。在一个方面，所公开的类似物可以具有以下式表示的结构：（I）。本摘要旨在作为在特定领域进行搜索的扫描工具，不打算限制本发明。

  公开号：

  WO2009152071A1

文献信息

• A novel class of H3 antagonists derived from the natural product guided synthesis of unnatural analogs of the marine bromopyrrole alkaloid dispyrin
  作者：J. Phillip Kennedy、P. Jeffrey Conn、Craig W. Lindsley

  DOI：10.1016/j.bmcl.2009.04.106

  日期：2009.6

  Letter describes the natural product guided synthesis of unnatural analogs of the marine bromopyrrole alkaloid dispyrin, and the resulting SAR of H3 antagonism. Multiple rounds of iterative parallel synthesis improved human H3 IC50 ∼33-fold, and afforded a new class of H3 antagonists based on the novel bromotyramine core of dispyrin.

  这封信描述了天然产物引导合成的海洋溴吡咯生物碱 dispyrin 的非天然类似物，以及由此产生的 H 3拮抗作用的SAR 。多轮迭代平行合成将人类 H 3 IC提高了50 ∼33 倍，并提供了一类新的 H 3拮抗剂，该拮抗剂基于新的双吡啉溴酪胺核心。
• Total Synthesis of Dispyrin, Purpurealidin E, and Aplysamine-1
  作者：Makoto Yoshida、Kentaro Yamaguchi

  DOI：10.1248/cpb.56.1362

  日期：——

  Bromotyrosine alkaloids dispyrin (1), purpurealidin E (2), and aplysamine-1 (3) isolated from marine sponge, were synthesized from commercially available tyramine (4) as a common starting material. The overall yield was 18%, 39%, and 22% for 1 from 4 in 5 steps, 2 in 5 steps, and 3 in 6 steps, respectively.

  以市面上常见的酪胺（4）为起始原料，合成了从海洋海绵中分离出来的溴代酪氨酸生物碱dispyrin（1）、purpurealidin E（2）和aplysamine-1（3）。通过 5 个步骤从 4 中合成 1，通过 5 个步骤合成 2，通过 6 个步骤合成 3，总收率分别为 18%、39% 和 22%。
• UNNATURAL DISPYRIN ANALOGUES, PREPARATION AND USES THEREOF
  申请人：Lindsley Craig W.

  公开号：US20100035929A1

  公开（公告）日：2010-02-11

  Disclosed are dispyrin analogue compounds useful as H3 receptor activity modulators, methods of making same, pharmaceutical compositions comprising same, and methods of treating neurological and psychiatric disorders associated with histamine H3 receptor activity using same. In one aspect, the disclosed analogues can have a structure represented by a formula: This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.