(3aR,6aR)-1-[4'-(5-methyl-octahydro-pyrrolo[3,4-b]pyrrol-1-yl)-biphenyl-4-yl]-ethanone | 948845-59-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,6aR)-1-[4'-(5-methyl-octahydro-pyrrolo[3,4-b]pyrrol-1-yl)-biphenyl-4-yl]-ethanone
• 英文别名: 1-[4'-((3aR,6aR)-5-methyl-octahydro-pyrrolo[3,4-b]pyrrol-1-yl)-biphenyl-4-yl]-ethanone；(3aR,6aR)-1-[40-(5-Methyl-hexahydro-pyrrolo[3,4-b]pyrrol-1-yl)-biphenyl-4-yl]-ethanone；1-[4-[4-[(3aR,6aR)-5-methyl-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrol-1-yl]phenyl]phenyl]ethanone
• CAS: 948845-59-8
• 化学式: C₂₁H₂₄N₂O
• 分子量: 320.434
• InChiKey: NCLNAQYDNSHAQF-CTNGQTDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aR,6aR)-1-[4'-(5-methyl-octahydro-pyrrolo[3,4-b]pyrrol-1-yl)-biphenyl-4-yl]-ethanone 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 (1E)-1-(4'-[(3aR,6aR)-5-methyl-octahydro-pyrrolo[3,4-b]pyrrol-1-yl]-biphenyl-4-yl)ethanone oxime
  参考文献：
  名称：

  WO2007/100990

  摘要：

  公开号：
• 作为产物：
  描述：

  (3aR,6aR)-5-methyl-2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-b]pyrrole 、 4-乙酰基-4-溴代联苯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 以53.2%的产率得到(3aR,6aR)-1-[4'-(5-methyl-octahydro-pyrrolo[3,4-b]pyrrol-1-yl)-biphenyl-4-yl]-ethanone
  参考文献：
  名称：

  Design of a New Histamine H₃ Receptor Antagonist Chemotype: (3aR,6aR)-5-Alkyl-1-aryl-octahydropyrrolo[3,4-b]pyrroles, Synthesis, and Structure−Activity Relationships

  摘要：

  A new histamine H-3 receptor (H3R) antagonist chemotype 1 was designed by combining key pharmacophoric elements from two different precursor structural series and then simplifying and optimizing the resulting combined structural features. First, analogues were made based oil a previously identified conessine-based H3R. antagonist series. While the first analogues 11 and 15 showed no antagonistic activity to H3R, the mere addition of a key moiety found in the reference compound 7 (ABT-239) elevated the series to high potency at H3R. The hybrid structure (16b) was judged too synthetically demanding to enable an extensive SAR study, thus forcing a strategy to simplify the chemical structure. The resulting (3aR,6aR)-5-alkyl-1-aryl-octahydropyrrolo[3,4-b]pyrrole series proved to be highly potent, as exemplified by 17a having a human H-3 K-i of 0.54 nM, rat H-3 K-i of 4.57 nM, and excellent pharmacokinetics (PK) profile in rats (oral bioavailability of 39% and t(1/2) of 2.4 h).

  DOI：

  10.1021/jm900480x

文献信息

• Octahydro-pyrrolo[3,4-b]pyrrole Derivatives
  申请人：Cowart D. Marlon

  公开号：US20070232612A1

  公开（公告）日：2007-10-04

  Octahydro-pyrrolo[3,4-b]pyrrole derivatives are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands, Octahydro-pyrrolo[3,4-b]pyrrole compounds, methods for using such compounds, compositions for making them, and processes for preparing such compounds are disclosed herein.

  本文披露了八氢吡咯并[3,4-b]吡咯衍生物在治疗由组胺-3受体配体预防或改善的疾病或疾患方面的用途，包括八氢吡咯并[3,4-b]吡咯化合物，使用这种化合物的方法，制备它们的组合物以及制备这种化合物的过程。
• OCTAHYDRO-PYRROLO[3,4-B]PYRROLE DERIVATIVES
  申请人：Cowart Marlon D.

  公开号：US20100222358A1

  公开（公告）日：2010-09-02

  Octahydro-pyrrolo[3,4-b]pyrrole derivatives are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Octahydro-pyrrolo[3,4-b]pyrrole compounds, methods for using such compounds, compositions for making them, and processes for preparing such compounds are disclosed herein.

  八氢吡咯并[3,4-b]吡咯衍生物在治疗因组胺-3受体配体预防或改善的疾病或疾患中具有用途。本文揭示了八氢吡咯并[3,4-b]吡咯化合物，使用这种化合物的方法，制备它们的组合物以及制备这种化合物的过程。
• US7728031B2
  申请人：——

  公开号：US7728031B2

  公开（公告）日：2010-06-01
• US8399468B2
  申请人：——

  公开号：US8399468B2

  公开（公告）日：2013-03-19
• WO2007/100990
  申请人：——

  公开号：——

  公开（公告）日：——