(3R,8aS)-3-甲基八氢吡咯并[1,2-a]吡嗪 | 740787-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: (3R,8aS)-3-甲基八氢吡咯并[1,2-a]吡嗪
• 英文名称: (3R,8AS)-3-methyloctahydropyrrolo[1,2-a]pyrazine
• 英文别名: (3R,8aS)-3-methyl-1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine
• CAS: 740787-48-8
• 化学式: C₈H₁₆N₂
• 分子量: 140.228
• InChiKey: ZUILOGVUGKBLHW-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 5-(chlorocarbonyl)-6,6-dimethyl-3-(picolinamido)-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate 、 (3R,8aS)-3-甲基八氢吡咯并[1,2-a]吡嗪 生成 C₂₅H₃₃N₇O₄
  参考文献：
  名称：

  Identification of novel pyrrolopyrazoles as protein kinase C β II inhibitors

  摘要：

  A novel series of pyrrolopyrazole-based protein kinase C beta II inhibitors has been identified from high-throughput screening. Herein, we report our initial structure-activity relationship studies with a focus on optimizing compound ligand efficiency and physicochemical properties, which has led to potent inhibitors with good cell permeability. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.032
• 作为产物：
  描述：

  3-甲基六氢吡咯并[1,2-a]吡嗪-1,4-二酮 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (3R,8aS)-3-甲基八氢吡咯并[1,2-a]吡嗪
  参考文献：
  名称：

  设计，合成和吲哚-3-羧酰胺双环哌嗪类似物作为新型大麻素CB1受体激动剂的结构-活性关系研究

  摘要：

  合成双环哌嗪衍生物作为N-烷基哌嗪的构象约束类似物，发现其为有效的CB1受体激动剂。CB1受体激动剂活性取决于双环系统手性中心的绝对构型。尽管构象约束不能保护化合物免受N-去烷基化作用的代谢，但发现一些双环类似物比不受约束的先导化合物更有效。化合物8b在体内显示出有效的抗伤害感受活性。

  DOI：

  10.1016/j.bmcl.2010.10.061

文献信息

• PYRROLOTRIAZOLOPYRIMIDINONE DERIVATIVES
  申请人：Laboratorios Almirall, S.A.

  公开号：EP1307458B1

  公开（公告）日：2007-10-03
• Identification of novel pyrrolopyrazoles as protein kinase C β II inhibitors
  作者：Hui Li、Yufeng Hong、Seiji Nukui、Jihong Lou、Sarah Johnson、Stephanie Scales、Iriny Botrous、Eileen Tompkins、Chunfeng Yin、Ru Zhou、Mingying He、Jordan Jensen、Djamal Bouzida、Gordon Alton、Jennifer Lafontaine、Stephan Grant

  DOI：10.1016/j.bmcl.2010.10.032

  日期：2011.1

  A novel series of pyrrolopyrazole-based protein kinase C beta II inhibitors has been identified from high-throughput screening. Herein, we report our initial structure-activity relationship studies with a focus on optimizing compound ligand efficiency and physicochemical properties, which has led to potent inhibitors with good cell permeability. (C) 2010 Elsevier Ltd. All rights reserved.
• Design, synthesis, and structure–activity relationship study of bicyclic piperazine analogs of indole-3-carboxamides as novel cannabinoid CB1 receptor agonists
  作者：Elizabeth M. Moir、Kazuya Yoshiizumi、Jim Cairns、Phillip Cowley、Morag Ferguson、Fiona Jeremiah、Takao Kiyoi、Richard Morphy、Jason Tierney、Grant Wishart、Mark York、James Baker、Jean E. Cottney、Andrea K. Houghton、Petula McPhail、Andrew Osprey、Glenn Walker、Julia M. Adam

  DOI：10.1016/j.bmcl.2010.10.061

  日期：2010.12

  Bicyclic piperazine derivatives were synthesized as conformationally constrained analogs of N-alkyl piperazines and were found to be potent CB1 receptor agonists. The CB1 receptor agonist activity was dependent upon the absolute configuration of the chiral center of the bicyclic ring system. Although the conformational constraint did not protect the compounds from metabolism by N-dealkylation, several

  合成双环哌嗪衍生物作为N-烷基哌嗪的构象约束类似物，发现其为有效的CB1受体激动剂。CB1受体激动剂活性取决于双环系统手性中心的绝对构型。尽管构象约束不能保护化合物免受N-去烷基化作用的代谢，但发现一些双环类似物比不受约束的先导化合物更有效。化合物8b在体内显示出有效的抗伤害感受活性。