5-(1-ethylpropyl)-3,7-dimethyl-2-(6-methyl-1,3-benzodioxol-5-yl)pyrrolo[1,2-b]pyridazine | 941693-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(1-ethylpropyl)-3,7-dimethyl-2-(6-methyl-1,3-benzodioxol-5-yl)pyrrolo[1,2-b]pyridazine
• 英文别名: 3,7-Dimethyl-2-(6-methyl-1,3-benzodioxol-5-yl)-5-pentan-3-ylpyrrolo[1,2-b]pyridazine
• CAS: 941693-99-8
• 化学式: C₂₂H₂₆N₂O₂
• 分子量: 350.461
• InChiKey: UBDBGSWWAIWABV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  35.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-(1-ethylpropenyl)-3,7-dimethyl-2-(6-methylbenzo[1,3]dioxol-5-yl)-pyrrolo[1,2-b]pyridazine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 5-(1-ethylpropyl)-3,7-dimethyl-2-(6-methyl-1,3-benzodioxol-5-yl)pyrrolo[1,2-b]pyridazine
  参考文献：
  名称：

  Pyrrolo[1,2-b]pyridazines, pyrrolo[2,1-f]triazin-4(3H)-ones, and related compounds as novel corticotropin-releasing factor 1 (CRF1) receptor antagonists

  摘要：

  To identify structurally novel corticotropin-releasing factor 1 (CRF1) receptor antagonists, a series of bicyclic core analogs pyrrolo[1,2-b]pyridazines and pyrrolo[2,1-f]triazin-4(3H)-ones, which were designed based on a monocyclic core antagonist, was synthesized and evaluated. Among the compounds tested, 2-difluoromethoxy-4-methylpyridin-5-yl analog 27 was found to show efficacy in a dose-dependent manner in an elevated plus maze test in rats. The discovery process and structure-activity relationship is presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.015

文献信息

• Bicyclic Heterocyclic Compound
  申请人：Nakai Hisao

  公开号：US20100184771A1

  公开（公告）日：2010-07-22

  A compound represented by the formula (I), a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrug thereof: wherein X 1 represents N and X 2 represents C, or X 1 represents C and X 2 represents N; Y 1 represents CR 4 or N; Y 2 represents CH or N; wherein both Y 1 and Y 2 do not represent N at the same time; R 1 represents (1) C3-10 branched alkyl which may be substituted or (2) —(CH 2 ) m —NR 5 R 6 ; R 2 , R 3 , and R 4 each independently represent H, C1-4 alkyl, a halo-substituted C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, or the like; R 5 and R 6 each independently represent C1-6 alkyl which may be substituted, or R 5 represents H, and R 6 represents C3-6 branched alkyl which may be substituted; and Ar represents an aromatic ring which may be substituted, is useful as a pharmacologically active ingredient having a CRF antagonistic activity in preventing and/or treating neuropsychiatric diseases, diseases of peripheral organs or the like.

  化合物的化学式为(I)，其盐，N-氧化物，溶剂合物或前药：其中X1代表N，X2代表C，或者X1代表C，X2代表N；Y1代表CR4或N；Y2代表CH或N；其中Y1和Y2不能同时代表N；R1代表(1) C3-10支链烷基，可以被取代或(2) -(CH2)m-NR5R6; R2、R3和R4各自独立地代表H、C1-4烷基、卤代C1-4烷基、C2-4烯基、C2-4炔基或类似物；R5和R6各自独立地代表C1-6烷基，可以被取代，或者R5代表H，R6代表C3-6支链烷基，可以被取代；Ar代表一个芳香环，可以被取代，其在预防和/或治疗神经精神疾病、外周器官疾病或类似疾病方面具有CRF拮抗活性的药理活性成分。
• BICYCLIC HETEROCYCLIC COMPOUND
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1961754A1

  公开（公告）日：2008-08-27

  A compound represented by the formula (I), a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrug thereof: wherein X1 represents N and X2 represents C, or X1 represents C and X2 represents N; Y1 represents CR4 or N; Y2 represents CH or N; wherein both Y1 and Y2 do not represent N at the same time; R1 represents (1) C3-10 branched alkyl which may be substituted or (2) -(CH2)m-NR5R6;R2, R3, and R4 each independently represent H, C1-4 alkyl, a halo-substituted C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, or the like; R5 and R6 each independently represent C1-6 alkyl which may be substituted, or R5 represents H, and R6 represents C3-6 branched alkyl which may be substituted; and Ar represents an aromatic ring which may be substituted, is useful as a pharmacologically active ingredient having a CRF antagonistic activity in preventing and/or treating neuropsychiatric diseases, diseases of peripheral organs or the like.

  由式 (I) 代表的化合物、其盐、其 N-氧化物、其溶液或其原药： 其中 X1 代表 N，X2 代表 C，或 X1 代表 C，X2 代表 N； Y1 代表 CR4 或 N Y2 代表 CH 或 N； 其中 Y1 和 Y2 不同时代表 N； R1代表(1)可被取代的C3-10支链烷基或(2)-(CH2)m-NR5R6；R2、R3和R4各自独立地代表H、C1-4烷基、卤代C1-4烷基、C2-4烯基、C2-4炔基或类似物； R5 和 R6 各自独立地代表可被取代的 C1-6 烷基，或 R5 代表 H，R6 代表可被取代的 C3-6 支链烷基；以及 Ar 代表可被取代的芳香环，可用作具有 CRF 拮抗活性的药理活性成分，用于预防和/或治疗神经精神疾病、外周器官疾病或类似疾病。
• Pyrrolo[1,2-b]pyridazines, pyrrolo[2,1-f]triazin-4(3H)-ones, and related compounds as novel corticotropin-releasing factor 1 (CRF1) receptor antagonists
  作者：Tetsuji Saito、Tetsuo Obitsu、Hiroshi Kohno、Isamu Sugimoto、Takeshi Matsushita、Taihei Nishiyama、Tomoko Hirota、Hiroyuki Takeda、Naoya Matsumura、Sonoko Ueno、Akihiro Kishi、Yoshifumi Kagamiishi、Hisao Nakai、Yoshikazu Takaoka

  DOI：10.1016/j.bmc.2011.11.015

  日期：2012.1

  To identify structurally novel corticotropin-releasing factor 1 (CRF1) receptor antagonists, a series of bicyclic core analogs pyrrolo[1,2-b]pyridazines and pyrrolo[2,1-f]triazin-4(3H)-ones, which were designed based on a monocyclic core antagonist, was synthesized and evaluated. Among the compounds tested, 2-difluoromethoxy-4-methylpyridin-5-yl analog 27 was found to show efficacy in a dose-dependent manner in an elevated plus maze test in rats. The discovery process and structure-activity relationship is presented. (C) 2011 Elsevier Ltd. All rights reserved.