6-Benzyl-7,8-dihydro-5H-1,6-naphthyridin-3-ol | 625098-87-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-Benzyl-7,8-dihydro-5H-1,6-naphthyridin-3-ol
• CAS: 625098-87-5
• 化学式: C₁₅H₁₆N₂O
• 分子量: 240.305
• InChiKey: HCPCPXTYFIXVOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Benzyl-7,8-dihydro-5H-1,6-naphthyridin-3-ol 在 盐酸 、 Pd/C 、 氢气 作用下， 以 乙醇 为溶剂， 生成 5,6,7,8-四氢-1,6-萘啶-3-醇盐酸盐
  参考文献：
  名称：

  An expeditious synthesis of 3-(difluoromethoxy)- and 3-(trifluoromethoxy)-5,6,7,8-tetrahydro-1,6-naphthyridines

  摘要：

  An expeditious and concise synthesis of 3-(difluoromethoxy)-5,6,7,8-tetrahydro-1,6-naphthyridine and 3-(trifluoromethoxy)-5,6,7,8-tetrahydro-1,6-naphthyridines is described. Starting from N-benzyl piperidone, the key intermediates leading to these two biologically desirable synthones were rapidly assembled by inverse electron demand Diels-Alder (IEDA) reaction utilizing microwave irradiation. The scope of the microwave methodology developed herein was extended to other ketones. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.083
• 作为产物：
  描述：

  6-苯甲基-5,6,7,8-四氢-1,6-二氮杂萘-3-胺 在 sodium nitrite 、 硫酸 作用下， 生成 6-Benzyl-7,8-dihydro-5H-1,6-naphthyridin-3-ol
  参考文献：
  名称：

  An expeditious synthesis of 3-(difluoromethoxy)- and 3-(trifluoromethoxy)-5,6,7,8-tetrahydro-1,6-naphthyridines

  摘要：

  An expeditious and concise synthesis of 3-(difluoromethoxy)-5,6,7,8-tetrahydro-1,6-naphthyridine and 3-(trifluoromethoxy)-5,6,7,8-tetrahydro-1,6-naphthyridines is described. Starting from N-benzyl piperidone, the key intermediates leading to these two biologically desirable synthones were rapidly assembled by inverse electron demand Diels-Alder (IEDA) reaction utilizing microwave irradiation. The scope of the microwave methodology developed herein was extended to other ketones. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.083

文献信息

• Design, synthesis, and evaluation of fused heterocyclic analogs of SCH 58261 as adenosine A2A receptor antagonists
  作者：Unmesh Shah、Claire M. Lankin、Craig D. Boyle、Samuel Chackalamannil、William J. Greenlee、Bernard R. Neustadt、Mary E. Cohen-Williams、Guy A. Higgins、Kwokei Ng、Geoffrey B. Varty、Hongtao Zhang、Jean E. Lachowicz

  DOI：10.1016/j.bmcl.2008.05.069

  日期：2008.7

  SCH 58261 is a reported adenosine A(2A) receptor antagonist which is active in rat in vivo models of Parkinson's Disease upon ip administration. However, it has poor selectivity versus the A(1) receptor and does not demonstrate oral activity. Quinoline analogs have improved upon the selectivity and pharmacokinetics of SCH 58261, but were difficult to handle due to poor aqueous solubility. We report the design and synthesis of fused heterocyclic analogs of SCH 58261 with aqueous solubility as well as improved A(2A) receptor binding selectivity and pharmacokinetic properties. In particular, the tetrahydronaphthyridine 4s has excellent A(2A) receptor in vitro binding affinity and selectivity, is active orally in a rat in vivo model of Parkinson's Disease, and has aqueous solubility of 100 mu M at physiological pH. (C) 2008 Elsevier Ltd. All rights reserved.
• US7230008B2
  申请人：——

  公开号：US7230008B2

  公开（公告）日：2007-06-12
• US7786305B2
  申请人：——

  公开号：US7786305B2

  公开（公告）日：2010-08-31
• An expeditious synthesis of 3-(difluoromethoxy)- and 3-(trifluoromethoxy)-5,6,7,8-tetrahydro-1,6-naphthyridines
  作者：Deodialsingh Guiadeen、Shankaran Kothandaraman、Lihu Yang、Sander G. Mills、Malcolm MacCoss

  DOI：10.1016/j.tetlet.2008.08.083

  日期：2008.10

  An expeditious and concise synthesis of 3-(difluoromethoxy)-5,6,7,8-tetrahydro-1,6-naphthyridine and 3-(trifluoromethoxy)-5,6,7,8-tetrahydro-1,6-naphthyridines is described. Starting from N-benzyl piperidone, the key intermediates leading to these two biologically desirable synthones were rapidly assembled by inverse electron demand Diels-Alder (IEDA) reaction utilizing microwave irradiation. The scope of the microwave methodology developed herein was extended to other ketones. (c) 2008 Elsevier Ltd. All rights reserved.