8-(2-Methoxyethoxy)-1,2,3,4-tetrahydroisoquinoline | 927021-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 8-(2-Methoxyethoxy)-1,2,3,4-tetrahydroisoquinoline
• CAS: 927021-15-6
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: JMKWHJHNYYELBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)ethyl 4-methylbenzenesulfonate 、 8-(2-Methoxyethoxy)-1,2,3,4-tetrahydroisoquinoline 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(furan-2-yl)-10-[2-[8-(2-methoxyethoxy)-3,4-dihydro-1H-isoquinolin-2-yl]ethyl]-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine
  参考文献：
  名称：

  Design, synthesis, and evaluation of fused heterocyclic analogs of SCH 58261 as adenosine A2A receptor antagonists

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.05.069
• 作为产物：
  描述：

  在 Pd(OH)2/C 、 甲酸铵 作用下， 以 甲醇 为溶剂， 生成 8-(2-Methoxyethoxy)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Design, synthesis, and evaluation of fused heterocyclic analogs of SCH 58261 as adenosine A2A receptor antagonists

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.05.069

文献信息

• [EN] PYRAZOLOTRIAZOLOPYRIMIDINE DERIVATIVES AS A2A RECEPTOR ANTAGONIST<br/>[FR] DÉRIVÉS DE PYRAZOLOTRIAZOLOPYRIMIDINE EN TANT QU'ANTAGONISTE DU RÉCEPTEUR A2A
  申请人：BEIGENE LTD

  公开号：WO2020020097A1

  公开（公告）日：2020-01-30

  Disclosed herein is a pyrazolotriazolopyrimidine derivative or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof useful as A2A receptor antagonist, and a pharmaceutical composition comprising the same. Also disclosed herein is a method of treating cancer using the pyrazolotriazolopyrimidine derivative or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof as A2A receptor antagonist.

  本文揭示了一种吡唑三唑吡嘧啶衍生物或其立体异构体，或其药学上可接受的盐，可用作A2A受体拮抗剂，以及包含该物质的药物组合物。本文还揭示了一种使用该吡唑三唑吡嘧啶衍生物或其立体异构体，或其药学上可接受的盐作为A2A受体拮抗剂治疗癌症的方法。
• PYRAZOLOTRIAZOLOPYRIMIDINE DERIVATIVES AS A2A RECEPTOR ANTAGONIST
  申请人：BEIGENE, LTD.

  公开号：US20210300936A1

  公开（公告）日：2021-09-30

  Disclosed herein is a pyrazolotriazolopyrimidine derivative or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof useful as A2A receptor antagonist, and a pharmaceutical composition comprising the same. Also disclosed herein is a method of treating cancer using the pyrazolotriazolopyrimidine derivative or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof as A2A receptor antagonist.
• 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.