1,2,3,4-Tetrahydro-1,8-naphthyridin-4-OL | 1379218-50-4

• 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: 1,2,3,4-Tetrahydro-1,8-naphthyridin-4-OL
• 英文别名: 1,2,3,4-tetrahydro-1,8-naphthyridin-4-ol
• CAS: 1379218-50-4
• 化学式: C₈H₁₀N₂O
• 分子量: 150.18
• InChiKey: PWEDXSQOXUIMEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2,3,4-Tetrahydro-1,8-naphthyridin-4-OL 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 6-bromo-1,2,3,4-tetrahydro-1,8-naphthyridin-4-ol
  参考文献：
  名称：

  WO2007/130468

  摘要：

  公开号：
• 作为产物：
  描述：

  7-bromo-1,2,3,4-tetrahydro-1,8-naphthyridin-4-ol 在 甲醇 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 1,2,3,4-Tetrahydro-1,8-naphthyridin-4-OL
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 1,2,3,4-tetrahydropyrido[2,3-b]pyrazines as potent and selective inhibitors of the anaplastic lymphoma kinase

  摘要：

  Dysregulation of the anaplastic lymphoma kinase (ALK) is implicated in a variety of cancers. A series of tetrahydropyrido[2,3-b]pyrazines was constructed as ring-constrained analogs of a known aminopyridine kinase scaffold. Chemistry was developed to rapidly elaborate the SAR, structural elements impacting ALK inhibitory activity were exploited, and kinase selective analogs were identified that inhibit ALK with IC50 values similar to 10 nM (enzyme) and similar to 150 nM (cell). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.087

文献信息

• [EN] A PROCESS FOR THE PREPARATION OF THE CORE STRUCTURE IN QUINOLONE AND NAPTHYRIDONE CLASS OF ANTIBIOTICS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE LA STRUCTURE CENTRALE D'ANTIBIOTIQUES APPARTENANT AUX CLASSES QUINOLONE ET NAPHTHYRIDONE
  申请人：INDIAN INST TECHNOLOGY MADRAS

  公开号：WO2013157018A1

  公开（公告）日：2013-10-24

  This invention relates to quinolone- and naphthyridone derivatives represented by the general formula VII, and a process for their preparation using Baylis-Hillman adducts from substituted aromatic or hetero-aromatic aldehydes and amines of interest as the starting materials. After the tandem Aza-Michael addition and SNAr cyclization, the resulting 4-hydroxy-1,2,3,4-tetrahydroquinoline or 4-hydroxy-1, 2,3,4- tetrahydro-1,8-naphthyridine derivative was subjected to oxidation to get the quinolone or naphthyridone skeleton in one step in good to excellent yields.

  本发明涉及通式VII所代表的喹诺酮和萘啶酮衍生物，以及使用取代芳香族或杂芳香族醛和感兴趣的胺作为起始材料，从Baylis-Hillman加合物开始制备它们的过程。在串联的Aza-Michael加成和SNAr环化之后，所得的4-羟基-1,2,3,4-四氢喹啉或4-羟基-1,2,3,4-四氢-1,8-萘啶衍生物被氧化，从而在一步中以良好至优异的收率得到喹诺酮或萘啶酮骨架。
• WO2007/130468
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and structure–activity relationships of 1,2,3,4-tetrahydropyrido[2,3-b]pyrazines as potent and selective inhibitors of the anaplastic lymphoma kinase
  作者：Karen L. Milkiewicz、Linda R. Weinberg、Mark S. Albom、Thelma S. Angeles、Mangeng Cheng、Arup K. Ghose、Renee C. Roemmele、Jay P. Theroff、Ted L. Underiner、Craig A. Zificsak

  DOI：10.1016/j.bmc.2010.04.087

  日期：2010.6.15

  Dysregulation of the anaplastic lymphoma kinase (ALK) is implicated in a variety of cancers. A series of tetrahydropyrido[2,3-b]pyrazines was constructed as ring-constrained analogs of a known aminopyridine kinase scaffold. Chemistry was developed to rapidly elaborate the SAR, structural elements impacting ALK inhibitory activity were exploited, and kinase selective analogs were identified that inhibit ALK with IC50 values similar to 10 nM (enzyme) and similar to 150 nM (cell). (C) 2010 Elsevier Ltd. All rights reserved.