6-benzyl-3-nitro-5,6,7,8-tetrahydro[1,6]naphthyridine

• 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-3-nitro-5,6,7,8-tetrahydro[1,6]naphthyridine
• 英文别名: 6-Benzyl-3-nitro-5,6,7,8-tetrahydro-1,6-naphthyridine；6-benzyl-3-nitro-7,8-dihydro-5H-1,6-naphthyridine
• 化学式: C₁₅H₁₅N₃O₂
• 分子量: 269.303
• InChiKey: ADYNDFLTYRSRDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 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：
  62
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-benzyl-3-nitro-5,6,7,8-tetrahydro[1,6]naphthyridine 在 Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 生成 6-苯甲基-5,6,7,8-四氢-1,6-二氮杂萘-3-胺
  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：

  N-苄基哌啶酮 、 1-甲基-3,5-二硝基-2-吡啶酮 在 氨 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以93%的产率得到6-benzyl-3-nitro-5,6,7,8-tetrahydro[1,6]naphthyridine
  参考文献：
  名称：

  3-氨基-5,6,7,8-四氢[1,6]萘啶体系和一些烷基化和多环同源物的简单合成

  摘要：

  3-氨基-5,6,7,8-四氢[1,6]萘啶系统 1 及其更多取代的同系物 2-5 通过单环和双环 4-哌啶酮 11a 的缩合的简易两步合成-c, 12-14 与 3,5-dinitro-1-methyl-2-pyridone 6 在氨存在下进行了描述。

  DOI：

  10.1081/scc-100103271

文献信息

• A FACILE SYNTHESIS OF THE 3-AMINO-5,6,7,8-TETRAHYDRO[1,6]NAPHTHYRIDINE SYSTEM AND SOME ALKYLATED AND POLYCYCLIC HOMOLOGUES
  作者：John D. Harling、Frank P. Harrington、Mervyn Thompson

  DOI：10.1081/scc-100103271

  日期：2001.1

  A facile, two step synthesis of the 3-amino-5,6,7,8-tetrahydro[1,6]naphthyridine system 1 and its more substituted homologues 2–5 via the condensation of mono- and bicyclic-4-piperidinones 11a–c, 12–14 with 3,5-dinitro-1-methyl-2-pyridone 6 in the presence of ammonia is described.

  3-氨基-5,6,7,8-四氢[1,6]萘啶系统 1 及其更多取代的同系物 2-5 通过单环和双环 4-哌啶酮 11a 的缩合的简易两步合成-c, 12-14 与 3,5-dinitro-1-methyl-2-pyridone 6 在氨存在下进行了描述。
• Imidazole and imidazoline derivatives and uses thereof
  申请人：Synaptic Pharmaceutical Corporation

  公开号：US20020019390A1

  公开（公告）日：2002-02-14

  This invention is directed to novel imidazole and imidazoline derivatives which are selective agonists for cloned human &agr; 2 adrenergic receptors. This invention is also related to the use of these compounds for the treatment of any disease where modulation of the &agr; 2 receptors may be useful. The invention further provides for a pharmaceutical composition comprising a therapeutically effective amount of the above-defined compounds and a pharmaceutically acceptable carrier.

  本发明涉及一种新型咪唑和咪唑啉衍生物，它们是选择性激动剂，适用于克隆的人类α2肾上腺素受体。本发明还涉及使用这些化合物治疗任何调节α2受体可能有用的疾病。本发明还提供了一种药物组合物，包括上述定义化合物的治疗有效量和药学上可接受的载体。
• 1,6-naphthyridine anti-convulsants
  申请人：SmithKline Beecham p.l.c.

  公开号：US06245778B1

  公开（公告）日：2001-06-12

  Compounds of formula (I) and pharmaceutically acceptable salts thereof: where R1 is hydrogen, C1-6 alkyl optionally substituted by hydroxy or C1-4alkoxy, or C1-6 alkylphenyl; R2 is hydrogen or up to three substituents selected from halogen, NO2, CN, N3, C1-6 alkylO-, C1-6 alkylS-, C1-6 alkyl, C3-6cycloalkyl, C3-6cycloalkyl-C1-4alkyl-, C1-6alkenyl, C1-6alkynyl, CF3, CF3O, CF3CO—, C1-6alkylCO-, C3-6cycloalkylCO-, C3-6cycloalkyl-C1-4alkylCO-, phenyl, phenoxy, benzyloxy, benzoyl, phenyl-C1-4alkyl-, or —NR3R4 where R3 is hydrogen or C1-4 alkyl, and R4 is hydrogen, C1-4alkyl, —CHO, —CO2C1-4alkyl or —COC1-4alkyl; or two R2 groups form a saturated carbocyclic ring optionally interrupted by oxygen; and X is selected from hydrogen, halogen, cyano, alkyl and alkoxy; are useful in the treatment and prophylaxis of inter alia epilepsy.

  化合物I式及其药学上可接受的盐：其中R1为氢，C1-6烷基（可选用羟基或C1-4烷氧基取代），或C1-6烷基苯基；R2为氢或最多三个取代基，所选取代基来自卤素、NO2、CN、N3、C1-6烷氧基、C1-6烷硫基、C1-6烷基、C3-6环烷基、C3-6环烷基-C1-4烷基、C1-6烯基、C1-6炔基、CF3、CF3O、CF3CO—、C1-6烷基CO-、C3-6环烷基CO-、C3-6环烷基-C1-4烷基CO-、苯基、苯氧基、苄氧基、苯甲酰基、苯基-C1-4烷基-，或—NR3R4，其中R3为氢或C1-4烷基，R4为氢、C1-4烷基、—CHO、—CO2C1-4烷基或—COC1-4烷基；或两个R2基团形成一个饱和的碳环，可选地被氧中断；X为氢、卤素、氰基、烷基或烷氧基。这些化合物在治疗和预防癫痫等方面有用。
• Imidazoline derivatives and uses thereof
  申请人：Synaptic Pharmaceutical Corporation

  公开号：US06294566B1

  公开（公告）日：2001-09-25

  This invention is directed to novel imidazole and imidazoline derivatives which are selective agonists for cloned human &agr;2 adrenergic receptors. This invention is also related to the use of these compounds for the treatment of any disease where modulation of the &agr;2 receptors may be useful. The invention further provides for a pharmaceutical composition comprising a therapeutically effective amount of the above-defined compounds and a pharmaceutically acceptable carrier.

  这项发明涉及新型咪唑和咪唑啉衍生物，它们是选择性激动剂，可作用于克隆的人类α2肾上腺素受体。此发明还涉及使用这些化合物治疗任何需要调节α2受体的疾病。此发明还提供了一种药物组合物，包括上述定义化合物的治疗有效量和药学可接受的载体。
• 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.