7-amino-2-chloro-3-phenyl-1,8-naphthyridine | 30167-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 7-amino-2-chloro-3-phenyl-1,8-naphthyridine
• 英文别名: 7-chloro-6-phenyl-[1,8]naphthyridin-2-ylamine；7-Chloro-6-phenyl-1,8-naphthyridin-2-amine
• CAS: 30167-77-2
• 化学式: C₁₄H₁₀ClN₃
• 分子量: 255.707
• InChiKey: FAVDFNAHKVXRGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-amino-2-chloro-3-phenyl-1,8-naphthyridine 在 吡啶 、 硫酸 、 sodium nitrite 作用下， 反应 49.0h， 生成 7-hydroxy-2-(4′-methoxybenzylamine)-6-nitro-3-phenyl-1,8-naphthyridine
  参考文献：
  名称：

  Antilipolytic effects of 1,8-naphthyridine derivatives β-adrenoceptor antagonists in rat white adipocytes

  摘要：

  The rat fat cell β‐adrenoceptors were investigated by studying the effects of new 1,8‐naphthyridine derivatives synthesized starting from 7‐amino‐2‐chloro‐3‐phenyl‐1,8‐naphthyridine on lipolysis induced by isoprenaline, and alprenolol. Lipolysis induced by isoprenaline agonist was competitively antagonized by the 1,8‐naphthyridine analogue with a 7‐hydroxy‐2‐(4′‐methoxybenzylamine)‐6‐nitro‐3‐phenyl substituent designated as 3. In contrast, 10, 50, and 100 μm of 7‐methoxy and 7‐ethoxy derivatives did not modify the concentration–response curve of isoprenaline. A rightward shift of the curve was, however, observed with 50 μm of a 7‐methoxy‐2‐(4′‐methoxybenzylamine)‐6‐amino‐3‐phenyl substituent designated as 10. The selective β1‐AR antagonist, 7‐hydroxy‐4‐morpholinomethyl‐2‐piperazino‐1,8‐naphthyridine slightly reduced isoprenaline‐induced lipolysis only at high doses. Alprenolol‐mediated lipolytic effect was antagonized by derivative 3, 10 and the selective β3‐AR antagonist SR 59,230A, but resistant to the selective β1‐AR antagonist 7‐hydroxy‐4‐morpholinomethyl‐2‐piperazino‐1,8‐naphthyridine. The results provide preliminary pharmacological evidence for the antilipolytic effect of the newly synthesized 1,8‐naphthyridine derivatives on rat fat cells. The analogues designated as 3 and 10 were the most potent antagonists of this series.

  DOI：

  10.1111/cbdd.12933

文献信息

• Unusual nitration of substituted 7-amino-1,8-naphthyridine in the synthesis of compounds with antiplatelet activity
  作者：Pier Luigi Ferrarini、Claudio Mori、Muwaffag Badawneh、Clementina Manera、Adriano Martinelli、Federico Romagnoli、Giuseppe Saccomanni、Mauro Miceli

  DOI：10.1002/jhet.5570340520

  日期：1997.9

  possible explanation of the effects induced by the nature of the substituents and of their position. Some of the compounds were tested for their ability to inhibit human platelet aggregation in vitro induced by arachidonic acid. Only compound 26 showed interesting antiplatelet activity.

  几种1，8-萘啶衍生物已被重氮化以获得相应的羟基衍生物或羟基和羟基硝基衍生物的混合物。羟基和羟基硝基衍生物的各自量取决于取代基的性质，它们在萘啶核上的位置，亚硝酸钠的量以及反应温度。对某些分子的电子密度的研究表明，可能是由取代基的性质及其位置引起的影响的解释。测试了某些化合物在体外抑制花生四烯酸诱导的人血小板聚集的能力。仅化合物26显示出令人感兴趣的抗血小板活性。
• Antilipolytic effects of 1,8-naphthyridine derivatives β-adrenoceptor antagonists in rat white adipocytes
  作者：Jalal A. Aljamal、Muwaffag Badawneh

  DOI：10.1111/cbdd.12933

  日期：2017.7

  The rat fat cell β‐adrenoceptors were investigated by studying the effects of new 1,8‐naphthyridine derivatives synthesized starting from 7‐amino‐2‐chloro‐3‐phenyl‐1,8‐naphthyridine on lipolysis induced by isoprenaline, and alprenolol. Lipolysis induced by isoprenaline agonist was competitively antagonized by the 1,8‐naphthyridine analogue with a 7‐hydroxy‐2‐(4′‐methoxybenzylamine)‐6‐nitro‐3‐phenyl substituent designated as 3. In contrast, 10, 50, and 100 μm of 7‐methoxy and 7‐ethoxy derivatives did not modify the concentration–response curve of isoprenaline. A rightward shift of the curve was, however, observed with 50 μm of a 7‐methoxy‐2‐(4′‐methoxybenzylamine)‐6‐amino‐3‐phenyl substituent designated as 10. The selective β1‐AR antagonist, 7‐hydroxy‐4‐morpholinomethyl‐2‐piperazino‐1,8‐naphthyridine slightly reduced isoprenaline‐induced lipolysis only at high doses. Alprenolol‐mediated lipolytic effect was antagonized by derivative 3, 10 and the selective β3‐AR antagonist SR 59,230A, but resistant to the selective β1‐AR antagonist 7‐hydroxy‐4‐morpholinomethyl‐2‐piperazino‐1,8‐naphthyridine. The results provide preliminary pharmacological evidence for the antilipolytic effect of the newly synthesized 1,8‐naphthyridine derivatives on rat fat cells. The analogues designated as 3 and 10 were the most potent antagonists of this series.