4-(7-Hydroxy-6-nitro-3-phenyl-[1,8]naphthyridin-2-yl)-piperazine-1-carboxylic acid ethyl ester | 199983-15-8

• 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: 4-(7-Hydroxy-6-nitro-3-phenyl-[1,8]naphthyridin-2-yl)-piperazine-1-carboxylic acid ethyl ester
• 英文别名: ethyl 4-(6-nitro-7-oxo-3-phenyl-8H-1,8-naphthyridin-2-yl)piperazine-1-carboxylate
• CAS: 199983-15-8
• 化学式: C₂₁H₂₁N₅O₅
• 分子量: 423.428
• InChiKey: IZSFCTXXCSPRBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(7-Hydroxy-6-nitro-3-phenyl-[1,8]naphthyridin-2-yl)-piperazine-1-carboxylic acid ethyl ester 在 sodium methylate 、 三氯氧磷 作用下， 反应 4.75h， 生成 4-(7-Methoxy-6-nitro-3-phenyl-[1,8]naphthyridin-2-yl)-piperazine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and antiplatelet activity of some 3-phenyl-1,8-naphthyridine derivatives

  摘要：

  A series of 2-cycloalkylamino-3-phenyl-1,8-naphthyridine derivatives, variously substituted in the 6- and 7-positions were synthesized and tested for their ability to inhibit human platelet aggregation in vitro induced by arachidonate, collagen and ADP. Compounds 5a,b, 7a,b, 8a and 10c,d showed a remarkable activity similar to that of indomethacin in the test with arachidonate and collagen. In the test with ADP only compound 8a showed a significant activity. The presence of a morpholinyl or piperidinyl group in position 2 and of a chloro or methoxy group in position 7 of the 1,8-naphthyridine nucleus seem to favour a higher activity. However on the basis of the pharmacological results, no structure-activity relationship can be deduced. Compounds 5b and 7b, which possess the best activity in the arachidonate test, were also shown to increase the c-AMP level significantly, without involving the adenylyl cyclase system. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00085-9
• 作为产物：
  描述：

  Ethyl 4-(7-amino-3-phenyl-1,8-naphthyridin-2-yl)piperazine-1-carboxylate 在 硫酸 、 sodium nitrite 作用下， 反应 1.0h， 以7%的产率得到4-(7-Hydroxy-6-nitro-3-phenyl-[1,8]naphthyridin-2-yl)-piperazine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  合成具有抗血小板活性的化合物中不寻常的取代7-氨基-1,8-萘啶的硝化反应

  摘要：

  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。

  DOI：

  10.1002/jhet.5570340520

文献信息

• Synthesis and antiplatelet activity of some 3-phenyl-1,8-naphthyridine derivatives
  作者：Pier Luigi Ferrarini、Claudio Mori、Muwaffag Badawneh、Flavia Franconi、Clementina Manera、Mauro Miceli、Giuseppe Saccomanni

  DOI：10.1016/s0014-827x(00)00085-9

  日期：2000.11

  A series of 2-cycloalkylamino-3-phenyl-1,8-naphthyridine derivatives, variously substituted in the 6- and 7-positions were synthesized and tested for their ability to inhibit human platelet aggregation in vitro induced by arachidonate, collagen and ADP. Compounds 5a,b, 7a,b, 8a and 10c,d showed a remarkable activity similar to that of indomethacin in the test with arachidonate and collagen. In the test with ADP only compound 8a showed a significant activity. The presence of a morpholinyl or piperidinyl group in position 2 and of a chloro or methoxy group in position 7 of the 1,8-naphthyridine nucleus seem to favour a higher activity. However on the basis of the pharmacological results, no structure-activity relationship can be deduced. Compounds 5b and 7b, which possess the best activity in the arachidonate test, were also shown to increase the c-AMP level significantly, without involving the adenylyl cyclase system. (C) 2000 Elsevier Science S.A. All rights reserved.
• 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。