4-(6-Amino-7-methoxy-3-phenyl-[1,8]naphthyridin-2-yl)-piperazine-1-carboxylic acid ethyl ester | 326802-25-9

• 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-(6-Amino-7-methoxy-3-phenyl-[1,8]naphthyridin-2-yl)-piperazine-1-carboxylic acid ethyl ester
• 英文别名: Ethyl 4-(6-amino-7-methoxy-3-phenyl-1,8-naphthyridin-2-yl)piperazine-1-carboxylate
• CAS: 326802-25-9
• 化学式: C₂₂H₂₅N₅O₃
• 分子量: 407.472
• InChiKey: GSBHYIISWZYKNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  93.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(6-Amino-7-methoxy-3-phenyl-[1,8]naphthyridin-2-yl)-piperazine-1-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以70%的产率得到2-Methoxy-6-phenyl-7-piperazin-1-yl-[1,8]naphthyridin-3-ylamine
  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：

  4-(7-Methoxy-6-nitro-3-phenyl-[1,8]naphthyridin-2-yl)-piperazine-1-carboxylic acid ethyl ester 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 反应 3.0h， 以79%的产率得到4-(6-Amino-7-methoxy-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

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.