4-(7-Chloro-6-nitro-3-phenyl-[1,8]naphthyridin-2-yl)-piperazine-1-carboxylic acid ethyl ester | 326802-13-5

• 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-Chloro-6-nitro-3-phenyl-[1,8]naphthyridin-2-yl)-piperazine-1-carboxylic acid ethyl ester
• 英文别名: Ethyl 4-(7-chloro-6-nitro-3-phenyl-1,8-naphthyridin-2-yl)piperazine-1-carboxylate
• CAS: 326802-13-5
• 化学式: C₂₁H₂₀ClN₅O₄
• 分子量: 441.874
• InChiKey: LYNQABCABMPNMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：
  104
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(7-Chloro-6-nitro-3-phenyl-[1,8]naphthyridin-2-yl)-piperazine-1-carboxylic acid ethyl ester 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 甲醇 为溶剂， 反应 35.0h， 生成 2-Morpholin-4-yl-6-phenyl-7-piperazin-1-yl-[1,8]naphthyridin-3-ylamine
  参考文献：
  名称：

  Synthesis and antiplatelet activity of some 2,7-di(N-cycloamino)-3-phenyl-1,8-naphthyridine derivatives

  摘要：

  Several 2,7-di(N-cycloamino)-3-phenyl-1,8-naphthyridine derivatives were synthesized and tested for their ability to inhibit human platelet aggregation in vitro induced by arachidonic acid, collagen and ADP. Only five compounds showed any appreciable activity, and the results of all the active derivatives were similar to those of papaverine in the test with arachidonic acid and collagen. Moreover, the most active compounds were investigated in the test with ADP and again showed a significant activity. The tested compounds that possessed the best activity were also shown to increase the c-AMP level significantly without involving the adenylyl cyclase system. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01075-8
• 作为产物：
  描述：

  4-(7-Hydroxy-6-nitro-3-phenyl-[1,8]naphthyridin-2-yl)-piperazine-1-carboxylic acid ethyl ester 在 三氯氧磷 作用下， 反应 0.75h， 以79%的产率得到4-(7-Chloro-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

文献信息

• Synthesis and antiplatelet activity of some 2,7-di(N-cycloamino)-3-phenyl-1,8-naphthyridine derivatives
  作者：Pier Luigi Ferrarini、Muwaffag Badawneh、Flavia Franconi、Clementina Manera、Mauro Miceli、Claudio Mori、Giuseppe Saccomanni

  DOI：10.1016/s0014-827x(01)01075-8

  日期：2001.4

  Several 2,7-di(N-cycloamino)-3-phenyl-1,8-naphthyridine derivatives were synthesized and tested for their ability to inhibit human platelet aggregation in vitro induced by arachidonic acid, collagen and ADP. Only five compounds showed any appreciable activity, and the results of all the active derivatives were similar to those of papaverine in the test with arachidonic acid and collagen. Moreover, the most active compounds were investigated in the test with ADP and again showed a significant activity. The tested compounds that possessed the best activity were also shown to increase the c-AMP level significantly without involving the adenylyl cyclase system. (C) 2001 Elsevier Science S.A. All rights reserved.
• 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.