5-[4-(4-fluorophenyl)-5-sulfanyl-4H-[1,2,4]-triazol-3-yl]-1H,3H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione | 1417340-48-7

• 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: 5-[4-(4-fluorophenyl)-5-sulfanyl-4H-[1,2,4]-triazol-3-yl]-1H,3H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione
• 英文别名: 5-[4-(4-fluorophenyl)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]-1,8-dihydropyrido[2,3-d]pyrimidine-2,4,7-trione
• CAS: 1417340-48-7
• 化学式: C₁₅H₉FN₆O₃S
• 分子量: 372.339
• InChiKey: OOIZAVZNJDWNFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  147
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-[4-(4-fluorophenyl)-5-sulfanyl-4H-[1,2,4]-triazol-3-yl]-1H,3H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione 、 氯乙酰氯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以70%的产率得到S-[3-(2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2.3-d]pyrimidin-5-yl)-4-(4-fluorophenyl)-4H-[1,2,4]-triazol-4-yl] 2-chloroethanethioate
  参考文献：
  名称：

  Synthesis and antitumor activity of new pyrido[2,3-d]pyrimidine derivatives

  摘要：

  New series of pyrido[2,3-d]pyrimidines such as; 5-(4-aryl-5-sulfanyl-4H-[1,2,4]triazol-3-yl) 1H,3H,8H-pyrido[2,3-d]pyrimidine-2,4,7-triones 6, 7; S-[3-(2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-yl)-4-(4-substituted phenyl)-4H-[1,2,4]triazol-5-yl]-2-(4-phenylpiperazin-1-yl)ethanethioates 10, 11; 2,4,7-trioxo-N'-[(4-substituted piperazin-1-yl)acetyl]-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidine-5-carbohydrazides 13-16 and N'-arylidene-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidine-5-carbohydrazides 17-19 was synthesized through the reaction of the key intermediate 2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidine-5-carbohydrazide 3 with different reagents. The structures of the newly synthesized compounds were elucidated through microanalysis, IR, H-1 NMR, C-13 NMR, and mass spectroscopy. These compounds have been subjected to in vitro antitumor evaluation by bleomycin-dependant DNA damage assay. The most active antitumor compound 6 was selected for further in vivo evaluation of antineoplastic activity against Ehrlich ascites carcinoma in mice. It was observed that our target compound has a potent antitumor activity.

  DOI：

  10.1007/s00044-012-0396-0
• 作为产物：
  描述：

  2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidine-5-carbohydrazide 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 26.0h， 生成 5-[4-(4-fluorophenyl)-5-sulfanyl-4H-[1,2,4]-triazol-3-yl]-1H,3H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione
  参考文献：
  名称：

  Synthesis and antitumor activity of new pyrido[2,3-d]pyrimidine derivatives

  摘要：

  New series of pyrido[2,3-d]pyrimidines such as; 5-(4-aryl-5-sulfanyl-4H-[1,2,4]triazol-3-yl) 1H,3H,8H-pyrido[2,3-d]pyrimidine-2,4,7-triones 6, 7; S-[3-(2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-yl)-4-(4-substituted phenyl)-4H-[1,2,4]triazol-5-yl]-2-(4-phenylpiperazin-1-yl)ethanethioates 10, 11; 2,4,7-trioxo-N'-[(4-substituted piperazin-1-yl)acetyl]-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidine-5-carbohydrazides 13-16 and N'-arylidene-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidine-5-carbohydrazides 17-19 was synthesized through the reaction of the key intermediate 2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidine-5-carbohydrazide 3 with different reagents. The structures of the newly synthesized compounds were elucidated through microanalysis, IR, H-1 NMR, C-13 NMR, and mass spectroscopy. These compounds have been subjected to in vitro antitumor evaluation by bleomycin-dependant DNA damage assay. The most active antitumor compound 6 was selected for further in vivo evaluation of antineoplastic activity against Ehrlich ascites carcinoma in mice. It was observed that our target compound has a potent antitumor activity.

  DOI：

  10.1007/s00044-012-0396-0

文献信息

• Synthesis and antitumor activity of new pyrido[2,3-d]pyrimidine derivatives
  作者：Magdy M. Gineinah、Magda N. A. Nasr、Sahar M. I. Badr、Walaa M. El-Husseiny

  DOI：10.1007/s00044-012-0396-0

  日期：2013.8

  New series of pyrido[2,3-d]pyrimidines such as; 5-(4-aryl-5-sulfanyl-4H-[1,2,4]triazol-3-yl) 1H,3H,8H-pyrido[2,3-d]pyrimidine-2,4,7-triones 6, 7; S-[3-(2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-yl)-4-(4-substituted phenyl)-4H-[1,2,4]triazol-5-yl]-2-(4-phenylpiperazin-1-yl)ethanethioates 10, 11; 2,4,7-trioxo-N'-[(4-substituted piperazin-1-yl)acetyl]-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidine-5-carbohydrazides 13-16 and N'-arylidene-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidine-5-carbohydrazides 17-19 was synthesized through the reaction of the key intermediate 2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidine-5-carbohydrazide 3 with different reagents. The structures of the newly synthesized compounds were elucidated through microanalysis, IR, H-1 NMR, C-13 NMR, and mass spectroscopy. These compounds have been subjected to in vitro antitumor evaluation by bleomycin-dependant DNA damage assay. The most active antitumor compound 6 was selected for further in vivo evaluation of antineoplastic activity against Ehrlich ascites carcinoma in mice. It was observed that our target compound has a potent antitumor activity.