ethyl2-(2-cyanoacetamido)-4-(5-amino-3-hydroxy-1Hpyrazol-1-yl)thiophene-3-carboxylate | 1444020-14-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: ethyl2-(2-cyanoacetamido)-4-(5-amino-3-hydroxy-1Hpyrazol-1-yl)thiophene-3-carboxylate
• CAS: 1444020-14-7
• 化学式: C₁₃H₁₃N₅O₄S
• 分子量: 335.343
• InChiKey: YIZNRJWLWMBSGF-UHFFFAOYSA-N

物化性质

• 熔点：
  230-233 °C
• 密度：
  1.509±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  143.26
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ethyl2-(2-cyanoacetamido)-4-(5-amino-3-hydroxy-1Hpyrazol-1-yl)thiophene-3-carboxylate 在 乙醇 、 sodium 作用下， 反应 8.0h， 以66%的产率得到3-(5-amino-3-hydroxy-1H-pyrazol-1-yl)-4,6-dihydroxythieno[2,3-b]pyridine-5-carbonitrile
  参考文献：
  名称：

  New approaches for the synthesis of pyrazole, thiophene, thieno[2,3-b]pyridine, and thiazole derivatives together with their anti-tumor evaluations

  摘要：

  The reaction of cyanoacetylhydrazine (1) with acetylchloride (2) gave the N-acyl derivative 3. The latter underwent ready cyclization in sodium ethoxide to give the pyrazole derivative 4 which was the key compound for the synthesis of thiophene, thieno[2,3-b]pyridine, and thiazole derivatives. The anti-tumor evaluations of the newly synthesized products against the three human tumor cell lines, namely, breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460), and CNS cancer (SF-268), were studied. Some of these compounds were found to exhibit much higher inhibitory effects toward the three tumor cell lines than the reference doxorubicin. Molecular modeling of the four compounds 12c, 12f, 16a, and 16d, which showed the maximum inhibitory effect, were done.

  DOI：

  10.1007/s00044-013-0664-7
• 作为产物：
  描述：

  氰基乙酸 2-乙酰基酰肼 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 乙醇 、 sodium 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 ethyl2-(2-cyanoacetamido)-4-(5-amino-3-hydroxy-1Hpyrazol-1-yl)thiophene-3-carboxylate
  参考文献：
  名称：

  New approaches for the synthesis of pyrazole, thiophene, thieno[2,3-b]pyridine, and thiazole derivatives together with their anti-tumor evaluations

  摘要：

  The reaction of cyanoacetylhydrazine (1) with acetylchloride (2) gave the N-acyl derivative 3. The latter underwent ready cyclization in sodium ethoxide to give the pyrazole derivative 4 which was the key compound for the synthesis of thiophene, thieno[2,3-b]pyridine, and thiazole derivatives. The anti-tumor evaluations of the newly synthesized products against the three human tumor cell lines, namely, breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460), and CNS cancer (SF-268), were studied. Some of these compounds were found to exhibit much higher inhibitory effects toward the three tumor cell lines than the reference doxorubicin. Molecular modeling of the four compounds 12c, 12f, 16a, and 16d, which showed the maximum inhibitory effect, were done.

  DOI：

  10.1007/s00044-013-0664-7