ethyl 5-acetamido-N-(4-chlorophenylsulfonyl)-1H-pyrazole-4-carboxylate | 1349199-16-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 5-acetamido-N-(4-chlorophenylsulfonyl)-1H-pyrazole-4-carboxylate
• CAS: 1349199-16-1
• 化学式: C₁₄H₁₄ClN₃O₅S
• 分子量: 371.801
• InChiKey: BHOQKIGVMDCPND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  107.36
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl 5-acetamido-N-(4-chlorophenylsulfonyl)-1H-pyrazole-4-carboxylate 在 一水合肼 、 溶剂黄146 作用下， 以 正丁醇 为溶剂， 反应 48.0h， 生成 (E)-1-(4-chlorophenylsulfonyl)-5-(4-methoxybenzylideneamino)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one
  参考文献：
  名称：

  Synthesis and in vitro cytotoxic activity of novel pyrazolo[3,4-d]pyrimidines and related pyrazole hydrazones toward breast adenocarcinoma MCF-7 cell line

  摘要：

  New series of pyrazolo[3,4-d]pyrimidines (7a-e and 13a-d) and pyrazole hydrazones 17a-d were synthesized and evaluated for their antiproliferative activity against human breast adenocarcinoma MCF-7 cell line. Most of the tested compounds exploited potent to moderate growth inhibitory activity, in particular compound 7e exhibited superior potency to the reference drug cisplatin (IC50 = 7.60 and 13.29 mu M, respectively). The antitumor activity of the new compounds was accompanied by significant increase in the activity of superoxide dismutase with concomitant decrease in the activities of catalase and glutathione peroxidase and reduced glutathione level. Accordingly, the overproduction of hydrogen peroxide, nitric oxide and other free radicals allowed reactive oxygen species (ROS)-mediated tumor cells death, as monitored by reduction in the synthesis of protein and nucleic acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.036
• 作为产物：
  描述：

  ethyl 5-amino-1-(4-chlorophenylsulfonyl)-1H-pyrazole-4-carboxylate 、 乙酸酐 反应 4.0h， 以60%的产率得到ethyl 5-acetamido-N-(4-chlorophenylsulfonyl)-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  Synthesis and in vitro cytotoxic activity of novel pyrazolo[3,4-d]pyrimidines and related pyrazole hydrazones toward breast adenocarcinoma MCF-7 cell line

  摘要：

  New series of pyrazolo[3,4-d]pyrimidines (7a-e and 13a-d) and pyrazole hydrazones 17a-d were synthesized and evaluated for their antiproliferative activity against human breast adenocarcinoma MCF-7 cell line. Most of the tested compounds exploited potent to moderate growth inhibitory activity, in particular compound 7e exhibited superior potency to the reference drug cisplatin (IC50 = 7.60 and 13.29 mu M, respectively). The antitumor activity of the new compounds was accompanied by significant increase in the activity of superoxide dismutase with concomitant decrease in the activities of catalase and glutathione peroxidase and reduced glutathione level. Accordingly, the overproduction of hydrogen peroxide, nitric oxide and other free radicals allowed reactive oxygen species (ROS)-mediated tumor cells death, as monitored by reduction in the synthesis of protein and nucleic acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.036