N'-(4-(pyridin-2-yl)piperazine-1-carbonothioyl)picolinohydrazonamide | 1538611-85-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N'-(4-(pyridin-2-yl)piperazine-1-carbonothioyl)picolinohydrazonamide
• 英文别名: N-[(E)-[amino(pyridin-2-yl)methylidene]amino]-4-pyridin-2-ylpiperazine-1-carbothioamide
• CAS: 1538611-85-6
• 化学式: C₁₆H₁₉N₇S
• 分子量: 341.44
• InChiKey: HRMMCOOJVLKXOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  82.67
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-氰基吡啶 、 4-(pyridin-2-yl)piperazine-1-carbothiohydrazide 在 sodium 作用下， 以 甲醇 为溶剂， 反应 4.5h， 以45%的产率得到N'-(4-(pyridin-2-yl)piperazine-1-carbonothioyl)picolinohydrazonamide
  参考文献：
  名称：

  Discovery of 2-pyridineformamide thiosemicarbazones as potent antiausterity agents

  摘要：

  Series of 2-pyridineformamide thiosemicarbazones were synthesized. Their preferential cytotoxicity in nutrient deprived medium (NDM) was evaluated using PANC-1 human pancreatic cancer cells by employing an antiausterity strategy. 2-Pyridineformamide thiosemicarbazones induced apoptosis and exhibited preferential cytotoxic activity toward PANC-1 cells in NDM, with potencies in the submicromolar range. These compounds are potential candidates for the development of therapeutics against pancreatic cancer. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.044

文献信息

• Discovery of 2-pyridineformamide thiosemicarbazones as potent antiausterity agents
  作者：Bhushan Shakya、Paras Nath Yadav、Jun-ya Ueda、Suresh Awale

  DOI：10.1016/j.bmcl.2013.12.044

  日期：2014.1

  Series of 2-pyridineformamide thiosemicarbazones were synthesized. Their preferential cytotoxicity in nutrient deprived medium (NDM) was evaluated using PANC-1 human pancreatic cancer cells by employing an antiausterity strategy. 2-Pyridineformamide thiosemicarbazones induced apoptosis and exhibited preferential cytotoxic activity toward PANC-1 cells in NDM, with potencies in the submicromolar range. These compounds are potential candidates for the development of therapeutics against pancreatic cancer. (C) 2013 Elsevier Ltd. All rights reserved.
• 2-Pyridineformamide N(4)-ring incorporated thiosemicarbazones inhibit MCF-7 cells by inhibiting JNK pathway
  作者：Bhushan Shakya、Nerina Shahi、Faiz Ahmad、Paras Nath Yadav、Yub Raj Pokharel

  DOI：10.1016/j.bmcl.2019.04.031

  日期：2019.7

  In an effort to develop a more potent anticancer therapeutic agent, a series of 2-pyridineformamide thiosemi-carbazones (R = H, 4-CH3, 5-F, 6-CH3 and[GRAPHICS]) have been synthesized and evaluated for their anti-cancer activities against the cancer cells MCF-7 (breast cancer cell line), A-431 and A375 (epidermoid carcinoma cell line), and HeLa (cervical cancer cell line) using MTT assay. All these 2-pyridineformamide thiosemicarbazones exhibited anti-proliferative activities towards these cell lines. 5FAmPyrr possess most profound effects against MCF-7 cells with IC50 of 0.9 mu M. In flow cytometry using Propidium Iodide, 5FAmPyrr was found to induce cell death significantly in a dose dependent manner (100 nM-3 mu M) and inhibited colony formation of MCF-7 cells. This compound induced pro-apoptotic protein Box and inhibited anti apoptotic protein Bcl-2 as well as both c-Jun and Jun N-terminal kinase (abbreviated as JNK) in concentration dependent manner. Further pro-caspase 3 and PARP were inhibited by 5FAmPyrr at concentration of 3 mu M. The results suggest that 5FAmPyrr exhibit anticancer potency and induced cell death by inhibiting MAPK signaling and inducing intrinsic apoptotic pathway. All these indicate that 2-pyridineformamide thiosemicarbazones could be developed as future therapeutics agents to treat cancer.[GRAPHICS].