N'-(thiomorpholine-4-carbonothioyl)picolinohydrazonamide | 1538611-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻嗪类
• 英文名称: N'-(thiomorpholine-4-carbonothioyl)picolinohydrazonamide
• 英文别名: N-[(Z)-[amino(pyridin-2-yl)methylidene]amino]thiomorpholine-4-carbothioamide
• CAS: 1538611-78-7
• 化学式: C₁₁H₁₅N₅S₂
• 分子量: 281.406
• InChiKey: VPUIZYHBRHCGNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.54
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-氰基吡啶 、 thiomorpholine-4-carbothiohydrazide 在 甲醇 、 sodium 作用下， 反应 5.5h， 以59%的产率得到N'-(thiomorpholine-4-carbonothioyl)picolinohydrazonamide
  参考文献：
  名称：

  2-Pyridineformamide N(4)-ring incorporated thiosemicarbazones inhibit MCF-7 cells by inhibiting JNK pathway

  摘要：

  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].

  DOI：

  10.1016/j.bmcl.2019.04.031

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].