N'-(pyrrolidine-1- carbonothioyl)picolinohydrazonamide | 1538611-64-1

• 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: N'-(pyrrolidine-1- carbonothioyl)picolinohydrazonamide
• 英文别名: N'-(Pyrrolidine-1-carbonothioyl)picolinohydrazonamide；N-[(Z)-[amino(pyridin-2-yl)methylidene]amino]pyrrolidine-1-carbothioamide
• CAS: 1538611-64-1
• 化学式: C₁₁H₁₅N₅S
• 分子量: 249.34
• InChiKey: HEZHPOBCAYUNOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  17.0
• 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：
  3.0

反应信息

• 作为产物：
  描述：

  3-氰基吡啶 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 N'-(pyrrolidine-1- carbonothioyl)picolinohydrazonamide
  参考文献：
  名称：

  显示结核活性的杂芳基二硫代咔唑酸衍生物的平面度：结构-活性关系。

  摘要：

  由于结核分枝杆菌对现有病原体的抗药性增强以及由此引起的病原体传播，寻找新的抗结核药是一个重要的问题。杂芳基二硫代咔唑酸衍生物已显示出潜在的抗结核活性，因此对这些化合物的结构方面的研究是有意义的。合成了三个新的例子。2- [氨基（吡啶-3-基）亚甲基]肼碳二硫代甲基酯C 8 H 10 N 4 S 2的结构在293 K时具有单斜晶（P 2 1 / n）对称。关于抗菌性能是令人感兴趣的。该结构显示N–H…N和N–H…S氢键。N '-（吡咯烷-1-碳硫基）吡啶并肼基酰胺的结构C 100 H（11 K 15 N 5 S）具有单斜（P 2 1 / n）对称性，并且在抗菌性能方面也很受关注。该结构显示NHS…氢键。（Z）-甲基2- [氨基（吡啶-2-基）亚甲基] -1-甲基肼碳二硫酸酯C 9 H 13 N 4 S 2的结构为三斜晶系（P）对称。结构显示出NHS氢键。

  DOI：

  10.1107/s205322961800284x

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].
• Planarity of heteroaryldithiocarbazic acid derivatives showing tuberculostatic activity: structure–activity relationships
  作者：Małgorzata Szczesio、Jolanta Gołka、Izabela Korona-Głowniak、Czesława Orlewska、Katarzyna Gobis、Andrzej Olczak

  DOI：10.1107/s205322961800284x

  日期：2018.3.1

  is an important issue due to the increasing resistance of Mycobacterium tuberculosis to existing agents and the resulting spread of the pathogen. Heteroaryldithiocarbazic acid derivatives have shown potential tuberculostatic activity and investigations of the structural aspects of these compounds are thus of interest. Three new examples have been synthesized. The structure of methyl 2‐[amino(pyridin

  由于结核分枝杆菌对现有病原体的抗药性增强以及由此引起的病原体传播，寻找新的抗结核药是一个重要的问题。杂芳基二硫代咔唑酸衍生物已显示出潜在的抗结核活性，因此对这些化合物的结构方面的研究是有意义的。合成了三个新的例子。2- [氨基（吡啶-3-基）亚甲基]肼碳二硫代甲基酯C 8 H 10 N 4 S 2的结构在293 K时具有单斜晶（P 2 1 / n）对称。关于抗菌性能是令人感兴趣的。该结构显示N–H…N和N–H…S氢键。N '-（吡咯烷-1-碳硫基）吡啶并肼基酰胺的结构C 100 H（11 K 15 N 5 S）具有单斜（P 2 1 / n）对称性，并且在抗菌性能方面也很受关注。该结构显示NHS…氢键。（Z）-甲基2- [氨基（吡啶-2-基）亚甲基] -1-甲基肼碳二硫酸酯C 9 H 13 N 4 S 2的结构为三斜晶系（P）对称。结构显示出NHS氢键。