N'-(piperidine-1-carbonothioyl)picolinohydrazonamide | 403823-10-9

• 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'-(piperidine-1-carbonothioyl)picolinohydrazonamide
• 英文别名: 2-pyridineformamide-3-piperidylthiosemicarbazone；N-[[amino(pyridin-2-yl)methylidene]amino]piperidine-1-carbothioamide
• CAS: 403823-10-9
• 化学式: C₁₂H₁₇N₅S
• 分子量: 263.366
• InChiKey: WUGXLKZMWVBROV-UHFFFAOYSA-N

物化性质

• 沸点：
  388.7±34.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  98.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N'-(piperidine-1-carbonothioyl)picolinohydrazonamide 、 zinc diacetate 以 乙醇 为溶剂， 以98.7%的产率得到[Zn(2-pyridineformamide-3-piperidylthiosemicarbazonato)(OAc)]2
  参考文献：
  名称：

  Coordination of ZnII, CdII, and HgII by 2-Pyridineformamide-3-piperidyl-thiosemicarbazone

  摘要：

  Sodium in dry methanol reduces 2-cyanopyridine in the presence of 3-piperidylthiosemicarbazide and produces 2-pyridineformamide-3-piperidylthiosemicarbazone, HAmpip. Complexes with zinc(II), cadmium(II), and mercury(II) have been prepared and characterized by elemental analyses and spectroscopic techniques. In addition, the crystal structures of [Zn(Ampip)(2)], [Zn(Ampip)(Oac)](2), [Cd(HAmpip)Cl-2].(CH3)(2)SO, [Cd(HAmpip)Br-2] (.) (CH3)(2)SO, [Cd(HAmpip)I-2].(CH3)(2)SO, [Cd(Ampip)(2)] and [Hg(HAmpip)Br-2].(CH3)(2)SO have been solved. Coordination of the anionic and neutral thiosemicarbazone ligand is via the pyridyl nitrogen, imine nitrogen and thiolato/thione sulfur atom, respectively. In [Zn(Ampip)(OAc)](2) one of the bridging acetato ligands has monodentate coordination and the other bridges in a bidentate manner. Cd-113 NMR studies were carried out on the [Cd(HAmpip)X-2] (X = Cl, Br or I) and [Cd(Ampip)(OAc)](2) complexes. The Cd-113 chemical shifts are affected by the halogen and range from 411 to 301 ppm, and the spectrum of [Cd(Ampip)(OAc)](2) shows two signals at 450 and 251 ppm. The Hg-199 NMR spectrum of [Hg(HAmpip)Cl-2] also is discussed.

  DOI：

  10.1002/1521-3749(200202)628:2<492::aid-zaac492>3.0.co;2-v
• 作为产物：
  描述：

  2-氰基吡啶 、 piperidine-1-carbothioic acid hydrazide 在 甲醇 、 sodium 作用下， 反应 5.5h， 以21%的产率得到N'-(piperidine-1-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

• Iron(III), cobalt(II,III), copper(II) and zinc(II) complexes of 2-pyridineformamide 3-piperidylthiosemicarbazone
  作者：Karen A. Ketcham、John K. Swearingen、Alfonso Castiñeiras、Isabel Garcia、Elena Bermejo、Douglas X. West

  DOI：10.1016/s0277-5387(01)00941-x

  日期：2001.12

  with iron(III), cobalt(II,III) copper(II) and zinc(II) have been prepared and characterized by molar conductivities, magnetic susceptibilities and spectroscopic techniques. In addition, the crystal structures of HAmpip, [Fe(Ampip)2]ClO4, [Cu(HAmpip)Cl2]·CH3OH and [Zn(HAmpip)Br2]·C2H6SO have been determined. Coordination is via the pyridyl nitrogen, imine nitrogen and thiolato or thione sulfur when coordinating

  摘要在3-哌啶硫代氨基脲存在下，用钠还原2-氰基吡啶可生成2-吡啶甲酰胺3-哌啶硫代氨基脲HAmpip。已经制备了与铁（III），钴（II，III），铜（II）和锌（II）的配合物，并通过摩尔电导率，磁化率和光谱技术对其进行了表征。此外，已经确定了HAmpip，[Fe（Ampip）2] ClO4，[Cu（HAmpip）Cl2]·CH3OH和[Zn（HAmpip）Br2]·C2H6SO的晶体结构。当分别配位为阴离子或中性配体时，配位是通过吡啶基氮，亚胺氮和硫醇基或硫酮硫进行的。
• 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.
• Spectral studies and X-ray crystal structures of three nickel(II) complexes of 2-pyridineformamide 3-piperidylthiosemicarbazone
  作者：Karen A Ketcham、Isabel Garcia、John K Swearingen、Ayman K El-Sawaf、Elena Bermejo、Alfonso Castiñeiras、Douglas X West

  DOI：10.1016/s0277-5387(02)00853-7

  日期：2002.4

  Reduction of 2-cyanopyridine by sodium in dry methanol in the presence of 3-piperidylthiosemicarbazide produces 2-pyridineformamide 3-piperidylthiosemicarbazone, HAmpip. Complexes with nickel(II) have been prepared and characterized by magnetic susceptibility and spectroscopic techniques. The crystal structures of [Ni(Ampip)(2)], [Ni(Ampip)OAc], and [Ni(HAmpip)Cl]Cl have been solved. Coordination of the anionic and neutral ligand is via the pyridyl nitrogen, imine nitrogen, and thiolatothione sulfur. [Ni(Ampip)(2)] is an approximately octahedral NiN4S2 center with the tridentate ligands in a meridonal arrangement. [Ni(Ampip)OAc] is essentially planar except for the acetato ligand, which is > 80degrees out of the coordination plane, and the ionic [Ni(HAmpip)Cl]Cl involves the neutral thiosemicarbazone ligand. (C) 2002 Published by Elsevier Science Ltd.
• 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].
• Coordination of ZnII, CdII, and HgII by 2-Pyridineformamide-3-piperidyl-thiosemicarbazone
  作者：Alfonso Castiñeiras、Isabel García、Elena Bermejo、Karen A. Ketcham、Douglas X. West、Ayman K. El-Sawaf

  DOI：10.1002/1521-3749(200202)628:2<492::aid-zaac492>3.0.co;2-v

  日期：2002.2

  Sodium in dry methanol reduces 2-cyanopyridine in the presence of 3-piperidylthiosemicarbazide and produces 2-pyridineformamide-3-piperidylthiosemicarbazone, HAmpip. Complexes with zinc(II), cadmium(II), and mercury(II) have been prepared and characterized by elemental analyses and spectroscopic techniques. In addition, the crystal structures of [Zn(Ampip)(2)], [Zn(Ampip)(Oac)](2), [Cd(HAmpip)Cl-2].(CH3)(2)SO, [Cd(HAmpip)Br-2] (.) (CH3)(2)SO, [Cd(HAmpip)I-2].(CH3)(2)SO, [Cd(Ampip)(2)] and [Hg(HAmpip)Br-2].(CH3)(2)SO have been solved. Coordination of the anionic and neutral thiosemicarbazone ligand is via the pyridyl nitrogen, imine nitrogen and thiolato/thione sulfur atom, respectively. In [Zn(Ampip)(OAc)](2) one of the bridging acetato ligands has monodentate coordination and the other bridges in a bidentate manner. Cd-113 NMR studies were carried out on the [Cd(HAmpip)X-2] (X = Cl, Br or I) and [Cd(Ampip)(OAc)](2) complexes. The Cd-113 chemical shifts are affected by the halogen and range from 411 to 301 ppm, and the spectrum of [Cd(Ampip)(OAc)](2) shows two signals at 450 and 251 ppm. The Hg-199 NMR spectrum of [Hg(HAmpip)Cl-2] also is discussed.