N(4)-methyl-2-pyrazineformamide thiosemicarbazone | 463962-51-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N(4)-methyl-2-pyrazineformamide thiosemicarbazone
• 英文别名: pyrazineformamide N4-methylthiosemicarbazone；1-[[Amino(pyrazin-2-yl)methylidene]amino]-3-methylthiourea；1-[[amino(pyrazin-2-yl)methylidene]amino]-3-methylthiourea
• CAS: 463962-51-8
• 化学式: C₇H₁₀N₆S
• 分子量: 210.263
• InChiKey: YSXWQFIPGZNVGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N(4)-methyl-2-pyrazineformamide thiosemicarbazone 、 镉 在 tetraethylammonium perchlorate 作用下， 以 乙腈 为溶剂， 生成 cadmium(II) bis(pyrazineformamide N4-methylthiosemicarbazone)
  参考文献：
  名称：

  Structural studies of pyrazineformamide N4-methylthiosemicarbazone and its zinc(II) and cadmium(II) complexes formed by electrochemical oxidation

  摘要：

  Reduction of cyanopyrazine by sodium in dry methanol in the presence of N(4)-methylthiosemicarbazide produces pyrazineformamide N(4)-methylthiosemicarbazone, HPzAm4M. Electrochemical synthesis in acetonitrile produced [Zn(PzAm(4)M)(2)](.)2CH(3)CN and (.)[Cd(PzAm4M)(2)](.)0.5CH(3)CN. The crystal Structures of HPzAm4M and the two complexes have been obtained. Coordination of anionic PzAm4M in the two complexes is via the pyridyl nitrogen, imine nitrogen and thiolato sulfur and the ligands are in a meridional arrangement with the imine nitrogens trans. Hydrogen-bonding interactions are an important property of HPzAm4M and its complexes. Both pyrazine nitrogens are involved in hydrogen-bonding in HPzAm4M, and the non-coordinated pyrazine nitrogen is involved in both complexes. HPzAm4M and the coordinated PzAm4M ligands are quite planar. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0277-5387(02)01019-7
• 作为产物：
  描述：

  2-氰基吡嗪 、 4-甲基氨基硫脲 在 sodium 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以80%的产率得到N(4)-methyl-2-pyrazineformamide thiosemicarbazone
  参考文献：
  名称：

  生物相关化合物中的超分子相互作用。2-吡嗪甲酰胺缩氨基硫脲及其环化产物

  摘要：

  摘要 2-氰基吡嗪与氨基硫脲或N-甲基氨基硫脲反应得到(Z)-2-(氨基(吡嗪-2-基)亚甲基)肼碳硫酰胺(HPzAm4DH)和(Z)-2-(氨基(吡嗪-2-基) )-N-甲基肼碳硫酰胺 (HPzAm4M)，分别。(2Z,N'E)-N'-(4-Oxothiazolidin-2-ylidene)pyrazine-2-carbohydrazonamide (HPzAmot, 5) 和 (2Z,N'E)-N'-(3-methyl-4-oxothiazolidin) -2-ylidene)pyrazine-2-carbohydrazonamide (MPzAmot, 7) 已从这些缩氨基硫脲与氯乙酸或溴乙酸合成，使用常规合成方法和微波辅助有机反应增强。缩氨基硫脲及其溶剂化物的晶体结构 [HPzAm4DH⋅1/2 MeOH (1), HPzAm4DH⋅H2O (2), HPzAm4M (3), HPzAm4M⋅2H2O

  DOI：

  10.1016/j.molstruc.2014.05.042

文献信息

• Bismuth(III) complexes with pyrazineformamide thiosemicarbazones: Investigation on the antimicrobial and cytotoxic effects
  作者：Jéssica C.L. Almeida、Raquel S. Amim、Claudia Pessoa、Maria C.S. Lourenço、Isolda C. Mendes、Josane A. Lessa

  DOI：10.1016/j.poly.2020.114709

  日期：2020.10

  Complexes [Bi(PzAm4DH)Cl-2] (1), [Bi(PzAm4M)Cl-2] (2), [Bi(PzAm4E)Cl-2] (3), [Bi(PzAm4Cy)Cl-2]center dot 3H(2)O (4) and [Bi(PzAm4Ph)Cl-2] (5) were prepared with 2-pyrazineformamide- (HPzAm4DH, L1), N(4)-methyl-2-pyrazineformamide- (HPzAm4M, L2), N(4)-ethyl-2-pyrazineformamide- (HPzAm4E, L3), N(4)-cyclohexyl-2-pyrazineformamide (HPzAm4Cy, L4) and N(4)-phenyl-2-pyrazineformamide (HPzAm4Ph, L5) thiosemicarbazones. L4 crystallized from methanol in monoclinic crystal system. All compounds were assayed for their cytotoxicity against SF-295 (glioblastoma multiforme) and HCT-116 (colon adenocarcinoma) human tumor cell lines and Mycobacterium tuberculosis H37Rv ATCC 27294 strain. Complexes 1-5 proved to have poor activity against the tumor cells at 5 mu g/mL, whereas for complexes 4 and 5, coordination to Bi(III) was an effective strategy to increase the antimycobacterial activity of the thiosemicarbazones L4 and L5. (C) 2020 Published by Elsevier Ltd.
• Supramolecular interactions in biologically relevant compounds. 2-Pyrazineformamide thiosemicarbazones and some products of their cyclization
  作者：Alfonso Castiñeiras、Isabel García-Santos、Silvia Nogueiras、Iria Rodríguez-González、Raúl Rodríguez-Riobó

  DOI：10.1016/j.molstruc.2014.05.042

  日期：2014.9

  (MPzAmot, 7) have been synthesized from these thiosemicarbazones with chloroacetic or bromoacetic acids, using a conventional synthetic methodology and microwave-assisted organic reaction enhancement. The crystal structures of the thiosemicarbazones and their solvates [HPzAm4DH⋅1/2 MeOH (1), HPzAm4DH⋅H2O (2), HPzAm4M (3), HPzAm4M⋅2H2O (4)] and the 1,3-thiazolidin-4-ones (5 and 7) have been studied by

  摘要 2-氰基吡嗪与氨基硫脲或N-甲基氨基硫脲反应得到(Z)-2-(氨基(吡嗪-2-基)亚甲基)肼碳硫酰胺(HPzAm4DH)和(Z)-2-(氨基(吡嗪-2-基) )-N-甲基肼碳硫酰胺 (HPzAm4M)，分别。(2Z,N'E)-N'-(4-Oxothiazolidin-2-ylidene)pyrazine-2-carbohydrazonamide (HPzAmot, 5) 和 (2Z,N'E)-N'-(3-methyl-4-oxothiazolidin) -2-ylidene)pyrazine-2-carbohydrazonamide (MPzAmot, 7) 已从这些缩氨基硫脲与氯乙酸或溴乙酸合成，使用常规合成方法和微波辅助有机反应增强。缩氨基硫脲及其溶剂化物的晶体结构 [HPzAm4DH⋅1/2 MeOH (1), HPzAm4DH⋅H2O (2), HPzAm4M (3), HPzAm4M⋅2H2O
• Structural studies of pyrazineformamide N4-methylthiosemicarbazone and its zinc(II) and cadmium(II) complexes formed by electrochemical oxidation
  作者：Elena Labisbal、Antonio Sousa-Pedrares、Alfonso Castiñeiras、John K. Swearingen、Douglas X. West

  DOI：10.1016/s0277-5387(02)01019-7

  日期：2002.7

  Reduction of cyanopyrazine by sodium in dry methanol in the presence of N(4)-methylthiosemicarbazide produces pyrazineformamide N(4)-methylthiosemicarbazone, HPzAm4M. Electrochemical synthesis in acetonitrile produced [Zn(PzAm(4)M)(2)](.)2CH(3)CN and (.)[Cd(PzAm4M)(2)](.)0.5CH(3)CN. The crystal Structures of HPzAm4M and the two complexes have been obtained. Coordination of anionic PzAm4M in the two complexes is via the pyridyl nitrogen, imine nitrogen and thiolato sulfur and the ligands are in a meridional arrangement with the imine nitrogens trans. Hydrogen-bonding interactions are an important property of HPzAm4M and its complexes. Both pyrazine nitrogens are involved in hydrogen-bonding in HPzAm4M, and the non-coordinated pyrazine nitrogen is involved in both complexes. HPzAm4M and the coordinated PzAm4M ligands are quite planar. (C) 2002 Elsevier Science Ltd. All rights reserved.