(4)N-methyl-2-[1-(pyrrol-2-yl)methylidene]hydrazine carbothiamide | 16431-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (4)N-methyl-2-[1-(pyrrol-2-yl)methylidene]hydrazine carbothiamide
• 英文别名: pyrrole-2-carbaldehyde N-methyl-thiosemicarbazone；Pyrrol-2-carbaldehyd-(4-methyl-thiosemicarbazon)；Pyrrol-2-carboxaldehyd-4-methyl-thiosemicarbazon；N-Methyl-2-[(2H-pyrrol-2-ylidene)methyl]hydrazine-1-carbothioamide；1-methyl-3-(1H-pyrrol-2-ylmethylideneamino)thiourea
• CAS: 16431-47-3
• 化学式: C₇H₁₀N₄S
• mdl: MFCD05053140
• 分子量: 182.249
• InChiKey: SYYWMKZEDFZNDB-UHFFFAOYSA-N

物化性质

• 熔点：
  191-192 °C (decomp)
• 沸点：
  338.0±34.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  84.3
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4)N-methyl-2-[1-(pyrrol-2-yl)methylidene]hydrazine carbothiamide 以 甲醇 、 氯仿 为溶剂， 生成
  参考文献：
  名称：

  钯 (II) 吡咯缩氨基脲配合物的合成和表征。[{Pd[C4H4NC(H)=NNC(S)NHMe](Cl)}2{μ-Ph2P(CH2)3PPh2}]和[Pd{C4H4NC(H)=NNC(S)NHMe}{Ph2P]的晶体结构(CH2)2PPh2-P,P}](Cl)

  摘要：

  缩氨基硫脲配体 C4H4NC(H)=NN(H)C(S)NHR (R = Me, a; Et, b) 与 Li2[PdCl4] 反应得到双核配合物 [Pd{C4H4NC(H)=NNC(S) )NHR}(μ-Cl)]2 (R = Me, 1a; Et, 1b) 具有中心 Pd2Cl2 核心和氨基硫脲在肼氮原子上的去质子化。用三苯基膦处理 1a 和 1b 得到单核化合物 [Pd{C4H4C(H)=NNC(S)NHR}(Cl)(PPh3)] (R = Me, 2a; Et, 2b)，而 1a 和 1b 的反应与叔二膦反应得到单核和双核化合物，视情况而定，相应的二膦充当单齿 (6b)、螯合 (3a) 和桥连配体 (4a, 5a, 4b, 5b)。用 (Ph2PCH2CH2PPh2)W(CO)5 处理 1a 和 1b 得到新的异质双金属配合物 7a 和 7b。描述了配合物 3a 和 4a 的晶体结构。

  DOI：

  10.1002/zaac.200570043
• 作为产物：
  描述：

  2-吡咯甲醛 、 4-甲基氨基硫脲 以 甲醇 为溶剂， 以67.8%的产率得到(4)N-methyl-2-[1-(pyrrol-2-yl)methylidene]hydrazine carbothiamide
  参考文献：
  名称：

  Inhibitory effect of synthetic aromatic heterocycle thiosemicarbazone derivatives on mushroom tyrosinase: Insights from fluorescence, 1 H NMR titration and molecular docking studies

  摘要：

  Three structurally similar aromatic heterocyclic compounds 2-thiophenecarboxaldehyde (a), 2-furaldehyde (b), 2-pyrrolecarboxaldehyde (c) were chosen and a series of their thiosemicarbazone derivatives(1a-3a, 1b-3b and 1c-3c) were synthesized to evaluate their biological activities as mushroom tyrosinase inhibitors. The inhibitory effects of these compounds on tyrosinase were investigated by using spectrofluorimetry, H-1 NMR titration and molecular docking techniques. From the results of fluorescence spectrum and H-1 NMR titration, it was found that forming complexes between the sulfur atom from thiourea and copper ion of enzyme center may play a key role for inhibition activity. Moreover, investigation of H-1 NMR spectra further revealed that formation of hydrogen bond between inhibitor and enzyme may be helpful to above complexes formation. The results were well coincident with the suggestion of molecular docking and obviously showed that 2-thiophone N(4)-thiosemicarbazone (1a), 2-furfuran N(4)-thiosemicarbazone (1b) and 2-pyrrole N(4)-thiosemicarbazone (1c) are potential inhibitors which deserves further investigation. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2015.05.124

文献信息

• Synthesis and Structural Characterization of Metal Complexes of 2-Formylpyrrole ⁴N-Methylthiosemicarbazone (4ML₁) and 2-Acetyl- pyrrole ⁴N-Methylthiosemicarbazone (4ML₂). The X-Ray Crystal Structures of [Ni(4ML₁-H)₂], [Pd(4ML₁-H)₂] and [Cd(4ML₂)₂I₂]
  作者：Ruben Alonso、Elena Bermejo、Rosa Carballo、Alfonso astiñeiras、Teresa Pérez

  DOI：10.1515/znb-2001-0301

  日期：2001.3.1

  Reaction of ⁴N-methyl-2-[1-(pyrrol-2-yl)methylidene]hydrazinecarbothioamide (4ML₁ and ⁴N-methyl-2-[1-(pyrrol-2-yl)-ethylidene]hydrazine carbothioamide (4ML₁) with zinc(II), cadmium(II) and mercury(II) halides afforded complexes with formulas [M(L)X₂] [(L; M; X) =(4ML₁; Cd; Cl) (4), (4ML₁; Hg; Cl, Br, I) (7 - 9), (4ML₂; Cd; Cl) (17), (4ML₂; Hg; Cl, Br, I) (20 - 22)] or [M(L)₂X₂] [(L; M; X) = (4ML₁; Zn; Cl, Br, I) (1 - 3), (4ML₁; Cd; Br, I) (5, 6), (4ML₂; Zn; Cl, Br, I) (14 - 16), (4ML₂; Cd; Br, I) (18, 19)]. Reaction of 4ML₁ with salts of copper(II), nickel(II), palladium(II) and platinum(II) afforded complexes of formula [M(4ML₁-H)₂] (10 -13). Crystals of 11, 12 and 19 were studied by X-ray diffractometry, and all new compounds were characterized by elemental analysis, mass spectrometry, and IR, electronic and ¹H and ¹³C NMR spectroscopy and, when pertinent and allowed by the solubility of the compound, ¹¹³Cd or ¹⁹⁹Hg NMR spectroscopy. In the complexes of Group 12 metals, both ligands are neutral and S-monodentate. In the complexes of copper or Group 10 metals, 4ML₁ is monodeprotonated and S,N-bidentate.

  将⁴N-甲基-2-[1-(吡咯-2-基)甲基亚氨基]羧硫酰胺(4ML₁)和⁴N-甲基-2-[1-(吡咯-2-基)乙基亚氨基]羧硫酰胺(4ML₂)与锌(II)、镉(II)和汞(II)卤化物反应，得到的配合物的化学式为[M(L)X₂] [(L; M; X) =(4ML₁; Cd; Cl) (4), (4ML₁; Hg; Cl, Br, I) (7 - 9), (4ML₂; Cd; Cl) (17), (4ML₂; Hg; Cl, Br, I) (20 - 22)]或[M(L)₂X₂] [(L; M; X) =(4ML₁; Zn; Cl, Br, I) (1 - 3), (4ML₁; Cd; Br, I) (5, 6), (4ML₂; Zn; Cl, Br, I) (14 - 16), (4ML₂; Cd; Br, I) (18, 19)]。将4ML₁与铜(II)、镍(II)、钯(II)和铂(II)的盐反应，得到的配合物的化学式为[M(4ML₁-H)₂] (10 -13)。11、12和19的晶体结构经过X射线衍射研究，所有新的化合物均通过元素分析、质谱、红外、电子和¹H和¹³C NMR光谱表征，当适用并且化合物的溶解度允许时，还使用¹¹³Cd或¹⁹⁹Hg NMR光谱。在12族金属的配合物中，两个配体均为中性的S-单齿配体。在铜或10族金属的配合物中，4ML₁为单去质子化的S、N-双齿配体。

• Pyrrole-2-carbaldehyde Thiosemicarbazonates of Nickel(II) and Palladium(II): Synthesis, Structure, and Spectroscopy
  作者：Tarlok S. Lobana、Poonam Kumari、Gagandeep Bawa、Geeta Hundal、Ray J. Butcher、Francisco J. Fernandez、Jerry P. Jasinski、James A. Golen

  DOI：10.1002/zaac.201200012

  日期：2012.4

  Complexes of pyrrole-2-carbaldehyde thiosemicarbazones, [(C4H4N4)(H)C2=N3–N2(H)–C1(=S)–N1HR; R = Ph, H2L1; Me, H2L2; H, H2L3] with nickel(II) and palladium(II) are described. The reaction of nickel(II) acetate with H2L1 in methanol in 1:1 molar ratio yielded a complex of composition, [Ni(κ2-N3,S-HL1)2] (1). Likewise reaction of NiCl2 with H2L2 in 1:1 molar ratio in acetonitrile in the presence of triethylamine

  吡咯-2-甲醛缩氨基硫脲复合物，[(C4H4N4)(H)C2=N3–N2(H)–C1(=S)–N1HR；R=Ph，H2L1；我，H2L2；H, H2L3] 与镍 (II) 和钯 (II) 进行了描述。乙酸镍 (II) 与 H2L1 在甲醇中以 1:1 的摩尔比反应生成复合物 [Ni(κ2-N3,S-HL1)2] (1)。同样，在三乙胺碱的存在下，NiCL2 与 H2L2 在乙腈中以 1:1 的摩尔比反应，然后加入吡啶，没有产生预期的 [Ni(κ3-N4,N3,S-L2)(py)] 络合物，此外，还形成了一个双方形平面复合物，[Ni(κ2-N3,S-HL2)2] (2)。然而，在联吡啶 (bipy) 的存在下，它产生了加成产物 [Ni(κ2-N3,S-HL2)2(κ2-N, N-bipy)] (3)。PdCL2(κ2-P, P–PPh2–CH2–PPh2) 与 H2L3 在甲苯中在三乙胺存在