Pyrrol-2-carboxaldehyd-4-phenyl-thiosemicarbazon | 16431-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: Pyrrol-2-carboxaldehyd-4-phenyl-thiosemicarbazon
• 英文别名: Pyrrol-2-carbaldehyd-(4-phenyl-thiosemicarbazon)；pyrrolecarboxaldehyde N-phenylthiosemicarbazone；(4)N-phenyl-2-[1-(pyrrol-2-yl)methylidene]-hydrazine carbothioamide；pyrrole-2-carbaldehyde N-phenyl-thiosemicarbazone；1-phenyl-3-(1H-pyrrol-2-ylmethylideneamino)thiourea
• CAS: 16431-49-5
• 化学式: C₁₂H₁₂N₄S
• 分子量: 244.32
• InChiKey: JOHDDABCJDTKEN-UHFFFAOYSA-N

物化性质

• 密度：
  1.2455 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  Pyrrol-2-carboxaldehyd-4-phenyl-thiosemicarbazon 、 三甲基镓 以 甲苯 为溶剂， 以80%的产率得到[(MeGa)(NC4H3CHNNC(S)NMe)(GaMe2)]
  参考文献：
  名称：

  杂环羧醛硫杂氨基甲酮的铝和镓配合物的合成与表征。[（MeAl）{NC 4 H 3 CHNNC（S）N iC 3 H 7 }（AlMe 2）] 2和（GaMe 2）2 [SC 4 H 3 CHNNC（S）NPh]

  摘要：

  分子式为[[MeM）{NC 4 H 3 CHNNC（S）NR}（MMe 2）] 2的新型四核金属配合物（M = Al，R = iC 3 H 7（1）；C 3 H 7（1）。M = Ga，R = iC 3 H 7（2）；C 3 H 7（2）。M = Al，R = Me（3）；当吡咯羧甲醛硫代半脲配体与三甲基铝和-镓混合时，M = Ga，R = Me（4））。四种具有式（MMe 2）2 [SC 4 H 3 CHNNC（S）NR]的双核金属化合物（M = Al，R = iC 3 H 7（5）；C 3 H 7（5）。M = Ga，R = iC 3 H 7（6）；C 3 H 7（6）。M ＝ Al，R ＝ C 6 H 5（7）；M ＝ Al，R ＝ C 6 H 5（7）。M ＝ Ga，R ＝ C 6 H 5（8））是通过噻吩甲醛甲醛缩氨基脲与三甲基铝和-镓的甲烷消除反应而合成的。描述了1和8的X射线

  DOI：

  10.1021/om970660l
• 作为产物：
  描述：

  2-吡咯甲醛 、 4-苯基-3-硫代氨基脲 以 甲醇 为溶剂， 以63.9%的产率得到Pyrrol-2-carboxaldehyd-4-phenyl-thiosemicarbazon
  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

• Group 12 Metal Complexes of 2-Formylpyrrole-(4PL₁) and 2-Acetylpyrrole-N(4)-phenylthiosemicarbazone (4Pl₂), as Examples form Different Donor Modes. Crystal and Molecular Structures of [Hg(4PL₁- H)Br]₂ and [Zn(4PL₂)₂Br₂] · 2 EtOH
  作者：Rosa Carballo、Alfonso Castiñeiras、Teresa Pérez

  DOI：10.1515/znb-2001-0904

  日期：2001.9.1

  The reactions of ⁴N-phenyl-2-[ 1 -(pyrrol-2-yl)methylidene]-hydrazine carbothioamide (4PL₁) and ⁴N-phenyl-2-[l-(pyrrol-2-yl)ethylidene]-hydrazine carbothioamide (4PL₂) with Group 12 metal halides afford complexes of types [M(L)₂X₂] [M = Zn, L = 4PL₁ or 4PL₂, X = Cl, Br or I; M = Cd, L = 4PL₁, and X = Cl, or L = 4PL₂ and X = Cl, Br or I] and [M(L)X₂] [M = Cd, L = 4PL₁, X = Br or I; M = Hg, L = 4PL₁ or 4PL₂, X = Cl, Br or I]. The new compounds were characterized by elemental analysis, FAB mass spectrometry, IR spectroscopy, and, in the case of sufficiently soluble compounds, ¹H, ¹³C and, when appropriate, ¹¹³Cd or ¹⁹⁹Hg NMR spectrometry. The structures of [Hg(4PL₁-H)Br] and [Zn(4PL₂)₂Br₂] · 2 EtOH were also studied by single-crystal X-ray diffractometry. In [Hg(4PL₁-H)Br] crystallized from the mother liquor of its synthesis, 4PL₁ behaves as a monodeprotonated S,N-bidentate ligand. Otherwise, with Hg(II), Zn(II) and Cd(II), 4PL₁ and 4PL₂ both behave as neutral S-monodentate ligands.

  摘要：对4N-苯基-2-[1-(吡咯-2-基)甲基亚胺基]硫代甲酰肼（4PL1）和4N-苯基-2-[1-(吡咯-2-基)乙基亚胺基]硫代甲酰肼（4PL2）与12族金属卤化物的反应得到了类型为[M(L)2X2]（M = Zn，L = 4PL1或4PL2，X = Cl，Br或I；M = Cd，L = 4PL1，X = Cl，或L = 4PL2，X = Cl，Br或I）和[M(L)X2]（M = Cd，L = 4PL1，X = Br或I；M = Hg，L = 4PL1或4PL2，X = Cl，Br或I）的配合物。新化合物通过元素分析、FAB质谱、红外光谱以及在溶解度足够的化合物中的1H、13C和适当情况下的113Cd或199Hg核磁共振光谱进行了表征。[Hg(4PL1-H)Br]和[Zn(4PL2)2Br2]·2乙醇的结构也通过单晶X射线衍射学进行了研究。在从合成母液中结晶的[Hg(4PL1-H)Br]中，4PL1表现为一种单去质子的S，N-双齿配体。否则，对于Hg(II)，Zn(II)和Cd(II)，4PL1和4PL2均表现为中性S-单齿配体。
• 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
• Inhibitory effect of synthetic aromatic heterocycle thiosemicarbazone derivatives on mushroom tyrosinase: Insights from fluorescence, 1 H NMR titration and molecular docking studies
  作者：Juan Xie、Huanhuan Dong、Yanying Yu、Shuwen Cao

  DOI：10.1016/j.foodchem.2015.05.124

  日期：2016.1

  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.
• Synthesis and Characterization of Aluminum and Gallium Complexes of Heterocyclic Carboxaldehyde Thiosemicarbazones. Single-Crystal Structure of [(MeAl){NC₄H₃CHNNC(S)N<i>ⁱ</i>C₃H₇}(AlMe₂)]₂ and (GaMe₂)₂[SC₄H₃CHNNC(S)NPh]
  作者：Youngjin Kang、Namkeun Yang、Sang Ook Kang、Jaejung Ko、Chai-Ho Lee、Young-Haeng Lee

  DOI：10.1021/om970660l

  日期：1997.12.1

  yde thiosemicarbazones with trimethylaluminum and -gallium. The X-ray crystal structures of 1 and 8 are described. The structural data revealed that 1 is a tetranuclear aluminum compound with an eight-membered ring system and 8 is a dinuclear gallium compound with a weak interaction between the pendant thiophene and the gallium center.

  分子式为[[MeM）NC 4 H 3 CHNNC（S）NR}（MMe 2）] 2的新型四核金属配合物（M = Al，R = iC 3 H 7（1）；C 3 H 7（1）。M = Ga，R = iC 3 H 7（2）；C 3 H 7（2）。M = Al，R = Me（3）；当吡咯羧甲醛硫代半脲配体与三甲基铝和-镓混合时，M = Ga，R = Me（4））。四种具有式（MMe 2）2 [SC 4 H 3 CHNNC（S）NR]的双核金属化合物（M = Al，R = iC 3 H 7（5）；C 3 H 7（5）。M = Ga，R = iC 3 H 7（6）；C 3 H 7（6）。M ＝ Al，R ＝ C 6 H 5（7）；M ＝ Al，R ＝ C 6 H 5（7）。M ＝ Ga，R ＝ C 6 H 5（8））是通过噻吩甲醛甲醛缩氨基脲与三甲基铝和-镓的甲烷消除反应而合成的。描述了1和8的X射线