2-furaldehyde-4-methylthiosemicarbazone | 27421-68-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-furaldehyde-4-methylthiosemicarbazone
• 英文别名: furan-2-carbaldehyde N¹-methylthiosemicarbazone；furan-2-carbaldehyde-N-methyl thiosemicarbazone；Furfural-(4-methyl-thiosemicarbazon)；furancarboxaldehyde N-methylthiosemicarbazone；1-(2-Furanylmethylideneamino)-3-methylthiourea；1-(furan-2-ylmethylideneamino)-3-methylthiourea
• CAS: 27421-68-7
• 化学式: C₇H₉N₃OS
• 分子量: 183.234
• InChiKey: HYXWOVSEEKCMOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 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：
  81.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-furaldehyde-4-methylthiosemicarbazone 、 三甲基镓 以 甲苯 为溶剂， 以65%的产率得到(Me2Ga)(OC4H3CHNNC(S)NHMe)
  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：

  糠醛 、 4-甲基氨基硫脲 在 溶剂黄146 作用下， 以92.45 %的产率得到2-furaldehyde-4-methylthiosemicarbazone
  参考文献：
  名称：

  一些含五元环缩氨基硫脲的合成、表征及 Hirshfeld 表面分析

  摘要：

  摘要 作为多齿配体的缩氨基硫脲被认为是最重要的一类有机化合物，因为它们具有广谱的药理作用和易于与金属离子配位的能力。四种缩氨基硫脲，呋喃-2-甲醛-N-甲基缩氨基硫脲 ( Hfmtsc )、噻吩-2-乙醛缩氨基硫脲 ( Hattsc )、噻吩-2-乙醛-N-甲基缩氨基硫脲 ( Hatmtsc ) 和噻吩-2-乙醛-N-乙基使用取代的醛和（未）取代的氨基硫脲通过缩合反应成功制备了氨基硫脲（Hatetsc ）。它们通过熔点、元素分析、摩尔电导率、FTIR、UV-Vis、1H 和13 C NMR 光谱技术。它们的晶体结构是通过使用单晶X射线衍射研究确定的。通过 Hirshfeld 表面分析研究分子间相互作用。化合物的分子结构通过 N–H⋯S、C–H⋯S、N–H⋯O 和 C–H⋯O 相互作用来稳定。在每个化合物中，分子通过成对的 N-H⋯S 相互作用连接成\(R_{2}^{2}(8)\)二聚体。

  DOI：

  10.1134/s0022476623050013

文献信息

• 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.
• Umapathy, P.; Budhkar, A. P.; Dorai, C. S., Journal of the Indian Chemical Society, 1986, vol. 63, p. 714 - 721
  作者：Umapathy, P.、Budhkar, A. P.、Dorai, C. S.

  DOI：——

  日期：——
• The influence of substituents (R) at N1 atom of furan-2-carbaldehyde thiosemicarbazones {(C4H3O)HC2N3–N(H)–C1(S)N1HR} on bonding, nuclearity, H-bonded networks of copper(I) complexes
  作者：Tarlok S. Lobana、Rekha Sharma、Geeta Hundal、A. Castineiras、Ray Jay Butcher

  DOI：10.1016/j.poly.2012.08.014

  日期：2012.10

  The chemistry of copper(I) halides (CuX) with furan-2-carbaldehyde-N-1-substituted thiosemicarbazones (C4H3O)HC2=(NNH)-N-3-H-2-C-1(=S)(NHR)-H-1, Hftsc-(NHR)-H-1) in presence of triphenyl phopshine is described. For methyl and ethyl substituents (R) at N-1 atom, and with X = I, Br, Cl, the halogen-bridged dimers, namely, [Cu-2(mu-X)(2)(eta(1)-S-Hftsc-(NHR)-H-1)(2)(PPh3)(2)] (R, X: Me, I, 1, Br 2, Cl 3; Et, I 4, Br 5, Cl 6) have been obtained. However, the presence of phenyl substituent at N-1 has favored a three coordinate complex, [Cul(eta(1)-S-Hftsc-(NHPh)-H-1)(2)] 7, and with copper(I) bromide/and chloride, it has formed sulfur-bridged dimers, [Cu2X2(-eta(1)-Hftsc-(NHPh)-H-1)(2)(mu-S-Hftsc-(NHPh)-H-1)(2)] (X = Br 8, Cl 9). In the latter three complexes (7-9), the Ph3P ligand did not take part in coordination. All these complexes have been characterized with the help of elemental analysis, IR, H-1 NMR spectroscopy and X-ray crystallography (1-3, 5, 7 and 9). The bonding and nuclearity of complexes has been found to vary with the substituents at N-1 atom. The intermolecular interactions have formed one dimensional (1,9) and two dimensional (2, 3 and 5) networks. (C) 2012 Elsevier Ltd. All rights reserved.
• Metal derivatives of N1-substituted thiosemicarbazones: Synthesis, structures and spectroscopy of nickel(II) and cobalt(III) complexes
  作者：Tarlok S. Lobana、Poonam Kumari、Geeta Hundal、Ray J. Butcher、A. Castineiras、Takashiro Akitsu

  DOI：10.1016/j.ica.2012.09.021

  日期：2013.1

  Reactions of nickel(II) and cobalt(II) salts with various N-1-substituted thiosemicarbazones [(RRC2)-R-1-C-2=N-3-(NH)-H-2-C-1(=S)-(NHR3)-H-1, (HL)-L-2; R-1 = C6H5-, R-2 = H, H2L1(R-3 = Me); H2L2(R-3 = Ph), R-1 = 2-OHC6H4-, R-2 = H, H2L3(R-3 = Me), H2L4(R-3 = Et), H2L5(R-3 = Ph); R-2 = Me, H2L6(R-3 = Me), R-2 = Me, H2L7(R-3 = Et) and R-2, R-3 = H, Me, H2L8(R-1 = C4H3S), H2L9(R-1 = C4H3O)] are described. Reactions of Ni(OAc)(2) with the ligands having R-1 as phenyl group at C-2 carbon (H2L1, H2L2) gave complexes, [Ni(kappa(2)-N-3, S-HL)(2)] (HL = HL1, 1; HL2, 2). Other ligands with R-1 as 2-hydroxyphenyl groups, namely, H2L3-H2L7, with Ni(OAc)(2) yielded rust colored compounds, Ni(kappa(3)-O, N-3, S-L)} (L-2 = L-3-L-7) which after the addition of PPh2-CH2-PPh2 yielded dinuclear, [Ni-2(kappa(3)-O, N-3, S-L)(2)(mu-P, P-PPh2-CH2-PPh2)] (L-2 = L-3, 3; L-4, 4; L-5, 5) and mononuclear, [Ni(kappa(3)-O, N-3, S-L)(kappa(1)-P-PPh2-CH2-PPh2)] (L-2 = L-6, 6; L-7, 7) complexes. Likewise, Ni(kappa(3)-O, N-3, S-L-5} with 2-phenylpyridine(2-Phpy) has yielded a mononuclear complex, [Ni(kappa(3)-O, N-3, S-L-5)(kappa(1)-N-2-Phpy)] 8. The geometry around Ni metal center can be formally described as square planar in each of complexes 1-8. Reactions of CoCl2 with H2L8 and H2L9 involved oxidation of Co-II to Co-III and yielded octahedral complexes, [Co(kappa(2)-N, S-HL)(3)] (HL = HL8, 9; HL9, 10). (C) 2012 Elsevier B. V. 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