thiophene-2-carbaldehyde-N-methyl thiosemicarbazone | 1434-96-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: thiophene-2-carbaldehyde-N-methyl thiosemicarbazone
• 英文别名: thiophene-2-carboxaldehyde-4-methyl-thiosemicarbazone；1-Methyl-3-(thiophen-2-ylmethylideneamino)thiourea
• CAS: 1434-96-4
• 化学式: C₇H₉N₃S₂
• 分子量: 199.301
• InChiKey: GVSCOAYJXHCUMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  96.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  thiophene-2-carbaldehyde-N-methyl thiosemicarbazone 、 三甲基镓 以 甲苯 为溶剂， 以68%的产率得到(Me2Ga)2(SC4H3CHNNC(S)NPh)
  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-噻吩甲醛 、 4-甲基氨基硫脲 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以90.6 %的产率得到thiophene-2-carbaldehyde-N-methyl thiosemicarbazone
  参考文献：
  名称：

  含噻吩-2-甲醛缩氨基硫脲的单核、双核和多核卤化铋 (III) 配合物的合成、表征和生物学特性

  摘要：

  为了研究铋化合物的配位化学和药理应用，合成了一系列新的卤化铋(III)缩氨基硫脲络合物。thiophene-2-carbaldehyde-N-取代的缩氨基硫脲与卤化铋 (III) 的反应导致形成 {[[BiCl 2 (η 1 -S-Httsc) 4 ] + .Cl − ][BiCl 2 (μ 2 -Cl)(η 1 -S-Httsc) 2 ] 2 } ( 1 ), {[BiCl 3 (η 1 -S-Htmtsc) 3 ].CH 3 OH} ( 2 ), {[BiCl3 (η 1 -S-Httsc) 3 ].CH 3 OH} ( 3 ), {[BiBr 2 (μ 2 -Br)(η 1 -S-Httsc) 2 ] 2 .CH 3 OH} ( 4 ), {[BiBr 2 (μ 2 -Br)(η 1 -S-Htmtsc) 2 ] n } ( 5 ), 和 {[BiI 2 (μ 2 -I)(η 1 -S-Httsc)

  DOI：

  10.1016/j.jinorgbio.2022.111987

文献信息

• 以2-噻吩甲醛缩氨基硫脲为配体的铜化合物 及其合成方法
  申请人：广西师范大学

  公开号：CN110790778B

  公开（公告）日：2021-05-28

  本发明公开了一种以2‑噻吩甲醛缩氨基硫脲为配体的铜化合物及其合成方法，合成方法是取氨基硫脲，加入无水乙醇搅拌溶解，溶解后，加入2‑噻吩甲醛，混合均匀，将混合溶液在水浴70℃条件下搅拌，室温挥发，有晶体析出，得到配体；取制得的配体加入无水乙醇搅拌溶解，溶解后，加入CuBr2·2H2O，在水浴70℃条件下搅拌，室温挥发，有晶体析出，得到配体的Cu化合物。本发明进一步对合成的铜化合物进行了体外增殖抑制活性实验，结果表明，合成的系列铜化合物对其体外活性普遍较好，特别是对人T24和HeLa细胞具有高度特异性，表现出很好的抑制活性，并且对人正常细胞毒性作用不大，适用于制备高效，低毒的抗肿瘤药物。
• Novel mono-, bi-, tri- and tetra-nuclear copper complexes that inhibit tumor growth through apoptosis and anti-angiogenesis
  作者：Xiaojun Wang、Minghui Zhu、Shanhe Li、Gang Xu、Zhenlei Zhang、Feng Yang

  DOI：10.1016/j.jinorgbio.2023.112403

  日期：2024.1

  To develop the next-generation metal agents for efficiently inhibiting tumor growth, a series of novel mononuclear, binuclear and trinuclear copper (Cu) thiophene-2-formaldehyde thiosemicarbazone complexes and a tetranuclear Cu 1,2,4-triazole-derived complex have been synthesized and their structure-activity relationships have been studied. The trinucleated Cu complex showed the strongest inhibitory

  为了开发有效抑制肿瘤生长的下一代金属制剂，一系列新型单核、双核和三核铜（Cu）噻吩-2-甲醛缩氨基硫脲配合物和四核Cu 1,2,4-三唑衍生配合物已被开发出来。并对其构效关系进行了研究。在所有Cu配合物中，三核Cu配合物对T24细胞表现出最强的抑制活性。其体内抗肿瘤作用优于顺铂，且副作用减少。进一步的抗肿瘤机制研究表明，Cu配合物不仅诱导癌细胞凋亡，还通过抑制血管内皮细胞的迁移和侵袭、阻断细胞周期于G1期、诱导自噬来抑制肿瘤血管生成。
• 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：——
• Synthesis, crystal structures, and biological activities of 2-thiophene N(4)-methylthiosemicarbazone and its unusual hexanuclear silver(I) cluster
  作者：Ming-Xue Li、Dong Zhang、Li-Zhi Zhang、Jing-Yang Niu

  DOI：10.1016/j.inoche.2010.07.012

  日期：2010.11

  2-Thiophene N(4)-methylthiosemicarbazone (HL) and its Ag(I) complex of formula [Ag-6(L)(6)center dot 4DMF] 1 have been synthesized and characterized by elemental analysis, IR spectra and single-crystal X-ray diffraction studies. The silver(I) complex 1 with a 1:1 metal-ligand molar ratio is an unusual hexanuclear cluster with 6 silver atoms in different environments: four silver atoms of them are considered to be 3-coordinate form, which are coordinated by two thiolate sulfur atoms and one imine nitrogen and the other two silver atoms are considered to be 4-coordinate form, which are coordinated by three thiolate sulfur atoms and one imine nitrogen, with four thiolate sulfur bridging two silver atoms and two thiolate sulfur bridging three silver atoms. Biological studies, carried out in vitro against bacteria, fungi and SMMC-7721 liver cancer cell line, respectively, have shown that the free ligand and the title complex show distinct difference in the biological property. (C) 2010 Elsevier B.V. All rights reserved.