1-[(1H-indol-2-yl)methylene]thiosemicarbazide | 6868-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-[(1H-indol-2-yl)methylene]thiosemicarbazide
• 英文别名: (1H-indol-2-ylmethylideneamino)thiourea
• CAS: 6868-27-5
• 化学式: C₁₀H₁₀N₄S
• 分子量: 218.282
• InChiKey: DMZWHYDVGXCMFS-UHFFFAOYSA-N

物化性质

• 熔点：
  231 °C (decomp)
• 沸点：
  453.3±37.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.3
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  异氰环已烷 、 1-[(1H-indol-2-yl)methylene]thiosemicarbazide 在 三甲基氯硅烷 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以90%的产率得到
  参考文献：
  名称：

  Synthesis of N1,N3-disubstituted formamidrazones via the TMSCl-promoted reaction of isocyanides with thiosemicarbazones

  摘要：

  A hitherto undescribed TMSCl-promoted reaction of thiosemicarbazones was found to give rare N-1,N-3-disubstituted formamidrazones in fair to excellent yields. The scope of this new reaction was investigated and a plausible mechanism proposed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.085
• 作为产物：
  描述：

  1H-吲哚-2-甲醛 、 氨基硫脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以72%的产率得到1-[(1H-indol-2-yl)methylene]thiosemicarbazide
  参考文献：
  名称：

  Refinement of arylthiosemicarbazone pharmacophore in inhibition of mushroom tyrosinase

  摘要：

  Melanin play a major role in human skin protection and their biosynthesis is vital. Due to their color, they contribute to the skin pigmentation. Tyrosinase is a key enzyme involved in the first stage of melanin biosynthesis, it catalyzes the transformation of tyrosine into L-dopaquinone. The aim of the present study was to study molecules able to inhibit tyrosinase to be used in treating depigmentation-related disorders. In this study, we targeted arylthiosemicarbazone analogs with the aim to contribute to the identification of the optimal aryl ring to be linked to the thiosemicarbazone moiety. The biological activity was evaluated on commercial mushroom tyrosinase which was purified prior use. The results demonstrated that several of our compounds (1a-h, 1j, 1r and 5) had more potent inhibitory activities than kojic acid which was used as the reference inhibitor. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.003

文献信息

• Synthesis of 1,2,4-triazoles employing isocyanides
  作者：Pakornwit Sarnpitak、Mikhail Krasavin

  DOI：10.1016/j.tet.2013.01.039

  日期：2013.3

  A conceptually new, two-step synthesis of medicinally important 1,2,4-triazoles from isocyanides and thiosemicarbazones was developed. The method is based on the recently discovered TMSCI-promoted reaction of isocyanides that yields rare N-1,N-3-disubstututed formamidrazones. (C) 2013 Elsevier Ltd. All rights reserved.
• In vitro and in silico antimalarial activity of 2-(2-hydrazinyl)thiazole derivatives
  作者：Parameshwar Makam、Prasoon Kumar Thakur、Tharanikkarasu Kannan

  DOI：10.1016/j.ejps.2013.11.001

  日期：2014.2

  A series of 2-(2-hydrazinyl)thiazole derivatives with a wide range of substitutions at 2-, 4- and 5-positions were synthesized, characterized and evaluated their inhibitory potentials against plasmodium falciparum, NF54, by in vitro blood stage assay. The compounds, ethyl-4-methyl-2-[(E)-2-[1-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1,3-thiazole-5-carboxylate, 4d, and 1-(4-methyl-2-[(E)-2-[1-(pyridin-2-yl)ethylidenelhydrazin-1-yl]-mu 3-thiazol-5-yliethan-1-one, 5d showed significant antimalarial activity with IC50 values of 0.725 mu M and 0.648 mu M respectively. To understand the mechanism, the binding interactions between 2-(2-hydrazinyl)thiazole derivatives and trans-2-enoyl acyl carrier protein reductase of P. falciparum were studied through docking studies. The half maximal inhibitory concentration (IC50) through docking studies for the compounds, 4d and 5d were found to be 22.88 mu M and 631.84 mu M respectively. (C) 2013 Elsevier B.V. All rights reserved.
• Refinement of arylthiosemicarbazone pharmacophore in inhibition of mushroom tyrosinase
  作者：Wei Yi、Carole Dubois、Samir Yahiaoui、Romain Haudecoeur、Catherine Belle、Huacan Song、Renaud Hardré、Marius Réglier、Ahcène Boumendjel

  DOI：10.1016/j.ejmech.2011.07.003

  日期：2011.9

  Melanin play a major role in human skin protection and their biosynthesis is vital. Due to their color, they contribute to the skin pigmentation. Tyrosinase is a key enzyme involved in the first stage of melanin biosynthesis, it catalyzes the transformation of tyrosine into L-dopaquinone. The aim of the present study was to study molecules able to inhibit tyrosinase to be used in treating depigmentation-related disorders. In this study, we targeted arylthiosemicarbazone analogs with the aim to contribute to the identification of the optimal aryl ring to be linked to the thiosemicarbazone moiety. The biological activity was evaluated on commercial mushroom tyrosinase which was purified prior use. The results demonstrated that several of our compounds (1a-h, 1j, 1r and 5) had more potent inhibitory activities than kojic acid which was used as the reference inhibitor. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis of N1,N3-disubstituted formamidrazones via the TMSCl-promoted reaction of isocyanides with thiosemicarbazones
  作者：Pakornwit Sarnpitak、Sergey Tsirulnikov、Mikhail Krasavin

  DOI：10.1016/j.tetlet.2012.09.085

  日期：2012.11

  A hitherto undescribed TMSCl-promoted reaction of thiosemicarbazones was found to give rare N-1,N-3-disubstituted formamidrazones in fair to excellent yields. The scope of this new reaction was investigated and a plausible mechanism proposed. (C) 2012 Elsevier Ltd. All rights reserved.