3-hydroxy-4-methoxy-benzaldehyde-thiosemicarbazone | 14453-26-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-hydroxy-4-methoxy-benzaldehyde-thiosemicarbazone
• 英文别名: 3-Hydroxy-4-methoxy-benzaldehyd-thiosemicarbazon；3-hydroxy-4-methoxybenzaldehyde thio semicarbazone；[(E)-(3-hydroxy-4-methoxyphenyl)methylideneamino]thiourea
• CAS: 14453-26-0
• 化学式: C₉H₁₁N₃O₂S
• 分子量: 225.271
• InChiKey: ARINKVDYBABITQ-VZUCSPMQSA-N

物化性质

• 熔点：
  176-177 °C(Solv: ethanol (64-17-5))
• 沸点：
  414.5±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxy-4-methoxy-benzaldehyde-thiosemicarbazone 、 2-氯乙酰乙酸乙酯 以 乙醇 为溶剂， 以80%的产率得到ethyl 2-[(E)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]hydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate
  参考文献：
  名称：

  2-(2-Hydrazinyl)thiazole derivatives: Design, synthesis and in vitro antimycobacterial studies

  摘要：

  In an attempt to discover new potent inhibitors for Mycobacterium tuberculosis (Mtb), a series of 2-(2hydrazinyl)thiazole derivatives with a wide range of substitutions at 2-, 4- and 5-positions were designed by considering Lipinski rule. The designed compounds were synthesized, characterized and evaluated for their inhibitory potential against Mtb, H(37)Rv, by in vitro assay. The compounds, ethyl-4methyl-2-[(E)-24]-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1,3-thiazole-5-carboxylate, 4d, and ethyl-2[(E)-2-[(2-hydroxyphenyl)methylidenelhydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate, 2i showed noticeable inhibitory activity against Mtb, H37Rv with minimum inhibitory concentration (MIC) of 12.5 pM and 25 1.1M respectively. An attempt has been made to understand the mechanism of action by binding interactions of these molecules with 0-ketoacyl-ACP synthase protein through docking studies. The inhibition constants for compounds 4d and 2i were found to be 1.46 pM and 0.177 pM respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.054
• 作为产物：
  描述：

  异香兰素 、 氨基硫脲 在 硫酸 作用下， 以 乙醇 为溶剂， 以80 %的产率得到3-hydroxy-4-methoxy-benzaldehyde-thiosemicarbazone
  参考文献：
  名称：

  Carbothioamides 衍生物作为碳酸酐酶 II 和 15-脂氧合酶抑制剂的合成、生物学评价和分子动力学。

  摘要：

  合成了一系列肼-1-硫代甲酰胺衍生物 (3a-3j)，并分析了对牛碳酸酐酶 II (b-CA II) 和 15-脂氧合酶 (15-LOX) 的抑制潜力。有趣的是，发现四种衍生物 3b、3d、3g 和 3j 是 CA II 的选择性抑制剂，而其他衍生物则表现出 CA II 和 15-LOX 抑制作用。对最有效的 b-CA II 和 15-LOX 抑制剂进行了计算机模拟研究，以发现化合物在其活性位点的可能结合模式。此外，MD模拟结果证实这些配体与两个靶标稳定结合，而结合能进一步证实了3h化合物的抑制作用。由于这些化合物可能与特定疾病有关，

  DOI：

  10.3390/molecules27248723

文献信息

• Synthesis, in vitro evaluation and molecular docking studies of thiazole derivatives as new inhibitors of α-glucosidase
  作者：Fazal Rahim、Hayat Ullah、Muhammad Tariq Javid、Abdul Wadood、Muhammad Taha、Muhammad Ashraf、Ayesha Shaukat、Muhammad Junaid、Shafqat Hussain、Wajid Rehman、Rashad Mehmood、Muhammad Sajid、Muhammad Naseem Khan、Khalid Mohammed Khan

  DOI：10.1016/j.bioorg.2015.06.006

  日期：2015.10

  A series of thiazole derivatives 1-21 were prepared, characterized by EI-MS and H-1 NMR and evaluated for alpha-glucosidase inhibitory potential. All twenty one derivatives showed good alpha-glucosidase inhibitory activity with IC50 value ranging between 18.23 +/- 0.03 and 424.41 +/- 0.94 mu M when compared with the standard acarbose (IC50, 38.25 +/- 0.12 mu M). Compound (8) (IC50, 18.23 +/- 0.03 mu M) and compound (7) (IC50 = 36.75 +/- 0.05 mu M) exhibited outstanding inhibitory potential much better than the standard acarbose (IC50, 38.25 +/- 0.12 mu M). All other analogs also showed good to moderate enzyme inhibition. Molecular docking studies were carried out in order to find the binding affinity of thiazole derivatives with enzyme. Studies showed these thiazole analogs as a new class of a-glucosidase inhibitors. (C) 2015 Elsevier Inc. All rights reserved.
• Structure-Based Discovery of Thiosemicarbazone Metalloproteinase Inhibitors for Hemorrhage Treatment in Snakebites
  作者：Francis B. Ferreira、Thiago M. Pereira、Dayane L. N. Souza、Daiana S. Lopes、Vitor Freitas、Veridiana M. R. Ávila、Arthur E. Kümmerle、Carlos Mauricio R. Sant’Anna

  DOI：10.1021/acsmedchemlett.7b00186

  日期：2017.11.9

  The venoms of snakes are composed by many toxins, which are responsible for various toxic effects including intense pain, bleeding disorders, and local tissue damage caused by hemorrhage and necrosis. The snake venom metalloproteinases (SVMPs) are proteolytic zinc-dependent enzymes acting in different hemostatic mechanisms. In this work, a structure-based molecular modeling strategy was used for the rational design, by means of a homology 3D model of an SVMP isolated from Bothrops pauloensis venom (BpMP-I), followed by synthesis and in vitro evaluation of new thiosemicarbazones as the first inhibitors of the B. pauloensis SVMP. Besides being effective for the SVMP inhibition, two molecules were shown to be effective also in vivo, inhibiting hemorrhage caused by the B. pauloensis whole venom. Docking studies on metalloproteinases from other snake species suggest that the thiosemicarbazones activity is not confined to BpMP-I, but seems to be a common feature of metzincins.
• Erdogan; Safak; Ertan, Journal of the Indian Chemical Society, 1989, vol. 66, # 1, p. 45 - 47
  作者：Erdogan、Safak、Ertan、Yulug

  DOI：——

  日期：——
• 2-(2-Hydrazinyl)thiazole derivatives: Design, synthesis and in vitro antimycobacterial studies
  作者：Parameshwar Makam、Ramakrishna Kankanala、Amresh Prakash、Tharanikkarasu Kannan

  DOI：10.1016/j.ejmech.2013.08.054

  日期：2013.11

  In an attempt to discover new potent inhibitors for Mycobacterium tuberculosis (Mtb), a series of 2-(2hydrazinyl)thiazole derivatives with a wide range of substitutions at 2-, 4- and 5-positions were designed by considering Lipinski rule. The designed compounds were synthesized, characterized and evaluated for their inhibitory potential against Mtb, H(37)Rv, by in vitro assay. The compounds, ethyl-4methyl-2-[(E)-24]-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1,3-thiazole-5-carboxylate, 4d, and ethyl-2[(E)-2-[(2-hydroxyphenyl)methylidenelhydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate, 2i showed noticeable inhibitory activity against Mtb, H37Rv with minimum inhibitory concentration (MIC) of 12.5 pM and 25 1.1M respectively. An attempt has been made to understand the mechanism of action by binding interactions of these molecules with 0-ketoacyl-ACP synthase protein through docking studies. The inhibition constants for compounds 4d and 2i were found to be 1.46 pM and 0.177 pM respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis, Biological Evaluation, and Molecular Dynamics of Carbothioamides Derivatives as Carbonic Anhydrase II and 15-Lipoxygenase Inhibitors
  作者：Pervaiz Ali Channar、Rima D. Alharthy、Syeda Abida Ejaz、Aamer Saeed、Jamshed Iqbal

  DOI：10.3390/molecules27248723

  日期：——

  A series of hydrazine-1-carbothioamides derivatives (3a-3j) were synthesized and analyzed for inhibitory potential towards bovine carbonic anhydrase II (b-CA II) and 15-lipoxygenase (15-LOX). Interestingly, four derivatives, 3b, 3d, 3g, and 3j, were found to be selective inhibitors of CA II, while other derivatives exhibited CA II and 15-LOX inhibition. In silico studies of the most potent inhibitors

  合成了一系列肼-1-硫代甲酰胺衍生物 (3a-3j)，并分析了对牛碳酸酐酶 II (b-CA II) 和 15-脂氧合酶 (15-LOX) 的抑制潜力。有趣的是，发现四种衍生物 3b、3d、3g 和 3j 是 CA II 的选择性抑制剂，而其他衍生物则表现出 CA II 和 15-LOX 抑制作用。对最有效的 b-CA II 和 15-LOX 抑制剂进行了计算机模拟研究，以发现化合物在其活性位点的可能结合模式。此外，MD模拟结果证实这些配体与两个靶标稳定结合，而结合能进一步证实了3h化合物的抑制作用。由于这些化合物可能与特定疾病有关，