3,4-methylenedioxy-6-nitro-benzaldehyde thiosemicarbazone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3,4-methylenedioxy-6-nitro-benzaldehyde thiosemicarbazone
• 英文别名: [(6-Nitro-1,3-benzodioxol-5-yl)methylideneamino]thiourea
• 化学式: C₉H₈N₄O₄S
• mdl: MFCD00556024
• 分子量: 268.253
• InChiKey: IOKYPDHGVZKBSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  五羰基溴化锰(I) 、 3,4-methylenedioxy-6-nitro-benzaldehyde thiosemicarbazone 以 丙酮 为溶剂， 反应 3.0h， 以80%的产率得到
  参考文献：
  名称：

  含硫半脲配体的锰碳释放分子的化学和生物学

  摘要：

  已经合成并表征了一系列带有6-硝基哌嗪硫半碳zone配体的锰配合物。配体的区别在于胺氮上的烷基取代基。这些配合物，配制成Mn（CO）3（TSC）Br（其中TSC代表硫代半碳胺配体）在暴露于光时显示出非常迅速的一氧化碳释放，将其确立为photoCORM（光活化的一氧化碳释放分子）。使用肌红蛋白测定法作为一氧化碳检测系统，已对复合物的光反应性进行了详细研究。使用了三种不同的光波长：365 nm（UV），405 nm（紫色）和435 nm（蓝色）。观察到，CO释放的半衰期取决于光的波长。这些半衰期约为10到100秒，对于这种类型的复合物而言非常快。通常，半衰期随着入射辐射能量的减少而增加。对于带有苯基取代胺基的化合物，UV的t½（以秒为单位）为44.54、59.59和65.90，紫色和蓝色的光。释放的CO的量也与波长有关，较高的能量波长通常释放更多的CO。UV光导致2当量的CO被释放，而紫色和蓝色光分别释放大约1

  DOI：

  10.1016/j.jphotochem.2019.01.037
• 作为产物：
  描述：

  胡椒醛 在 硫酸 、 硝酸 作用下， 以 乙醇 、 水 为溶剂， 反应 4.5h， 生成 3,4-methylenedioxy-6-nitro-benzaldehyde thiosemicarbazone
  参考文献：
  名称：

  Novel 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones: Synthesis and antileishmanial effects against Leishmania amazonensis

  摘要：

  A series of eleven 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones (16-27) was synthesised as part of a study to search for potential new drugs with a leishmanicidal effect. The thiosemicarbazones, ten of which are new compounds, were prepared in good yields (85-98%) by the reaction of 3,4-methylenedioxyde-6-benzaldehydes (6-X-piperonal), previously synthesised for this work by several methodologies, and thiosemicarbazide in ethanol with a few drops of H2SO4. These compounds were evaluated against Leishmania amazonensis promastigotes, and derivatives where X = I (22) and X = CN (23) moieties showed impressive results, having IC50 = 20.74 mu M and 16.40 mu M, respectively. The intracellular amastigotes assays showed IC50 = 22.00 mu M (22) and 17.00 mu M (23), and selectivity index >5.7 and >7.4, respectively, with a lower toxicity compared to pentamidine (positive control, SI = 4.5). The results obtained from the preliminary QSAR study indicated the hydrophobicity (log P) as a fundamental parameter for the 2D-QSAR linear model. A molecular docking study demonstrated that both compounds interact with flavin mononucleotide (FMN), important binding site of NO synthase. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.09.009

文献信息

• Copper complexes containing thiosemicarbazones derived from 6-nitropiperonal: Antimicrobial and biophysical properties
  作者：Floyd A. Beckford、Kelsey R. Webb

  DOI：10.1016/j.saa.2017.04.057

  日期：2017.8

  A series of four thiosemicarbazones from 6-nitropiperonal along with the corresponding copper complexes were synthesized. The biophysical characteristics of the complexes were investigated by the binding to DNA and human serum albumin. The binding to DNA is moderate; the binding constants run from (0.49-7.50)×104M-1. In relation to HSA, the complexes interact strongly with binding constants on the

  合成了一系列由6-硝基胡椒醛形成的四个硫代半脲酮以及相应的铜配合物。通过与DNA和人血清白蛋白的结合来研究复合物的生物物理特性。与DNA的结合是中等的；结合常数为（0.49-7.50）×104M-1。关于HSA，复合物与结合常数强烈相互作用，为105M-1。该复合物还表现出抗氧化行为，这取决于清除二苯基吡啶甲基肼基（dpph）和一氧化氮自由基的能力。测试了该化合物的抗微生物特性，针对的微生物包括5种ESKAPE病原体（金黄色葡萄球菌，MRSA，大肠杆菌，肺炎克雷伯菌，MDR，鲍曼不动杆菌，还描述了铜绿假单胞菌和两种酵母（白色念珠菌和新隐球菌var。grubii）。这些化合物的核心部分类似于草酸，后者是靶向DNA促旋酶和拓扑异构酶（IV）的喹诺酮类抗生素。通过计算方法，主要是对接研究，研究了复合物与这些重要抗菌靶标之间的结合相互作用。与DNA促旋酶B（来自金黄色葡萄球菌）的相互作用的计算解离常数范围为4
• Chemistry and biology of manganese carbon-releasing molecules containing thiosemicarbazone ligands
  作者：Hannah G. Daniels、Olivia G. Fast、Steven M. Shell、Floyd A. Beckford

  DOI：10.1016/j.jphotochem.2019.01.037

  日期：2019.4

  TSC represents the thiosemicarbazone ligand, show very rapid release of carbon monoxide upon exposure to light, establishing them as photoCORMs (light activated carbon monoxide-releasing molecules). The photo-reactivity profile of the complexes have been studied in detail using the myoglobin assay as a detection system for carbon monoxide. Three different wavelengths of light were used: 365 nm (UV),

  已经合成并表征了一系列带有6-硝基哌嗪硫半碳zone配体的锰配合物。配体的区别在于胺氮上的烷基取代基。这些配合物，配制成Mn（CO）3（TSC）Br（其中TSC代表硫代半碳胺配体）在暴露于光时显示出非常迅速的一氧化碳释放，将其确立为photoCORM（光活化的一氧化碳释放分子）。使用肌红蛋白测定法作为一氧化碳检测系统，已对复合物的光反应性进行了详细研究。使用了三种不同的光波长：365 nm（UV），405 nm（紫色）和435 nm（蓝色）。观察到，CO释放的半衰期取决于光的波长。这些半衰期约为10到100秒，对于这种类型的复合物而言非常快。通常，半衰期随着入射辐射能量的减少而增加。对于带有苯基取代胺基的化合物，UV的t½（以秒为单位）为44.54、59.59和65.90，紫色和蓝色的光。释放的CO的量也与波长有关，较高的能量波长通常释放更多的CO。UV光导致2当量的CO被释放，而紫色和蓝色光分别释放大约1
• Novel 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones: Synthesis and antileishmanial effects against Leishmania amazonensis
  作者：Jorge Luiz R. de Melos、Eduardo Caio Torres-Santos、Viviane dos S. Faiões、Catarina de Nigris Del Cistia、Carlos Maurício R. Sant'Anna、Cláudio Eduardo Rodrigues-Santos、Aurea Echevarria

  DOI：10.1016/j.ejmech.2015.09.009

  日期：2015.10

  A series of eleven 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones (16-27) was synthesised as part of a study to search for potential new drugs with a leishmanicidal effect. The thiosemicarbazones, ten of which are new compounds, were prepared in good yields (85-98%) by the reaction of 3,4-methylenedioxyde-6-benzaldehydes (6-X-piperonal), previously synthesised for this work by several methodologies, and thiosemicarbazide in ethanol with a few drops of H2SO4. These compounds were evaluated against Leishmania amazonensis promastigotes, and derivatives where X = I (22) and X = CN (23) moieties showed impressive results, having IC50 = 20.74 mu M and 16.40 mu M, respectively. The intracellular amastigotes assays showed IC50 = 22.00 mu M (22) and 17.00 mu M (23), and selectivity index >5.7 and >7.4, respectively, with a lower toxicity compared to pentamidine (positive control, SI = 4.5). The results obtained from the preliminary QSAR study indicated the hydrophobicity (log P) as a fundamental parameter for the 2D-QSAR linear model. A molecular docking study demonstrated that both compounds interact with flavin mononucleotide (FMN), important binding site of NO synthase. (C) 2015 Elsevier Masson SAS. All rights reserved.