4-methyl-1-(2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetyl)thiosemicarbazide | 181482-66-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-methyl-1-(2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetyl)thiosemicarbazide
• 英文别名: 1-Methyl-3-[[2-(4-methyl-2-oxochromen-7-yl)oxyacetyl]amino]thiourea
• CAS: 181482-66-6
• 化学式: C₁₄H₁₅N₃O₄S
• 分子量: 321.357
• InChiKey: SRLQQMZGKMBOQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methyl-1-(2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetyl)thiosemicarbazide 在 磷酸 作用下， 反应 0.5h， 生成 4-Methyl-7-(5-methylamino-[1,3,4]thiadiazol-2-ylmethoxy)-chromen-2-one
  参考文献：
  名称：

  Eltamany; El-Deen; El-Fattah, M. F. Abd, Journal of the Indian Chemical Society, 1996, vol. 73, # 7, p. 367 - 369

  摘要：

  DOI：
• 作为产物：
  描述：

  (4-甲基-香豆素-7-基氧代)乙酸乙酯 在 肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 4-methyl-1-(2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetyl)thiosemicarbazide
  参考文献：
  名称：

  4-Methyl-7-hydroxycoumarin antifungal and antioxidant activity enhancement by substitution with thiosemicarbazide and thiazolidinone moieties

  摘要：

  According to literature data, thiosemicarbazide and thiazolidinone moieties should enhance biological properties of coumarin. Antioxidant, metal-chelating and antifungal activities of all compounds were investigated and compared to the activity of the starting material, 7-hydroxy-4-methylcoumarin, and were proven to possess potent antioxidant and antifungal activity. In general, thiosemicarbazides showed higher scavenging activity towards DPPH and galvinoxyl radicals than did 4-thiazolidinones and some of them had the same or even better activity than had ascorbic acid itself, depending on the free radical used. In antifungal activity tests towards four foodborne mycotoxigenic fungi, Aspergillus flavus, Aspergillus ochraceus. Fusarium graminearum and Fusarium verticillioides, coumarin derivatives were proven to possess a very high activity in terms of growth inhibition, depending on the fungi investigated. In general, 4-thiazolidinones showed better antifungal activity than did thiosemicarbazides. F. graminearum was the most susceptible to the compounds investigated and F. verticillioides was proven to be the most resistant. Two compounds, both coumarinyl thiosemicarbazides, were found to possess both antifungal and antioxidant activity which could be useful for applications in medicine, food industry and agriculture. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2013.01.027

文献信息

• Design and Synthesis of Some New 1,3,4-Thiadiazines with Coumarin Moieties and Their Antioxidative and Antifungal Activity
  作者：Milan Čačić、Valentina Pavić、Maja Molnar、Bojan Šarkanj、Elizabeta Has-Schön

  DOI：10.3390/molecules19011163

  日期：——

  A series of newly disubstituted (compounds 4a,b) and trisubstituted 1,3,4-thiadiazines 5a–l with various substituents was prepared utilizing different thiosemicarbazides and 3-α-bromoacetylcoumarins as starting compounds. The structures of the synthesized 1,3,4-thiadiazines are elucidated and confirmed utilizing the corresponding analytical and spectroscopic data. All of the new thiadiazine derivatives were tested for their antioxidant activity, employing different antioxidant assays (DPPH scavenging activity, iron chelating activity, power reducing activity). Compounds 5b, 5f, 5j and 4b were proven to be the best DPPH radical scavengers, while compounds 5h and 5j have shown the best iron chelating activity. Thiadiazine derivatives were also tested on their antifungal activity against four mycotoxicogenic fungi, Aspergillus flavus, A. ochraceus, Fusarium graminearum and F. verticillioides. The best antifungal against A. flavus was proven to be compound 5e, while compounds 4a and 5c were the best antifungals on A. ochraceus, and compound 5g showed the best antifungal activity on F. verticillioides.

  一系列新合成的二取代（化合物4a,b）和三取代的1,3,4-噻二嗪化合物5a–l，采用不同的硫代氨基脲和3-α-溴乙酰香豆素作为起始化合物进行制备。利用相应的分析和光谱数据阐明并确认了合成的1,3,4-噻二嗪的结构。所有的新噻二嗪衍生物均进行了抗氧化活性的测试，采用不同的抗氧化测定方法（DPPH清除活性、铁螯合活性、还原能力）。化合物5b、5f、5j和4b被证实为最佳的DPPH自由基清除剂，而化合物5h和5j显示出最佳的铁螯合活性。噻二嗪衍生物还被测试其对四种产霉毒素真菌的抗真菌活性，包括黄曲霉、鼠尾草霉、镰刀菌及旋链镰刀菌。化合物5e被证明对黄曲霉具有最佳的抗真菌活性，化合物4a和5c是对鼠尾草霉的最佳抗真菌剂，而化合物5g在旋链镰刀菌上显示出最佳的抗真菌活性。
• Eltamany, S. H.; El-Deen, I. M.; El-Fattah, M. E. Abd, Pakistan Journal of Scientific and Industrial Research, 1995, vol. 38, # 3-4, p. 115 - 118
  作者：Eltamany, S. H.、El-Deen, I. M.、El-Fattah, M. E. Abd

  DOI：——

  日期：——
• 4-Methyl-7-hydroxycoumarin antifungal and antioxidant activity enhancement by substitution with thiosemicarbazide and thiazolidinone moieties
  作者：Bojan Šarkanj、Maja Molnar、Milan Čačić、Lars Gille

  DOI：10.1016/j.foodchem.2013.01.027

  日期：2013.8

  According to literature data, thiosemicarbazide and thiazolidinone moieties should enhance biological properties of coumarin. Antioxidant, metal-chelating and antifungal activities of all compounds were investigated and compared to the activity of the starting material, 7-hydroxy-4-methylcoumarin, and were proven to possess potent antioxidant and antifungal activity. In general, thiosemicarbazides showed higher scavenging activity towards DPPH and galvinoxyl radicals than did 4-thiazolidinones and some of them had the same or even better activity than had ascorbic acid itself, depending on the free radical used. In antifungal activity tests towards four foodborne mycotoxigenic fungi, Aspergillus flavus, Aspergillus ochraceus. Fusarium graminearum and Fusarium verticillioides, coumarin derivatives were proven to possess a very high activity in terms of growth inhibition, depending on the fungi investigated. In general, 4-thiazolidinones showed better antifungal activity than did thiosemicarbazides. F. graminearum was the most susceptible to the compounds investigated and F. verticillioides was proven to be the most resistant. Two compounds, both coumarinyl thiosemicarbazides, were found to possess both antifungal and antioxidant activity which could be useful for applications in medicine, food industry and agriculture. (C) 2013 Elsevier Ltd. All rights reserved.
• Eltamany; El-Deen; El-Fattah, M. F. Abd, Journal of the Indian Chemical Society, 1996, vol. 73, # 7, p. 367 - 369
  作者：Eltamany、El-Deen、El-Fattah, M. F. Abd

  DOI：——

  日期：——