4-(4-methoxyphenyl)-1-(2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetyl)thiosemicarbazide | 69321-34-2

• 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-(4-methoxyphenyl)-1-(2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetyl)thiosemicarbazide
• 英文别名: N-(4-methoxyphenyl)-2-(2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetyl)hydrazinecarbothioamide；1-(4-Methoxyphenyl)-3-[[2-(4-methyl-2-oxochromen-7-yl)oxyacetyl]amino]thiourea
• CAS: 69321-34-2
• 化学式: C₂₀H₁₉N₃O₅S
• 分子量: 413.454
• InChiKey: LRHQZUAIEKLURC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(4-methoxyphenyl)-1-(2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetyl)thiosemicarbazide 在 sodium hydroxide 作用下， 反应 0.05h， 以78%的产率得到7-((5-mercapto-4-(4-methoxyphenyl)-4H-1,2,4-triazol-3-yl)-methoxy)-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  某些三唑，噻二唑和恶二唑取代的香豆素的合成及抑菌活性

  摘要：

  由7-羟基-4-甲基-2-香豆素制备2-2-（4-甲基-2-氧代-2-香豆素-7-香豆基）乙酸酯1，将其在沸腾的乙醇中用水合肼进一步处理后得到酰肼化合物2。使所得的酰肼与取代的异硫氰酸芳基酯反应形成硫代氨基脲化合物3a，3b，3c，3d，3e。1-（2-（4-甲基-2-氧代-2-香豆素-7-基氧基）乙酰基）-4-芳基硫代氨基脲3在不同的反应条件下用不同的试剂环化以提供具有三唑4a，4b，4c的香豆素衍生物，4d，4e，噻二唑5a，5b，5c，5d，5e和恶二唑6a，6b，6c，6d，6e， 分别。所有化合物的结构均已通过元素分析和光谱研究确定。筛选合成的化合物的抗菌镇痛活性。非常规控制的微波辐射合成是在70°C（200 W）下进行的。该方法在方法学，高产收率，短反应时间，温和的反应条件，对环境无害且易于后处理方面具有许多优势。

  DOI：

  10.1002/jhet.1745
• 作为产物：
  描述：

  (4-甲基-2-氧代-2H-色烯-7-氧基)-乙酸肼 以56%的产率得到
  参考文献：
  名称：

  HUSAIN M. I.; SHUKLA M. K., J. INDIAN CHEM. SOC., 1978, 55, NO 8, 826-828

  摘要：

  DOI：

文献信息

• 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.
• Bhavsar, S. B.; Shinde, D. B.; Shingare, M. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 1, p. 70 - 74
  作者：Bhavsar, S. B.、Shinde, D. B.、Shingare, M. S.

  DOI：——

  日期：——