2-(2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetyl)-N-phenylhydrazine carbothioamide | 69321-29-5

• 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: 2-(2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetyl)-N-phenylhydrazine carbothioamide
• 英文别名: 1-(2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetyl)-4-phenylthiosemicarbazide；2-(2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetyl)-N-phenylhydrazinecarbothioamide；N⁴-phenyl-N¹-(4-methyl-7-coumarinyloxymethylcarbonyl)thiosemicarbazide；1-[[2-(4-Methyl-2-oxochromen-7-yl)oxyacetyl]amino]-3-phenylthiourea
• CAS: 69321-29-5
• 化学式: C₁₉H₁₇N₃O₄S
• 分子量: 383.428
• InChiKey: DINMZLGVZDAVRJ-UHFFFAOYSA-N

物化性质

• 熔点：
  256-258 °C
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  2-(2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetyl)-N-phenylhydrazine carbothioamide 在 sodium hydroxide 作用下， 反应 2.0h， 以92%的产率得到4-methyl-7-((4-phenyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methoxy)-2H-chromen-2-one
  参考文献：
  名称：

  具有抗菌活性的新型 7-取代 4-甲基香豆素衍生物的合成

  摘要：

  已经合成了衍生自 4-甲基-7-香豆素酰氧基乙酸酰肼的新环状衍生物。筛选了一些代表性实例的抗微生物活性。

  DOI：

  10.1002/ardp.19943270404
• 作为产物：
  描述：

  (4-甲基-2-氧代-2H-色烯-7-氧基)-乙酸肼 以60%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

• Synthesis and Antimicrobial Activities of Some Triazole, Thiadiazole, and Oxadiazole Substituted Coumarins
  作者：K. Rajasekhar Reddy、R. Mamatha、M. S. Surendra Babu、K. Shiva Kumar、K. N. Jayaveera、G. Narayanaswamy

  DOI：10.1002/jhet.1745

  日期：2014.1

  furnish coumarin derivatives possessing triazoles 4a, 4b, 4c, 4d, 4e, thiadiazoles 5a, 5b, 5c, 5d, 5e, and oxadiazoles 6a, 6b, 6c, 6d, 6e, respectively. The structures of all the compounds have been assigned by elemental analysis and spectral studies. The synthesized compounds were screened for their antimicrobial analgesic activities. The nonconventional controlled microwave irradiation synthesis is carried

  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。
• Access to new antimicrobial 4-methylumbelliferone derivatives
  作者：MARWA ZAYANE、ANIS ROMDHANE、MEJDA DAAMI-REMADI、HICHEM BEN JANNET

  DOI：10.1007/s12039-015-0927-6

  日期：2015.9

  Synthesis of some novel coumarin esters has been accomplished through iodine-catalyzed method using 4-methylumbelliferone as the starting material. Condensation of hydrazide, which was obtained in two steps from 4-methylumbelliferone, with some arylaldhydes provided hydrazone derivatives, while the reaction with phenylthioisocyanate leads to the thiosemicarbazide that evolved into two new compounds

  以4-甲基伞形酮为原料，通过碘催化的方法完成了一些香豆素的合成。从4-甲基伞形酮分两步获得的酰肼与一些芳基醛的缩合提供了derivatives衍生物，而与苯硫异氰酸酯的反应导致了硫代氨基脲，后者演变成两种新化合物。最后，酰肼与三种二酮的缩合反应得到新的吡咯和吡唑衍生物。根据包括1 H NMR，13 C NMR和ES-HRMS在内的光谱方法，确定了所有合成化合物的结构。最后对它们的抗菌活性进行了测试，并讨论了它们的构效关系。 从4-甲基伞形酮合成了一系列新的化合物。所有新化合物均通过光谱数据进行表征，然后评估其抗菌活性。
• 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。
• Choline Chloride Based Deep Eutectic Solvents as a Tuneable Medium for Synthesis of Coumarinyl 1,2,4-Triazoles: Effect of Solvent Type and Temperature
  作者：Maja Molnar、Ivana Periš、Mario Komar

  DOI：10.1002/ejoc.201900249

  日期：2019.4.24

  Pure 1, 2, 4‐ triazoles were obtained in choline chloride:urea (1:2) and choline chloride:N‐ methyl urea (1:3) deep eutectic solvents at 80°C. Pure thiosemicarbazides were obtained in choline chloride:ethane‐1, 2‐diol (1:2), choline chloride:malic acid (1:1), choline chloride:malonic acid (1:1), choline chloride:butane‐1, 4‐diol (1:3) and choline chloride:glycerole (1:2) at 40°C. The ratio of 1, 2,

  由 2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy) acetohydrazide (1) 或 2-(7-hydroxy-2-oxo-) 合成 1, 2, 4-三唑的研究2H-chromen-4-yl)乙酰肼 (2) 和各种异硫氰酸酯，在低共熔溶剂中进行。为了找到 1, 2, 4-三唑形成的最佳条件，在 14 种不同的基于氯化胆碱的低共熔溶剂中，在两种不同的温度（40°C 和 80°C）下，对 1 和异硫氰酸苯酯进行了模型反应。在 80°C 的氯化胆碱:尿素 (1:2) 和氯化胆碱:N-甲基尿素 (1:3) 低共熔溶剂中获得纯 1, 2, 4- 三唑。在氯化胆碱:乙烷-1、2-二醇 (1:2)、氯化胆碱:苹果酸 (1:1)、氯化胆碱:丙二酸 (1:1)、氯化胆碱:丁烷-1、 4-二醇 (1:3) 和氯化胆碱:甘油 (1:2) 在 40°C。通过 HPLC 和 1H
• 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.