4-hydroxythidiazuron | 65647-48-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-hydroxythidiazuron
• 英文别名: 4-Hydroxyphenyl-thidiazuron；1-(4-hydroxy-phenyl)-3-[1,2,3]thiadiazol-5-yl-urea；Urea, N-(4-hydroxyphenyl)-N'-1,2,3-thiadiazol-5-yl-；1-(4-hydroxyphenyl)-3-(thiadiazol-5-yl)urea
• CAS: 65647-48-5
• 化学式: C₉H₈N₄O₂S
• 分子量: 236.254
• InChiKey: BRISYSJIMKTDJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(4-Methoxyphenyl)-N'-1,2,3-thiadiazol-5-yl-urea 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 4-hydroxythidiazuron
  参考文献：
  名称：

  Identification, Synthesis, and Safety Assessment of Thidiazuron [1-Phenyl-3-(1,2,3-thidiazol-5-yl)urea] and Its Metabolites in Kiwifruits

  摘要：

  The quality of kiwifruit became worse as a result of the abuse of plant growth regulators (PGRs). The safety of the fruits treated with PGRs also worried consumers. Therefore, the present study analyzed the structure of thidiazuron [TDZ, (1-phenyl-3-(1,2,3-thidiazol-5-yl)-urea)] (1) and its metabolites of biotransformation in kiwifruits using liquid chromatography hybrid ion trap time-of-flight mass spectrometry (LC-IT-TOF-MS). Standard compounds were also synthesized and used for structural identification of those metabolites. In addition, cytotoxicity of TDZ and its metabolites was tested through sulforhodamine B assays against normal Chinese hamster ovary (CHO) cells. Four metabolites were identified. They were 4-hydroxy-thidiazuron (2), 3-hydroxy-thidiazuron (3), thidiazuron-4-O-beta-D-glucoside (4), and thidiazuron-3-O-beta-D-glucoside (5). Values of IC50 of compounds 1, 2, and 3 to CHO cells were 18.3 +/- 1.8, 37.56 +/- 1.5, and 23.36 +/- 1.59 mu M, respectively. Compounds 4 and 5 had no effect on CHO cells.

  DOI：

  10.1021/acs.jafc.7b03522

文献信息

• Identification, Synthesis, and Safety Assessment of Thidiazuron [1-Phenyl-3-(1,2,3-thidiazol-5-yl)urea] and Its Metabolites in Kiwifruits
  作者：Zhiwei Zhang、Haihua Yang、Zhenhong Gao、Yahong Yuan、Jing Dong、Yuan Wang、Tianli Yue

  DOI：10.1021/acs.jafc.7b03522

  日期：2017.12.27

  The quality of kiwifruit became worse as a result of the abuse of plant growth regulators (PGRs). The safety of the fruits treated with PGRs also worried consumers. Therefore, the present study analyzed the structure of thidiazuron [TDZ, (1-phenyl-3-(1,2,3-thidiazol-5-yl)-urea)] (1) and its metabolites of biotransformation in kiwifruits using liquid chromatography hybrid ion trap time-of-flight mass spectrometry (LC-IT-TOF-MS). Standard compounds were also synthesized and used for structural identification of those metabolites. In addition, cytotoxicity of TDZ and its metabolites was tested through sulforhodamine B assays against normal Chinese hamster ovary (CHO) cells. Four metabolites were identified. They were 4-hydroxy-thidiazuron (2), 3-hydroxy-thidiazuron (3), thidiazuron-4-O-beta-D-glucoside (4), and thidiazuron-3-O-beta-D-glucoside (5). Values of IC50 of compounds 1, 2, and 3 to CHO cells were 18.3 +/- 1.8, 37.56 +/- 1.5, and 23.36 +/- 1.59 mu M, respectively. Compounds 4 and 5 had no effect on CHO cells.