1-(3-chlorophenyl)-3-[[(E)-3-(4-methoxyphenyl)prop-2-enoyl]amino]thiourea

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(3-chlorophenyl)-3-[[(E)-3-(4-methoxyphenyl)prop-2-enoyl]amino]thiourea
• 化学式: C₁₇H₁₆ClN₃O₂S
• 分子量: 361.852
• InChiKey: FUILCSHJBQDCQZ-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  94.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 6.0h， 生成 1-(3-chlorophenyl)-3-[[(E)-3-(4-methoxyphenyl)prop-2-enoyl]amino]thiourea
  参考文献：
  名称：

  Synthesis, Antifungal Activity and 3D‐QSAR Study of Novel Anisaldehyde‐Derived Amide‐Thiourea Compounds

  摘要：

  AbstractSuccinate dehydrogenase (SDH) is an important target enzyme for designing agricultural chemical fungicides. In order to explore novel natural product‐based antifungal agents, twenty‐one unreported anisaldehyde‐derived amide‐thiourea compounds were designed and synthesized using the principle of active splicing, and structurally confirmed by 1H‐NMR, 13C‐NMR, ESI‐MS, FT‐IR, and element analysis. In vitro antifungal activity of the target compounds was evaluated by the agar dilution method. The results showed that some target compounds exhibited better or comparable antifungal activity than that of the commercial fungicide chlorothalonil, in which compounds 5c, 5o, and 5r displayed excellent antifungal activity of 92.6 %, 92.6 % and 99.1 % against P. piricola, respectively, better than that of the positive control. In addition, 3D‐QSAR analysis was carried out by the CoMFA method to reveal the relationship between the structures of the target compounds and their inhibitory activities. The simulative binding mode of the target compounds and SDH was also studied by molecular docking.

  DOI：

  10.1002/cbdv.202101025

文献信息

• Synthesis, Antifungal Activity and 3D‐QSAR Study of Novel Anisaldehyde‐Derived Amide‐Thiourea Compounds
  作者：Rong Li、Bo Cen、Wengui Duan、Guishan Lin

  DOI：10.1002/cbdv.202101025

  日期：2022.4

  AbstractSuccinate dehydrogenase (SDH) is an important target enzyme for designing agricultural chemical fungicides. In order to explore novel natural product‐based antifungal agents, twenty‐one unreported anisaldehyde‐derived amide‐thiourea compounds were designed and synthesized using the principle of active splicing, and structurally confirmed by 1H‐NMR, 13C‐NMR, ESI‐MS, FT‐IR, and element analysis. In vitro antifungal activity of the target compounds was evaluated by the agar dilution method. The results showed that some target compounds exhibited better or comparable antifungal activity than that of the commercial fungicide chlorothalonil, in which compounds 5c, 5o, and 5r displayed excellent antifungal activity of 92.6 %, 92.6 % and 99.1 % against P. piricola, respectively, better than that of the positive control. In addition, 3D‐QSAR analysis was carried out by the CoMFA method to reveal the relationship between the structures of the target compounds and their inhibitory activities. The simulative binding mode of the target compounds and SDH was also studied by molecular docking.