3-benzoyl-1{[(phenylformamido)methanethioyl]amino}thiourea

• 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: 3-benzoyl-1{[(phenylformamido)methanethioyl]amino}thiourea
• 英文别名: 1,6-dibenzoyldithiohydrazodicarbonamide；N-[(benzoylcarbamothioylamino)carbamothioyl]benzamide
• 化学式: C₁₆H₁₄N₄O₂S₂
• 分子量: 358.445
• InChiKey: XLWFXXDIGMEMMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 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：
  146
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-benzoyl-1{[(phenylformamido)methanethioyl]amino}thiourea 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到N,N′-(1,3,4-thiadiazole-2,5-diyl)dibenzamide
  参考文献：
  名称：

  Novel and Efficient Cyclization Procedure for the Synthesis of 2,5-Disubstituted-1,3,4-thiadiazoles Without Using Any Ring-Closing Reagents

  摘要：

  A novel method for the synthesis of 2,5-disubstituted-1,3,4-thiadiazoles via direct ring closure of 1,6-disubstituted-2,5-dithioureas in dimethylformanide without using any ring-closing reagents has been accidentally discovered. Repeated and extended experiments confirmed that this is a very simple and efficient way to synthesize these kinds of fine chemicals. A series of novel 2,5-disubstituted-1,3,4-thiadiazoles have been synthesized via this method in good yields.

  DOI：

  10.1080/00397911.2010.548891
• 作为产物：
  描述：

  苯甲酰基异硫氰酸酯 在 一水合肼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-benzoyl-1{[(phenylformamido)methanethioyl]amino}thiourea
  参考文献：
  名称：

  Phase Transfer Catalyzed Synthesis of 1,6-Diaroyldithiohydrazodicarbonamide Derivatives

  摘要：

  Reaction of hydrazine hydrate with aroyl chloride and ammonium thiocyanate under the condition of solid-liquid phase transfer catalysis using polyethylene glycol-600 (PEG-600) as the catalyst yielded 1,6-diaroyldithiohydrazodicarbonamides 3a - 3h in good to excellent yield.

  DOI：

  10.1080/00397919808004429

文献信息

• Synthesis, Characterization and Biological Activity of Some Dithiourea Derivatives
  作者：Felix Odame、Eric Hosten、Jason Krause、Michelle Isaacs、Heinrich Hoppe、Setshaba D. Khanye、Yasien Sayed、Carminita Frost、Kevin Lobb、Zenixole Tshentu

  DOI：10.17344/acsi.2019.5689

  日期：——

  Novel dithiourea derivatives have been designed as HIV-1 protease inhibitors using Auto dock 4.2, synthesized and characterized by spectroscopic methods and microanalysis. 1-(3-Bromobenzoyl)-3- [2-([(3-bromophenyl)form amido] methanethioyllamino)phenyl] thiourea (10) and 3-benzoyl-1 [(phenylformamido)methanethioyl] amino}thiourea (12) gave a percentage viability of 17.9 +/- 5.6% and 11.2 +/- 0.9% against Trypanosoma brucei. Single crystal X-ray diffraction analysis of 1-benzoyl-3-(5-methyl-2-[(phenylformamido)methanethioyl]amino}phenyl)thiourea (1), 3-benzoyl-1- (2-[(phenylformamido)methanethioyl]amino}ethyl)thiourea (11), 3-benzoyl-1-[(phenylformamido)methanethioyl]amino}thiourea (12) and 3-benzoyl-1- (4- [(phenylformamido)methanethioyl] amino}butyl)thioure a (14) have been presented. 1-(3-Bromobenzoyl) 3 [2-([(3-bromophenyl)formamido]methanethioyl}amino)phenyl]thiourea (10) gave a percentage inhibition of 97.03 +/- 0.37% against HIV-1 protease enzyme at a concentration of 100 mu M.