N-(m-chlorobenzamido)-N'-benzoylthiourea | 648860-52-0

• 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: N-(m-chlorobenzamido)-N'-benzoylthiourea
• 英文别名: 4-benzoyl-1-(3-chlorobenzoyl)thiosemicarbazide；N-[[(3-chlorobenzoyl)amino]carbamothioyl]benzamide
• CAS: 648860-52-0
• 化学式: C₁₅H₁₂ClN₃O₂S
• 分子量: 333.798
• InChiKey: FSAVRJZFBMPEIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 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：
  102
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(m-chlorobenzamido)-N'-benzoylthiourea 在 sodium hydroxide 作用下， 反应 10.0h， 以74%的产率得到5-(3-氯苯)-4H-1,2,4-三唑-3-硫醇
  参考文献：
  名称：

  Synthesis, characterization and preliminary anticonvulsant evaluation of some 4-alkyl-1,2,4-triazoles

  摘要：

  Designed and synthesized 4-alkyl-1,2,4-triazole-3-thione derivatives showed significant anticonvulsant activity, determined in the maximal electroshock-induced seizure (MES) test. The chemical structure of all new compounds was confirmed by spectral methods (H-1 NMR, C-13 NMR, IR, MS). A sensitive and selective method was elaborated for the determination of the anticonvulsant compounds levels in mice brain tissue, based on HPLC with diode array detector (DAD). Chromatographic tests showed that lack of anticonvulsant effect of two derivatives (15,16) with long alkyl chains at N-4 position of the 1,2,4-triazole ring was due to the inability to cross the blood brain barrier (BBB). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.026
• 作为产物：
  描述：

  苯甲酰基异硫氰酸酯 、 3-氯苯甲酰肼 以 乙腈 为溶剂， 反应 8.0h， 生成 N-(m-chlorobenzamido)-N'-benzoylthiourea
  参考文献：
  名称：

  分子内氢键和阴离子结合的ň -Benzamido- ñ “-benzoylthioureas

  摘要：

  ñ - （p二甲基氨基）苯甲酰基Ñ “-phenylthiourea作为ñ -acylthiourea已知是不能结合的阴离子由于强的分子内氢键（IHB）。我们在这里表明，通过在N'-苯基侧插入一个酰胺基，尽管有这种IHB，新设计的N-苯甲酰胺基-N'-苯甲酰硫脲也能以10 6 -10 7 mol的结合常数牢固地与阴离子结合- 1个L.结果表明，潜在的阴离子受体或有机催化剂可能具有广泛的结构多样性这一框架的基础上进行开发。

  DOI：

  10.1021/jo702159r

文献信息

• Synthesis, characterization and preliminary anticonvulsant evaluation of some 4-alkyl-1,2,4-triazoles
  作者：Tomasz Plech、Jarogniew J. Luszczki、Monika Wujec、Jolanta Flieger、Magdalena Pizoń

  DOI：10.1016/j.ejmech.2012.11.026

  日期：2013.2

  Designed and synthesized 4-alkyl-1,2,4-triazole-3-thione derivatives showed significant anticonvulsant activity, determined in the maximal electroshock-induced seizure (MES) test. The chemical structure of all new compounds was confirmed by spectral methods (H-1 NMR, C-13 NMR, IR, MS). A sensitive and selective method was elaborated for the determination of the anticonvulsant compounds levels in mice brain tissue, based on HPLC with diode array detector (DAD). Chromatographic tests showed that lack of anticonvulsant effect of two derivatives (15,16) with long alkyl chains at N-4 position of the 1,2,4-triazole ring was due to the inability to cross the blood brain barrier (BBB). (C) 2012 Elsevier Masson SAS. All rights reserved.
• Intramolecular Hydrogen Bonding and Anion Binding of <i>N</i>-Benzamido-<i>N</i>‘-benzoylthioureas
  作者：Wen-Xia Liu、Yun-Bao Jiang

  DOI：10.1021/jo702159r

  日期：2008.2.1

  N-acylthiourea is known to be unable to bind anions due to a strong intramolecular hydrogen bond (IHB). We show here that by inserting an amido group in the N‘-phenyl side the newly designed N-benzamido-N‘-benzoylthioureas, despite this IHB too, bind strongly to anions with binding constants on the order of 106−107 mol-1 L. Results suggest that potential anion receptors or organocatalysts could be developed

  ñ - （p二甲基氨基）苯甲酰基Ñ “-phenylthiourea作为ñ -acylthiourea已知是不能结合的阴离子由于强的分子内氢键（IHB）。我们在这里表明，通过在N'-苯基侧插入一个酰胺基，尽管有这种IHB，新设计的N-苯甲酰胺基-N'-苯甲酰硫脲也能以10 6 -10 7 mol的结合常数牢固地与阴离子结合- 1个L.结果表明，潜在的阴离子受体或有机催化剂可能具有广泛的结构多样性这一框架的基础上进行开发。