1-(4-chlorobenzoyl)-4-(3,4-dichlorophenyl)thiosemicarbazide | 891643-96-2

• 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: 1-(4-chlorobenzoyl)-4-(3,4-dichlorophenyl)thiosemicarbazide
• 英文别名: 4-(3″,4″-dichlorophenyl)-1-[(4′-chlorophenyl)carbonyl]thiosemicarbazide；1-(4-Chlorobenzoyl)-4-(3,4-dichlorophenyl)thiosemicarbazide；1-[(4-chlorobenzoyl)amino]-3-(3,4-dichlorophenyl)thiourea
• CAS: 891643-96-2
• 化学式: C₁₄H₁₀Cl₃N₃OS
• 分子量: 374.678
• InChiKey: VRCGVMCOURVUOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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：
  85.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-chlorobenzoyl)-4-(3,4-dichlorophenyl)thiosemicarbazide 在 sodium hydroxide 作用下， 反应 2.0h， 以86%的产率得到4-(3,4-dichlorophenyl)-5-(4-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  The antinociceptive effect of 4-substituted derivatives of 5-(4-chlorophenyl)-2-(morpholin-4-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione in mice

  摘要：

  The aim of the present experiments was to examine the antinociceptive activity of 4-substituted derivatives of 5-(4-chlorophenyl)-2-(morpholin-4-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione in mice. The compounds were synthesized using the so-called Mannich reaction and their structures were confirmed using IR and 1H-NMR spectra. The antinociceptive activity was investigated in two behavioral tests: the hot plate test and the writhing test. For preliminary estimation of other behavioral effects, the locomotor activity of mice, the motor coordination in the rota-rod test, and the myorelaxation in the chimney test were also studied. The changes in body temperature of animals were also recorded. We demonstrated that all examined compounds produced antinociceptive effect, both in the hot plate test and in the writhing test, without impact on the motor coordination and myorelaxation of animals. The pharmacological effect of all drugs has been developed within 60 min after administration of drugs; and in two cases (T-103 and T-104), it has been a short-lasting effect (up to 90 min). Two compounds (T-100 and T-102) also inhibited the locomotor activity of animals. T-104 induced the changes in body temperature of mice. Generally, we demonstrated that combination of two different heterocyclic systems (morpholine and 1,2,4-triazole) might be beneficial for reduction of nociception.

  DOI：

  10.1007/s00210-013-0938-0
• 作为产物：
  描述：

  3,4-二氯异硫氰酸苯酯 、 4-氯苯甲酰肼 以 乙醇 为溶剂， 以82%的产率得到1-(4-chlorobenzoyl)-4-(3,4-dichlorophenyl)thiosemicarbazide
  参考文献：
  名称：

  1-[（4'-氯苯基）羰基-4-（芳基）硫代氨基脲衍生物作为有效的脲酶抑制剂：合成，体外和计算机研究

  摘要：

  合成了一系列1-[（（4'-氯苯基）羰基-4-（芳基）硫代氨基脲] 1 – 25，并通过光谱技术（例如EI-MS和1 H NMR）进行了表征。 与标准硫脲（IC 50  = 21.25± 0.13μM）相比，所有化合物的体外尿素酶抑制活性均得到筛选，并在IC 50 = 0.32±0.01–25.13±0.13μM范围内表现出优异的抑制活性。在有效的类似物中，化合物3（IC 50  = 2.31±0.01μM），6（IC 50  = 2.14±0.04μM），10（IC 50  = 1.14±0.06μM），20（IC50  = 2.15±0.05μM）和25（IC 50  = 0.32±0.01μM）的活性比标准品高很多倍。通过考察不同取代的芳基环对抑制电位的影响来合理化结构-活性关系（SAR），该效应预测，不管取代基的性质如何，它们在芳基环上的位置对于有效活性都很重要。此外，为验证这些解

  DOI：

  10.1016/j.bioorg.2018.05.017

文献信息

• 1-[(4′-Chlorophenyl) carbonyl-4-(aryl) thiosemicarbazide derivatives as potent urease inhibitors: Synthesis, in vitro and in silico studies
  作者：Basharat Ali、Khalid Mohammed Khan、Uzma Salar、Kanwal、Safdar Hussain、Muhammad Ashraf、Muhammad Riaz、Abdul Wadood、Muhammad Taha、Shahnaz Perveen

  DOI：10.1016/j.bioorg.2018.05.017

  日期：2018.9

  compared to the standard thiourea (IC50 = 21.25 ± 0.13 μM). Amongst the potent analogs, compounds 3 (IC50 = 2.31 ± 0.01 μM), 6 (IC50 = 2.14 ± 0.04 μM), 10 (IC50 = 1.14 ± 0.06 μM), 20 (IC50 = 2.15 ± 0.05 μM), and 25 (IC50 = 0.32 ± 0.01 μM) are many folds more active than the standard. Structure-activity relationship (SAR) was rationalized by looking at the effect of diversely substituted aryl ring on inhibitory

  合成了一系列1-[（（4'-氯苯基）羰基-4-（芳基）硫代氨基脲] 1 – 25，并通过光谱技术（例如EI-MS和1 H NMR）进行了表征。 与标准硫脲（IC 50  = 21.25± 0.13μM）相比，所有化合物的体外尿素酶抑制活性均得到筛选，并在IC 50 = 0.32±0.01–25.13±0.13μM范围内表现出优异的抑制活性。在有效的类似物中，化合物3（IC 50  = 2.31±0.01μM），6（IC 50  = 2.14±0.04μM），10（IC 50  = 1.14±0.06μM），20（IC50  = 2.15±0.05μM）和25（IC 50  = 0.32±0.01μM）的活性比标准品高很多倍。通过考察不同取代的芳基环对抑制电位的影响来合理化结构-活性关系（SAR），该效应预测，不管取代基的性质如何，它们在芳基环上的位置对于有效活性都很重要。此外，为验证这些解
• The antinociceptive effect of 4-substituted derivatives of 5-(4-chlorophenyl)-2-(morpholin-4-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione in mice
  作者：Listos Joanna、Sylwia Talarek、Jolanta Orzelska、Sylwia Fidecka、Monika Wujec、Tomasz Plech

  DOI：10.1007/s00210-013-0938-0

  日期：2014.4

  The aim of the present experiments was to examine the antinociceptive activity of 4-substituted derivatives of 5-(4-chlorophenyl)-2-(morpholin-4-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione in mice. The compounds were synthesized using the so-called Mannich reaction and their structures were confirmed using IR and 1H-NMR spectra. The antinociceptive activity was investigated in two behavioral tests: the hot plate test and the writhing test. For preliminary estimation of other behavioral effects, the locomotor activity of mice, the motor coordination in the rota-rod test, and the myorelaxation in the chimney test were also studied. The changes in body temperature of animals were also recorded. We demonstrated that all examined compounds produced antinociceptive effect, both in the hot plate test and in the writhing test, without impact on the motor coordination and myorelaxation of animals. The pharmacological effect of all drugs has been developed within 60 min after administration of drugs; and in two cases (T-103 and T-104), it has been a short-lasting effect (up to 90 min). Two compounds (T-100 and T-102) also inhibited the locomotor activity of animals. T-104 induced the changes in body temperature of mice. Generally, we demonstrated that combination of two different heterocyclic systems (morpholine and 1,2,4-triazole) might be beneficial for reduction of nociception.