4,4'-bis(1-acetyl-semicarbazide)diphenylmethane | 1130206-80-2

• 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: 4,4'-bis(1-acetyl-semicarbazide)diphenylmethane
• 英文别名: 1-Acetamido-3-[4-[[4-(acetamidocarbamoylamino)phenyl]methyl]phenyl]urea
• CAS: 1130206-80-2
• 化学式: C₁₉H₂₂N₆O₄
• 分子量: 398.421
• InChiKey: QZHWGFJFVMBBHF-UHFFFAOYSA-N

物化性质

• 熔点：
  320-321 °C(Solvent: Ethanol)
• 密度：
  1.339±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  141
• 氢给体数：
  6
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-bis(1-acetyl-semicarbazide)diphenylmethane 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 15.0h， 以83%的产率得到4,4'-bis(3-methyl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)diphenylmethane
  参考文献：
  名称：

  一些新的 4,4'-双（3-取代-4,5-二氢-1H-1,2,4-三唑-5-one-4-yl）二苯基甲烷衍生物的合成、实验和理论研究

  摘要：

  摘要 通过氨基脲衍生物2的环化反应合成了4,4'-双(3-取代-4,5-二氢-1H-1,2,4-三唑-5-酮-4-基)二苯甲烷衍生物3。在碱性溶液中。合成的化合物通过元素分析、IR、1H 和 13C NMR 以及 MS 进行表征。化合物3a的分子结构由X射线分析确定。对所有最终（环状）化合物进行了分子结构的理论计算（DFT/B3LYP/6-311G**）。此外，通过单参数和 SQM 缩放方法再现了 3a 的振动谱，并提出了频带分配。研究的新化合物表现出镇痛特性。

  DOI：

  10.1016/j.molstruc.2008.09.002
• 作为产物：
  描述：

  乙酰肼 、 4,4'-二苯甲烷二异氰酸酯、2,4'-二苯甲烷二异氰酸酯和2,2'-二苯甲烷二异氰酸酯的混合物 以 乙醚 为溶剂， 反应 24.0h， 以80%的产率得到4,4'-bis(1-acetyl-semicarbazide)diphenylmethane
  参考文献：
  名称：

  一些新的 4,4'-双（3-取代-4,5-二氢-1H-1,2,4-三唑-5-one-4-yl）二苯基甲烷衍生物的合成、实验和理论研究

  摘要：

  摘要 通过氨基脲衍生物2的环化反应合成了4,4'-双(3-取代-4,5-二氢-1H-1,2,4-三唑-5-酮-4-基)二苯甲烷衍生物3。在碱性溶液中。合成的化合物通过元素分析、IR、1H 和 13C NMR 以及 MS 进行表征。化合物3a的分子结构由X射线分析确定。对所有最终（环状）化合物进行了分子结构的理论计算（DFT/B3LYP/6-311G**）。此外，通过单参数和 SQM 缩放方法再现了 3a 的振动谱，并提出了频带分配。研究的新化合物表现出镇痛特性。

  DOI：

  10.1016/j.molstruc.2008.09.002

文献信息

• Synthesis, Experimental and Theoretical Study on the Structure of Some Semicarbazides with Potential Antibacterial Activity
  作者：Monika Pitucha、Zbigniew Karczmarzyk、Urszula Kosikowska、Anna Malm

  DOI：10.1515/znb-2011-0511

  日期：2011.5.1

  A series of 1,4-disubstituted semicarbazide and 4,4’-bis[1-substituted semicarbazide]diphenylmethane derivatives were synthesized to explore their antibacterial activity. New compounds were characterized by elemental analysis and spectroscopic data. In order to find the tautomeric equilibrium for the molecules energy calculations for each possible tautomeric form of model compound 2, and for the most antibacterially active compound 7 in the investigated series, were calculated for the gas phase at the RHF/SCF/6-31G** level of theory

  合成了一系列1,4-二取代半胱氨酸和4,4'-双[1-取代半胱氨酸]二苯甲烷衍生物，以探索它们的抗菌活性。新化合物通过元素分析和光谱数据进行表征。为了找到分子的互变平衡，对模型化合物2的每种可能的互变形式和对研究系列中最具抗菌活性的化合物7进行了在RHF/SCF/6-31G**水平的气相能量计算。
• Antioxidant Evaluation of Some Semicarbazide, 1,2,4-Triazolone and Pyrazolone Derivatives
  作者：Monika Pitucha、Renata Nowak

  DOI：10.2174/157018011797655188

  日期：2011.12.1

  heterocyclic ring 1-14 were synthesized as compounds with interesting pharmacological profiles. All were investigated in vitro for their antioxidant activity. Some compounds showed significant effect in the above assay. The most promising was a group of pyrazolone. The effect was dependent mainly on the substituent on the amide group. It was found that compounds 8 and 10 showed the highest antioxidant capacity

  合成具有杂环1-14的1,2,4-三唑，吡唑和氨基脲为具有有趣药理学特征的化合物。所有的人都进行了体外抗氧化活性研究。一些化合物在上述测定中显示出显著作用。最有希望的是一组吡唑啉酮。 该作用主要取决于酰胺基上的取代基。发现化合物8和10显示出与广泛使用的参比抗氧化剂6-羟基-2,5,7,8-四甲基苯并-2-羧酸（Trolox）相当的最高抗氧化剂容量。
• Synthesis and antinociceptive activity of 4,4′-bis(1-substituted-semicarbazidyl)diphenylmethane and 4,4′-bis(5-substituted-2,4-dihydro-3-oxo-3H-1,2,4-triazol-4-yl)diphenylmethane derivatives
  作者：Monika Pitucha、Anna Chodkowska、Mariusz Maciejewski、Ewa Jagiello-Wójtowicz、Anna Pachuta-Stec

  DOI：10.1007/s00706-009-0242-3

  日期：2010.2

  In the reaction of 4,4'-diphenylmethane diisocyanate with carboxylic acid hydrazides, 4,4'-bis(1-substituted-semicarbazidyl) diphenylmethane derivatives were obtained. Depending on their chemical nature, cyclization of these compounds in alkaline medium led to the formation of two groups of compounds: bis(2,4-dihydro-3H-1,2,4-triazol-3-one) derivatives or carboxylic acids. The pharmacological effects of the selected compounds on the central nervous system in mice were investigated. Strong antinociceptive properties of some derivatives, at a wide range of doses, were observed.
• Synthesis and RP HPLC studies of biologically active semicarbazides and their cyclic analogues 1,2,4-triazol-3-ones
  作者：Monika Pitucha、Joanna Matysiak、Bogdan Senczyna

  DOI：10.1007/s00706-011-0715-z

  日期：2012.4

  The retention behaviour of semicarbazides and their cyclic analogues 1,2,4-triazol-3-ones, has been investigated by RP-8, RP-18 and IAM HPLC. The structures of new derivatives were proved by elemental analyses, IR, H-1 NMR and C-13 NMR spectroscopy. The compounds showed regular retention behaviour in three chromatographic systems; their log k values decreased linearly with the increasing concentration of an organic modifier in the mobile phase. The ratio of the intercept (log k (w)) to the slope of compounds is constant and the same for both groups of compounds on C18 and IAM stationary phases. Differences between log k (w) values from the octadecyl stationary phase of corresponding cyclic and linear derivatives are constant, and they are related to the mechanism of synthesis of 1,2,4-triazol-3-ones from linear substrate semicarbazides, which was confirmed by modelling studies. Good correlations between log k (w) parameters obtained by RP-8 or RP-18 and determined by the computational approach log P were found.
• Synthesis, experimental and theoretical investigations of some new 4,4′-bis(3-substituted-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)diphenylmethane derivatives
  作者：Monika Pitucha、Piotr Borowski、Zbigniew Karczmarzyk、Andrzej Fruziński

  DOI：10.1016/j.molstruc.2008.09.002

  日期：2009.2

  5-dihydro-1H-1,2,4-triazol-5-one-4-yl)diphenylmethane derivatives 3 were synthesized in the cyclization reaction of semicarbazide derivatives 2 in alkaline solution. The synthesized compounds were characterized by elemental analyses, IR, 1H and 13C NMR, as well as MS. Molecular structure of compound 3a was determined by the X-ray analysis. Theoretical calculations (DFT/B3LYP/6-311G∗∗) of molecular structures

  摘要 通过氨基脲衍生物2的环化反应合成了4,4'-双(3-取代-4,5-二氢-1H-1,2,4-三唑-5-酮-4-基)二苯甲烷衍生物3。在碱性溶液中。合成的化合物通过元素分析、IR、1H 和 13C NMR 以及 MS 进行表征。化合物3a的分子结构由X射线分析确定。对所有最终（环状）化合物进行了分子结构的理论计算（DFT/B3LYP/6-311G**）。此外，通过单参数和 SQM 缩放方法再现了 3a 的振动谱，并提出了频带分配。研究的新化合物表现出镇痛特性。