4-(4-bromophenyl)-1-[(1-methylpyrrol-2-yl)acetyl]semicarbazide | 891005-41-7

• 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-bromophenyl)-1-[(1-methylpyrrol-2-yl)acetyl]semicarbazide
• 英文别名: 1-(4-Bromophenyl)-3-[[2-(1-methylpyrrol-2-yl)acetyl]amino]urea
• CAS: 891005-41-7
• 化学式: C₁₄H₁₅BrN₄O₂
• 分子量: 351.203
• InChiKey: STRQQSPUDMVMBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  75.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-bromophenyl)-1-[(1-methylpyrrol-2-yl)acetyl]semicarbazide 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Synthesis and RP HPLC studies of biologically active semicarbazides and their cyclic analogues 1,2,4-triazol-3-ones

  摘要：

  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.

  DOI：

  10.1007/s00706-011-0715-z
• 作为产物：
  描述：

  1-甲基吡咯-2-乙酸乙酯 在 一水合肼 作用下， 以 乙醚 、 乙醇 、 N,N-二甲基乙酰胺 为溶剂， 生成 4-(4-bromophenyl)-1-[(1-methylpyrrol-2-yl)acetyl]semicarbazide
  参考文献：
  名称：

  Synthesis, Experimental and Theoretical Study on the Structure of Some Semicarbazides with Potential Antibacterial Activity

  摘要：

  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。

  DOI：

  10.1515/znb-2011-0511

文献信息

• 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。
• Anticancer Screening and Structure Activity Relationship Study of Some Semicarbazides and 1,2,4-Triazolin-5-ones
  作者：Monika Pitucha、Jolanta Rzymowska

  DOI：10.2174/157018012800673047

  日期：2012.5.1

  In this paper some semicarbazide and 1,2,4-triazolin-5-one derivatives are evaluated in vitro for their anticancer activity towards human tumour cell line: ovary (TOV 112D), lung (A 549), breast (T47D) and uterus (Hela). Compounds 2-4 have been found to show the most effective in vitro activity against ovary cancer cell line. For compound 4 the growth inhibition (80% and 70%) is observed in two concentrations (100 μg/ml and 50 μg/ml). The cytotoxic effect of examined compounds seems to be dose-dependent and time-dependent. Compound 7 has GI=80% values towards the breast cancer cell line in concentration of 100 μg/ml. Structure-activity relationship (SAR) studies are carried out for all the compounds of the series. Compounds 2-4 show an activity profile that can be improved through medicinal chemistry strategies.

  本文评估了一些半咔嗪和 1,2,4-三唑啉-5-酮衍生物对人类肿瘤细胞株（卵巢（TOV 112D）、肺（A 549）、乳腺（T47D）和子宫（Hela））的体外抗癌活性。研究发现，化合物 2-4 对卵巢癌细胞株具有最有效的体外活性。在两种浓度（100 微克/毫升和 50 微克/毫升）下，化合物 4 的生长抑制率分别为 80% 和 70%。所研究化合物的细胞毒性作用似乎是剂量依赖性和时间依赖性的。浓度为 100 μg/ml 的化合物 7 对乳腺癌细胞株的 GI 值为 80%。对该系列的所有化合物都进行了结构-活性关系（SAR）研究。化合物 2-4 显示出了可通过药物化学策略加以改进的活性特征。
• Determination of the Lipophilicity of Some New Derivatives of Semicarbazide and 1,2,4-Triazol-5-one with Potential Antibacterial Activity
  作者：Monika Pitucha、Beata Polak、Ryszard Świebodac、Urszula Kosikowska、Anna Malm

  DOI：10.1515/znb-2009-0514

  日期：2009.5.1

  The chromatographic behavior of new derivatives of 1,2,4-triazol-5-one and semicarbazide was determined. The lipophilicity was confirmed by the use of a RP-TLC method. The partition coefficients were calculated by use of theoretical procedures. The correlation between theoretical and experimental lipophilicity was determined. All obtained compounds were tested for their antimicrobial activity.

  新的1,2,4-三唑-5-酮和半卡巴肼衍生物的色谱行为已被确定。使用RP-TLC方法确认了它们的亲脂性。使用理论程序计算了它们的分配系数。确定了理论和实验亲脂性之间的相关性。对所有获得的化合物进行了抗微生物活性测试。
• Experimental and theoretical investigations on the keto–enol tautomerism of 4-substituted 3-[1-methylpyrrol-2-yl)methyl]-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives
  作者：Monika Pitucha、Zbigniew Karczmarzyk、Waldemar Wysocki、Agnieszka A. Kaczor、Dariusz Matosiuk

  DOI：10.1016/j.molstruc.2011.03.041

  日期：2011.5

  possessing the carbonyl group. In the present study we use X-ray analysis, IR spectroscopy as well as quantum chemical calculation to address the keto–enol tautomerism of 4-substituted 3-[1-methylpyrrol-2-yl)methyl]-4,5-dihydro-1 H -1,2,4-triazol-5-one derivatives with antimicrobial activity. In the gas phase and in the crystalline state all the investigated molecules exist in the keto form while in the

  摘要 酮-烯醇互变异构是决定具有羰基的化合物药理活性的关键现象。在本研究中，我们使用 X 射线分析、红外光谱以及量子化学计算来解决 4-取代 3-[1-甲基吡咯-2-基)甲基]-4,5-二氢- 1 H -1,2,4-triazol-5-one 衍生物，具有抗菌活性。在气相和结晶状态下，所有研究的分子都以酮形式存在，而在氯仿溶液中，观察到少量与酮形式平衡的烯醇形式。计算结果与在 KBr 中从 X 射线分析和红外光谱获得的实验数据非常一致，但不能证实互变异构平衡在氯仿溶液中转变为烯醇形式。
• 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。