2-(1-甲基-1H-吡咯-2-基)乙酰肼 | 158144-17-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-(1-甲基-1H-吡咯-2-基)乙酰肼
• 中文别名: 2-(1-甲基吡咯-2-基)乙酰肼；2-(1-甲基吡咯-2-基)乙烷肼；2-(1-甲基-2-吡咯基)乙酰肼
• 英文名称: (1-methyl-pyrrol-2-yl)acetic acid hydrazide
• 英文别名: 1-methyl-pyrrol-2-ylacetic acid hydrazide；1-methylpyrrol-2-ylacetic acid hydrazide；2-(1-methyl-1H-pyrrol-2-yl)acetohydrazide；2-(1-methylpyrrol-2-yl)acetohydrazide
• CAS: 158144-17-3
• 化学式: C₇H₁₁N₃O
• mdl: MFCD01335800
• 分子量: 153.184
• InChiKey: UWUDAKQYIYHYGD-UHFFFAOYSA-N

物化性质

• 沸点：
  390.8±25.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(1-甲基-1H-吡咯-2-基)乙酰肼 在 sodium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 反应 44.0h， 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 在 一水合肼 作用下， 生成 2-(1-甲基-1H-吡咯-2-基)乙酰肼
  参考文献：
  名称：

  Determination of the Lipophilicity of Some New Derivatives of Semicarbazide and 1,2,4-Triazol-5-one with Potential Antibacterial Activity

  摘要：

  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。

  DOI：

  10.1515/znb-2009-0514

文献信息

• Synthesis and structural study of some N-acyl-4-allylsemicarbazides and the product of their cyclization with a potential antimicrobial activity
  作者：Monika Pitucha、Zbigniew Karczmarzyk、Marta Swatko-Ossor、Monika Drozd、Waldemar Wysocki、Grazyna Ginalska、Zofia Urbanczyk-Lipkowska、Dorota Kowalczuk、Maja Morawiak

  DOI：10.1016/j.molstruc.2020.128552

  日期：2020.11

  physico-chemicals (logP) and electronic properties (MEP distribution, energy localization of HOMO and LUMO orbitals) are related to observed antimicrobial activity of investigated compounds. The molecular docking study carried out for the most active against M. tuberculosis compound 3b using the M. tuberculosis cytochrome P450 CYP121 showed that this compound binds to the active site of P450 by hydrogen bonds via

  摘要 本文合成了带有烯丙基的氨基脲(2a-2h)和1,2,4-四唑(3a-3h)衍生物。所有化合物的体外抗微生物活性都进行了测试，显示出对大肠杆菌、金黄色葡萄球菌、表皮葡萄球菌、耻垢分枝杆菌、草本分枝杆菌和结核分枝杆菌 H37Ra 的不同活性。抗菌活性表现出对表皮葡萄球菌2g，对大肠杆菌和表皮葡萄球菌3g，对大肠杆菌3h。测定2b、2d、3b、3c和3e的晶体结构是为了确认合成途径并鉴定它们在结晶状态下的互变异构形式。理论计算表明，物理化学 (logP) 和电子特性（MEP 分布、HOMO 和 LUMO 轨道的能量定位）与观察到的研究化合物的抗菌活性有关。
• Substituted imidazo-[1,5-a][1,2,4]triazolo[1,5-d][1,4] benzodiazepine derivatives
  申请人：Buettelmann Bernd

  公开号：US20070082890A1

  公开（公告）日：2007-04-12

  The present invention is concerned with substituted imidazo[1,5-a][1,2,4]triazolo[1,5-d][1,4]benzodiazepine derivatives of the following formula wherein the definition of substituents is described in the claims. This class of compounds shows high affinity and selectivity for GABA A α5 receptor binding sites and might be useful as a cognitive enhancer or for the treatment of cognitive disorders like Alzheimer's disease.

  本发明涉及以下式的取代咪唑[1,5-a][1,2,4]三唑[1,5-d][1,4]苯二氮䓬啉衍生物，其中取代基的定义在权利要求中描述。这类化合物对GABA A α5受体结合位点表现出高亲和力和选择性，可能有助于作为认知增强剂或治疗认知障碍如阿尔茨海默病的药物。
• 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。
• Synthesis of 1,6-bis(semicarbazide)hexanes and 1,6-bis(1,2,4-triazol-5-one)hexanes and their antiproliferative and antimicrobial activity
  作者：M. Pitucha、J. Rzymowska、A. Olender、L. Grzybowska-Szatkowska

  DOI：10.2298/jsc110212157p

  日期：——

  A series of 1,6-bis(3-substituted-4,5-dihydro-1H-1,2,4-triazol-5-on-4- yl)hexanes (3a-g) were synthesized by the cyclization reaction of 1,6-bis(1- substituted-semicarbazide-4-yl)hexanes (2a-g) in alkaline medium. New derivatives (3a-c) were screened in vitro for their antiproliferative and anticancer activity in human tumor cell lines derived from breast and lung carcinoma cells. Compounds 3a (in concentration of 0.18 mM), 3b (in concentrations of 0.12 mM and 0.02 mM) and 3c (in concentrations of 0.23 mM and 0.11 mM) were found to be the most effective against lung cell line. The compound (3a) had the most antiproliferative effect on breast carcinoma cell line. Representative compounds were established and evaluated as antimicrobial agents. All tested derivatives showed MIC in range 1.87-7.5 (?g/mL). The compound (3b) was the most effective against C. albicans (MIC 1.87 ?g/mL).

  通过环化反应合成了一系列 1,6-双(3-取代-4,5-二氢-1H-1,2,4-三唑-5-酮-4-基)己烷(3a-g)。 环化反应合成了一系列 1,6-双(3-取代-4,5-二氢-1H-1,2,4-三唑-5-酮-4-基)己烷（3a-g）。 1,6-双(1-取代-氨基脲-4-基)己烷(2a-g)在碱性介质中发生环化反应而合成。新 衍生物（3a-c）的体外抗增殖和抗癌活性进行了筛选。 人肿瘤细胞系中的抗增殖和抗癌活性。 癌细胞的抗增殖和抗癌活性。化合物 3a（浓度为 0.18 mM）、3b（浓度为 0.12 mM 浓度分别为 0.12 毫摩尔和 0.02 毫摩尔）和 3c （浓度分别为 0.23 毫摩尔和 0.11 毫摩尔 和 0.11 mM）对肺癌细胞株最有效。化合物 化合物（3a）对乳腺癌细胞株的抗增殖作用最强。 系。具有代表性的化合物被确立并评估为 抗菌剂。所有受试衍生物的 MIC 值范围为 1.87-7.5 (克/毫升）。化合物（3b）对白僵菌最有效（MIC 1.87毫克/毫升）。
• 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。