(9ci)-5-甲基-1H-咪唑-4-羧酸肼 | 71704-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (9ci)-5-甲基-1H-咪唑-4-羧酸肼
• 英文名称: 4-methylimidazole-5-carbohydrazide
• 英文别名: 4-methyl-1H-imidazole-5-carbohydrazide；5-methyl-1H-imidazole-4-carbohydrazide
• CAS: 71704-67-1
• 化学式: C₅H₈N₄O
• mdl: MFCD04107872
• 分子量: 140.145
• InChiKey: WAWTVTOLBUMOFH-UHFFFAOYSA-N

物化性质

• 熔点：
  220 °C
• 密度：
  1.337±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  83.8
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  (9ci)-5-甲基-1H-咪唑-4-羧酸肼 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 22.0h， 生成 (4-bromobenzylidene)-5-methyl-imidazole-4-carbohydrazide
  参考文献：
  名称：

  Design and Synthesis of Novel Potent Antinociceptive Agents: Methyl-imidazolyl N-Acylhydrazone Derivatives

  摘要：

  This paper describes recent results of design, synthesis and pharmacological evaluation of new N-heterocyclic functionalized N-acylhydrazone compounds, belonging to the 2-methyl-imidazolyl-3-acylhydrazone class (4a-e). These compounds were planned by applying the molecular simplification strategy to propose the structural modifications on the previously described functionalized imidazo[1,2-a]pyridine 3-acylhydrazone series (2), which presented an important analgesic profile. This new series (4) was synthesized in order to investigate the possible pharmacophoric contribution of the N-heteroaromatic ring and N-acylhydrazone moieties to the analgesic activity. Compounds 4a-b are the most potent antinociceptive agents from this series. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00152-8
• 作为产物：
  描述：

  4-羟甲基-5-甲基咪唑 在 manganese(IV) oxide 、 氰化钠 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 (9ci)-5-甲基-1H-咪唑-4-羧酸肼
  参考文献：
  名称：

  Design and Synthesis of Novel Potent Antinociceptive Agents: Methyl-imidazolyl N-Acylhydrazone Derivatives

  摘要：

  This paper describes recent results of design, synthesis and pharmacological evaluation of new N-heterocyclic functionalized N-acylhydrazone compounds, belonging to the 2-methyl-imidazolyl-3-acylhydrazone class (4a-e). These compounds were planned by applying the molecular simplification strategy to propose the structural modifications on the previously described functionalized imidazo[1,2-a]pyridine 3-acylhydrazone series (2), which presented an important analgesic profile. This new series (4) was synthesized in order to investigate the possible pharmacophoric contribution of the N-heteroaromatic ring and N-acylhydrazone moieties to the analgesic activity. Compounds 4a-b are the most potent antinociceptive agents from this series. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00152-8

文献信息

• A Search for Dual Action HIV-1 Reverse Transcriptase, Bacterial RNA Polymerase Inhibitors
  作者：Agata Paneth、Tomasz Frączek、Agnieszka Grzegorczyk、Dominika Janowska、Anna Malm、Piotr Paneth

  DOI：10.3390/molecules22111808

  日期：——

  Using molecular modeling approach, potential antibacterial agents with triazole core were proposed. A moderate to weak level of antibacterial activity in most of the compounds have been observed, with best minimal inhibitory concentration (MIC) value of 0.003 mg/mL, as shown by the 15 against S. epidermidis. Studied compounds were also submitted to the antifungal assay. The best antifungal activity

  使用分子建模方法，提出了具有三唑核的潜在抗菌剂。已观察到大多数化合物具有中等至微弱的抗菌活性，最佳最小抑菌浓度 (MIC) 值为 0.003 mg/mL，如针对表皮葡萄球菌的 15 所示。所研究的化合物也进行了抗真菌试验。对 16 种检测到最佳抗真菌活性，MIC 分别为 0.125 和 0.25 mg/mL，分别对抗白色念珠菌和近平滑念珠菌。
• Study of direction of cyclization of 1-azolil-4-aryl/alkyl-thiosemicarbazides
  作者：Agata Siwek、Monika Wujec、Maria Dobosz、Irena Wawrzycka-Gorczyca

  DOI：10.1002/hc.20643

  日期：——

  , a study on the influence of azole moiety on the capability for intramolecular cyclization and its direction was carried out. It was found that for 4-aryl/alkyl-thiosemicabazides with triazole, imidazole, or pyrrole moiety at N-1 nitrogen atom possible products were only s-triazoles, both in alkaline and acidic medium. Successful dehydrocyclization of 1-azolil-4-aryl/alkyl-thiosemicarbazides leading

  对四个系列的1-唑啉-4-芳基/烷基-氨基硫脲进行了唑基对分子内环化能力的影响及其方向的研究。发现对于在 N-1 个氮原子上具有三唑、咪唑或吡咯部分的 4-芳基/烷基-氨基硫脲，在碱性和酸性介质中，可能的产物仅为 s-三唑。仅针对一系列 1-(4-甲基-1,2,3-噻二唑-5-基-羰基)-4- 1-唑基-4-芳基/烷基-氨基硫脲成功脱氢环化生成噻二唑芳基/烷基氨基硫脲。可以推测，1-唑啉-4-芳基/烷基-氨基硫脲的氧原子pKa值的测定可能是预测脱氢环化形成噻二唑的可能性的非常有价值的参数。© 2010 威利期刊公司。杂原子化学 21:521–532, 2010; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.20643
• Self-assembled polymetallic square grids ([2 × 2] M₄, [3 × 3] M₉) and trigonal bipyramidal clusters (M₅)—structural and magnetic properties
  作者：Louise N. Dawe、Tareque S. M. Abedin、Timothy L. Kelly、Laurence K. Thompson、David O. Miller、Liang Zhao、Claire Wilson、Michael A. Leech、Judith A. K. Howard

  DOI：10.1039/b602595a

  日期：——

  New self-assembled grids and clusters are reported, with square [2 × 2] M4 (M = Mn(II)4, Cu(II)4), trigonal-bipyramidal Mn(II)5, and square [3 × 3] M9 (M = Mn(II), Cu(II)) examples. These are based on a series of ditopic and tritopic hydrazone ligands involving pyridine, pyrimidine and imidazole end groups. In all cases the metal centres are bridged by hydrazone oxygen atoms with large (>125°) bridge angles, leading to antiferromagnetic exchange for all the Mn systems (J = −2 to −5 cm−1), which results in S = 0 (Mn4), and S = 5/2 (Mn5, Mn9) ground states. The copper systems have a 90° alternation of the Jahn–Teller axes within the Cu4 and Cu8 grid rings (Cu9), which leads to magnetic orbital orthogonality, and dominant ferromagnetic coupling. For the Cu9 grid antiferromagnetic exchange between the ring and the central copper leads to a S = 7/2 ground state, while for the Cu4 grids S = 4/2 ground states are observed. The magnetic data have been treated using isotropic exchange models in the cases of the Cu4 and Cu9 grids, and the Mn5 clusters. However due to the enormity of a fully isotropic calculation a simplified model is used for the Mn9 grid, in which the outer Mn8 ring is treated as the equivalent of an isolated magnetic chain, with no coupling to the central metal ion.

  报道了一些新的自组装网格和簇，包括方形 [2 × 2] M4 (M = Mn(II)4, Cu(II)4)、三角双锥 Mn(II)5 以及方形 [3 × 3] M9 (M = Mn(II), Cu(II)) 的例子。这些基于一系列包含吡啶、嘧啶和咪唑末端基团的双位和三位肼酮配体。在所有情况下，金属中心由肼酮氧原子桥接，桥角大于125°，这导致所有 Mn 系统呈现反铁磁交换（J = -2 到 -5 cm⁻¹），最终结果为基态 S = 0 (Mn4)，和 S = 5/2 (Mn5, Mn9)。铜系统在 Cu4 和 Cu8 网格环 (Cu9) 中表现出 Jahn-Teller 轴的 90° 交替，导致磁轨道正交性和主导的铁磁耦合。对于 Cu9 网格，环和中心铜之间的反铁磁交换导致 S = 7/2 的基态，而对于 Cu4 网格则观察到 S = 4/2 的基态。对于 Cu4 和 Cu9 网格以及 Mn5 簇，磁数据使用各向同性交换模型进行处理。然而，由于完全各向同性计算的复杂性，对于 Mn9 网格采用了简化模型，其中外层 Mn8 环被视作一个孤立磁链的等效体，与中心金属离子没有耦合。
• Complete and ‘incomplete’ [2 × 2] grids by self-assembly with a sterically hindered ditopic imidazole hydrazone ligand—structural and magnetic studies
  作者：Louise N. Dawe、Laurence K. Thompson

  DOI：10.1039/b800529j

  日期：——

  carboxylic acid hydrazide with the iminoester of 2-pyridinecarbonitrile formed targeted [2 x 2] M(4)L(4) (M = Cu(II), Ni(II); L = ioap) grids, and a mixed oxidation state dinuclear cobalt complex. An 'incomplete' trinuclear M(3)L(4) (M = Mn(II)) grid, based on a [2 x 2] grid architecture, resulting from steric congestion of the imidazole methyl-substituent, was also produced. These results lead to the

  由4-甲基-5-咪唑羧酸酰肼与2-吡啶甲腈的亚氨基酯缩合合成的对位配体（ioap）形成目标[2 x 2] M（4）L（4）（M = Cu（II ），Ni（II）; L = ioap）网格和混合氧化态双核钴配合物。还产生了基于[2 x 2]网格结构的“不完全”三核M（3）L（4）（M = Mn（II））网格，该网格结构是由咪唑甲基取代基的空间拥堵引起的。这些结果提示了一种可能的途径，可以通往[2 x 2]网格的自组装路径。Mn（II），Ni（II）和Cu（II）配合物在金属中心之间具有氧桥，这会在Mn（II）（3）和Ni（II）（4）情况下导致反铁磁交换，但是，由于存在正交桥接连接，以Cu（II）（4）为例进行铁磁交换。基于桥接连接讨论了结构和磁性能。
• Systematic Identification of Thiosemicarbazides for Inhibition of Toxoplasma gondii Growth In Vitro
  作者：Agata Paneth、Lidia Węglińska、Adrian Bekier、Edyta Stefaniszyn、Monika Wujec、Nazar Trotsko、Katarzyna Dzitko

  DOI：10.3390/molecules24030614

  日期：——

  One of the key stages in the development of new therapies in the treatment of toxoplasmosis is the identification of new non-toxic small molecules with high specificity to Toxoplasma gondii. In the search for such structures, thiosemicarbazide-based compounds have emerged as a novel and promising leads. Here, a series of imidazole-thiosemicarbazides with suitable properties for CNS penetration was

  开发治疗弓形虫病的新疗法的关键阶段之一是鉴定对弓形虫具有高度特异性的新型无毒小分子。在寻找这样的结构时，已经出现了基于硫代氨基脲的化合物，这是一种新颖且有前途的线索。在这里，评估了一系列具有适合CNS渗透的特性的咪唑-硫代氨基脲，以确定有效的抗弓形虫活性所需的结构要求。当与磺胺嘧啶相比对宿主细胞无毒时，最好的4-芳基硫代氨基脲3和4表现出更高的效能，表明它们的抗弓形虫活性具有很高的选择性。