(1H-咪唑-4-基)-苯基-甲酮 | 61985-32-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1H-咪唑-4-基)-苯基-甲酮
• 英文名称: (1H‐imidazol‐5‐yl)(phenyl)methanone
• 英文别名: (1H-imidazol-5-yl)(phenyl)methanone；5-Benzoylimidazol；(1(3)H-imidazol-4-yl)-phenyl-methanone；4-Benzoylimidazol；1H-Imidazol-5-yl(phenyl)methanone
• CAS: 61985-32-8
• 化学式: C₁₀H₈N₂O
• mdl: MFCD04541434
• 分子量: 172.186
• InChiKey: DECHVIXTYBTMBL-UHFFFAOYSA-N

物化性质

• 溶解度：
  25.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 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：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1H-咪唑-4-基)-苯基-甲酮 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 phenyl[1-(prop-2-yn-1-yl)-1H-imidazol-5-yl]methanol
  参考文献：
  名称：

  咪唑-1,4-恶嗪的简单合成方案及其毒性评估

  摘要：

  AbstractImidazo‐1,5‐alkynyl alcohol derivatives were synthesized, and they were cyclized to imidazo‐1,4‐oxazines by means of cesium carbonate. Propargyl‐allene isomerization was examined, and the reaction mechanism was proposed. Moreover, cytotoxicity of synthesized molecules against LN405 cell lines was investigated by means of structure‐activity relationship (SAR). With SAR study, toxicities of some functional groups have been shown. In addition, two lead compounds were tested against DNA damaging.

  DOI：

  10.1002/hc.21412
• 作为产物：
  描述：

  1-(Dimethylsulfamoyl)-5-imidazol 在 sodium dichromate 、 水 、 碳酸氢钠 作用下， 反应 44.5h， 生成 (1H-咪唑-4-基)-苯基-甲酮
  参考文献：
  名称：

  Effenberger, Franz; Roos, Michael; Ahmad, Roshan, Chemische Berichte, 1991, vol. 124, p. 1639 - 1650

  摘要：

  DOI：

文献信息

• Synthesis of novel imidazopyridines and their biological evaluation as potent anticancer agents: A promising candidate for glioblastoma
  作者：Dilek Güçlü、Burak Kuzu、İsrafil Tozlu、Filiz Taşpınar、Hande Canpınar、Mehmet Taşpınar、Nurettin Menges

  DOI：10.1016/j.bmcl.2018.06.033

  日期：2018.8

  results of these two tests showed that both lead compounds affected the G0/G1 phase and did not allow the cells to reach the synthesis phase. The log BB (blood–brain barrier) and Caco-2 permeability of the synthesized molecules were calculated and it was shown that imidazopyridine derivatives taken orally are likely to pass through gastrointestinal membrane and the blood–brain barrier.

  根据非常简单的方案合成了新的咪唑并吡啶衍生物，然后对其进行针对LN-405细胞的细胞毒性测试。其中两种化合物在10和75 µM时对LN-405细胞具有抗增殖作用，因此被选作进一步研究的先导化合物。在WS1上进行了铅化合物的安全性实验，并获得了IC 50值分别计算为480和844 µM。将LN-405细胞系与先导化合物一起孵育，然后通过彗星试验检测DNA损伤，并使用流式细胞仪检测其对细胞周期的影响。这两个测试的结果表明，两种先导化合物都影响G0 / G1相，并且不允许细胞进入合成相。计算了合成分子的log BB（血脑屏障）和Caco-2渗透性，结果表明，口服的咪唑并吡啶衍生物很可能会穿过肠胃膜和血脑屏障。
• Mono- or di-substituted imidazole derivatives for inhibition of acetylcholine and butyrylcholine esterases
  作者：Burak Kuzu、Meltem Tan、Parham Taslimi、İlhami Gülçin、Mehmet Taşpınar、Nurettin Menges

  DOI：10.1016/j.bioorg.2019.01.044

  日期：2019.5

  Mono- or di-substituted imidazole derivatives were synthesized using a one-pot, two-step strategy. All imidazole derivatives were tested for AChE and BChE inhibition and showed nanomolar activity similar to that of the test compound donepezil and higher than that of tacrine. Structure activity relationship studies, docking studies to on X-ray crystal structure of AChE with PDB code 1B41, and adsorption

  使用一锅两步策略合成单或二取代的咪唑衍生物。测试了所有咪唑衍生物的AChE和BChE抑制作用，并显示出与测试化合物多奈哌齐相似的纳摩尔活性，但比他克林的纳摩尔活性更高。进行了结构活性关系研究，对具有PDB代码1B41的AChE的X射线晶体结构的对接研究以及吸附，分布，代谢和排泄（ADME）的预测。合成的核心骨架被绑定到AChE活性位点的重要区域，例如外围阴离子位点（PAS），氧阴离子孔（OH）和阴离子亚位点（AS）。计算出报告的测试化合物的选择性，酶动力学研究表明它们具有竞争性抑制剂的作用，而其中两种测试化合物则显示出非竞争性抑制行为。ADME的预测表明，合成的分子可能会穿过血脑屏障和肠上皮屏障，并在血流中自由循环而不与人血清白蛋白结合。一种化合物对WS1（皮肤成纤维细胞）细胞系的毒性为1790 µM，而对SH-SY5Y（神经母细胞瘤）细胞系的毒性为950 µM。
• Diastereoselective Synthesis Process with 6-Bromo-4-(3-Chlorophenyl)-2-Methoxy-Quinoline
  申请人：Filliers Ferdinand Maria Walter

  公开号：US20070293680A1

  公开（公告）日：2007-12-20

  A diastereoselective synthesis process for the preparation of (R)-(+)-6-[amino(4chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methyl2(1H)-quinolinone which comprises the preparation of a compound of formula (XVII): and the stereochemically isomeric forms thereof wherein R is C1-6alkyl or C1-6alkylphenyl.

  一种对映选择性合成过程，用于制备(R)-(+)-6-[氨基(4-氯苯基)(1-甲基-1H-咪唑-5-基)甲基]-4-(3-氯苯基)-1-甲基-2(1H)-喹啉酮，其中包括制备化合物公式(XVII)和其立体化学异构体，其中R为C1-6烷基或C1-6烷基苯基。
• 4-Benzyl- and 4-benzoylimidazole derivatives, processes for their preparation and pharmaceutical compositions comprising the same
  申请人：Farmos-Yhtyma Oy

  公开号：EP0024829A1

  公开（公告）日：1981-03-11

  The invention provides compounds of the formula: wherein R1, R2 and R3, which can be the same or different, are each selected from hydrogen, chloro, bromo, fluoro, methyl, ethyl, methoxy, amino, hydroxy and nitro; R4 is hydrogen or alkyl of 1 to 7 carbon atoms; -X- is wherein R5 is hydrogen, hydroxy or-OR6, and R6 is alkyl of 1 to 7 carbon atoms or aryl of 6 to 10 carbon atoms; and their non-toxic pharmaceutically acceptable acid addition salts and mixtures thereof. Processes for the preparation and use of the subject compounds are described, as are novel pharmaceutical compositions comprising at least one of the subject compounds or their salts. The compounds and their non-toxic salts exhibit valuable pharmacological activity and are useful in the treatment of mammals, particularly as anti-hypertensive or anti-ulcer agents. Furthermore, they are useful as diuretic, sedative, analgesic, anti-inflammatory and tranquilizing agents.

  本发明提供了如下式的化合物： 其中R1、R2和R3可以相同或不同，它们各自选自氢、氯、溴、氟、甲基、乙基、甲氧基、氨基、羟基和硝基；R4是氢或1至7个碳原子的烷基；-X-是 其中 R5 是氢、羟基或-OR6，R6 是 1 至 7 个碳原子的烷基或 6 至 10 个碳原子的芳基；以及它们的无毒药学上可接受的酸加成盐及其混合物。描述了制备和使用上述化合物的工艺，以及包含至少一种上述化合物或其盐的新型药物组合物。这些化合物及其无毒盐具有宝贵的药理活性，可用于治疗哺乳动物，特别是作为抗高血压或抗溃疡药物。此外，它们还可用作利尿剂、镇静剂、镇痛剂、消炎剂和镇定剂。
• Substituted imidazole derivatives and their preparation and use
  申请人：Farmos Group Ltd.

  公开号：EP0072615B1

  公开（公告）日：1985-12-27