(Z)-5-benzylidene-2-methyl-3,5-dihydro-imidazol-4-one | 101820-88-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-5-benzylidene-2-methyl-3,5-dihydro-imidazol-4-one
• 英文别名: 2-Methyl-4-benzyliden-2-imidazolin-5-on；(Z)-4-benzylidene-2-methyl-4,5-dihydro-1H-imidazol-5-one；5-benzylidene-2-methyl-3,5-dihydro-imidazol-4-one；5-Benzyliden-2-methyl-3,5-dihydro-imidazol-4-on；(4Z)-4-benzylidene-2-methyl-1H-imidazol-5-one
• CAS: 101820-88-6
• 化学式: C₁₁H₁₀N₂O
• 分子量: 186.213
• InChiKey: OZFVYSVTMXKDOZ-YFHOEESVSA-N

物化性质

• 熔点：
  178-180 °C
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-5-benzylidene-2-methyl-3,5-dihydro-imidazol-4-one 在 溶剂黄146 、 二乙胺 、 苯 作用下， 生成 3-acetyl-5-benzylidene-2-styryl-3,5-dihydro-imidazol-4-one
  参考文献：
  名称：

  Pfleger; Markert, Chemische Berichte, 1957, vol. 90, p. 1494,1498

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-4-亚苄基-2-甲基噁唑-5(4h)-酮 在 ammonium hydroxide 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 (Z)-5-benzylidene-2-methyl-3,5-dihydro-imidazol-4-one
  参考文献：
  名称：

  绿色荧光蛋白发色团衍生物作为新型醛糖还原酶抑制剂

  摘要：

  已合成了许多与水母绿色荧光蛋白（GFP）的荧光发色团有关的（Z）-4-芳基亚甲基-1 H-咪唑-5（4 H）-，并对其体外抑制作用进行了评估。重组人醛糖还原酶的活性首次获得证实。GFP生色团模型1a在4-亚苄基上具有对羟基，在N1位置上具有羧甲基，具有很强的生物活性，IC 50值为0.36μM。该功效高于已知的高效醛糖还原酶抑制剂山梨醇的功效。化合物1h，即1a的2-萘基亚甲基类似物，在被测化合物中表现出最佳的抑制作用，IC 50值为0.10μM 。结构-活性关系研究与对接模拟相结合，揭示了新合成的抑制剂与靶蛋白的相互作用模式以及获得高抑制活性所需的结构特征。总之，本研究中合成的GFP生色团模型化合物已被证明是糖尿病并发症的潜在药物。

  DOI：

  10.1016/j.ejmech.2016.10.016

文献信息

• Biomimetic Oxidation of 2-Methylimidazole Derivative with a Chemical Model System for Cytochrome P-450.
  作者：Hiroyuki Miyachi、Yoshio Nagatsu

  DOI：10.1248/cpb.50.1137

  日期：——

  A chemical model system for cytochrome P-450, consisting of tetraphenylporphyrin manganese chloride (TPPMnCl) and iodosylbenzene, efficiently oxidized 2-methylimidazole to 2-methylimidazolone. This system was next applied to 4-(2-methyl-1-imidazolyl)-2,2-diphenylbutyramide, a muscarinic acetylcholine receptor antagonist under clinical trial, affording the previously unisolated imidazole ring 5-mono-oxidized

  一种由四苯基卟啉氯化锰（TPPMnCl）和碘基苯组成的细胞色素P-450的化学模型系统，将2-甲基咪唑有效地氧化为2-甲基咪唑酮。然后将该系统应用于临床试验中的毒蕈碱乙酰胆碱受体拮抗剂4-（2-甲基-1-咪唑基）-2,2-二苯基丁酰胺，提供了以前未被分离的咪唑环5-单氧化衍生物。主要代谢物的前体。该系统优于抗坏血酸铜系统，应适用于含有2-甲基咪唑部分的各种药物的体外研究。
• Synthesis of Alaninyl andN-(2-Aminoethyl)glycinyl Amino Acid Derivatives Containing the Green Fluorescent Protein Chromophore in Their Side Chains for Incorporation into Peptides and Peptide Nucleic Acids
  作者：Thorsten Stafforst、Ulf Diederichsen

  DOI：10.1002/ejoc.200600729

  日期：2007.2

  Artificial amino acids carrying either the chromophore of the Green Fluorescent Protein (GFP) or a modification as their side chains have been synthesized: Boc-protected alaninyl derivatives and Fmoc-protected N-(2-aminoethyl)glycine-functionalized amino acids were obtained and could be applied in solid-phase peptide synthesis. The incorporation of the GFP chromophore into N-(2-aminoethyl)glycine-PNA

  合成了带有绿色荧光蛋白 (GFP) 发色团或其侧链修饰的人工氨基酸：获得了 Boc 保护的丙氨酸衍生物和 Fmoc 保护的 N-（2-氨基乙基）甘氨酸功能化氨基酸，并且可用于固相多肽合成。实现了 GFP 发色团与 N-(2-氨基乙基) 甘氨酸-PNA 的结合，并研究了作为与互补 DNA 杂交的函数的荧光。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Simple and Efficient Copper-Catalyzed Approach to 2,4-Disubstituted Imidazolones
  作者：Xiaoyu Gong、Haijun Yang、Hongxia Liu、Yuyang Jiang、Yufen Zhao、Hua Fu

  DOI：10.1021/ol1008813

  日期：2010.7.16

  Some imidazolone derivatives are biological and pharmaceutical active molecules and the chromophores of the fluorescent proteins. In this communication, a simple and efficient approach to 4-arylidene-2-alkyl-4,5-dihydro-1H-imidazol-5-ones (2,4-disubstituted imidazolones) has been developed, and the protocol uses readily available 2-bromo-3-alkylacrylic acids and amidines as the starting materials without addition of any ligand or additive. The reactions were performed under mild conditions. Therefore, the present method will be of wide application in organic chemistry and medicinal chemistry.
• Kjaer, Acta Chemica Scandinavica (1947), 1953, vol. 7, p. 889,896
  作者：Kjaer

  DOI：——

  日期：——
• Photochromic DNA having fluorescent protein-inspired nucleosides
  作者：Akio Kobori、Taichiro Arai、Yuya Sakata、Takayuki Sugita、Asako Yamayoshi、Akira Murakami

  DOI：10.1016/j.tetlet.2018.08.064

  日期：2018.10

  Molecular switches controlled by light stimuli can be applicable to the variety of the biological application. In this study, skeletal structures of a chromophore of fluorescent protein were applied as aglycones of newly designed photochromic nucleosides, "Fluorescent protein-inspired nuceloside: FIN". Phosphoramidite units of the photochromic nucleosides having imidazolinone derivatives with benzylidene or 3-pyridilidene groups were successfully synthesized for FIN-containing ODNs. Thermodynamic studies of the FIN-containing ODNs revealed that photo-irradiation with specific wavelength induced stability change of the duplexes. (C) 2018 Elsevier Ltd. All rights reserved.