1-(benzofuran-2-yl)-2-(1H-imidazol-1-yl)ethanone | 80170-20-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 1-(benzofuran-2-yl)-2-(1H-imidazol-1-yl)ethanone
• 英文别名: 1-(1-Benzofuran-2-yl)-2-imidazol-1-ylethanone
• CAS: 80170-20-3
• 化学式: C₁₃H₁₀N₂O₂
• mdl: MFCD12061432
• 分子量: 226.235
• InChiKey: FNVRZRNVPKSFGR-UHFFFAOYSA-N

物化性质

• 沸点：
  456.4±25.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(benzofuran-2-yl)-2-(1H-imidazol-1-yl)ethanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以74%的产率得到1-苯并呋喃-2-基-2-咪唑-1-基-乙醇
  参考文献：
  名称：

  Aromatic ethers of 1-aryl 2-(1H-azolyl)ethanol: study of antifungal activity

  摘要：

  Aromatic ethers related to antifungal azole miconazole were synthesized and tested against various strains of Candida. We found that activity is related to the nature of the aromatic ring and the position of substituents on this ring. Activity is more strongly dependent on the substituent in the 2 position of the ethyl chain than on the aromatic group linked through the oxygen. Triazoles were always less potent than the corresponding imidazole analogues.

  DOI：

  10.1016/0223-5234(96)88315-2
• 作为产物：
  描述：

  2-乙酰基苯并呋喃 在 溴 、 溶剂黄146 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 1-(benzofuran-2-yl)-2-(1H-imidazol-1-yl)ethanone
  参考文献：
  名称：

  Aromatic ethers of 1-aryl 2-(1H-azolyl)ethanol: study of antifungal activity

  摘要：

  Aromatic ethers related to antifungal azole miconazole were synthesized and tested against various strains of Candida. We found that activity is related to the nature of the aromatic ring and the position of substituents on this ring. Activity is more strongly dependent on the substituent in the 2 position of the ethyl chain than on the aromatic group linked through the oxygen. Triazoles were always less potent than the corresponding imidazole analogues.

  DOI：

  10.1016/0223-5234(96)88315-2

文献信息

• Structure-activity relationships of (arylalkyl)imidazole anticonvulsants: comparison of the (fluorenylalkyl)imidazoles with nafimidone and denzimol
  作者：David W. Robertson、Joseph H. Krushinski、E. E. Beedle、J. David Leander、David T. Wong、R. C. Rathbun

  DOI：10.1021/jm00159a004

  日期：1986.9

  fluorenyl, benzo[b]thienyl, and benzofuranyl aryl groups provided several highly active (arylalkyl)imidazole anticonvulsants. These structurally diverse aryl moieties, and comparable anticonvulsant activities, lend credence to the hypothesis that the pharmacophore of this class of anticonvulsants is the alkylimidazole portion of the molecule, with the lipophilic aryl portion enabling penetration of the

  （芳烷基）咪唑类是最近发现的并且在结构上不同的一类抗癫痫药。此类的两个独立发现的代表：地摩尔（α-[4-（2-苯基乙基）苯基] -1H-咪唑-1-乙醇）和萘啶酮（2-（1H-咪唑-1-基）-1-（2 -萘基萘酮）正在接受临床评估。我们的结构活性关系（SAR）研究表明，除了萘啶酮和苯并萘酚的萘基和苯乙基苯基芳基部分之外，芴基，苯并[b]噻吩基和苯并呋喃基芳基分别提供了几种高活性的（芳烷基）咪唑抗惊厥剂。这些结构上不同的芳基部分和可比较的抗惊厥活性使这一类抗惊厥药效基团是分子的烷基咪唑部分这一假设得到了证实，亲脂性芳基部分具有能够穿透血脑屏障的能力。我们将SAR研究的重点放在了（芴基烷基）咪唑系列上。该系列的代表性化合物是1-（9H-芴-2-基）-2-（1H-咪唑-1-基）乙酮。这种药物在抑制小鼠最大电击惊厥方面的功效是萘啶酮的两倍（分别为po ED50分别为25和56 mg / kg），而在
• Synthesis and cell imaging applications of fluorescent mono/di/tri-heterocyclyl-2,6-dicyanoanilines
  作者：Mahesh M. Pisal、Ritesh A. Annadate、Meghana C. Athalye、Deepak Kumar、Subhash P. Chavan、Dhiman Sarkar、Hanumant B. Borate

  DOI：10.1016/j.bmcl.2016.12.074

  日期：2017.2

  contact but not the nucleus while the compound 12 showed affinity to apoptotic cells resulting in blue fluorescence. The cell imaging results with compound 12 were similar to Annexin V-FITC, a known reagent containing recombinant Annexin V conjugated to green-fluorescent FITC dye, used for detection of apoptotic cells. These compounds were found to be non-cytotoxic and have potential application as cell

  描述了从杂环醛和1,2-二杂环取代的乙酮开始的3,4,5-三杂环基-2,6-二氰基苯胺的合成。还已经合成了具有一个或两个杂环取代基的2，6-二氰基苯胺。发现这些分子中的一些具有对细胞成像应用有用的选择性细胞染色特性。化合物1克，10F和11被发现在接触细胞的细胞质染色但不同时化合物核12产生蓝色荧光凋亡细胞显示出亲和力。化合物12的细胞成像结果与膜联蛋白V-FITC相似，膜联蛋白V-FITC是一种已知试剂，包含与绿色荧光FITC染料偶联的重组膜联蛋白V，用于检测凋亡细胞。发现这些化合物是无细胞毒性的，并且具有作为细胞显像剂的潜在应用。
• SCHERM, A.;PETERI, D.;DEUSCHLE, E.;SCHATTON, W.
  作者：SCHERM, A.、PETERI, D.、DEUSCHLE, E.、SCHATTON, W.

  DOI：——

  日期：——
• Aromatic ethers of 1-aryl 2-(1H-azolyl)ethanol: study of antifungal activity
  作者：Y Wahbi、R Caujolle、C Tournaire、M Payard、M.D. Linas、J.P. Seguela

  DOI：10.1016/0223-5234(96)88315-2

  日期：1995.1

  Aromatic ethers related to antifungal azole miconazole were synthesized and tested against various strains of Candida. We found that activity is related to the nature of the aromatic ring and the position of substituents on this ring. Activity is more strongly dependent on the substituent in the 2 position of the ethyl chain than on the aromatic group linked through the oxygen. Triazoles were always less potent than the corresponding imidazole analogues.