1-(2-苯基-3H-苯并咪唑-5-基)乙酮 | 91437-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1-(2-苯基-3H-苯并咪唑-5-基)乙酮
• 英文名称: 5-acetyl-2-phenylbenzimidazole
• 英文别名: Ethanone, 1-(2-phenyl-1H-benzimidazol-5-YL)-；1-(2-phenyl-3H-benzimidazol-5-yl)ethanone
• CAS: 91437-90-0
• 化学式: C₁₅H₁₂N₂O
• 分子量: 236.273
• InChiKey: ZACVEKOHHBZAQJ-UHFFFAOYSA-N

物化性质

• 熔点：
  179-182 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  459.8±37.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  1-(2-苯基-3H-苯并咪唑-5-基)乙酮 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以75%的产率得到1-(2-phenyl-1H-benzimidazol-5-yl)ethanone oxime
  参考文献：
  名称：

  5-Acetyl-2-arylbenzimidazoles as antiviral agents. Part 4

  摘要：

  Within a project aimed at discovering new Flaviviridae inhibitors, new variously substituted 2-phenylbenzimidazoles were synthesized and evaluated in cell-based assays for cytotoxicity and antiviral activity against viruses representatives of the three genera of the Flaviviridae family, i.e.: Pestivirus (BVDV), Flavivirus (YFV) and Hepacivirus (HCV). Title compounds were also tested against RNA viruses representative of other single-stranded, positive-sense (ssRNA(+)) negative-sense (RNA(-)), or double-stranded (dsRNA) genomes, as well as against representatives of two DNA virus families.Nine compounds showed activity against BVDV (EC50 = 0.8-8.0 mu M), compound 31 being the most potent (EC50 = 0.80 mu M) and selective (SI = CC50/EC50 = >100). When tested in an HCV replicon assay, compound 31 resulted again the most potent, displaying an EC50 value of 1.11 mu M and an SI of 100. Besides inhibiting BVDV, two compounds (35 and 38) showed a moderate activity also against YFV (EC50 = 13 mu M). Interestingly, 35 was moderately active also against RSV (EC50 = 25 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.038
• 作为产物：
  描述：

  4-氨基-3-硝基苯乙酮 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 1-(2-苯基-3H-苯并咪唑-5-基)乙酮
  参考文献：
  名称：

  5-Acetyl-2-arylbenzimidazoles as antiviral agents. Part 4

  摘要：

  Within a project aimed at discovering new Flaviviridae inhibitors, new variously substituted 2-phenylbenzimidazoles were synthesized and evaluated in cell-based assays for cytotoxicity and antiviral activity against viruses representatives of the three genera of the Flaviviridae family, i.e.: Pestivirus (BVDV), Flavivirus (YFV) and Hepacivirus (HCV). Title compounds were also tested against RNA viruses representative of other single-stranded, positive-sense (ssRNA(+)) negative-sense (RNA(-)), or double-stranded (dsRNA) genomes, as well as against representatives of two DNA virus families.Nine compounds showed activity against BVDV (EC50 = 0.8-8.0 mu M), compound 31 being the most potent (EC50 = 0.80 mu M) and selective (SI = CC50/EC50 = >100). When tested in an HCV replicon assay, compound 31 resulted again the most potent, displaying an EC50 value of 1.11 mu M and an SI of 100. Besides inhibiting BVDV, two compounds (35 and 38) showed a moderate activity also against YFV (EC50 = 13 mu M). Interestingly, 35 was moderately active also against RSV (EC50 = 25 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.038

文献信息

• Transforming Oxadiazolines through Nitrene Intermediates by Energy Transfer Catalysis: Access to Sulfoximines and Benzimidazoles
  作者：Do Dam Park、Kwan Hong Min、Jihee Kang、Ho Seong Hwang、Vineet Kumar Soni、Cheon-Gyu Cho、Eun Jin Cho

  DOI：10.1021/acs.orglett.9b04646

  日期：2020.2.7

  compounds, sulfoximines and benzimidazoles, were ingeniously prepared from oxadiazolines via nitrene intermediates by photocatalytic N-O/C-N bond cleavages. The synthesis of sulfoximines was realized through intermolecular N-S bond formation between nitrene intermediates and sulfoxides, whereas benzimidazoles were obtained via intramolecular aromatic substitution of the nitrene to the tethered aryl substituent

  反应条件的细微差别通过能量转移催化促进了恶二唑啉空前的光催化反应。一组化合物，亚砜亚砜和苯并咪唑，是通过恶唑中间体通过光催化的NO / CN键裂解，由恶二唑啉巧妙地制备的。亚砜中间体通过亚砜中间体和亚砜之间的分子间NS键形成来实现亚砜肟的合成，而苯并咪唑则是通过将亚硝基的分子内芳族取代成束缚的芳基取代基而获得的。
• [EN] BENZIMIDAZOL DERIVATIVES FOR TREATING FILOVIRUS INFECTION<br/>[FR] DÉRIVÉS DE BENZIMIDAZOLE POUR LE TRAITEMENT D'UNE INFECTION PAR FILOVIRUS
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2018050771A1

  公开（公告）日：2018-03-22

  The present invention relates to compounds comprising a benzimidazole scaffold, and the use of such compounds for the treatment of viral diseases. The invention also relates to pharmaceutical compositions comprising said compounds as an active ingredient. In particular the compounds of the invention comprising a benzimidazole scaffold are used for the treatment of filoviruses or retroviruses, and preferably for the treatment of Ebola virus or HIV virus.

  本发明涉及含有苯并咪唑骨架的化合物，以及利用这些化合物治疗病毒性疾病。该发明还涉及包含上述化合物作为活性成分的药物组合物。特别是，本发明涉及含有苯并咪唑骨架的化合物用于治疗丝状病毒或逆转录病毒，尤其是用于治疗埃博拉病毒或艾滋病毒。
• Assembly of Substituted 1<i>H</i>-Benzimidazoles and 1,3-Dihydrobenzimidazol-2-ones via CuI/<scp>l</scp>-Proline Catalyzed Coupling of Aqueous Ammonia with 2-Iodoacetanilides and 2-Iodophenylcarbamates
  作者：Xiaoqiong Diao、Yuji Wang、Yongwen Jiang、Dawei Ma

  DOI：10.1021/jo9017183

  日期：2009.10.16

  CuI/l-proline catalyzed coupling of aqueous ammonia with 2-iodoacetanilides and 2-iodophenylcarbamates affords the aryl amination products at room temperature, which undergo in situ additive cyclization under acidic conditions or heating to give substituted 1H-benzimidazoles and 1,3-dihydrobenzimidazol-2-ones, respectively. A wide range of functional groups including ketone, nitro, iodo, bromo, and

  CuI / l-脯氨酸催化氨水与2-碘乙酰苯胺和2-碘苯基氨基甲酸酯的偶联在室温下提供芳基胺化产物，将其在酸性条件下进行原位加成环化或加热以生成取代的1 H-苯并咪唑和1,3-二氢苯并咪唑-2-酮。在这些反应条件下，可以耐受包括酮，硝基，碘，溴和酯在内的各种官能团，从而为这些杂环提供了极大的多样性。
• Paglietti; Pirisi; Loriga, Farmaco, Edizione Scientifica, 1988, vol. 43, # 3, p. 215 - 226
  作者：Paglietti、Pirisi、Loriga、Grella、Sparatore、Satta、Manca

  DOI：——

  日期：——
• PAGLIETTI, G.;PIRISI, M. A.;LORIGA, M.;GRELLA, G. E.;SPARATORE, F.;SATTA,+, FARMACO. ED. SCI., 43,(1988) N 3, C. 215-226
  作者：PAGLIETTI, G.、PIRISI, M. A.、LORIGA, M.、GRELLA, G. E.、SPARATORE, F.、SATTA,+

  DOI：——

  日期：——