2-(1H-benzimidazol-2-yl)-3-(4-diethylaminophenyl)acrylonitrile | 51553-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(1H-benzimidazol-2-yl)-3-(4-diethylaminophenyl)acrylonitrile
• 英文别名: 2-(1H-benzoimidazol-2-yl)-3-(4-diethylamino-phenyl)-acrylonitrile；2-(1H-benzimidazol-2-yl)-3-[4-(diethylamino)phenyl]prop-2-enenitrile
• CAS: 51553-32-3
• 化学式: C₂₀H₂₀N₄
• 分子量: 316.406
• InChiKey: UJJAHCUHQPONAR-UHFFFAOYSA-N

物化性质

• 熔点：
  227-230 °C(Solv: 1,4-dioxane (123-91-1))
• 沸点：
  547.8±60.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-benzimidazol-2-yl)-3-(4-diethylaminophenyl)acrylonitrile 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以42%的产率得到2-(1H-benzimidazol-2-yl)-3-(4-diethylaminophenyl)propanenitrile
  参考文献：
  名称：

  Development of benzimidazole derivatives to inhibit HIV-1 replication through protecting APOBEC3G protein

  摘要：

  Human APOBEC3G (apolipoprotein B mRNA-editing enzyme, catalytic polypeptide-like 3G, MG) is a potent restriction factor against human immunodeficiency virus type 1 (HIV-1) by inducing hypermutation of G to A in viral genome after its incorporation into virions. HIV-1 Vif (Virion Infectivity Factor) counteracts A3G by inducing ubiquitination and proteasomal degradation of MG protein. Vif-A3G axis therefore is a promising therapeutic target of HIV-1. Here we report the screening, synthesis and SAR studies of benzimidazole derivatives as potent inhibitors against HIV-1 replication via protecting MG protein. Based on the steep SAR of the benzimidazole scaffold, we identified compound 14 and 26 which provided the best potency, with IC50 values of 3.45 nM and 58.03 nM respectively in the anti-HIV-1 replication assay in H9 cells. Compound 14 and 26 also afforded protective effects on MG protein level. Both compounds have been proved to be safe in acute toxicological studies. Taken together, we suggest that these two benzimidazole derivatives can be further developed as a new category of anti-HIV-1 leads. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.050
• 作为产物：
  描述：

  邻苯二胺 在 哌嗪 作用下， 以 乙醇 为溶剂， 反应 4.5h， 生成 2-(1H-benzimidazol-2-yl)-3-(4-diethylaminophenyl)acrylonitrile
  参考文献：
  名称：

  Development of benzimidazole derivatives to inhibit HIV-1 replication through protecting APOBEC3G protein

  摘要：

  Human APOBEC3G (apolipoprotein B mRNA-editing enzyme, catalytic polypeptide-like 3G, MG) is a potent restriction factor against human immunodeficiency virus type 1 (HIV-1) by inducing hypermutation of G to A in viral genome after its incorporation into virions. HIV-1 Vif (Virion Infectivity Factor) counteracts A3G by inducing ubiquitination and proteasomal degradation of MG protein. Vif-A3G axis therefore is a promising therapeutic target of HIV-1. Here we report the screening, synthesis and SAR studies of benzimidazole derivatives as potent inhibitors against HIV-1 replication via protecting MG protein. Based on the steep SAR of the benzimidazole scaffold, we identified compound 14 and 26 which provided the best potency, with IC50 values of 3.45 nM and 58.03 nM respectively in the anti-HIV-1 replication assay in H9 cells. Compound 14 and 26 also afforded protective effects on MG protein level. Both compounds have been proved to be safe in acute toxicological studies. Taken together, we suggest that these two benzimidazole derivatives can be further developed as a new category of anti-HIV-1 leads. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.050

文献信息

• 氰基亚乙烯类衍生物荧光染料及其制备方法和应用
  申请人：西北大学

  公开号：CN111057009B

  公开（公告）日：2022-03-25

  氰基亚乙烯类衍生物荧光染料及其制备方法和应用，本发明公开了结构通式（I）所示的化合物，该化合物R1独立地选自H，NH2，OH，CN，CH3，COOH，SO3H，F，Cl，Br或NO2；R2为。本发明化合物探针分子能够实现缓冲溶液测试体系中β‑Gal的定量检测且不受其他蛋白酶、生物硫醇、活性氧以及常见阳离子的干扰，已被成功应用于SKOV3细胞进行生物细胞内β‑Gal的原位检测。
• Activatable Formation of Emissive Excimers for Highly Selective Detection of β-Galactosidase
  作者：Yang Li、Lulu Ning、Fang Yuan、Tian Zhang、Jianjian Zhang、Zhigang Xu、Xiao-Feng Yang

  DOI：10.1021/acs.analchem.9b04806

  日期：2020.4.21

  concentration or aggregation-induced fluorescence quenching effect has usually hindered the development of traditional fluorescence dyes. Herein, a new fluorophore cyanovinylene dye BMZ with excimer emission property has been constructed. It shows an obvious enhanced and red-shift emission upon aggregation in aqueous solution, which overmatches the conventional pyrene with longer absorption and emission wavelengths

  小分子荧光传感器因其高灵敏度，出色的时间和空间分辨率以及低细胞毒性而在许多领域中成为有前途的检测工具。然而，高浓度或聚集诱导的荧光猝灭作用通常阻碍了传统荧光染料的发展。在此，已经构造了具有准分子发射性能的新型荧光团氰基亚乙烯基染料BMZ。它在水溶液中聚集后显示出明显的增强和红移发射，这与具有更长吸收和发射波长的常规pyr不匹配。利用这种独特的光学特性，开发了一种新型荧光探针BMZ-Gal，用于捕获β-半乳糖苷酶（β-Gal）活性，具有高选择性，0.17 U的低检出限和快速识别，这是基于β-Gal诱导的发红移准分子的形成。β-Gal对BMZ-Gal具有很强的亲和力，这已通过Michaelis-Menten常数（Km，1.87μM）和水解效率（Kcat / Km，1.78×103 M-1 s-1）进行了验证。此外，该测定系统已经成功地用于检测活的卵巢癌细胞中的内源性β-Gal，并且可以被动地靶