ethyl 2-(2-(furan-2-yl)-1H-benzo[d]imidazol-1-yl)acetate | 955431-92-2

• 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: ethyl 2-(2-(furan-2-yl)-1H-benzo[d]imidazol-1-yl)acetate
• 英文别名: Ethyl 2-[2-(furan-2-yl)benzimidazol-1-yl]acetate
• CAS: 955431-92-2
• 化学式: C₁₅H₁₄N₂O₃
• 分子量: 270.288
• InChiKey: MDUIGYFALPTWMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 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：
  57.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-(furan-2-yl)-1H-benzo[d]imidazol-1-yl)acetate 在 hydrazine hydrate 、 sodium hydride 、 potassium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成
  参考文献：
  名称：

  Part I. Synthesis, biological evaluation and docking studies of new 2-furylbenzimidazoles as antiangiogenic agents

  摘要：

  2-(2-Furyl)-1H-benzimidazoles 3-11 were synthesized and tested for their in vitro VEGF inhibition in MCF-7 cancer cell line. Compound 5a was more potent than Tamoxifen, and compounds 3b, 5a, 5c, 6b, 7a and 10 showed promising potency. Furthermore, compounds (6b, 7a and 10) showed remarkable selective inhibition of COX-2 enzyme close to that of Celecoxcib. Additionally, docking studies were performed using AutoDock 4.2 into the VEGFR2 kinase. Significant correlation exists between the biological activity (IC50 and %VEGF inhibition) against MCF-7 cell line and the molecular docking results (K-i and Delta G(b)) with correlation coefficients (R-2) of 0.5513 and 0.4623 respectively. Accordingly, most of the synthesized 2-(2-furyl)-1H-benzimidazoles showed strong antiangiogenic activity against VEGFR2 kinase. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.063
• 作为产物：
  描述：

  邻苯二胺 在 sodium metabisulfite 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 2-(2-(furan-2-yl)-1H-benzo[d]imidazol-1-yl)acetate
  参考文献：
  名称：

  具有 1,3,4-恶二唑部分的新型苯并咪唑衍生物作为潜在的胸苷酸合成酶抑制剂的设计、合成、抗癌活性和分子对接研究

  摘要：

  目前的工作描述了作为胸苷酸合酶抑制剂的新型苯并咪唑衍生物的合成和抗癌活性，这些衍生物带有 1,3,4-恶二唑。新合成的分子通过 NMR、质量、FT-IR 和元素分析得到证实。从抗癌活性结果来看，与标准药物 5-氟尿嘧啶相比，化合物10和14对肺 A549、卵巢 SKOV3 和乳腺 MDA-MB 231 癌细胞表现出更高的敏感性和更好的 IC 50值，范围为 1.15-6.27 μM。 IC 50：10.65–15.48 μM）。此外，这两种化合物对 TS 酶有显着抑制作用，与​​ 5FU (IC 50: 1.91 微米)。通过流式细胞术对化合物10和14对细胞周期进程和细胞凋亡诱导的机理研究表明，化合物10和14在乳腺 MDA-MB-231 细胞中，在肺 A549 和卵巢 SKOV3 细胞中均将细胞周期阻滞在 G1 期，化合物10阻止 G2 相，而化合物14阻止 G1 和 S 阶段。此外，这些化合物在

  DOI：

  10.1039/d2nj01980a

文献信息

• Design, synthesis, molecular docking and cytotoxic evaluation of novel 2-furybenzimidazoles as VEGFR-2 inhibitors
  作者：Mona A. Abdullaziz、Heba T. Abdel-Mohsen、Ahmed M. El Kerdawy、Fatma A.F. Ragab、Mamdouh M. Ali、Sherifa M. Abu-bakr、Adel S. Girgis、Hoda I. El Diwani

  DOI：10.1016/j.ejmech.2017.04.068

  日期：2017.8

  the allosteric hydrophobic back pocket in a type III inhibitors-like binding mode. The binding interaction is augmented by a ring substituent with long chain extension at position 1 of the benzimidazole due to its hydrophobic interaction with the hydrophobic side chains of the amino acids at the interface between the ATP binding site and the allosteric back pocket. Structure-activity relationship (SAR)

  通过抑制血管内皮生长因子受体2（VEGFR-2）抑制血管生成已被应用于癌症治疗，因为它在促进癌症生长和转移中起着重要的作用。在本研究中，通过简便的合成途径设计并合成了一系列苯并咪唑-呋喃杂种。评估合成的化合物对乳腺癌（MCF-7）和肝细胞癌（HepG2）癌细胞的体外细胞毒活性。与他莫昔芬（IC50 = 21.57μM）相比，两种合成的缀合物10b和15对MCF-7细胞系表现出有效的抗增殖特性（分别为IC50 = 21.25、21.35μM）。此外，化合物10a，10b，15和17还显示出有希望的效价（IC50 = 25.95、22.58、26.94和31.06μM，与顺铂相反（分别为IC50 = 31.16μM）针对肝癌细胞HepG2。而且，对合成化合物对MCF-7细胞系中VEGFR-2水平的影响的体外评价显示出相对于未处理的对照细胞，它们具有有效的抑制活性。四种化合物10a，10b，14
• Jerchel et al., Justus Liebigs Annalen der Chemie, 1954, vol. 590, p. 232,238
  作者：Jerchel et al.

  DOI：——

  日期：——
• Crystal Structures of 2-Furylbenzimidazoles with Antiangiogenic Inhibition of VEGF in Cell Line MCF-7
  作者：Mathias O. Senge、Keith J. Flanagan、Yasser M. Shaker、Ahmed Temirak、Hoda I. El Diwani

  DOI：10.3987/com-15-13258

  日期：——

  The first crystal structures of four 2-furylbenzimidazole acetohydrazide derivatives are reported herein. The compounds have been shown to be planar with a small cant that varies from 4 to 30 degrees. The X-ray crystal structure of the compounds 7-10 revealed that compounds are oriented in the cis configuration which suggests that the acid hydrazide group is essential for the enhanced potency of 2-furylbenzimidazoles as anti-angiogenic agents.
• Part I. Synthesis, biological evaluation and docking studies of new 2-furylbenzimidazoles as antiangiogenic agents
  作者：Ahmed Temirak、Yasser M. Shaker、Fatma A.F. Ragab、Mamdouh M. Ali、Hamed I. Ali、Hoda I. El Diwani

  DOI：10.1016/j.ejmech.2014.01.063

  日期：2014.11

  2-(2-Furyl)-1H-benzimidazoles 3-11 were synthesized and tested for their in vitro VEGF inhibition in MCF-7 cancer cell line. Compound 5a was more potent than Tamoxifen, and compounds 3b, 5a, 5c, 6b, 7a and 10 showed promising potency. Furthermore, compounds (6b, 7a and 10) showed remarkable selective inhibition of COX-2 enzyme close to that of Celecoxcib. Additionally, docking studies were performed using AutoDock 4.2 into the VEGFR2 kinase. Significant correlation exists between the biological activity (IC50 and %VEGF inhibition) against MCF-7 cell line and the molecular docking results (K-i and Delta G(b)) with correlation coefficients (R-2) of 0.5513 and 0.4623 respectively. Accordingly, most of the synthesized 2-(2-furyl)-1H-benzimidazoles showed strong antiangiogenic activity against VEGFR2 kinase. (c) 2014 Elsevier Masson SAS. All rights reserved.
• Design, synthesis, anticancer activity and molecular docking studies of new benzimidazole derivatives bearing 1,3,4-oxadiazole moieties as potential thymidylate synthase inhibitors
  作者：Abdulraheem SA Almalki、Syed Nazreen、Serag Eldin I. Elbehairi、Mohammad Asad、Ali A. Shati、Mohammad Y. Alfaifi、Abdulrahman Alhadhrami、Ahmed A. Elhenawy、Ali Q. Alorabi、Abdullah M. Asiri、Mohammad Mahboob Alam

  DOI：10.1039/d2nj01980a

  日期：——

  The present work describes the synthesis and anticancer activity of new benzimidazole derivatives bearing 1,3,4-oxadiazoles as thymidylate synthase inhibitors. The newly synthesized molecules were confirmed by NMR, mass, FT-IR and elemental analyses. From the anticancer activity results, compounds 10 and 14 showed higher sensitivity and better IC50 values in the range of 1.15–6.27 μM against lung A549

  目前的工作描述了作为胸苷酸合酶抑制剂的新型苯并咪唑衍生物的合成和抗癌活性，这些衍生物带有 1,3,4-恶二唑。新合成的分子通过 NMR、质量、FT-IR 和元素分析得到证实。从抗癌活性结果来看，与标准药物 5-氟尿嘧啶相比，化合物10和14对肺 A549、卵巢 SKOV3 和乳腺 MDA-MB 231 癌细胞表现出更高的敏感性和更好的 IC 50值，范围为 1.15-6.27 μM。 IC 50：10.65–15.48 μM）。此外，这两种化合物对 TS 酶有显着抑制作用，与​​ 5FU (IC 50: 1.91 微米)。通过流式细胞术对化合物10和14对细胞周期进程和细胞凋亡诱导的机理研究表明，化合物10和14在乳腺 MDA-MB-231 细胞中，在肺 A549 和卵巢 SKOV3 细胞中均将细胞周期阻滞在 G1 期，化合物10阻止 G2 相，而化合物14阻止 G1 和 S 阶段。此外，这些化合物在