ethyl [3-(2-ethoxy-2-oxoethyl)-2-imino-5-benzoyl-2,3-dihydro-1H-benzimidazol-1-yl]acetate | 1441402-23-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl [3-(2-ethoxy-2-oxoethyl)-2-imino-5-benzoyl-2,3-dihydro-1H-benzimidazol-1-yl]acetate
• 英文别名: Ethyl 2-[5-benzoyl-3-(2-ethoxy-2-oxoethyl)-2-iminobenzimidazol-1-yl]acetate；ethyl 2-[5-benzoyl-3-(2-ethoxy-2-oxoethyl)-2-iminobenzimidazol-1-yl]acetate
• CAS: 1441402-23-8
• 化学式: C₂₂H₂₃N₃O₅
• 分子量: 409.442
• InChiKey: AFKRZEFIMMNSGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-benzoyl-1H-benzimidazole-2-sulfonic acid 在 ammonium hydroxide 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 ethyl [3-(2-ethoxy-2-oxoethyl)-2-imino-5-benzoyl-2,3-dihydro-1H-benzimidazol-1-yl]acetate
  参考文献：
  名称：

  一些新型苯并咪唑的合成，电子性能，抗氧化剂和抗菌活性。

  摘要：

  使用5（6）-取代的2-巯基苯并咪唑-硫醇作为前体合成了两组苯并咪唑衍生物，并使用TBA-MDA试验研究了它们的抗氧化活性。在1，3-二取代的苯并咪唑-2-亚胺组中，最高的脂质过氧化抑制作用为74.04％（IC₅₀= 141.89μg/ mL），显示乙基[3-（2-乙氧基-2-氧代乙基）-2-亚氨基- 5-苯甲酰基-2,3-二氢-1H-苯并咪唑-1-基]乙酸酯12，而在2-取代的1,3-噻唑并[3,2-a]苯并咪唑酮类中，最高的抑制作用显示为2-（ 4-氟亚苄基）-7-（苯基羰基）[1，3]噻唑并[3，2-a]苯并咪唑-3（2H）-1 17 90.76％（IC 50 ＝53.70μg/ mL）。为了估计所研究的苯并咪唑用作自由基清除剂的能力，在B3LYP / 6-311 ++ G（∗∗）水平上优化了两个亚系列中最活跃的衍生物的结构，并计算了各自的键解离焓。提出了用于抗氧化活性的HAT和SE

  DOI：

  10.1016/j.bmc.2015.08.029

文献信息

• Design, synthesis and antiproliferative properties of some new 5-substituted-2-iminobenzimidazole derivatives
  作者：Anelia Ts. Mavrova、Diana Wesselinova、Nikolay Vassilev、Jordan A. Tsenov

  DOI：10.1016/j.ejmech.2013.03.010

  日期：2013.5

  Some new 1,3,5-substituted-2,3-dihydro-2-imino-benzimidazoles were synthesized under solid-liquid phase transfer catalysis conditions using 5-substituted-2-aminobenzimidazoles as precursors in order to assess their cytotoxicity respectively proliferative activity. The structures of the compounds were confirmed by IR, H-1 NMR, C-13 NMR and elemental analysis.Compounds 9-10, 12 and 16-17 were evaluated for their cytotoxical effect on four cancer cell lines: HT-29, breast cancer cells MDA-MB-231, HeLa, HepG2 and as well as human diploid cell line Lep-3.Significant cytotoxicity of hydrazone 16 against MDA-MB-231 was established by biologically study, the IC50 was 6.2 nM while the EC50 value to Lep 3 is 0.21 nM. Relative high antiproliferative effects of the acetate 12 and compound 16 against HT-29 were ascertained and the calculated IC50 values were IC50 - 0.85 nM and IC50 - 2.83 nM respectively. Cytotoxic activity against HeLa and HepG2 cells was demonstrated by hydrazone 17, IC50 was 7.2 nM and 117 nM respectively. All tested compounds revealed proliferative activities to human diploid cell line Lep-3. The EC50 values were in the range from 0.05 to 16.91 nM. The obtained results prove the selective cytotoxicity of the tested compounds and are promising for further evaluation of the investigated compounds in vivo experiments using experimentally induced tumors in laboratory animals. (c) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis, electronic properties, antioxidant and antibacterial activity of some new benzimidazoles
  作者：Anelia Ts. Mavrova、Denitsa Yancheva、Neda Anastassova、Kamelya Anichina、Jelena Zvezdanovic、Aleksandra Djordjevic、Dejan Markovic、Andrija Smelcerovic

  DOI：10.1016/j.bmc.2015.08.029

  日期：2015.10

  in the group of 2-substituted-1,3-thiazolo[3,2-a]benzimidazolones the highest inhibition effect showed 2-(4-fluorobenzylidene)-7-(phenylcarbonyl)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one 17 90.76% (IC₅₀=53.70 μg/mL). In order to estimate the capability of the studied benzimidazoles to act as radical scavengers the structure of the most active derivative within the both subseries was optimized at B3LYP/6-311++G(∗∗)

  使用5（6）-取代的2-巯基苯并咪唑-硫醇作为前体合成了两组苯并咪唑衍生物，并使用TBA-MDA试验研究了它们的抗氧化活性。在1，3-二取代的苯并咪唑-2-亚胺组中，最高的脂质过氧化抑制作用为74.04％（IC₅₀= 141.89μg/ mL），显示乙基[3-（2-乙氧基-2-氧代乙基）-2-亚氨基- 5-苯甲酰基-2,3-二氢-1H-苯并咪唑-1-基]乙酸酯12，而在2-取代的1,3-噻唑并[3,2-a]苯并咪唑酮类中，最高的抑制作用显示为2-（ 4-氟亚苄基）-7-（苯基羰基）[1，3]噻唑并[3，2-a]苯并咪唑-3（2H）-1 17 90.76％（IC 50 ＝53.70μg/ mL）。为了估计所研究的苯并咪唑用作自由基清除剂的能力，在B3LYP / 6-311 ++ G（∗∗）水平上优化了两个亚系列中最活跃的衍生物的结构，并计算了各自的键解离焓。提出了用于抗氧化活性的HAT和SE