2-[3-(2-hydrazino-2-oxoethyl)-2-imino-5-nitro-2,3-dihydro-1H-benzimidazol-1-yl]acetohydrazide | 1441402-42-1

• 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-[3-(2-hydrazino-2-oxoethyl)-2-imino-5-nitro-2,3-dihydro-1H-benzimidazol-1-yl]acetohydrazide
• 英文别名: 2-[3-(2-Hydrazinyl-2-oxoethyl)-2-imino-5-nitrobenzimidazol-1-yl]acetohydrazide；2-[3-(2-hydrazinyl-2-oxoethyl)-2-imino-5-nitrobenzimidazol-1-yl]acetohydrazide
• CAS: 1441402-42-1
• 化学式: C₁₁H₁₄N₈O₄
• 分子量: 322.283
• InChiKey: IFBQJPGTGNWKHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  186
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[3-(2-hydrazino-2-oxoethyl)-2-imino-5-nitro-2,3-dihydro-1H-benzimidazol-1-yl]acetohydrazide 、 对氟苯甲醛 以 乙醇 为溶剂， 以72%的产率得到N'-[4-(fluorophenyl)methylene]-2-(3-{2-[2-(4-fluorophenyl)methylenehydrazino]-2-oxoethyl}-2-imino-5-nitro-2,3-dihydro-1H-benzimidazol-1-yl)acetohydrazide
  参考文献：
  名称：

  Design, synthesis and antiproliferative properties of some new 5-substituted-2-iminobenzimidazole derivatives

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2013.03.010
• 作为产物：
  描述：

  2-氨基-6-硝基苯并咪唑 在 四丁基溴化铵 、 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 2.0h， 生成 2-[3-(2-hydrazino-2-oxoethyl)-2-imino-5-nitro-2,3-dihydro-1H-benzimidazol-1-yl]acetohydrazide
  参考文献：
  名称：

  Design, synthesis and antiproliferative properties of some new 5-substituted-2-iminobenzimidazole derivatives

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2013.03.010