1-Methyl-2-amino-3-ethoxycarbonylmethylbenzimidazolium bromide

• 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: 1-Methyl-2-amino-3-ethoxycarbonylmethylbenzimidazolium bromide
• 英文别名: Ethyl 2-(2-imino-3-methylbenzimidazol-1-yl)acetate;hydrobromide
• 化学式: Br*C₁₂H₁₆N₃O₂
• 分子量: 314.182
• InChiKey: ZPIAAYDXTYXTMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.38
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Methyl-2-amino-3-ethoxycarbonylmethylbenzimidazolium bromide 在 N-溴代丁二酰亚胺(NBS) 、 sodium acetate 作用下， 以 四氯化碳 为溶剂， 反应 6.0h， 生成 2-Bromomethyl-3-ethoxycarbonyl-9-methylimidazo<1,2-a>benzimidazole
  参考文献：
  名称：

  Synthesis and neuro-psychotropic activity of adamantylimidazo[1,2-a]benzimidazoles

  摘要：

  DOI：

  10.1007/bf00763524
• 作为产物：
  描述：

  1-甲基苯并-2-磺酸 在 ammonium hydroxide 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 1-Methyl-2-amino-3-ethoxycarbonylmethylbenzimidazolium bromide
  参考文献：
  名称：

  Synthesis, characterization and cytotoxicity of some novel 1,3-disubstituted-2,3-dihydro-2-iminobenzimidazoles

  摘要：

  Some new 1,3-disubstituted-2,3-dihydro-2-iminobenzimidazoles were synthesized using 1-(un) substituted-2-aminobenzimidazoles as precursors in order to determine their cytotoxicity. The structures of the compounds were confirmed by IR, H-1 NMR, C-13 NMR and elemental analysis.Compounds 4, 7-11 and 13-14 were evaluated for their cytotoxical effect on two cancer cell lines: human colorectal cancer cell line HT-29, breast cancer cells MDA-MB-231 and as well as normal spleen cells. The distinctly marked antiproliferative activity of 1,3-bis(3-phenylpropyl-1)-1,3-dihydro-2H-benzimidazol-2-imine hydro bromide 7, N-(aminopropyl)-2-(3-{2-[(aminopropyl)-amino]-2-oxoethyl}-2-imino-2,3-dihydro-1H-benzimidazol-1-yl)acetamide 9 and 1,3-bis[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2,3-dihydro-2H-benzimidazol-2-imine 11 against human colorectal cancer cell line HT-29 was ascertained and the calculated IC50 were 926, 0.56 and 0.013 nM respectively. Compounds 4, 9, 10 and 13 exhibited relative high cytotoxic activity against MDA-MB-231 cells. The calculated IC50 values were in the range 0.123-1.65 nM. All tested compounds excluding compound 1,3-bis[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2,3-dihydro-2H-benzimidazol-2-imine (11) revealed proliferative activities to normal spleen cells. The computed EC50 values varied from 0.05 to 16.91 nM. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.061

文献信息

• MOROZOV, I. S.;ANISIMOVA, V. A.;AVDYUNINA, N. I.;LUKOVA, O. A.;PYATIN, B.+, XIM.-FARMATS. ZH., 22,(1988) N 7, 815-819
  作者：MOROZOV, I. S.、ANISIMOVA, V. A.、AVDYUNINA, N. I.、LUKOVA, O. A.、PYATIN, B.+

  DOI：——

  日期：——
• Synthesis, characterization and cytotoxicity of some novel 1,3-disubstituted-2,3-dihydro-2-iminobenzimidazoles
  作者：Anelia Ts. Mavrova、Diana Wesselinova、Nikolay Vassilev、Jordan A. Tsenov

  DOI：10.1016/j.ejmech.2011.04.061

  日期：2011.8

  Some new 1,3-disubstituted-2,3-dihydro-2-iminobenzimidazoles were synthesized using 1-(un) substituted-2-aminobenzimidazoles as precursors in order to determine their cytotoxicity. The structures of the compounds were confirmed by IR, H-1 NMR, C-13 NMR and elemental analysis.Compounds 4, 7-11 and 13-14 were evaluated for their cytotoxical effect on two cancer cell lines: human colorectal cancer cell line HT-29, breast cancer cells MDA-MB-231 and as well as normal spleen cells. The distinctly marked antiproliferative activity of 1,3-bis(3-phenylpropyl-1)-1,3-dihydro-2H-benzimidazol-2-imine hydro bromide 7, N-(aminopropyl)-2-(3-2-[(aminopropyl)-amino]-2-oxoethyl}-2-imino-2,3-dihydro-1H-benzimidazol-1-yl)acetamide 9 and 1,3-bis[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2,3-dihydro-2H-benzimidazol-2-imine 11 against human colorectal cancer cell line HT-29 was ascertained and the calculated IC50 were 926, 0.56 and 0.013 nM respectively. Compounds 4, 9, 10 and 13 exhibited relative high cytotoxic activity against MDA-MB-231 cells. The calculated IC50 values were in the range 0.123-1.65 nM. All tested compounds excluding compound 1,3-bis[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2,3-dihydro-2H-benzimidazol-2-imine (11) revealed proliferative activities to normal spleen cells. The computed EC50 values varied from 0.05 to 16.91 nM. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis and neuro-psychotropic activity of adamantylimidazo[1,2-a]benzimidazoles
  作者：I. S. Morozov、V. A. Anisimova、N. I. Avdyunina、O. A. Lukova、B. M. Pyatin、N. A. Militareva、N. P. Bykov、É. G. Dvalishvili、A. A. Khranilov

  DOI：10.1007/bf00763524

  日期：1988.7