Synthesis, characterization and cytotoxicity of some novel 1,3-disubstituted-2,3-dihydro-2-iminobenzimidazoles
| Autor: | Diana Wesselinova, Nikolay Vassilev, Anelia Ts. Mavrova, J. A. Tsenov |
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| Rok vydání: | 2011 |
| Předmět: |
Magnetic Resonance Spectroscopy
Cell Survival Stereochemistry Antineoplastic Agents Breast Neoplasms Chemical synthesis Monocytes Inhibitory Concentration 50 chemistry.chemical_compound Bromide Cell Line Tumor Drug Discovery Humans Cytotoxic T cell Cytotoxicity Pharmacology Organic Chemistry Biological activity General Medicine Carbon-13 NMR chemistry Cell culture Benzimidazoles Female Imines Drug Screening Assays Antitumor Colorectal Neoplasms Acetamide |
| Zdroj: | European Journal of Medicinal Chemistry. 46:3362-3367 |
| ISSN: | 0223-5234 |
| DOI: | 10.1016/j.ejmech.2011.04.061 |
| Popis: | 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, 1 H NMR, 13 C 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 IC 50 were 9.26, 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 IC 50 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 EC 50 values varied from 0.05 to 16.91 nM. |
| Databáze: | OpenAIRE |
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