期刊
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
卷 46, 期 9, 页码 4062-4070出版社
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
DOI: 10.1016/j.ejmech.2011.06.006
关键词
Nucleophilic aromatic substitution; Pyrazole derivatives; Trisubstituted benzimidazoles; Solvent free reaction conditions; Antitumor agents
资金
- Colciencias
- Universidad del Valle
- Consejeria de Innovacion
- Ciencia y Empresa (Junta de Andalucia, Spain)
- Universidad de Jaen
Novel methyl 1-(5-tert-butyl-1H-pyrazol-3-yl)-2-(aryl)-1H-benzo[d]imidazole-5-carboxylates 11 were synthesized by following a four-step strategy involving a nucleophilic aromatic displacement (SNAr) and a solvent free approach as key steps for the formation of the desired products. Structure of intermediates and products were confirmed by X-ray diffraction as well as the tautomeric rearrangement suffered by the pyrazole moiety during the curse of the final cyclization process. Several of the obtained compounds were screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines. Products 11b and 11n exhibited the highest activity against a range of cancer cell lines with remarkable values in panels of Non-Small Cell Lung Cancer, Melanoma and Leukemia, with GI(50) range of 1.15-7.33 mu M and 0.167-7.59 mu M, respectively, and suitable LC50 with values greater than 100 mu M. (C) 2011 Elsevier Masson SAS. All rights reserved.
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