Isoprenyl-thiourea and urea derivatives as new farnesyl diphosphate analogues: Synthesis and in vitro antimicrobial and cytotoxic activities
| Autor: | José M. Vega-Pérez, Margarita Vega-Holm, Ignacio Periñán, Carlos Palo-Nieto, Estefanía Burgos-Morón, Fernando Iglesias-Guerra, Joaquín J. Nieto, Carmen Vargas, Miguel López-Lázaro, Montserrat Argandoña |
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| Rok vydání: | 2012 |
| Předmět: |
Antifungal Agents
Stereochemistry Antineoplastic Agents Microbial Sensitivity Tests Gram-Positive Bacteria Structure-Activity Relationship chemistry.chemical_compound Polyisoprenyl Phosphates Candida albicans Gram-Negative Bacteria Drug Discovery Humans Urea Organic chemistry Alkyl Cell Proliferation Pharmacology chemistry.chemical_classification Dose-Response Relationship Drug Molecular Structure Aryl Organic Chemistry Aromaticity General Medicine Antimicrobial Isocyanate Anti-Bacterial Agents chemistry Thiourea Isothiocyanate Proton NMR Drug Screening Assays Antitumor HT29 Cells Sesquiterpenes |
| Zdroj: | European Journal of Medicinal Chemistry. 58:591-612 |
| ISSN: | 0223-5234 |
| DOI: | 10.1016/j.ejmech.2012.10.042 |
| Popis: | A series of new isoprenyl-thiourea and urea derivatives were synthesized by the reaction of alkyl or aryl isothiocyanate or isocyanate and primary amines. The structures of the compounds were established by 1 H NMR, 13 C NMR, MS, HRMS and elemental analysis. The new compounds were screened for in vitro antimicrobial activity against seven strains representing different types of gram-positive and gram-negative bacteria. More than a third of the synthesized compounds showed variable inhibition activities against the tested strains. Best antimicrobial activities were found for those thiourea analogues with 3-methyl-2-butenyl, isobutyl or isopentyl groups and aromatic rings possessing electron withdrawing substituents. The new compounds were also subjected to a preliminary screening for antitumoral activity. The presence of a highly lipophilic group and an electron withdrawing group in the aromatic rings enhanced anticancer activity of the synthesized compounds, showing in most cases more activity than that of the controls. |
| Databáze: | OpenAIRE |
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