Synthesis and Toxicity Evaluation of New Pyrroles Obtained by the Reaction of Activated Alkynes with 1-Methyl-3-(cyanomethyl)benzimidazolium Bromide
| Autor: | Robert Ancuceanu, Octavian Tudorel Olaru, Denisa Dumitrescu, Adriana Iuliana Anghel, Beatrice-Cristina Ivan, Mihaela Dinu, Constantin Draghici, Florea Dumitrascu, Sergiu Shova, George Mihai Nitulescu, Stefania-Felicia Barbuceanu |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Bromides
Models Molecular Daphnia magna Substituent Pharmaceutical Science Organic chemistry Chemistry Techniques Synthetic Toxicology benzimidazolium bromide alkynes Medicinal chemistry Article Analytical Chemistry toxicity evaluation chemistry.chemical_compound QD241-441 Bromide pyrroles Toxicity Tests Drug Discovery Physical and Theoretical Chemistry Molecular Structure biology Spectrum Analysis fungi Biological activity Nuclear magnetic resonance spectroscopy biology.organism_classification Acute toxicity X-ray diffraction chemistry Chemistry (miscellaneous) Reagent 1 3-dipolar cycloaddition Toxicity Molecular Medicine Benzimidazoles |
| Zdroj: | Molecules Molecules, Vol 26, Iss 6435, p 6435 (2021) Volume 26 Issue 21 |
| ISSN: | 1420-3049 |
| Popis: | A series of new pyrrole derivatives were designed as chemical analogs of the 1,4-dihydropyridines drugs in order to develop future new calcium channel blockers. The new tri- and tetra-substituted N-arylpyrroles were synthesized by the one-pot reaction of 1-methyl-3-cyanomethyl benzimidazolium bromide with substituted alkynes having at least one electron-withdrawing substituent, in 1,2-epoxybutane, acting both as the solvent and reagent to generate the corresponding benzimidazolium N3-ylide. The structural characterization of the new substituted pyrroles was based on IR, NMR spectroscopy as well as on single crystal X-ray analysis. The toxicity of the new compounds was assessed on the plant cell using Triticum aestivum L. species and on the animal cell using Artemia franciscana Kellogg and Daphnia magna Straus crustaceans. The compounds showed minimal phytotoxicity on Triticum rootlets and virtually no acute toxicity on Artemia nauplii, while on Daphnia magna, it induced moderate to high toxicity, similar to nifedipine. Our research indicates that the newly synthetized pyrrole derivatives are promising molecules with biological activity and low acute toxicity. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
| Nepřihlášeným uživatelům se plný text nezobrazuje | K zobrazení výsledku je třeba se přihlásit. |