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- Title
Synthesis and Toxicity Evaluation of New Pyrroles Obtained by the Reaction of Activated Alkynes with 1-Methyl-3-(cyanomethyl)benzimidazolium Bromide.
- Authors
Ivan, Beatrice-Cristina; Dumitrascu, Florea; Anghel, Adriana Iuliana; Ancuceanu, Robert Viorel; Shova, Sergiu; Dumitrescu, Denisa; Draghici, Constantin; Olaru, Octavian Tudorel; Nitulescu, George Mihai; Dinu, Mihaela; Barbuceanu, Stefania-Felicia
- Abstract
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.
- Subjects
KELLOGG Co.; TOXICITY testing; PYRROLES; PYRROLE derivatives; DAPHNIA magna; ALKYNES; CALCIUM antagonists
- Publication
Molecules, 2021, Vol 26, Issue 21, p6435
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules26216435