Journal
MOLECULES
Volume 26, Issue 21, Pages -Publisher
MDPI
DOI: 10.3390/molecules26216435
Keywords
benzimidazolium bromide; alkynes; 1,3-dipolar cycloaddition; pyrroles; X-ray diffraction; toxicity evaluation
Funding
- Carol Davila University of Medicine and Pharmacy, Bucharest, Romania
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A series of new pyrrole derivatives were designed as chemical analogs of 1,4-dihydropyridines drugs to develop future new calcium channel blockers. The compounds showed minimal phytotoxicity on Triticum rootlets and induced moderate to high toxicity on Daphnia magna, similar to nifedipine. The newly synthesized pyrrole derivatives are promising molecules with biological activity and low acute toxicity.
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.
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