Synthesis and Toxicity Evaluation of New Pyrroles Obtained by the Reaction of Activated Alkynes with 1-Methyl-3-(cyanomethyl)benzimidazolium Bromide

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 <i>N</i>-arylpyrroles were synthesized by the one-pot reaction of 1-methyl-3-cyanomethyl ben...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Beatrice-Cristina Ivan, Florea Dumitrascu, Adriana Iuliana Anghel, Robert Viorel Ancuceanu, Sergiu Shova, Denisa Dumitrescu, Constantin Draghici, Octavian Tudorel Olaru, George Mihai Nitulescu, Mihaela Dinu, Stefania-Felicia Barbuceanu
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	benzimidazolium bromide alkynes 1,3-dipolar cycloaddition pyrroles X-ray diffraction toxicity evaluation Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/50ba9b3b4d214fd69a0031ea6801b023
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:doaj.org-article:50ba9b3b4d214fd69a0031ea6801b023
record_format	dspace
spelling	oai:doaj.org-article:50ba9b3b4d214fd69a0031ea6801b0232021-11-11T18:27:01ZSynthesis and Toxicity Evaluation of New Pyrroles Obtained by the Reaction of Activated Alkynes with 1-Methyl-3-(cyanomethyl)benzimidazolium Bromide10.3390/molecules262164351420-3049https://doaj.org/article/50ba9b3b4d214fd69a0031ea6801b0232021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6435https://doaj.org/toc/1420-3049A 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 <i>N</i>-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 <i>Triticum aestivum</i> L. species and on the animal cell using <i>Artemia franciscana</i> Kellogg and <i>Daphnia magna</i> Straus crustaceans. The compounds showed minimal phytotoxicity on <i>Triticum</i> rootlets and virtually no acute toxicity on <i>Artemia</i> nauplii, while on <i>Daphnia magna</i>, 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.Beatrice-Cristina IvanFlorea DumitrascuAdriana Iuliana AnghelRobert Viorel AncuceanuSergiu ShovaDenisa DumitrescuConstantin DraghiciOctavian Tudorel OlaruGeorge Mihai NitulescuMihaela DinuStefania-Felicia BarbuceanuMDPI AGarticlebenzimidazolium bromidealkynes1,3-dipolar cycloadditionpyrrolesX-ray diffractiontoxicity evaluationOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6435, p 6435 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	benzimidazolium bromide alkynes 1,3-dipolar cycloaddition pyrroles X-ray diffraction toxicity evaluation Organic chemistry QD241-441
spellingShingle	benzimidazolium bromide alkynes 1,3-dipolar cycloaddition pyrroles X-ray diffraction toxicity evaluation Organic chemistry QD241-441 Beatrice-Cristina Ivan Florea Dumitrascu Adriana Iuliana Anghel Robert Viorel Ancuceanu Sergiu Shova Denisa Dumitrescu Constantin Draghici Octavian Tudorel Olaru George Mihai Nitulescu Mihaela Dinu Stefania-Felicia Barbuceanu Synthesis and Toxicity Evaluation of New Pyrroles Obtained by the Reaction of Activated Alkynes with 1-Methyl-3-(cyanomethyl)benzimidazolium Bromide
description	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 <i>N</i>-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 <i>Triticum aestivum</i> L. species and on the animal cell using <i>Artemia franciscana</i> Kellogg and <i>Daphnia magna</i> Straus crustaceans. The compounds showed minimal phytotoxicity on <i>Triticum</i> rootlets and virtually no acute toxicity on <i>Artemia</i> nauplii, while on <i>Daphnia magna</i>, 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.
format	article
author	Beatrice-Cristina Ivan Florea Dumitrascu Adriana Iuliana Anghel Robert Viorel Ancuceanu Sergiu Shova Denisa Dumitrescu Constantin Draghici Octavian Tudorel Olaru George Mihai Nitulescu Mihaela Dinu Stefania-Felicia Barbuceanu
author_facet	Beatrice-Cristina Ivan Florea Dumitrascu Adriana Iuliana Anghel Robert Viorel Ancuceanu Sergiu Shova Denisa Dumitrescu Constantin Draghici Octavian Tudorel Olaru George Mihai Nitulescu Mihaela Dinu Stefania-Felicia Barbuceanu
author_sort	Beatrice-Cristina Ivan
title	Synthesis and Toxicity Evaluation of New Pyrroles Obtained by the Reaction of Activated Alkynes with 1-Methyl-3-(cyanomethyl)benzimidazolium Bromide
title_short	Synthesis and Toxicity Evaluation of New Pyrroles Obtained by the Reaction of Activated Alkynes with 1-Methyl-3-(cyanomethyl)benzimidazolium Bromide
title_full	Synthesis and Toxicity Evaluation of New Pyrroles Obtained by the Reaction of Activated Alkynes with 1-Methyl-3-(cyanomethyl)benzimidazolium Bromide
title_fullStr	Synthesis and Toxicity Evaluation of New Pyrroles Obtained by the Reaction of Activated Alkynes with 1-Methyl-3-(cyanomethyl)benzimidazolium Bromide
title_full_unstemmed	Synthesis and Toxicity Evaluation of New Pyrroles Obtained by the Reaction of Activated Alkynes with 1-Methyl-3-(cyanomethyl)benzimidazolium Bromide
title_sort	synthesis and toxicity evaluation of new pyrroles obtained by the reaction of activated alkynes with 1-methyl-3-(cyanomethyl)benzimidazolium bromide
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/50ba9b3b4d214fd69a0031ea6801b023
work_keys_str_mv	AT beatricecristinaivan synthesisandtoxicityevaluationofnewpyrrolesobtainedbythereactionofactivatedalkyneswith1methyl3cyanomethylbenzimidazoliumbromide AT floreadumitrascu synthesisandtoxicityevaluationofnewpyrrolesobtainedbythereactionofactivatedalkyneswith1methyl3cyanomethylbenzimidazoliumbromide AT adrianaiulianaanghel synthesisandtoxicityevaluationofnewpyrrolesobtainedbythereactionofactivatedalkyneswith1methyl3cyanomethylbenzimidazoliumbromide AT robertviorelancuceanu synthesisandtoxicityevaluationofnewpyrrolesobtainedbythereactionofactivatedalkyneswith1methyl3cyanomethylbenzimidazoliumbromide AT sergiushova synthesisandtoxicityevaluationofnewpyrrolesobtainedbythereactionofactivatedalkyneswith1methyl3cyanomethylbenzimidazoliumbromide AT denisadumitrescu synthesisandtoxicityevaluationofnewpyrrolesobtainedbythereactionofactivatedalkyneswith1methyl3cyanomethylbenzimidazoliumbromide AT constantindraghici synthesisandtoxicityevaluationofnewpyrrolesobtainedbythereactionofactivatedalkyneswith1methyl3cyanomethylbenzimidazoliumbromide AT octaviantudorelolaru synthesisandtoxicityevaluationofnewpyrrolesobtainedbythereactionofactivatedalkyneswith1methyl3cyanomethylbenzimidazoliumbromide AT georgemihainitulescu synthesisandtoxicityevaluationofnewpyrrolesobtainedbythereactionofactivatedalkyneswith1methyl3cyanomethylbenzimidazoliumbromide AT mihaeladinu synthesisandtoxicityevaluationofnewpyrrolesobtainedbythereactionofactivatedalkyneswith1methyl3cyanomethylbenzimidazoliumbromide AT stefaniafeliciabarbuceanu synthesisandtoxicityevaluationofnewpyrrolesobtainedbythereactionofactivatedalkyneswith1methyl3cyanomethylbenzimidazoliumbromide
_version_	1718431821985742848

Synthesis and Toxicity Evaluation of New Pyrroles Obtained by the Reaction of Activated Alkynes with 1-Methyl-3-(cyanomethyl)benzimidazolium Bromide

Ejemplares similares