One-Pot Multicomponent Synthesis of Methoxybenzo[<i>h</i>]quinoline-3-carbonitrile Derivatives; Anti-Chagas, X-ray, and In Silico ADME/Tox Profiling Studies

Several methoxybenzo[<i>h</i>]quinoline-3-carbonitrile analogs were designed and synthesized in a repositioning approach to developing compounds with anti-prostate cancer and anti-Chagas disease properties. The compounds were synthesized through a sequential multicomponent reaction of ar...

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Autores principales:	Hegira Ramírez, Katiuska Charris, Esteban Fernandez-Moreira, Benjamín Nogueda-Torres, Mario V. Capparelli, Jorge Ángel, Jaime Charris
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	cancer chagas one-pot synthesis methoxybenzo[<i>h</i>]quinoline Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/0f2d6485eb5242a790cfbcc301783a96
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spelling	oai:doaj.org-article:0f2d6485eb5242a790cfbcc301783a962021-11-25T18:28:52ZOne-Pot Multicomponent Synthesis of Methoxybenzo[<i>h</i>]quinoline-3-carbonitrile Derivatives; Anti-Chagas, X-ray, and In Silico ADME/Tox Profiling Studies10.3390/molecules262269771420-3049https://doaj.org/article/0f2d6485eb5242a790cfbcc301783a962021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/6977https://doaj.org/toc/1420-3049Several methoxybenzo[<i>h</i>]quinoline-3-carbonitrile analogs were designed and synthesized in a repositioning approach to developing compounds with anti-prostate cancer and anti-Chagas disease properties. The compounds were synthesized through a sequential multicomponent reaction of aromatic aldehydes, malononitrile, and 1-tetralone in the presence of ammonium acetate and acetic acid (catalytic). The effect of the one-pot method on the generation of the target product has been studied. The compounds were in vitro screened against bloodstream trypomastigotes of <i>T. cruzi</i> (NINOA and INC-5 strains) and were most effective at showing a better activity profile than nifurtimox and benznidazole (reference drugs). A study in silico on absorption, distribution, metabolism, excretion, and toxicity (ADME/Tox) profiling to help describe the molecular properties related to the pharmacokinetic aspects in the human body of these compounds was reported. In addition, <i>X-ray</i> data for the compound 2-Amino-5,6-dihydro-4-(3-hydroxy-4-methoxy-phenyl)-8-methoxybenzo[<i>h</i>]quinoline-3-carbonitrile <b>6</b> was being reported. Spectral (IR, NMR, and elemental analyses) data on all final compounds were consistent with the proposed structures.Hegira RamírezKatiuska CharrisEsteban Fernandez-MoreiraBenjamín Nogueda-TorresMario V. CapparelliJorge ÁngelJaime CharrisMDPI AGarticlecancerchagasone-pot synthesismethoxybenzo[<i>h</i>]quinolineOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6977, p 6977 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	cancer chagas one-pot synthesis methoxybenzo[<i>h</i>]quinoline Organic chemistry QD241-441
spellingShingle	cancer chagas one-pot synthesis methoxybenzo[<i>h</i>]quinoline Organic chemistry QD241-441 Hegira Ramírez Katiuska Charris Esteban Fernandez-Moreira Benjamín Nogueda-Torres Mario V. Capparelli Jorge Ángel Jaime Charris One-Pot Multicomponent Synthesis of Methoxybenzo[<i>h</i>]quinoline-3-carbonitrile Derivatives; Anti-Chagas, X-ray, and In Silico ADME/Tox Profiling Studies
description	Several methoxybenzo[<i>h</i>]quinoline-3-carbonitrile analogs were designed and synthesized in a repositioning approach to developing compounds with anti-prostate cancer and anti-Chagas disease properties. The compounds were synthesized through a sequential multicomponent reaction of aromatic aldehydes, malononitrile, and 1-tetralone in the presence of ammonium acetate and acetic acid (catalytic). The effect of the one-pot method on the generation of the target product has been studied. The compounds were in vitro screened against bloodstream trypomastigotes of <i>T. cruzi</i> (NINOA and INC-5 strains) and were most effective at showing a better activity profile than nifurtimox and benznidazole (reference drugs). A study in silico on absorption, distribution, metabolism, excretion, and toxicity (ADME/Tox) profiling to help describe the molecular properties related to the pharmacokinetic aspects in the human body of these compounds was reported. In addition, <i>X-ray</i> data for the compound 2-Amino-5,6-dihydro-4-(3-hydroxy-4-methoxy-phenyl)-8-methoxybenzo[<i>h</i>]quinoline-3-carbonitrile <b>6</b> was being reported. Spectral (IR, NMR, and elemental analyses) data on all final compounds were consistent with the proposed structures.
format	article
author	Hegira Ramírez Katiuska Charris Esteban Fernandez-Moreira Benjamín Nogueda-Torres Mario V. Capparelli Jorge Ángel Jaime Charris
author_facet	Hegira Ramírez Katiuska Charris Esteban Fernandez-Moreira Benjamín Nogueda-Torres Mario V. Capparelli Jorge Ángel Jaime Charris
author_sort	Hegira Ramírez
title	One-Pot Multicomponent Synthesis of Methoxybenzo[<i>h</i>]quinoline-3-carbonitrile Derivatives; Anti-Chagas, X-ray, and In Silico ADME/Tox Profiling Studies
title_short	One-Pot Multicomponent Synthesis of Methoxybenzo[<i>h</i>]quinoline-3-carbonitrile Derivatives; Anti-Chagas, X-ray, and In Silico ADME/Tox Profiling Studies
title_full	One-Pot Multicomponent Synthesis of Methoxybenzo[<i>h</i>]quinoline-3-carbonitrile Derivatives; Anti-Chagas, X-ray, and In Silico ADME/Tox Profiling Studies
title_fullStr	One-Pot Multicomponent Synthesis of Methoxybenzo[<i>h</i>]quinoline-3-carbonitrile Derivatives; Anti-Chagas, X-ray, and In Silico ADME/Tox Profiling Studies
title_full_unstemmed	One-Pot Multicomponent Synthesis of Methoxybenzo[<i>h</i>]quinoline-3-carbonitrile Derivatives; Anti-Chagas, X-ray, and In Silico ADME/Tox Profiling Studies
title_sort	one-pot multicomponent synthesis of methoxybenzo[<i>h</i>]quinoline-3-carbonitrile derivatives; anti-chagas, x-ray, and in silico adme/tox profiling studies
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/0f2d6485eb5242a790cfbcc301783a96
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One-Pot Multicomponent Synthesis of Methoxybenzo[<i>h</i>]quinoline-3-carbonitrile Derivatives; Anti-Chagas, X-ray, and In Silico ADME/Tox Profiling Studies

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