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Nanomaterial assisted bulk scale synthesis of 2-methyl-6-nitroquinoline

Quinolines are an interesting class of moieties with various medicinal chemistry uses. The most prominent is their ability to be used as the last line of therapy for bacterial and viral infections including recent COVID-19. The synthesis of quinoline is through a cyclization reaction and overall rea...

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Autores principales: Chandrappa, M., Swathi, Korrapati, Girish Kumar, S., Pullela, Phani Kumar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier Ltd. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7415172/
https://www.ncbi.nlm.nih.gov/pubmed/32837922
http://dx.doi.org/10.1016/j.matpr.2020.07.103
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author Chandrappa, M.
Swathi, Korrapati
Girish Kumar, S.
Pullela, Phani Kumar
author_facet Chandrappa, M.
Swathi, Korrapati
Girish Kumar, S.
Pullela, Phani Kumar
author_sort Chandrappa, M.
collection PubMed
description Quinolines are an interesting class of moieties with various medicinal chemistry uses. The most prominent is their ability to be used as the last line of therapy for bacterial and viral infections including recent COVID-19. The synthesis of quinoline is through a cyclization reaction and overall reaction yields are about 20%. The bulky ring and the associated crowding of functional groups limit the catalyst options. In this publication, the use of Fe(3)O(4)@SiO(2) for enhancing yield improvements, especially for heterocyclics is reported. The use of the 40 nm sized silica functionalized magnetite nanoparticles seems to help in both condensation and cyclization steps of representative 2-methyl-6-nitroquinoline. Reaction time reduction due to surface enabled catalysis of nanoparticles is 110 min to 80 min. The reaction yield has doubled due to the presence of catalyst and the mechanism suggests this drastic result is due to stabilization of unstable intermediate on the acidic surface of the silica coating. This near homogeneous catalysis of 40 nm sized, silica functionalized, magnetite nanoparticles have far reaching applications in bulk drug industry for drugs like chloroquine & hydroxychloroquine, the two essential drugs for prophylactic use for COVID-1.
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spelling pubmed-74151722020-08-10 Nanomaterial assisted bulk scale synthesis of 2-methyl-6-nitroquinoline Chandrappa, M. Swathi, Korrapati Girish Kumar, S. Pullela, Phani Kumar Mater Today Proc Article Quinolines are an interesting class of moieties with various medicinal chemistry uses. The most prominent is their ability to be used as the last line of therapy for bacterial and viral infections including recent COVID-19. The synthesis of quinoline is through a cyclization reaction and overall reaction yields are about 20%. The bulky ring and the associated crowding of functional groups limit the catalyst options. In this publication, the use of Fe(3)O(4)@SiO(2) for enhancing yield improvements, especially for heterocyclics is reported. The use of the 40 nm sized silica functionalized magnetite nanoparticles seems to help in both condensation and cyclization steps of representative 2-methyl-6-nitroquinoline. Reaction time reduction due to surface enabled catalysis of nanoparticles is 110 min to 80 min. The reaction yield has doubled due to the presence of catalyst and the mechanism suggests this drastic result is due to stabilization of unstable intermediate on the acidic surface of the silica coating. This near homogeneous catalysis of 40 nm sized, silica functionalized, magnetite nanoparticles have far reaching applications in bulk drug industry for drugs like chloroquine & hydroxychloroquine, the two essential drugs for prophylactic use for COVID-1. Elsevier Ltd. 2021 2020-08-09 /pmc/articles/PMC7415172/ /pubmed/32837922 http://dx.doi.org/10.1016/j.matpr.2020.07.103 Text en © 2020 Elsevier Ltd. All rights reserved. Selection and peer-review under responsibility of the scientific committee of the International Conference on Newer Trends and Innovation in Mechanical Engineering: Materials Science. Since January 2020 Elsevier has created a COVID-19 resource centre with free information in English and Mandarin on the novel coronavirus COVID-19. The COVID-19 resource centre is hosted on Elsevier Connect, the company's public news and information website. Elsevier hereby grants permission to make all its COVID-19-related research that is available on the COVID-19 resource centre - including this research content - immediately available in PubMed Central and other publicly funded repositories, such as the WHO COVID database with rights for unrestricted research re-use and analyses in any form or by any means with acknowledgement of the original source. These permissions are granted for free by Elsevier for as long as the COVID-19 resource centre remains active.
spellingShingle Article
Chandrappa, M.
Swathi, Korrapati
Girish Kumar, S.
Pullela, Phani Kumar
Nanomaterial assisted bulk scale synthesis of 2-methyl-6-nitroquinoline
title Nanomaterial assisted bulk scale synthesis of 2-methyl-6-nitroquinoline
title_full Nanomaterial assisted bulk scale synthesis of 2-methyl-6-nitroquinoline
title_fullStr Nanomaterial assisted bulk scale synthesis of 2-methyl-6-nitroquinoline
title_full_unstemmed Nanomaterial assisted bulk scale synthesis of 2-methyl-6-nitroquinoline
title_short Nanomaterial assisted bulk scale synthesis of 2-methyl-6-nitroquinoline
title_sort nanomaterial assisted bulk scale synthesis of 2-methyl-6-nitroquinoline
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7415172/
https://www.ncbi.nlm.nih.gov/pubmed/32837922
http://dx.doi.org/10.1016/j.matpr.2020.07.103
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