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Facile synthesis of pyrazolopyridine pharmaceuticals under mild conditions using an algin-functionalized silica-based magnetic nanocatalyst (Alg@SBA-15/Fe(3)O(4))
Pyrazolopyridines are common scaffolds in various bioactive compounds, which have several therapeutic effects and unique pharmacological properties. In this study, we fabricated a novel environmentally friendly silica-based nanocomposite as a multifunctional catalytic system for the synthesis of pyr...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10068431/ https://www.ncbi.nlm.nih.gov/pubmed/37020883 http://dx.doi.org/10.1039/d2ra07228a |
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author | Hassanzadeh-Afruzi, Fereshte Amiri-Khamakani, Zeinab Saeidirad, Mahdi Salehi, Mohammad Mehdi Taheri-Ledari, Reza Maleki, Ali |
author_facet | Hassanzadeh-Afruzi, Fereshte Amiri-Khamakani, Zeinab Saeidirad, Mahdi Salehi, Mohammad Mehdi Taheri-Ledari, Reza Maleki, Ali |
author_sort | Hassanzadeh-Afruzi, Fereshte |
collection | PubMed |
description | Pyrazolopyridines are common scaffolds in various bioactive compounds, which have several therapeutic effects and unique pharmacological properties. In this study, we fabricated a novel environmentally friendly silica-based nanocomposite as a multifunctional catalytic system for the synthesis of pyrazolopyridine derivatives. This novel heterogeneous nanocomposite named Alg@SBA-15/Fe(3)O(4) (Alg stands for alginic acid), was prepared in several steps. In this regard, SBA-15 was synthesized by the hydrothermal method. Next, it was magnetized by Fe(3)O(4) nanoparticles via an in situ co-precipitation process. Then, SBA-15/Fe(3)O(4) particles were functionalized with 3-minopropyltriethoxysilane (APTES). Afterward, Alg@SBA-15/Fe(3)O(4) was obtained by a nucleophilic substitution reaction between SBA-15/Fe(3)O(4)–NH(2) and an as-synthesized methyl-esterified alginic. Different analyses such as Fourier-transform infrared (FTIR), energy-dispersive X-ray (EDX) spectroscopy, field-emission scanning-electron microscopy (FESEM), vibrating-sample magnetometer (VSM), X-ray diffraction (XRD), thermogravimetric analysis (TGA), and BET (Brunauer–Emmett–Teller) have been used to confirm the structure of the fabricated catalyst. The magnetic properties of the Alg@SBA-15/Fe(3)O(4) catalytic system imparted by Fe(3)O(4) MNPs enable it to be conveniently isolated from the reaction mixture by using an external magnet. According to the obtained results, the prepared nanocatalyst has high thermal stability and it lost approximately 26% of its weight up to 800 °C. Interestingly, a small amount of prepared nanocatalyst (0.02 g) has shown excellent catalytic performance in the synthesis of pyrazolopyridine derivatives (90–97%) in a short reaction time (20–30 min) at room temperature which can be attributed to its porous structure and large surface area, and the presence of many acidic and basic functional groups. In general, it can be argued that the Alg@SBA-15/Fe(3)O(4) nanocomposite deserves more attention due to its non-toxicity, ease of preparation, good recyclability, and its high catalytic efficiency. |
format | Online Article Text |
id | pubmed-10068431 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-100684312023-04-04 Facile synthesis of pyrazolopyridine pharmaceuticals under mild conditions using an algin-functionalized silica-based magnetic nanocatalyst (Alg@SBA-15/Fe(3)O(4)) Hassanzadeh-Afruzi, Fereshte Amiri-Khamakani, Zeinab Saeidirad, Mahdi Salehi, Mohammad Mehdi Taheri-Ledari, Reza Maleki, Ali RSC Adv Chemistry Pyrazolopyridines are common scaffolds in various bioactive compounds, which have several therapeutic effects and unique pharmacological properties. In this study, we fabricated a novel environmentally friendly silica-based nanocomposite as a multifunctional catalytic system for the synthesis of pyrazolopyridine derivatives. This novel heterogeneous nanocomposite named Alg@SBA-15/Fe(3)O(4) (Alg stands for alginic acid), was prepared in several steps. In this regard, SBA-15 was synthesized by the hydrothermal method. Next, it was magnetized by Fe(3)O(4) nanoparticles via an in situ co-precipitation process. Then, SBA-15/Fe(3)O(4) particles were functionalized with 3-minopropyltriethoxysilane (APTES). Afterward, Alg@SBA-15/Fe(3)O(4) was obtained by a nucleophilic substitution reaction between SBA-15/Fe(3)O(4)–NH(2) and an as-synthesized methyl-esterified alginic. Different analyses such as Fourier-transform infrared (FTIR), energy-dispersive X-ray (EDX) spectroscopy, field-emission scanning-electron microscopy (FESEM), vibrating-sample magnetometer (VSM), X-ray diffraction (XRD), thermogravimetric analysis (TGA), and BET (Brunauer–Emmett–Teller) have been used to confirm the structure of the fabricated catalyst. The magnetic properties of the Alg@SBA-15/Fe(3)O(4) catalytic system imparted by Fe(3)O(4) MNPs enable it to be conveniently isolated from the reaction mixture by using an external magnet. According to the obtained results, the prepared nanocatalyst has high thermal stability and it lost approximately 26% of its weight up to 800 °C. Interestingly, a small amount of prepared nanocatalyst (0.02 g) has shown excellent catalytic performance in the synthesis of pyrazolopyridine derivatives (90–97%) in a short reaction time (20–30 min) at room temperature which can be attributed to its porous structure and large surface area, and the presence of many acidic and basic functional groups. In general, it can be argued that the Alg@SBA-15/Fe(3)O(4) nanocomposite deserves more attention due to its non-toxicity, ease of preparation, good recyclability, and its high catalytic efficiency. The Royal Society of Chemistry 2023-04-03 /pmc/articles/PMC10068431/ /pubmed/37020883 http://dx.doi.org/10.1039/d2ra07228a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Hassanzadeh-Afruzi, Fereshte Amiri-Khamakani, Zeinab Saeidirad, Mahdi Salehi, Mohammad Mehdi Taheri-Ledari, Reza Maleki, Ali Facile synthesis of pyrazolopyridine pharmaceuticals under mild conditions using an algin-functionalized silica-based magnetic nanocatalyst (Alg@SBA-15/Fe(3)O(4)) |
title | Facile synthesis of pyrazolopyridine pharmaceuticals under mild conditions using an algin-functionalized silica-based magnetic nanocatalyst (Alg@SBA-15/Fe(3)O(4)) |
title_full | Facile synthesis of pyrazolopyridine pharmaceuticals under mild conditions using an algin-functionalized silica-based magnetic nanocatalyst (Alg@SBA-15/Fe(3)O(4)) |
title_fullStr | Facile synthesis of pyrazolopyridine pharmaceuticals under mild conditions using an algin-functionalized silica-based magnetic nanocatalyst (Alg@SBA-15/Fe(3)O(4)) |
title_full_unstemmed | Facile synthesis of pyrazolopyridine pharmaceuticals under mild conditions using an algin-functionalized silica-based magnetic nanocatalyst (Alg@SBA-15/Fe(3)O(4)) |
title_short | Facile synthesis of pyrazolopyridine pharmaceuticals under mild conditions using an algin-functionalized silica-based magnetic nanocatalyst (Alg@SBA-15/Fe(3)O(4)) |
title_sort | facile synthesis of pyrazolopyridine pharmaceuticals under mild conditions using an algin-functionalized silica-based magnetic nanocatalyst (alg@sba-15/fe(3)o(4)) |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10068431/ https://www.ncbi.nlm.nih.gov/pubmed/37020883 http://dx.doi.org/10.1039/d2ra07228a |
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