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核心技术专利:CN118964589B侵权必究
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Facile synthesis of pyrazolopyridine pharmaceuticals under mild conditions using an algin-functionalized silica-based magnetic nanocatalyst (Alg@SBA-15/FeO).

作者信息

Hassanzadeh-Afruzi Fereshte, Amiri-Khamakani Zeinab, Saeidirad Mahdi, Salehi Mohammad Mehdi, Taheri-Ledari Reza, Maleki Ali

机构信息

Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology Tehran 16846-13114 Iran

出版信息

RSC Adv. 2023 Apr 3;13(15):10367-10378. doi: 10.1039/d2ra07228a. eCollection 2023 Mar 27.


DOI:10.1039/d2ra07228a
PMID:37020883
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10068431/
Abstract

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/FeO (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 FeO nanoparticles an co-precipitation process. Then, SBA-15/FeO particles were functionalized with 3-minopropyltriethoxysilane (APTES). Afterward, Alg@SBA-15/FeO was obtained by a nucleophilic substitution reaction between SBA-15/FeO-NH 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/FeO catalytic system imparted by FeO 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/FeO nanocomposite deserves more attention due to its non-toxicity, ease of preparation, good recyclability, and its high catalytic efficiency.

摘要
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/4a813f22916b/d2ra07228a-f10.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/33ff48f419ab/d2ra07228a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/d714af46a931/d2ra07228a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/05efde322fca/d2ra07228a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/b62ff138daad/d2ra07228a-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/119d1678a4bb/d2ra07228a-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/1fb7619b4c2a/d2ra07228a-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/abf35504dd4f/d2ra07228a-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/7a52cd9e40c3/d2ra07228a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/77ca5c5142bf/d2ra07228a-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/4ce59af1c179/d2ra07228a-f9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/4a813f22916b/d2ra07228a-f10.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/33ff48f419ab/d2ra07228a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/d714af46a931/d2ra07228a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/05efde322fca/d2ra07228a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/b62ff138daad/d2ra07228a-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/119d1678a4bb/d2ra07228a-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/1fb7619b4c2a/d2ra07228a-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/abf35504dd4f/d2ra07228a-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/7a52cd9e40c3/d2ra07228a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/77ca5c5142bf/d2ra07228a-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/4ce59af1c179/d2ra07228a-f9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14cd/10068431/4a813f22916b/d2ra07228a-f10.jpg

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引用本文的文献

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Sci Rep. 2024-5-16

[2]
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Sci Rep. 2023-12-13

[3]
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本文引用的文献

[1]
Functionalized hybrid magnetic catalytic systems on micro- and nanoscale utilized in organic synthesis and degradation of dyes.

Nanoscale Adv. 2022-2-9

[2]
High-performance sono/nano-catalytic system: CTSN/FeO-Cu nanocomposite, a promising heterogeneous catalyst for the synthesis of -arylimidazoles.

RSC Adv. 2019-12-5

[3]
Urease covalently immobilized on cotton-derived nanocellulose-dialdehyde for urea detection and urea-based multicomponent synthesis of tetrahydro-pyrazolopyridines in water.

RSC Adv. 2019-12-17

[4]
Cu(ii) immobilized on FeO@HNTs-tetrazole (CFHT) nanocomposite: synthesis, characterization, investigation of its catalytic role for the 1,3 dipolar cycloaddition reaction, and antibacterial activity.

RSC Adv. 2020-7-15

[5]
Tungsten anchored onto functionalized SBA-15: an efficient catalyst for diastereoselective synthesis of 2-azapyrrolizidine alkaloid scaffolds.

RSC Adv. 2019-6-24

[6]
Tetrahydropyrazolopyridines as antifriction and antiwear agents: experimental and DFT calculations.

RSC Adv. 2020-3-10

[7]
Assessment of catalytic and antibacterial activity of biocompatible agar supported ZnS/CuFeO magnetic nanotubes.

Sci Rep. 2022-3-16

[8]
Guanidinylated SBA-15/FeO mesoporous nanocomposite as an efficient catalyst for the synthesis of pyranopyrazole derivatives.

Sci Rep. 2021-10-6

[9]
Plasmonic photothermal release of docetaxel by gold nanoparticles incorporated onto halloysite nanotubes with conjugated 2D8-E3 antibodies for selective cancer therapy.

J Nanobiotechnology. 2021-8-11

[10]
Metals and Antibiotics as Aqueous Sequestration Targets for Magnetic Polyamidoamine-Grafted SBA-15.

Langmuir. 2021-7-6

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