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Chitosan–Cu Catalyzed Novel Ferrocenated Spiropyrrolidines: Green Synthesis, Single Crystal X-ray Diffraction, Hirshfeld Surface and Antibacterial Studies
Chitosan-bounded copper (chitosan–Cu) was introduced for green synthesis of novel ferrocenated spiropyrrolidine hybrids, namely 3′-(4-.bromobenzoyl)-5′-(4-hydroxybenzyl)-4′-ferrocenylspiro[indoline-3,2′-pyrrolidin]-2-one and 3′-(4-bromobenzoyl)-4′-ferrocenylspiro[indoline-3,2′-pyrrolidin]-2-one, in...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9867216/ https://www.ncbi.nlm.nih.gov/pubmed/36679308 http://dx.doi.org/10.3390/polym15020429 |
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author | Asad, Mohammad Arshad, Muhammad Nadeem Asiri, Abdullah M. Rahman, Mohammed M. Kumaran, Snigdha Thorakkattil Neerankuzhiyil, Mohammed Musthafa |
author_facet | Asad, Mohammad Arshad, Muhammad Nadeem Asiri, Abdullah M. Rahman, Mohammed M. Kumaran, Snigdha Thorakkattil Neerankuzhiyil, Mohammed Musthafa |
author_sort | Asad, Mohammad |
collection | PubMed |
description | Chitosan-bounded copper (chitosan–Cu) was introduced for green synthesis of novel ferrocenated spiropyrrolidine hybrids, namely 3′-(4-.bromobenzoyl)-5′-(4-hydroxybenzyl)-4′-ferrocenylspiro[indoline-3,2′-pyrrolidin]-2-one and 3′-(4-bromobenzoyl)-4′-ferrocenylspiro[indoline-3,2′-pyrrolidin]-2-one, in good yield. A one-pot three-component 1,3-dipolar cycloaddition reaction was employed for the formation of spiropyrrolidines from 1-(4-bromophenyl)-ferrocene-prop-2-en-1-one and azomethine ylides, which were developed in situ from tyrosine, glycine, and isatin, respectively. Various spectroscopic methods were used to establish the structures of spiropyrrolidines, and a single crystal X-ray diffraction study of a spiropyrrolidine provided additional confirmation. The crystallographic study revealed that compound 3a has one independent molecule in its unit cell, which is correlated with Hirshfeld surface analysis, and describes intramolecular contacts adversely. The highly yielded products in green conditions were determined for their antibacterial significance and were found to have good activity against Gram-positive and Gram-negative bacterial strains. |
format | Online Article Text |
id | pubmed-9867216 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-98672162023-01-22 Chitosan–Cu Catalyzed Novel Ferrocenated Spiropyrrolidines: Green Synthesis, Single Crystal X-ray Diffraction, Hirshfeld Surface and Antibacterial Studies Asad, Mohammad Arshad, Muhammad Nadeem Asiri, Abdullah M. Rahman, Mohammed M. Kumaran, Snigdha Thorakkattil Neerankuzhiyil, Mohammed Musthafa Polymers (Basel) Article Chitosan-bounded copper (chitosan–Cu) was introduced for green synthesis of novel ferrocenated spiropyrrolidine hybrids, namely 3′-(4-.bromobenzoyl)-5′-(4-hydroxybenzyl)-4′-ferrocenylspiro[indoline-3,2′-pyrrolidin]-2-one and 3′-(4-bromobenzoyl)-4′-ferrocenylspiro[indoline-3,2′-pyrrolidin]-2-one, in good yield. A one-pot three-component 1,3-dipolar cycloaddition reaction was employed for the formation of spiropyrrolidines from 1-(4-bromophenyl)-ferrocene-prop-2-en-1-one and azomethine ylides, which were developed in situ from tyrosine, glycine, and isatin, respectively. Various spectroscopic methods were used to establish the structures of spiropyrrolidines, and a single crystal X-ray diffraction study of a spiropyrrolidine provided additional confirmation. The crystallographic study revealed that compound 3a has one independent molecule in its unit cell, which is correlated with Hirshfeld surface analysis, and describes intramolecular contacts adversely. The highly yielded products in green conditions were determined for their antibacterial significance and were found to have good activity against Gram-positive and Gram-negative bacterial strains. MDPI 2023-01-13 /pmc/articles/PMC9867216/ /pubmed/36679308 http://dx.doi.org/10.3390/polym15020429 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Asad, Mohammad Arshad, Muhammad Nadeem Asiri, Abdullah M. Rahman, Mohammed M. Kumaran, Snigdha Thorakkattil Neerankuzhiyil, Mohammed Musthafa Chitosan–Cu Catalyzed Novel Ferrocenated Spiropyrrolidines: Green Synthesis, Single Crystal X-ray Diffraction, Hirshfeld Surface and Antibacterial Studies |
title | Chitosan–Cu Catalyzed Novel Ferrocenated Spiropyrrolidines: Green Synthesis, Single Crystal X-ray Diffraction, Hirshfeld Surface and Antibacterial Studies |
title_full | Chitosan–Cu Catalyzed Novel Ferrocenated Spiropyrrolidines: Green Synthesis, Single Crystal X-ray Diffraction, Hirshfeld Surface and Antibacterial Studies |
title_fullStr | Chitosan–Cu Catalyzed Novel Ferrocenated Spiropyrrolidines: Green Synthesis, Single Crystal X-ray Diffraction, Hirshfeld Surface and Antibacterial Studies |
title_full_unstemmed | Chitosan–Cu Catalyzed Novel Ferrocenated Spiropyrrolidines: Green Synthesis, Single Crystal X-ray Diffraction, Hirshfeld Surface and Antibacterial Studies |
title_short | Chitosan–Cu Catalyzed Novel Ferrocenated Spiropyrrolidines: Green Synthesis, Single Crystal X-ray Diffraction, Hirshfeld Surface and Antibacterial Studies |
title_sort | chitosan–cu catalyzed novel ferrocenated spiropyrrolidines: green synthesis, single crystal x-ray diffraction, hirshfeld surface and antibacterial studies |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9867216/ https://www.ncbi.nlm.nih.gov/pubmed/36679308 http://dx.doi.org/10.3390/polym15020429 |
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