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Keywords = benzylidene-3-pyrroline

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31 pages, 12346 KiB  
Review
Phosphorylated Nitrones—Synthesis and Applications
by Iwona Rozpara, José Marco-Contelles, Dorota G. Piotrowska and Iwona E. Głowacka
Molecules 2025, 30(6), 1333; https://doi.org/10.3390/molecules30061333 - 16 Mar 2025
Cited by 1 | Viewed by 1411
Abstract
Phosphorylated nitrones belong to an important class of compounds with several applications, such as their therapeutic potency to reduce oxidative stress or as spin-trapping agents. This review covers available synthetic methods for the preparation of both non-cyclic and cyclic phosphorylated nitrones, including the [...] Read more.
Phosphorylated nitrones belong to an important class of compounds with several applications, such as their therapeutic potency to reduce oxidative stress or as spin-trapping agents. This review covers available synthetic methods for the preparation of both non-cyclic and cyclic phosphorylated nitrones, including the possibilities of the modification of structures with selected functional groups, as well as examples of their application. As reported, the incorporation of diethoxyphosphoryl function into the structure of PBN and DMPO resulted in obtaining their phosphorylated analogs, i.e., N-benzylidene-1-diethoxyphosphoryl-1-methylethylamine N-oxide (PPN) and 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline-N-oxide (DEPMPO), respectively, both forming spin adducts of improved stability in comparison to the reference non-phosphorus nitrones. Moreover, antioxidant and neuroprotective activity observed in the group of phosphorylated nitrones makes them promising candidates for therapeutics. Full article
(This article belongs to the Special Issue Design, Synthesis, and Analysis of Potential Drugs, 3rd Edition)
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7 pages, 1308 KiB  
Article
Synthesis of 2-Benzylidene-3-Pyrrolines and Their Synthetic Transformation
by Ming-Tsung Hsu, Yi-Hung Liu and Shiuh-Tzung Liu
Reactions 2020, 1(2), 47-53; https://doi.org/10.3390/reactions1020005 - 16 Oct 2020
Cited by 5 | Viewed by 3183
Abstract
A series of benzylidene-3-pyrrolines were prepared from chalcone derivatives, arylacetylene and sulfonamide via a three-step sequence without the isolation of intermediates. Typically, the reaction of 1,3-di-p-tolylprop-2-en-1-one with lithium phenylacetylide was followed by substitution with tosylamide and then silver-catalyzed 5-exo-dig cyclization to [...] Read more.
A series of benzylidene-3-pyrrolines were prepared from chalcone derivatives, arylacetylene and sulfonamide via a three-step sequence without the isolation of intermediates. Typically, the reaction of 1,3-di-p-tolylprop-2-en-1-one with lithium phenylacetylide was followed by substitution with tosylamide and then silver-catalyzed 5-exo-dig cyclization to give N-tosyl-2-benzylidene-3,5-di-p-tolyl-2,5-dihydro-1H-pyrrole with a 86% yield. Furthermore, transformation to the corresponding substituted 3-pyrrolin-2-one and pyrrole by m-chloroperbenzoic acid (mcpba)-oxidation and acid-catalyzed aromatization, respectively, was investigated. Full article
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