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Isoxazolines in Medicinal Chemistry and Natural Products

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: closed (31 January 2023) | Viewed by 4725

Special Issue Editors


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Guest Editor
Department of Pharmaceutical Sciences, University of Milan, Via L. Mangiagalli 25, 20133 Milan, Italy
Interests: medicinal chemistry; chemical biology; photopharmacology; translational chemistry; GPCRs; biased signaling; ion channels; acetylcholine; muscarinic receptors; nicotinic receptors; dopamine; dopamine receptors; multi-target ligands; bifunctional ligands; dual-acting agents; dualsteric ligands; bitopic ligands; photoswitches; cancer; antibiotics; neurodegeneration
Special Issues, Collections and Topics in MDPI journals

E-Mail Website
Guest Editor
Department of Pharmaceutical Sciences, University of Milan, Via Luigi Mangiagalli 25, 20133 Milan, Italy
Interests: medicinal chemistry; chemical biology; GPCRs; biased signaling; ion channels; acetylcholine; muscarinic receptors; nicotinic receptors; dopamine; dopamine receptors; multi-target ligands; bifunctional ligands; dual-acting agents; dualsteric ligands; bitopic ligands; neurodegeneration

E-Mail Website
Guest Editor
Department of Pharmaceutical Sciences, University of Milan, Via Luigi Mangiagalli 25, 20133 Milan, Italy
Interests: rational drug design; organic synthesis; structure-activity relationships; nicotinic acetylcholine receptors; muscarinic acetylcholine receptors; cholinesterase inhibitors; bifunctional and bitopic ligands
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

We cordially invite you to contribute original research papers or reviews to this Special Issue of Molecules entitled “Isoxazolines in Medicinal Chemistry and Natural Products”. Obtained from natural sources or by synthetic routes, Δ2-isoxazolines (4,5-dihydroisoxazoles) are a class of five-membered heterocyclic compounds that have gained much interest in the field of medicinal chemistry due to their wide range of biological properties, including anti-inflammatory, anticancer, antifungal, antibacterial, antituberculosis, antimalarial, cholinergic, and glutamatergic activities, among others. The structural features of isoxazolines make them suitable for multiple non-covalent interactions, especially hydrogen bonds and hydrophobic interactions. The introduction of an isoxazoline ring in synthetic or natural bioactive compounds often results in increased efficacy, decreased toxicity, and improved pharmacokinetics.

This Special Issue aims to provide a broad survey of the most recent advances in this topic. We invite you to submit original research and review articles related to up-to-date and ongoing studies focusing on the design of isoxazoline bioactive compounds, their preparation, and pharmacological evaluation, as well as on the isolation, identification, synthesis, and biological characterization of isoxazoline-containing natural products. Papers that cover new methodologies for the synthesis and functionalization of isoxazolines are also welcome.
 
Dr. Carlo Matera
Prof. Dr. Marco De Amici
Prof. Dr. Clelia Dallanoce
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • isoxazoline
  • heterocyclic compound
  • five-membered ring
  • small molecule
  • synthetic drug
  • natural product
  • anti-inflammatory
  • anticancer
  • antifungal
  • antibacterial
  • antituberculosis
  • antimalarial
  • cholinergic
  • nicotinic receptor
  • muscarinic receptor
  • glutamate receptor
  • 1,3-dipolar cycloaddition

Published Papers (1 paper)

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Review

144 pages, 82695 KiB  
Review
Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines
by Stanisław Krompiec, Piotr Lodowski, Aneta Kurpanik-Wójcik, Bogumiła Gołek, Angelika Mieszczanin, Aleksandra Fijołek, Marek Matussek and Klaudia Kaszuba
Molecules 2023, 28(6), 2547; https://doi.org/10.3390/molecules28062547 - 10 Mar 2023
Cited by 4 | Viewed by 3966
Abstract
The involvement of 1,3-dipolar cycloaddition (1,3-DP), double bond migration, metathesis, and nitrile oxide (including in situ-generated nitrile oxide) as dipoles, together with the C=C bond containing dipolarophiles, in the syntheses of 2-isoxazolines is presented. Methods for synthesizing isoxazolines (other than 1,3-DP cycloaddition) were [...] Read more.
The involvement of 1,3-dipolar cycloaddition (1,3-DP), double bond migration, metathesis, and nitrile oxide (including in situ-generated nitrile oxide) as dipoles, together with the C=C bond containing dipolarophiles, in the syntheses of 2-isoxazolines is presented. Methods for synthesizing isoxazolines (other than 1,3-DP cycloaddition) were also presented briefly. Various methods of nitrile oxide preparation, especially in situ-generated procedures, are presented. Special attention was paid to the application of various combinations of 1,3-DP cycloaddition with double bond migration (DBM) and with alkene metathesis (AM) in the syntheses of trisubstituted isoxazolines. Allyl compounds of the type QCH2CH=CH2 (Q = ArO, ArS, Ar, and others) play the role of dipolarophile precursors in the combinations of DPC mentioned, DBM and AM. Mechanistic aspects of cycloadditions, i.e., concerted or stepwise reaction mechanism and their regio- and stereoselectivity are also discussed from experimental and theoretical points of view. Side reactions accompanying cycloaddition, especially nitrile oxide dimerization, are considered. 2-Isoxazoline applications in organic synthesis and their biological activity, broad utility in medicine, agriculture, and other fields were also raised. Some remaining challenges in the field of 1,3-DP cycloaddition in the syntheses of isoxazolines are finally discussed. Full article
(This article belongs to the Special Issue Isoxazolines in Medicinal Chemistry and Natural Products)
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