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Dear Colleagues,

We are delighted to announce a call for submissions to a Special Issue of the International Journal of Molecular Sciences on the topic of transformations of electron-rich aromatic compounds into bioactive precursors.

For a variety of pharmacological targets and disorders, medicinal chemistry focuses on drug design and the synthesis of biologically active compounds. Several electron-rich aromatic ring-systems, such as hydroxyquinoline, indole or β-carbolines, have privileged positions in biochemistry. By being part of the molecules in enzymatic processes, neurotransmitters or plant-derived pharmacophores, these structures bear a high importance. Nonetheless, they may also take part in specific reactions that require an electron-rich donor, such as a Mannich reaction or Knoevenagel condensation. Applying these electron-rich aromatic starting compounds in such transformations may aid in the discovery of novel bioactive agents.

We encourage the submission of both original research articles and topical reviews on all aspects of synthesis and pharmacological studies on electron-rich aromatic compounds, such as the aforementioned hydroxyquinoline, indole or β-carboline derivatives. All submitted articles will undergo a peer review.

Prof. Dr. István Szatmári
Guest Editor

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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. International Journal of Molecular Sciences is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. There is an Article Processing Charge (APC) for publication in this open access journal. For details about the APC please see here. 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

electron-rich
hydroxyquinoline
indole
β-carboline
bioactive compounds
neuroprotection
antiproloferative activity

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32 pages, 11800 KiB

Open AccessArticle

Synthesis of β-Carbolines with Electrocyclic Cyclization of 3-Nitrovinylindoles

by Nicolai A. Aksenov, Nikolai A. Arutiunov, Alexander V. Aksenov, Nikita K. Kirilov, Inna V. Aksenova, Dmitrii A. Aksenov, Elena V. Aleksandrova, Michael Rubin and Alexander Kornienko

Int. J. Mol. Sci. 2023, 24(17), 13107; https://doi.org/10.3390/ijms241713107 - 23 Aug 2023

Viewed by 807

Abstract

The β-carboline motif is common in drug discovery and among numerous biologically active natural products. However, its synthetic preparation relies on multistep sequences and heavily depends on the type of substitution required in the core of the desired β-carboline target. Herein, we demonstrate that this structural motif can be accessed with the microwave-assisted electrocyclic cyclization of heterotrienic aci (alkylideneazinic acid) forms of 3-nitrovinylindoles. The reaction can start with 3-nitrovinylindoles themselves under two sets of conditions. The first one involves microwave irradiation of butanolic solutions of 3-nitrovinylindoles, whereas the second one consists of prior Boc protection of indolic nitrogen, where the protecting group cleanly comes off during the course of the reaction. Alternatively, the reaction can start with 3-nitrovinylindoles prepared in situ using various processes. Finally, the reaction may utilize indoles with β-nitrostyrenes, likely involving the intermediacy of spirocyclic oxazolines, which rearrange to similar heterotrienic systems undergoing cyclization to β-carbolines. As part of this study, several natural products, namely, alkaloids norharmane, harmane, and eudistomin N, were synthesized. Full article

(This article belongs to the Special Issue Transformations of Electron-Rich Aromatic Compounds toward Bioactive Precursors)

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