Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
6.7
4.6
Journals
Molecules
Special Issues
Asymmetric Synthesis of Pharmaceutically Relevant and Natural Compounds
molecules-logo
Submit to Molecules Review for Molecules Propose a Special Issue

Journal Menu

► Journal Menu

Journal Browser

► Journal Browser
share announcement

Asymmetric Synthesis of Pharmaceutically Relevant and Natural Compounds

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

Deadline for manuscript submissions: closed (28 February 2022) | Viewed by 7780

Special Issue Editor

Prof. Dr. Vladimir Dimitrov

E-Mail Website
Guest Editor
Institute of Organic Chemistry With Centre of Phytochemistry, Bulgarian Academy of Sciences, BG-1113 Sofia, Bulgaria
Interests: organometallic chemistry; organic chemistry; chiral ligands; asymmetric synthesis

Special Issue Information

Asymmetric synthesis is perhaps the field of organic synthesis that has experienced the most impressive development in the last few decades. As the majority of therapeutics and active natural products are in one enantiomeric form, the development of asymmetric synthetic methodologies plays a crucial role in the chemical production of these compounds of interest. Therefore, the development of efficient asymmetric methodologies using economical starting materials and/or catalysts, suitable to render very high or total asymmetric bias, and employing mild reaction conditions, remains nowadays a topic of the highest interest. Of course, we should add the present environmental concerns to these considerations—safe reagents and solvents, recyclability, etc. Asymmetric synthesis still remains a big (but rewarding) challenge for any synthetic chemist.

This Special Issue aims to provide a broad overview of the latest developments to asymmetric synthesis of pharmaceutically relevant and natural compounds of interest.

Prof. Dr. Vladimir Dimitrov
Guest Editor

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

  • Asymmetric catalysis
  • Asymmetric synthesis
  • Stereoselective synthesis
  • Chiral
  • Natural compounds
  • Pharmaceuticals

Published Papers (3 papers)

Download All Papers
Order results
Result details
Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:

Research

17 pages, 1968 KiB  
Article
Iboga Inspired N-Indolylethyl-Substituted Isoquinuclidines as a Bioactive Scaffold: Chemoenzymatic Synthesis and Characterization as GDNF Releasers and Antitrypanosoma Agents
by Mariana Pazos, Estefania Dibello, Juan Manuel Mesa, Dalibor Sames, Marcelo Alberto Comini, Gustavo Seoane and Ignacio Carrera
Molecules 2022, 27(3), 829; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27030829 - 27 Jan 2022
Cited by 2 | Viewed by 2962
Abstract
The first stage of the drug discovery process involves the identification of small compounds with biological activity. Iboga alkaloids are monoterpene indole alkaloids (MIAs) containing a fused isoquinuclidine-tetrahydroazepine ring. Both the natural products and the iboga-inspired synthetic analogs have shown a wide variety [...] Read more.
The first stage of the drug discovery process involves the identification of small compounds with biological activity. Iboga alkaloids are monoterpene indole alkaloids (MIAs) containing a fused isoquinuclidine-tetrahydroazepine ring. Both the natural products and the iboga-inspired synthetic analogs have shown a wide variety of biological activities. Herein, we describe the chemoenzymatic preparation of a small library of novel N-indolylethyl-substituted isoquinuclidines as iboga-inspired compounds, using toluene as a starting material and an imine Diels–Alder reaction as the key step in the synthesis. The new iboga series was investigated for its potential to promote the release of glial cell line-derived neurotrophic factor (GDNF) by C6 glioma cells, and to inhibit the growth of infective trypanosomes. GDNF is a neurotrophic factor widely recognized by its crucial role in development, survival, maintenance, and protection of dopaminergic neuronal circuitries affected in several neurological and psychiatric pathologies. Four compounds of the series showed promising activity as GDNF releasers, and a leading structure (compound 11) was identified for further studies. The same four compounds impaired the growth of bloodstream Trypanosoma brucei brucei (EC50 1–8 μM) and two of them (compounds 6 and 14) showed a good selectivity index. Full article
(This article belongs to the Special Issue Asymmetric Synthesis of Pharmaceutically Relevant and Natural Compounds)
►▼ Show Figures

Graphical abstract

19 pages, 3462 KiB  
Article
Chiral Aminoalcohols and Squaric Acid Amides as Ligands for Asymmetric Borane Reduction of Ketones: Insight to In Situ Formed Catalytic System by DOSY and Multinuclear NMR Experiments
by Yana Nikolova, Georgi M. Dobrikov, Zhanina Petkova and Pavletta Shestakova
Molecules 2021, 26(22), 6865; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26226865 - 14 Nov 2021
Cited by 3 | Viewed by 2258
Abstract
A series of squaric acid amides (synthesized in 66–99% isolated yields) and a set of chiral aminoalcohols were comparatively studied as ligands in a model reaction of reduction of α-chloroacetophenone with BH3•SMe2. In all cases, the aminoalcohols demonstrated better [...] Read more.
A series of squaric acid amides (synthesized in 66–99% isolated yields) and a set of chiral aminoalcohols were comparatively studied as ligands in a model reaction of reduction of α-chloroacetophenone with BH3•SMe2. In all cases, the aminoalcohols demonstrated better efficiency (up to 94% ee), while only poor asymmetric induction was achieved with the corresponding squaramides. A mechanistic insight on the in situ formation and stability at room temperature of intermediates generated from ligands and borane as possible precursors of the oxazaborolidine-based catalytic system has been obtained by 1H DOSY and multinuclear 1D and 2D (1H, 10/11B, 13C, 15N) NMR spectroscopy of equimolar mixtures of borane and selected ligands. These results contribute to better understanding the complexity of the processes occurring in the reaction mixture prior to the possible oxazaborolidine formation, which play a crucial role on the degree of enantioselectivity achieved in the borane reduction of α-chloroacetophenone. Full article
(This article belongs to the Special Issue Asymmetric Synthesis of Pharmaceutically Relevant and Natural Compounds)
►▼ Show Figures

Graphical abstract

14 pages, 2803 KiB  
Article
Synthesis and Oxidative Transformations of New Chiral Pinane-Type γ-Ketothiols: Stereochemical Features of Reactions
by Olga M. Lezina, Svetlana N. Subbotina, Larisa L. Frolova, Svetlana A. Rubtsova and Denis V. Sudarikov
Molecules 2021, 26(17), 5245; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26175245 - 29 Aug 2021
Cited by 2 | Viewed by 1889
Abstract
Chiral γ-ketothiols, thioacetates, thiobenzoate, disulfides, sulfones, thiosulfonates, and sulfonic acids were obtained from β-pinene for the first time. New compounds open up prospects for the synthesis of other polyfunctional compounds combining a biologically active pinane fragment with various pharmacophore groups. It was shown [...] Read more.
Chiral γ-ketothiols, thioacetates, thiobenzoate, disulfides, sulfones, thiosulfonates, and sulfonic acids were obtained from β-pinene for the first time. New compounds open up prospects for the synthesis of other polyfunctional compounds combining a biologically active pinane fragment with various pharmacophore groups. It was shown that the syntheses of sulfanyl and sulfonyl derivatives based on 2-norpinanone are characterized by high stereoselectivity in comparison with similar reactions of pinocarvone. The conditions for the preparation of diastereomerically pure thioacetyl and thiobenzoyl derivatives based on pinocarvone, as well as for the chemoselective oxidation of γ-ketothiols with chlorine dioxide to the corresponding thiolsulfonates and sulfonic acids, were selected. The effect of the VO(acac)2 catalyst on the increase in the yields of thiosulfonates was shown. A new direction of the transformation of thiosulfonates with the formation of sulfones was revealed. In the case of pinocarvone-based sulfones, the configuration is inversed at the C2 atom. An epimerization scheme is proposed. Full article
(This article belongs to the Special Issue Asymmetric Synthesis of Pharmaceutically Relevant and Natural Compounds)
►▼ Show Figures

Graphical abstract

Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:
 
Displaying articles 1-3
Back to TopTop