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Special Issue "Focusing on Sulfur in Medicinal Chemistry"

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

Deadline for manuscript submissions: 20 March 2018

Special Issue Editor

Guest Editor
Prof. Dr. Thierry Besson

Normandie Univ, Univ Rouen; INSA Rouen, CNRS, Laboratoire COBRA UMR6014, Bâtiment IRCOF, 1 rue Tesnière, F-76821 Mont Saint-Aignan Cedex, France
Website | E-Mail
Interests: N,O,S-Heterocycles for therapeutic applications; microwave assisted chemistry; microwave-assisted chemistry; active drugs for cancer and central nervous system; cancer and CNS drugs

Special Issue Information

Dear Colleagues,

The presence of heterocycles in all kinds of organic compounds of interest in biology, pharmacology and medicine, is well known. Among them, sulphur-containing heterocyclic compounds have maintained the interest of researchers, and their unique structures have led to several applications in different areas; especially in the design of drugs. The presence of heteroatoms results in significant changes in the cyclic molecular structure and the number of synthetic methods to afford sulphur-containing molecules is, in practice, restricted to the availability of the appropriate sulphur reagent. Sometimes, the preparation of theses heterocyclic systems by conventional ways is a hard work that implies many synthetic steps and extensive starting material. For all these reasons, the various possibilities offered by innovative technologies are particularly attractive. This Special Issue aims to review recent developments in the synthesis of bioactive sulphur-containing heteroaromatic compounds under conditions that may include the application of new technology or techniques (e.g., microwave irradiation, flow chemistry) in the ring-forming step.

Prof. Dr. Thierry Besson
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 papers will be 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 monthly 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 1800 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

  • thiophenes
  • thiazoles
  • thiazines
  • thiadiazines
  • thiazepines
  • thiadiazepines

Published Papers (3 papers)

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Research

Open AccessArticle Syntheses of Novel 4-Substituted N-(5-amino-1H-1,2,4-triazol-3-yl)pyridine-3-sulfonamide Derivatives with Potential Antifungal Activity
Molecules 2017, 22(11), 1926; doi:10.3390/molecules22111926
Received: 10 October 2017 / Revised: 2 November 2017 / Accepted: 3 November 2017 / Published: 7 November 2017
PDF Full-text (5615 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Candidiasis represent a serious threat for patients with altered immune responses. Therefore, we have undertaken the synthesis of compounds comprising a pyridine-3-sulfonamide scaffold and known antifungally active 1,2,4-triazole substituents. Thus a series of novel 4-substituted N-(5-amino-1H-1,2,4-triazol-3-yl)pyridine-3-sulfonamides have been synthesized by
[...] Read more.
Candidiasis represent a serious threat for patients with altered immune responses. Therefore, we have undertaken the synthesis of compounds comprising a pyridine-3-sulfonamide scaffold and known antifungally active 1,2,4-triazole substituents. Thus a series of novel 4-substituted N-(5-amino-1H-1,2,4-triazol-3-yl)pyridine-3-sulfonamides have been synthesized by multistep reactions starting from 4-chloropyridine-3-sulfonamide via N′-cyano-N-[(4-substitutedpyridin-3-yl)sulfonyl]carbamimidothioates which were further converted with hydrazine hydrate to the corresponding 1,2,4-triazole derivatives 2636. The final compounds were evaluated for antifungal activity against strains of the genera Candida, Geotrichum, Rhodotorula, and Saccharomycess isolated from patients with mycosis. Many of them show greater efficacy than fluconazole, mostly towards Candida albicans and Rhodotorula mucilaginosa species, with MIC values ≤ 25 µg/mL. A docking study of the most active compounds 26, 34 and 35 was performed showing the potential mode of binding to Candida albicans lanosterol 14α-demethylase. Also in vitro cytotoxicity of selected compounds have been evaluated on the NCI-60 cell line panel. Full article
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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Open AccessArticle New 2-Phenylthiazoles as Potential Sortase A Inhibitors: Synthesis, Biological Evaluation and Molecular Docking
Molecules 2017, 22(11), 1827; doi:10.3390/molecules22111827
Received: 5 October 2017 / Accepted: 22 October 2017 / Published: 27 October 2017
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Abstract
Sortase A inhibition is a well establish strategy for decreasing bacterial virulence by affecting numerous key processes that control biofilm formation, host cell entry, evasion and suppression of the immune response and acquisition of essential nutrients. A meta-analysis of structures known to act
[...] Read more.
Sortase A inhibition is a well establish strategy for decreasing bacterial virulence by affecting numerous key processes that control biofilm formation, host cell entry, evasion and suppression of the immune response and acquisition of essential nutrients. A meta-analysis of structures known to act as Sortase A inhibitors provided the starting point for identifying a new potential scaffold. Based on this template a series of new potential Sortase A inhibitors, that contain the 2-phenylthiazole moiety, were synthesized. The physicochemical characterisation confirmed the identity of the proposed structures. Antibacterial activity evaluation showed that the new compounds have a reduced activity against bacterial cell viability. However, the compounds prevent biofilm formation at very low concentrations, especially in the case of E. faecalis. Molecular docking studies performed estimate that this is most likely due to the inhibition of Sortase A. The new compounds could be used as add-on therapies together with known antibacterial agents in order to combat multidrug-resistance enterococcal infections. Full article
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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Figure 1

Open AccessArticle Evaluation of LPS-Induced Acute Lung Injury Attenuation in Rats by Aminothiazole-Paeonol Derivatives
Molecules 2017, 22(10), 1605; doi:10.3390/molecules22101605
Received: 1 September 2017 / Revised: 20 September 2017 / Accepted: 21 September 2017 / Published: 25 September 2017
PDF Full-text (2754 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Paeonol is a key phenolic compound in the root bark of Moutan Cortex Radicis that has been used in traditional Chinese Medicine to ameliorate inflammation. A series of aminothiazole-paeonol derivatives (APDs) were synthesized in this work and subjected to preliminary evaluation in cells
[...] Read more.
Paeonol is a key phenolic compound in the root bark of Moutan Cortex Radicis that has been used in traditional Chinese Medicine to ameliorate inflammation. A series of aminothiazole-paeonol derivatives (APDs) were synthesized in this work and subjected to preliminary evaluation in cells followed by verification in animals. Quantification of monocyte chemotactic protein-1 (MCP-1) and interleukin-6 (IL-6) in culture media of LPS-activated A549 cells, a lung epithelial adenocarcinoma cell line, were used to investigate the anti-inflammatory capability of APDs. ALI-bearing rats were employed to verify therapeutic efficacy of APDs according to observations of total cells, protein amounts, MCP-1 and IL-6 in bronchoalveolar lavage fluid (BALF). Histopathological examinations of lung tissues were consequently applied for validation of APDs. Among these compounds, 2-(2-aminothiazol-4-yl)-5-methoxyphenol (4) had the most potent activity, showing comparable inhibition of MCP-1/IL-6 and superior elimination of neutrophil infiltration and protein exudation in lungs compared to others as well as dexamethasone. This study demonstrated a comprehensive strategy to evaluate APDs through integration of cell-based screening and animal-based verification. In order to fulfill unmet needs of treating acute lung injury (ALI) and acute respiratory distress syndrome (ARDS), APDs introduced in this work could be promising lead compounds to develop high potent anti-inflammation agents. Full article
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Title: In vitro evaluation of the sulforaphane and its analog as a potent inducers of 5-fluorouracil anticancer activity
Author: Katarzyna Wiktorska, et al.
Abstract: Isothiocyanates (R-NCS) are sulphur-containing phytochemicals. They main source are plants of the Brassicaceae family. The best known plant-derived isothiocyanate is sulforaphane that exhibit anticancer activity in both in vivo and in vitro studies. Recent attempt to evaluate their use in cancer therapy is to combine them with standard chemotherapeutic in order to increase the therapy efficacy. The aim of this paper is to determine the impact of sulforaphane and its natural analog alyssin on the anticancer activity of anticancer drug 5-fluorouracil. The type of drug-drug interactions was determined in prostate and colon cancer cell lines. The methods of confocal microscopy, western blot and flow cytometry were employed to determine the mechanism of cytotoxic and cytostatic action of the combination. The study revealed that additive or synergistic interaction were observed between 5-fluorouracil and both isothiocyanates which enhanced the anticancer activity of 5-fluorouracil in particular in colon cancer cell lines. The increased cytostatic effect was observed in case of alyssin while for sulforaphane the synergistic interaction with 5-fluorouracil was the effect of intensification of apoptotic death of the cell.

Title: Novel 3H-1,2-dithiole-3-thiones as antivirals targeting the nucleocapsid zinc finger containing protein of the feline immunodeficiency virus (FIV) as a model of HIV infection
Authors: Asquith C. R. M.,1,2 Konstantinova L. S.,3,4 Laitinen T,5 Poso A,5 Rakitin OA,3,4 Hofmann-Lehmann R,2 Hilton S. T.1*
Affiliation:
1. School of Pharmacy, Faculty of Life Sciences, University College London, London, WC1N 1AX, United Kingdom.
2. Clinical Laboratory & Center for Clinical Studies, Vetsuisse Faculty, University of Zurich, 8057, Zurich, Switzerland.
3. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 119991, Russian Federation.
4. Nanotechnology Education and Research Center, South Ural State, University, Lenina Ave. 76, Chelyabinsk, 454080, Russian Federation.
5. School of Pharmacy, Faculty of Health Sciences, University of Eastern, Finland, Kuopio, 70211, Finland.
Abstract: The substituted 3H-1,2-dithiole-3-thione has been utilised for a number of medicinal chemistry applications. The most recent development has been the identification of extrusion of hydrogen sulfide as a ubiquitous gasotransmitter, which can be produced directly by 3H-1,2-dithiole-3-thione in vivo. We were interested in probing the reactivity of the disulfide bridge of the 3H-1,2-dithiole-3-thione as a zinc abstracter in the nucleocapsid protein of Feline Immunodeficiency Virus (FIV). A series of 3H-1,2-dithiole-3-thione were prepared for evaluation of activity against the of FIV. The compounds display potent nanomolar activity and low toxicity against this key model of HIV infection.

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