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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: closed (30 April 2018)

Special Issue Editor

Guest Editor
Prof. Dr. Thierry Besson

Normandie Univ, Univ Rouen; INSA Rouen, CNRS, Laboratoire COBRA UMR6014Bâtiment 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; 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

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Keywords

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

Published Papers (15 papers)

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Research

Jump to: Review

Open AccessArticle In Vitro Evaluation of Sulforaphane and a Natural Analog as Potent Inducers of 5-Fluorouracil Anticancer Activity
Molecules 2018, 23(11), 3040; https://doi.org/10.3390/molecules23113040
Received: 26 October 2018 / Revised: 13 November 2018 / Accepted: 19 November 2018 / Published: 21 November 2018
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Abstract
Isothiocyanates (R-NCS) are sulphur-containing phytochemicals. The main source are plants of the Brassicaceae family. The best known plant-derived isothiocyanate is sulforaphane that has exhibited anticancer activity in both in vivo and in vitro studies. Recent attempts to expand their use in cancer therapy
[...] Read more.
Isothiocyanates (R-NCS) are sulphur-containing phytochemicals. The main source are plants of the Brassicaceae family. The best known plant-derived isothiocyanate is sulforaphane that has exhibited anticancer activity in both in vivo and in vitro studies. Recent attempts to expand their use in cancer therapy involve combining them with standard chemotherapeutics in order to increase their therapeutic efficacy. The aim of this paper is to determine the impact of sulforaphane and its natural analog alyssin on the anticancer activity of the well-known anticancer drug 5-fluorouracil. The type of drug-drug interactions was determined in prostate and colon cancer cell lines. Confocal microscopy, western blot and flow cytometry methods were employed to determine the mechanism of cytotoxic and cytostatic action of the combinations. The study revealed that additive or synergistic interactions were observed between 5-fluorouracil and both isothiocyanates, which enhanced the anticancer activity of 5-fluorouracil, particularly in colon cancer cell lines. An increased cytostatic effect was observed in case of alyssin while for sulforaphane the synergistic interaction with 5-fluorouracil involved an intensification of apoptotic cell death. Full article
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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Open AccessFeature PaperArticle Development of Kinase Inhibitors via Metal-Catalyzed C–H Arylation of 8-Alkyl-thiazolo[5,4-f]-quinazolin-9-ones Designed by Fragment-Growing Studies
Molecules 2018, 23(9), 2181; https://doi.org/10.3390/molecules23092181
Received: 9 August 2018 / Revised: 24 August 2018 / Accepted: 27 August 2018 / Published: 29 August 2018
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Abstract
Efficient metal catalyzed C–H arylation of 8-alkyl-thiazolo[5,4-f]-quinazolin-9-ones was explored for SAR studies. Application of this powerful chemical tool at the last stage of the synthesis of kinase inhibitors allowed the synthesis of arrays of molecules inspired by fragment-growing studies generated by
[...] Read more.
Efficient metal catalyzed C–H arylation of 8-alkyl-thiazolo[5,4-f]-quinazolin-9-ones was explored for SAR studies. Application of this powerful chemical tool at the last stage of the synthesis of kinase inhibitors allowed the synthesis of arrays of molecules inspired by fragment-growing studies generated by molecular modeling calculations. Among the potentially active compounds designed through this strategy, FC162 (4c) exhibits nanomolar IC50 values against some kinases, and is the best candidate for the development as a DYRK kinase inhibitor. Full article
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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Open AccessFeature PaperArticle Synthesis of 2-Mercapto-(2-Oxoindolin-3-Ylidene)Acetonitriles from 3-(4-Chloro-5H-1,2,3-Dithiazol-5-Ylidene)Indolin-2-ones
Molecules 2018, 23(6), 1390; https://doi.org/10.3390/molecules23061390
Received: 23 May 2018 / Revised: 4 June 2018 / Accepted: 6 June 2018 / Published: 8 June 2018
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Abstract
Alkylidene oxindoles are important functional moieties and building blocks in pharmaceutical and synthetic chemistry. Our interest in biologically active compounds focused our studies on the synthesis of novel oxindoles, bearing on the exocyclic double bond at the C8, CN, and S groups. Extending
[...] Read more.
Alkylidene oxindoles are important functional moieties and building blocks in pharmaceutical and synthetic chemistry. Our interest in biologically active compounds focused our studies on the synthesis of novel oxindoles, bearing on the exocyclic double bond at the C8, CN, and S groups. Extending the potential applications of Appel’s salt, we developed a new synthetic approach by investigating the reactions of C5-substituted 2-oxindoles with 4,5-dichloro-1,2,3-dithiazolium chloride (Appel’s salt) to give original (Z)-3-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)indolin-2-one derivatives, and new 2-mercapto-(2-oxoindolin-3-ylidene)acetonitriles via a dithiazole ring-opening reaction. The work described in this article represents further applications of Appel’s salt in the conception of novel heterocyclic rings, in an effort to access original bioactive compounds. Fifteen new compounds were prepared and fully characterized. Full article
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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Open AccessArticle 1,2,6-Thiadiazinones as Novel Narrow Spectrum Calcium/Calmodulin-Dependent Protein Kinase Kinase 2 (CaMKK2) Inhibitors
Molecules 2018, 23(5), 1221; https://doi.org/10.3390/molecules23051221
Received: 29 April 2018 / Revised: 15 May 2018 / Accepted: 15 May 2018 / Published: 19 May 2018
Cited by 1 | PDF Full-text (13494 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
We demonstrate for the first time that 4H-1,2,6-thiadiazin-4-one (TDZ) can function as a chemotype for the design of ATP-competitive kinase inhibitors. Using insights from a co-crystal structure of a 3,5-bis(arylamino)-4H-1,2,6-thiadiazin-4-one bound to calcium/calmodulin-dependent protein kinase kinase 2 (CaMKK2), several
[...] Read more.
We demonstrate for the first time that 4H-1,2,6-thiadiazin-4-one (TDZ) can function as a chemotype for the design of ATP-competitive kinase inhibitors. Using insights from a co-crystal structure of a 3,5-bis(arylamino)-4H-1,2,6-thiadiazin-4-one bound to calcium/calmodulin-dependent protein kinase kinase 2 (CaMKK2), several analogues were identified with micromolar activity through targeted displacement of bound water molecules in the active site. Since the TDZ analogues showed reduced promiscuity compared to their 2,4-dianilinopyrimidine counter parts, they represent starting points for development of highly selective kinase inhibitors. Full article
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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Open AccessArticle First Metal-Free Synthesis of Tetracyclic Pyrido and Pyrazino Thienopyrimidinone Molecules
Molecules 2018, 23(5), 1159; https://doi.org/10.3390/molecules23051159
Received: 24 April 2018 / Revised: 4 May 2018 / Accepted: 8 May 2018 / Published: 11 May 2018
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Abstract
We report herein a new metal free synthetic pathway to generate tetracyclic compounds from 3-aminothieno[3,2-b]pyridine-2-carboxylate. To enlarge the molecular diversity, we studied the Suzuki coupling of 9-chloro-6H-pyrido[1,2-a]pyrido[2′,3′:4,5]thieno[3,2-d]pyrimidin-6-one and several boronic acids were easily introduced. Full article
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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Open AccessArticle Molecular Docking Evaluation of (E)-5-arylidene-2-thioxothiazolidin-4-one Derivatives as Selective Bacterial Adenylate Kinase Inhibitors
Molecules 2018, 23(5), 1076; https://doi.org/10.3390/molecules23051076
Received: 21 March 2018 / Revised: 27 April 2018 / Accepted: 1 May 2018 / Published: 3 May 2018
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Abstract
Multi-drug resistant microorganism infections with emerging problems that require not only a prevention strategy, but also the development of new inhibitory compounds. Six previously synthesized 5-arylidene-2-thioxothiazolidin-4-one derivatives 1af, were screened for inhibitory activity on adenylate kinases of different origins by
[...] Read more.
Multi-drug resistant microorganism infections with emerging problems that require not only a prevention strategy, but also the development of new inhibitory compounds. Six previously synthesized 5-arylidene-2-thioxothiazolidin-4-one derivatives 1af, were screened for inhibitory activity on adenylate kinases of different origins by molecular docking. The compounds 1c and 1d were the most efficient inhibitors of bacterial and some archean adenylate kinases. Hydrogen bond interactions were observed with the residues belonging to the ATP binding site. Moreover human adenylate kinases are poor targets, suggesting that this selectivity offers promising prospectives for refining the structure of our compounds. Full article
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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Open AccessArticle ω-Methylsulfanylalkyl Glucosinolates: A General Synthetic Pathway
Molecules 2018, 23(4), 786; https://doi.org/10.3390/molecules23040786
Received: 9 March 2018 / Revised: 20 March 2018 / Accepted: 21 March 2018 / Published: 28 March 2018
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Abstract
A general pathway was devised to synthesize ω-methylsulfanylalkyl glucosinolates, which represent an important class of structurally homogeneous plant secondary metabolites. The required thiofunctionalized hydroximoyl chlorides were obtained from the corresponding α,ω-nitroalkyl methylsulfide precursors, involving as the key-step, a nitronate chlorination strategy. A coupling
[...] Read more.
A general pathway was devised to synthesize ω-methylsulfanylalkyl glucosinolates, which represent an important class of structurally homogeneous plant secondary metabolites. The required thiofunctionalized hydroximoyl chlorides were obtained from the corresponding α,ω-nitroalkyl methylsulfide precursors, involving as the key-step, a nitronate chlorination strategy. A coupling reaction with 1-thio-beta-d-glucopyranose, followed by O-sulfation of the intermediate thiohydroximate and final deprotection of the sugar moiety afforded the target compounds. Full article
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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Open AccessArticle A Greener and Efficient Method for Nucleophilic Aromatic Substitution of Nitrogen-Containing Fused Heterocycles
Molecules 2018, 23(3), 684; https://doi.org/10.3390/molecules23030684
Received: 27 February 2018 / Revised: 12 March 2018 / Accepted: 16 March 2018 / Published: 18 March 2018
Cited by 1 | PDF Full-text (5163 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A simple and efficient methodology for the nucleophilic aromatic substitution of nitrogen-containing fused heterocycles with interesting biological activities has been developed in an environmentally sound manner using polyethylene glycol (PEG-400) as the solvent, leading to the expected compounds in excellent yields in only
[...] Read more.
A simple and efficient methodology for the nucleophilic aromatic substitution of nitrogen-containing fused heterocycles with interesting biological activities has been developed in an environmentally sound manner using polyethylene glycol (PEG-400) as the solvent, leading to the expected compounds in excellent yields in only five minutes. Full article
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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Open AccessArticle Non-Imidazole Histamine H3 Ligands. Part VII. Synthesis, In Vitro and In Vivo Characterization of 5-Substituted-2-thiazol-4-n-propylpiperazines
Molecules 2018, 23(2), 326; https://doi.org/10.3390/molecules23020326
Received: 18 January 2018 / Revised: 31 January 2018 / Accepted: 1 February 2018 / Published: 3 February 2018
Cited by 2 | PDF Full-text (1553 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
H3 receptors present on histaminergic and non-histaminergic neurons, act as autoreceptors or heteroreceptors controlling neurotransmitter release and synthesis. Previous, studies have found that the compound N-methyl-N-3-phenylalkyl-2-[2-(4-n-propylpiperazin-1-yl)-1,3-thiazol-5-yl]ethan-1-amine (ADS-531, 2c) exhibits high in vitro potency toward H3 guinea
[...] Read more.
H3 receptors present on histaminergic and non-histaminergic neurons, act as autoreceptors or heteroreceptors controlling neurotransmitter release and synthesis. Previous, studies have found that the compound N-methyl-N-3-phenylalkyl-2-[2-(4-n-propylpiperazin-1-yl)-1,3-thiazol-5-yl]ethan-1-amine (ADS-531, 2c) exhibits high in vitro potency toward H3 guinea pig jejunal receptors, with pA2 = 8.27. To optimize the structure of the lead compound ADS-531, a series of 5-substituted-2-thiazol-4-n-propylpiperazines 3 were synthesized and subjected to in vitro pharmacological characterization; the alkyl chain between position 2 of the thiazole ring and the terminal secondary N-methylamino function was elongated from three to four methylene groups and the N-methylamino functionality was substituted by benzyl-, 2-phenylethyl-, and 3-phenyl-propyl- moieties. SAR studies on novel non-imidazole, 5-substituted-2-thiazol-4-n-propyl-piperazines 3 showed that the most active compound 3a (pA2 = 8.38), additionally possessed a weak competitive H1-antagonistic activity. Therefore, compound ADS-531, which did not exhibit any H1-antagonistic activity, was chosen for further evaluation for its affinity to the recombinant rat and human histamine H3 receptors (rH3R and hH3R, respectively). ADS-531 exhibited nanomolar affinity for both rH3R and hH3R receptors. It was also shown that, ADS-531 given subchronically to rats (s.c. 3 mg/kg, 5 days) penetrated the brain, where it affected dopamine, noradrenaline and serotonin concentration; however, it did not affect histamine concentration nor feeding behavior. Full article
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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Open AccessArticle Synthesis and Evaluation of Thiochroman-4-One Derivatives as Potential Leishmanicidal Agents
Molecules 2017, 22(12), 2041; https://doi.org/10.3390/molecules22122041
Received: 24 October 2017 / Revised: 20 November 2017 / Accepted: 20 November 2017 / Published: 29 November 2017
Cited by 2 | PDF Full-text (1230 KB) | HTML Full-text | XML Full-text
Abstract
The S-containing heterocyclic compounds benzothiopyrans or thiochromones stand out as having promising biological activities due to their structural relationship with chromones (benzopyrans), which are widely known as privileged scaffolds in medicinal chemistry. In this work, we report the synthesis of 35 thiochromone derivatives
[...] Read more.
The S-containing heterocyclic compounds benzothiopyrans or thiochromones stand out as having promising biological activities due to their structural relationship with chromones (benzopyrans), which are widely known as privileged scaffolds in medicinal chemistry. In this work, we report the synthesis of 35 thiochromone derivatives and the in vitro antileishmanial and cytotoxic activities. Compounds were tested against intracellular amastigotes of Leishmania panamensis and cytotoxic activity against human monocytes (U-937 ATCC CRL-1593.2). Compounds bearing a vinyl sulfone moiety, 4h, 4i, 4j, 4k, 4l and 4m, displayed the highest antileishmanial activity, with EC50 values lower than 10 μM and an index of selectivity over 100 for compounds 4j and 4l. When the double bond or the sulfone moiety was removed, the activity decreased. Our results show that thiochromones bearing a vinyl sulfone moiety are endowed with high antileishmanial activity and low cytotoxicity. Full article
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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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; https://doi.org/10.3390/molecules22111926
Received: 10 October 2017 / Revised: 2 November 2017 / Accepted: 3 November 2017 / Published: 7 November 2017
Cited by 3 | 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; https://doi.org/10.3390/molecules22111827
Received: 5 October 2017 / Accepted: 22 October 2017 / Published: 27 October 2017
Cited by 4 | PDF Full-text (3319 KB) | HTML Full-text | XML Full-text
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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Open AccessArticle Evaluation of LPS-Induced Acute Lung Injury Attenuation in Rats by Aminothiazole-Paeonol Derivatives
Molecules 2017, 22(10), 1605; https://doi.org/10.3390/molecules22101605
Received: 1 September 2017 / Revised: 20 September 2017 / Accepted: 21 September 2017 / Published: 25 September 2017
Cited by 2 | 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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Review

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Open AccessReview Transient Sulfenic Acids in the Synthesis of Biologically Relevant Products
Molecules 2018, 23(5), 1030; https://doi.org/10.3390/molecules23051030
Received: 5 April 2018 / Revised: 20 April 2018 / Accepted: 24 April 2018 / Published: 27 April 2018
Cited by 1 | PDF Full-text (3964 KB) | HTML Full-text | XML Full-text
Abstract
Sulfenic acids as small molecules are too unstable to be isolated and their transient nature offers the possibility to involve them in concerted processes that lead to the obtainment of functional groups such as sulfoxides, sulfones, and disulfides. All these functions are present
[...] Read more.
Sulfenic acids as small molecules are too unstable to be isolated and their transient nature offers the possibility to involve them in concerted processes that lead to the obtainment of functional groups such as sulfoxides, sulfones, and disulfides. All these functions are present in a number of natural and synthetic drugs and can represent structural motives inducing biologically relevant properties. In this small review the generation and reactions of sulfenic acid bearing naturally occurring residues are described. Carbohydrate and aminoacid-derived sulfenic acids have been used in concerted addition with triple bonds to obtain alliin derivatives and thiosugars in enantiomerically pure form. Glycoconjugates with sulfinyl, sulfonyl, and disulfane functional groups and pyridine-derived disulfides have been obtained from bis- and tris-sulfinyl precursors of sulfenic acids. Small families of such compounds have been subjected to preliminary biological tests. Starting from the evidence that the control of molecular architecture and the presence of suitable functional groups can play a significant role on the exhibition of biological properties, apoptotic effects on malignant cells by glycoconjugates and inhibitory activity against the important human pathogen S. aureus by pyrimidine-derived disulfides have been found. Full article
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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Open AccessFeature PaperReview Isothiocyanates: An Overview of Their Antimicrobial Activity against Human Infections
Molecules 2018, 23(3), 624; https://doi.org/10.3390/molecules23030624
Received: 31 January 2018 / Revised: 3 March 2018 / Accepted: 3 March 2018 / Published: 9 March 2018
Cited by 4 | PDF Full-text (430 KB) | HTML Full-text | XML Full-text
Abstract
The use of plant-derived products as antimicrobial agents has been investigated in depth. Isothiocyanates (ITCs) are bioactive products resulting from enzymatic hydrolysis of glucosinolates (GLs), the most abundant secondary metabolites in the botanical order Brassicales. Although the antimicrobial activity of ITCs against foodborne
[...] Read more.
The use of plant-derived products as antimicrobial agents has been investigated in depth. Isothiocyanates (ITCs) are bioactive products resulting from enzymatic hydrolysis of glucosinolates (GLs), the most abundant secondary metabolites in the botanical order Brassicales. Although the antimicrobial activity of ITCs against foodborne and plant pathogens has been well documented, little is known about their antimicrobial properties against human pathogens. This review collects studies that focus on this topic. Particular focus will be put on ITCs’ antimicrobial properties and their mechanism of action against human pathogens for which the current therapeutic solutions are deficient and therefore of prime importance for public health. Our purpose was the evaluation of the potential use of ITCs to replace or support the common antibiotics. Even though ITCs appear to be effective against the most important human pathogens, including bacteria with resistant phenotypes, the majority of the studies did not show comparable results and thus it is very difficult to compare the antimicrobial activity of the different ITCs. For this reason, a standard method should be used and further studies are needed. Full article
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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