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Synthesis and Biological Activity of the Derivatives of Sulfuric Acid including Sulfonamides and Sulfonimidamides

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

Deadline for manuscript submissions: closed (31 January 2023) | Viewed by 7865

Special Issue Editors


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Guest Editor
Avidin Ltd., Alsó kikötő sor 11/D, H6726 Szeged, Hungary
Interests: antitumor small membered heterocycles; multicomponent reaction; multisubstituted aziridine/aziridine fused heterocycles; C-H oxidation/intramolecular cyclisation

Special Issue Information

Dear Colleagues,

Though absent in nature, the sulfonamide motif has emerged as an essential unit in numerous synthesized non-cyclic and cyclic architectures possessing pharmaceutical impact. So far, they have been included in more than 100 FDA-approved drugs and potential drug candidates. Whereas the preparation of non-cyclic sulfonamides with simple synthetic methodologies has been achieved and it is possible to obtain the desired substitution patterns in target structures, cyclic structures containing the sulfonamide motif are still challenging to produce. On the other hand, sulfonamides as carboxyl group bioisosteres can rapidly form in chemical reactions carried out during medicinal chemistry or drug discovery research. In contrast, their bioisosteres including sulfonimidamides or sulfonimides are less investigated in synthetic or medicinal chemistry studies. Indeed, their synthesis is more challenging, since it requires multistep synthetic procedures.

This Special Issue will publish works describing synthetic routes for the production of novel sulfonamide derivatives and investigating their bioactivity, e.g., their anti-cancer effects. The submission of research articles is mainly expected, as well as access towards cytotoxic chemical libraries including bioactive compounds with novel substitution patterns. Because of the recent developments in drug design and synthetic chemistry, review articles on these topics will also be considered.

Dr. Gabor J. Szebeni
Dr. Ivan Kanizsai
Guest Editors

Manuscript Submission Information

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Keywords

  • sulfuric acid
  • sulfonamides
  • sulfonimidamides
  • bioactive compounds

Published Papers (3 papers)

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Research

15 pages, 1513 KiB  
Article
Ursolic Acid and Solasodine as Potent Anti-Mycobacterial Agents for Combating Paratuberculosis: An Anti-Inflammatory and In Silico Analysis
by Manthena Navabharath, Varsha Srivastava, Saurabh Gupta, Shoor Vir Singh and Sayeed Ahmad
Molecules 2023, 28(1), 274; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28010274 - 29 Dec 2022
Cited by 3 | Viewed by 1601
Abstract
Mycobacterium avium subspecies paratuberculosis (MAP) infection in domestic livestock causes persistent diarrhea, weight loss, and death and is also a potential cause of Crohn’s disease (CD) in humans; notably, treatments against MAP are insufficient, costly, and can cause adverse reactions. Hence, plant-derived bioactive [...] Read more.
Mycobacterium avium subspecies paratuberculosis (MAP) infection in domestic livestock causes persistent diarrhea, weight loss, and death and is also a potential cause of Crohn’s disease (CD) in humans; notably, treatments against MAP are insufficient, costly, and can cause adverse reactions. Hence, plant-derived bioactive constituents have been taken into consideration in this regard. Herein, we present the results of two bioactive constituents (Solasodine and Ursolic acid) that were evaluated for their safety and efficacy against MAP protein (Dephospho-Coenzyme A kinase (DPCK) by utilizing in vitro assays and different tools of in silico biology. The ADME/t-test, the drug-likeness property test, pharmacophore modelling, and PASS prediction have proven that both the constituents have better binding capacities than the available antibiotic drugs used to target protein inhibition pathways. Through our observations, it can be inferred that these two phytochemicals can be adequately used to treat paratuberculosis, thereby combating inflammatory bowel disorders (IBD) of an autoimmune nature. Full article
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25 pages, 4279 KiB  
Article
Synthesis, Antimicrobial, Anti-Virulence and Anticancer Evaluation of New 5(4H)-Oxazolone-Based Sulfonamides
by Ahmad J. Almalki, Tarek S. Ibrahim, Ehab S. Taher, Mamdouh F. A. Mohamed, Mahmoud Youns, Wael A. H. Hegazy and Amany M. M. Al-Mahmoudy
Molecules 2022, 27(3), 671; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27030671 - 20 Jan 2022
Cited by 31 | Viewed by 2943
Abstract
Since the synthesis of prontosil the first prodrug shares their chemical moiety, sulfonamides exhibit diverse modes of actions to serve as antimicrobials, diuretics, antidiabetics, and other clinical applications. This inspiring chemical nucleus has promoted several research groups to investigate the synthesis of new [...] Read more.
Since the synthesis of prontosil the first prodrug shares their chemical moiety, sulfonamides exhibit diverse modes of actions to serve as antimicrobials, diuretics, antidiabetics, and other clinical applications. This inspiring chemical nucleus has promoted several research groups to investigate the synthesis of new members exploring new clinical applications. In this study, a novel series of 5(4H)-oxazolone-based-sulfonamides (OBS) 9ak were synthesized, and their antibacterial and antifungal activities were evaluated against a wide range of Gram-positive and -negative bacteria and fungi. Most of the tested compounds exhibited promising antibacterial activity against both Gram-positive and -negative bacteria particularly OBS 9b and 9f. Meanwhile, compound 9h showed the most potent antifungal activity. Moreover, the OBS 9a, 9b, and 9f that inhibited the bacterial growth at the lowest concentrations were subjected to further evaluation for their anti-virulence activities against Pseudomonas aeruginosa and Staphylococcus aureus. Interestingly, the three tested compounds reduced the biofilm formation and diminished the production of virulence factors in both P. aeruginosa and S. aureus. Bacteria use a signaling system, quorum sensing (QS), to regulate their virulence. In this context, in silico study has been conducted to assess the ability of OBS to compete with the QS receptors. The tested OBS showed marked ability to bind and hinder QS receptors, indicating that anti-virulence activities of OBS could be due to blocking QS, the system that controls the bacterial virulence. Furthermore, anticancer activity has been further performed for such derivatives. The OBS compounds showed variable anti-tumor activities, specifically 9a, 9b, 9f and 9k, against different cancer lines. Conclusively, the OBS compounds can serve as antimicrobials, anti-virulence and anti-tumor agents. Full article
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24 pages, 5031 KiB  
Article
The Anticancer Action of a Novel 1,2,4-Triazine Sulfonamide Derivative in Colon Cancer Cells
by Agnieszka Gornowicz, Anna Szymanowska, Mariusz Mojzych, Robert Czarnomysy, Krzysztof Bielawski and Anna Bielawska
Molecules 2021, 26(7), 2045; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26072045 - 02 Apr 2021
Cited by 15 | Viewed by 2657
Abstract
Cancer therapy is one of the most important challenges of modern medical and chemical sciences. Among the many methods of combating cancer, chemotherapy plays a special role. Imperfect modern chemotherapy justifies continuing the search for new, more effective, and safe drugs. Sulfonamides are [...] Read more.
Cancer therapy is one of the most important challenges of modern medical and chemical sciences. Among the many methods of combating cancer, chemotherapy plays a special role. Imperfect modern chemotherapy justifies continuing the search for new, more effective, and safe drugs. Sulfonamides are the classic group of chemotherapeutic drugs with a broad spectrum of pharmacological activity. Recent literature reports show that sulfonamide derivatives have anti-tumor activity in vitro and in vivo. The aim of the study was to synthesize a novel 1,2,4-triazine sulfonamide derivative and check its anticancer potential in DLD-1 and HT-29 colon cancer cells. The biological studies included MTT assay, DNA biosynthesis, cell cycle analysis, Annexin V binding assay, ethidium bromide/acridine orange staining, and caspase-8, -9, and -3/7 activity. The concentrations of important molecules (sICAM-1, mTOR, Beclin-1, cathepsin B) involved in the pathogenesis and poor prognosis of colorectal cancer were also evaluated by ELISA. We demonstrated that the novel compound was able to induce apoptosis through intrinsic and extrinsic pathways and was capable of decreasing sICAM-1, mTOR, cathepsin B concentrations, whereas increased Beclin-1 concentration was detected in both colon cancer cell lines. The novel compound represents promising multi-targeted potential in colorectal cancer, but further in vivo examinations are needed to confirm the claim. Full article
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