Sulfa drug analogs: new classes of N-sulfonyl aminated azines and their biological and preclinical importance in medicinal chemistry (2000–2018)

Elgemeie, Galal H.; Azzam, Rasha A.; Elsayed, Rasha E.

doi:10.1007/s00044-019-02378-6

Cited by 66 publications

(40 citation statements)

References 52 publications

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Section: Figurementioning

confidence: 99%

“…Sulfonamide moietiesa re ubiquitous in pharmaceuticals due to the high metabolic stability,w ater solubility,a nd biological response elicited by thesep harmacophores (Figure 1). [1] Of the numerous sulfur-containing drugs, 30 %a re known to contain as ulfonamide functional group. [2] As ar esult, these motifs have becomei ncreasingly prevalent throughout small molecule libraries and pharmaceutical discoveryp rograms.…”

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confidence: 99%

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Late‐Stage ¹⁸O Labeling of Primary Sulfonamides via a Degradation–Reconstruction Pathway

Reilly

Bennett

Fier

et al. 2020

Chemistry A European J

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A late‐stage 18O labeling approach of sulfonamides that employs the corresponding unlabeled molecule as the starting material was developed. Upon deamination of the sulfonamide, a sulfinate intermediate was isotopically enriched using eco‐friendly reagents H218O and 15NH3(aq) to afford a M+5 isotopologue of the parent compound. This degradation–reconstruction approach afforded isolated yields of up to 96 % for the stable isotope labeled (SIL) sulfonamides, and was compatible with multiple marketed therapeutics, including celecoxib, on a gram scale. The SIL products also exhibited no 18O/16O back exchange under extreme conditions, further validating the utility of this green strategy for drug labeling for both in vitro and in vivo use. This procedure was also adapted to include pharmaceutically relevant methyl sulfones by using 13CH3, affording M+5 isotopic enrichment, thereby illustrating the broad utility of this methodology.

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Section: Figurementioning

confidence: 99%

mentioning

confidence: 99%

Late‐Stage ¹⁸O Labeling of Primary Sulfonamides via a Degradation–Reconstruction Pathway

Reilly

Bennett

Fier

et al. 2020

Chemistry A European J

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“…Sulfonamide antibioticsare used as veterinary medicines to treat infectionsin livestock herds [9,10]. Additionally, sulfonamides are extremely useful pharmaceutical compounds because they exhibit a good range of biological activities like anticancer, anti-inflammatory, and antiviral activity [11][12][13][14][15]. The sulphonylation of amines with sulphonyl chlorides within the presence of a base remains getting used because the method of choice due to high efficiency and ease of the reaction [16].Sulfonamide are used as protecting groups of OH or NH functionalities for straightforward removal under mild conditions [17,18].…”

Section: Fig 1; Prontosilmentioning

confidence: 99%

“…It was found that non-peptidic protease inhibitors display higher bioavailability as well as slower excretion rate compared to the conventional peptide-base protease inhibitors. Among those protease inhibitors Amprenavir and Tipranavir aresulfonamide derived drugs[11][104,105].…”

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confidence: 99%

Sulfonamides: Synthesis and the recent applications in Medicinal Chemistry

et al. 2020

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This review spotlights on sulfonamides from different sides, including history, structure-activity relationship, chemistry, methods of classification and up to date ways for their synthesis. Moreover, the review includes a discussion of the varied pharmacological effects of sulfonamides. Sulfonamides have a good range of pharmacological activities like oral diuretics (furosemide, indapamide, chlorthalidone, thiazides); anticancer (E7070), carbonic anhydrase (CA) inhibitors (CAIs) (acetazolamide, dichlorophenamide, dorzolamide and brinzolamide), antiepileptics (zonisamide and sulthiame), for rheumatoid arthritis (Sulfasalazine) antiviral (Darunavir) anti-inflammatory (celecoxib), antibacterial (Sulfadizine), as ophthamologicals (Dorzolamide) anticonvulsant (Zonisamide) cycloxygenase 2 (COX2) inhibitors (valdecoxib). These days, novel pills are launched, like apricoxib and pazopanib, which additionally include this organization. The sulfonamides competitively inhibit vitamin Bc synthesis in microorganisms and subsequently inhibit multiplication of bacteria but donot actively kill them. They need been used against most gram-positive and lots of gram-negative bacteria, also as some fungi.

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“…Recently, we conducted numerous research investigations to develop different innovative synthetic methods for the preparation of N -sulfonylamino and N -sulfonyl-based heterocyclic compounds that have come into application as new forms for antiviral and antimicrobial agents. 1 − 4 Series of N -sulfonylpyrazole, synthesized by our group, 5 , 6 were evaluated against the enzyme cathepsin B.16 and breast adenocarcinoma MCF-7 cell line. 7 , 8 Similarly, the N -arylsulfonylpyrazole series was also identified to be active as inhibitors of the NS2B-NS3 enzyme.…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of a New Class of Pyridine-Based N-Sulfonamides Exhibiting Antiviral, Antimicrobial, and Enzyme Inhibition Characteristics

2020

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A new strategy for designing and assembling a novel class of functionalized pyridine-based benzothiazole and benzimidazole incorporating sulfonamide moieties was developed. The synthesis was carried out by reacting N -cyanoacetoarylsulfonylhydrazide with various electrophiles such as 2-(benzo[ d ]thiazol-2-yl)-3,3-bis(alkylthio)acrylonitriles and 2-(benzo[ d ]imidazol-2-yl)-3,3-bis(methylthio)-acrylonitriles, as well as 2-ethoxyl acrylonitrile derivatives. The synthesized compounds were tested for their antiviral and antimicrobial potency. Two of the synthesized compounds, 15c and 15d , showed more than 50% viral reduction against HSV-1 and CBV4, with significant IC 50 and CC 50 values. The two potent compounds 15c and 15d have also shown inhibitory activity against Hsp90α protein with IC 50 values of 10.24 and 4.48 μg/mL, respectively. A combination of 15c and 15d with acyclovir has led to IC 50 values that are lower than that of acyclovir alone. Molecular modeling studies were used to identify the interactions between the 15c and 15d compounds and the active site of Hsp90α enzyme. The antimicrobial investigation of the new compounds has also shown that 8b and 15d exhibited a higher inhibition zone (IZ) than sulfadiazine and gentamicin against Klebsiella pneumonia, whereas 9a showed higher IZ than ampicillin against Staphylococcus aureus . According to the enzyme assay study on dihydrofolate reductase, 9a was shown to be the most potent compound among all examined compounds.

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Sulfa drug analogs: new classes of N-sulfonyl aminated azines and their biological and preclinical importance in medicinal chemistry (2000–2018)

Cited by 66 publications

References 52 publications

Late‐Stage ¹⁸O Labeling of Primary Sulfonamides via a Degradation–Reconstruction Pathway

Late‐Stage ¹⁸O Labeling of Primary Sulfonamides via a Degradation–Reconstruction Pathway

Sulfonamides: Synthesis and the recent applications in Medicinal Chemistry

Design and Synthesis of a New Class of Pyridine-Based N-Sulfonamides Exhibiting Antiviral, Antimicrobial, and Enzyme Inhibition Characteristics

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Sulfa drug analogs: new classes of N-sulfonyl aminated azines and their biological and preclinical importance in medicinal chemistry (2000–2018)

Cited by 66 publications

References 52 publications

Late‐Stage 18O Labeling of Primary Sulfonamides via a Degradation–Reconstruction Pathway

Late‐Stage 18O Labeling of Primary Sulfonamides via a Degradation–Reconstruction Pathway

Sulfonamides: Synthesis and the recent applications in Medicinal Chemistry

Design and Synthesis of a New Class of Pyridine-Based N-Sulfonamides Exhibiting Antiviral, Antimicrobial, and Enzyme Inhibition Characteristics

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Product

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Late‐Stage ¹⁸O Labeling of Primary Sulfonamides via a Degradation–Reconstruction Pathway

Late‐Stage ¹⁸O Labeling of Primary Sulfonamides via a Degradation–Reconstruction Pathway