Chiral sulfonamides with various N-heterocyclic and aromatic units – Synthesis and antiviral activity evaluation

Iwan, Dominika; Kamińska, Karolina; Denel-Bobrowska, Marta; Olejniczak, Agnieszka B.; Wojaczyńska, Elżbieta

doi:10.1016/j.biopha.2022.113473

Cited by 8 publications

(4 citation statements)

References 26 publications

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“…Lower activity of 2-azabicyclo[2.2.1]heptanesulfonamide 6 was also observed against AdV5 and HPIV-3 with IC 50 = 7.5 ± 0.8 µM (SI = 1.8) and IC 50 = 1.5 ± 0.2 µM (SI = 2.8). At the same time, 2-azabiycolo[3.2.1]octane 3 showed minor antiviral activity against HPIV-3 [30].…”

Section: Antiviral Sulfonamide Derivativesmentioning

confidence: 91%

“…In their work, [30] presented the synthesis of chiral N-heterocycles based on arylsulfonamides. 2-Azabicyloalkane derivatives (2-azabicyclo[2.2.1]heptane and 2-azabicyclo[3.2.1]octane) contained dansyl-and biphenylsulfonamide fragments (compounds 3 and 6).…”

Section: Antiviral Sulfonamide Derivativesmentioning

confidence: 99%

“…Compounds 3 and 6 were obtained by the classical method for sulfonamide chemistry, which consists in the treatment of amines (in this case, bicyclic amines 2 or 5) with available aryl-substituted sulfonyl chlorides (1 or 4). Substrates 2 and 5 were obtained by a stereoselective aza-Diels-Alder reaction (cyclopentadiene with in situ generated Shiff base reaction [30,31]). The most significant antiviral activity of compounds 3 and 6 was observed against EMCV with IC 50 = 22.0 ± 2.6 µM and IC 50 = 18.3 ± 2.0 µM, respectively, with selectivity indexes (SI) of 40.3 and 19.6.…”

Section: Antiviral Sulfonamide Derivativesmentioning

confidence: 99%

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Sulfonamides with Heterocyclic Periphery as Antiviral Agents

Moskalik

2022

Molecules

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Sulfonamides are the basic motifs for a whole generation of drugs from a large group of antibiotics. Currently, research in the field of the new sulfonamide synthesis has received a “second wind”, due to the increase in the synthetic capabilities of organic chemistry and the study of their medical and biological properties of a wide spectrum of biological activity. New reagents and new reactions make it possible to significantly increase the number of compounds with a sulfonamide fragment in combination with other important pharmacophore groups, such as, for example, a wide class of N-containing heterocycles. The result of these synthetic possibilities is the extension of the activity spectrum—along with antibacterial activity, many of them exhibit other types of biological activity. Antiviral activity is also observed in a wide range of sulfonamide derivatives. This review provides examples of the synthesis of sulfonamide compounds with antiviral properties that can be used to develop drugs against coxsackievirus B, enteroviruses, encephalomyocarditis viruses, adenoviruses, human parainfluenza viruses, Ebola virus, Marburg virus, SARS-CoV-2, HIV and others. Since over the past three years, viral infections have become a special problem for public health throughout the world, the development of new broad-spectrum antiviral drugs is an extremely important task for synthetic organic and medicinal chemistry. Sulfonamides can be both sources of nitrogen for building a nitrogen-containing heterocyclic core and the side chain substituents of a biologically active substance. The formation of the sulfonamide group is often achieved by the reaction of the N-nucleophilic center in the substrate molecule with the corresponding sulfonylchloride. Another approach involves the use of sulfonamides as the reagents for building a nitrogen-containing framework.

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Section: Antiviral Sulfonamide Derivativesmentioning

confidence: 91%

Section: Antiviral Sulfonamide Derivativesmentioning

confidence: 99%

Section: Antiviral Sulfonamide Derivativesmentioning

confidence: 99%

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Sulfonamides with Heterocyclic Periphery as Antiviral Agents

Moskalik

2022

Molecules

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“…While a pioneer study in the utilization of the 2-azabicyclo[3.2.1]octane system in asymmetric organocatalysis, the des and ees obtained were not outstanding, and no other studies were performed in this topic. The free amine additionally proved useful for the synthesis of chiral thioureas ( 151 ) 31 and sulfonamides ( 152 ), the latter displaying promising antiviral 32 and antiproliferative activity, 18 g and also cytotoxicity to cancer cell lines. 7…”

Section: Synthesis Of 2-azabicyclo[321]octanes By Rearrangementsmentioning

confidence: 99%