Iodine-promoted direct thiolation (selenylation) of imidazole with disulfides (diselenide): A convenient and metal-free protocol for the synthesis of 2-arylthio(seleno)imidazole

Yi, Rongnan; Liu, Sen; Gao, Hongxia; Liang, Zhiwu; Xu, Xinhua

doi:10.1016/j.tet.2020.130951

Cited by 18 publications

(12 citation statements)

References 59 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[2,3] The heterocyclic derivatives of imidazole (C 3 H 4 N 2 ), which is an important member of the heterocyclic aromatic compounds, have been widely studied in the field of pharmaceutical chemistry and other fields due to their versatile use and various biological activities. [4][5][6][7][8] Thiadiazole is a heterocyclic aromatic compound that has a five-member ring with 2 nitrogen atoms and one sulfur atom, in addition to carbon and hydrogen atoms. There are four different isomers of thiadiazoles named 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, and 1,3,4-thiadiazole, according to the Hantzsch-Widman nomenclature.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural characterization, biological activity, and theoretical studies of some novel thioether‐bridged 2,6‐disubstituted imidazothiadiazole analogues

Tunel

Alıcı

et al. 2021

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

In this study, thioether-bridged imidazo [2,1-b][1,3,4]thiadiazole derivatives that contained both imidazole and 1,3,4-thiadiazole (compounds 7a-7i and 8a-8i) were synthesized from the reactions of 2-amino-1,3,4-thiadiazole with phenacyl bromide (6a-6i) (at yields of 59% to 74%). The structure of the synthesized compounds was characterized using 1 H NMR, 13 C NMR, Fouriertransform infrared spectroscopy, elemental analysis, mass spectroscopy, and Xray diffraction analysis. Mycelial growth, mycelial growth inhibition, minimum inhibitory concentration, minimum fungicidal concentration, and lethal dose values against various plant pathogenic fungi were determined for all of the target compounds synthesized in the study. The test results showed that most of the compounds had moderate to good antifungal activity. In addition, the absorption, distribution, metabolism, excretion (ADME) parameters of the compounds were calculated, and it was observed that all of the compounds met the drug-likeness rules in general. Finally, using docking simulations, it was found that compounds 7h, 7i, 8h, and 8i showed high affinity to PDB ID:5TZ1, which is an CYP51 antifungal target structure.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis, structural characterization, biological activity, and theoretical studies of some novel thioether‐bridged 2,6‐disubstituted imidazothiadiazole analogues

Tunel

Alıcı

et al. 2021

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…Imidazole and its derivatives are also widely studied in the field of pharmaceutical chemistry due to their versatile use and various biological activities. [10] Heterocyclic systems in which imidazole and 1,3,4-thiadiazole rings are fused to each other with a bridgehead nitrogen atom are referred to as imidazo [2,1-b] [1,3,4]thiadiazoles. [11][12][13] Imidazo [2,1-b] [1,3,4]thiadiazoles and their derivatives have become widely used compounds in pharmaceutical chemistry due to their broad spectrum of biological activities such as antimicrobial, antibacterial, antifungal, antiviral, antioxidant, anticonvulsant, antidepressant, anti-inflammatory, antituberculosis, antihypertensive, and antiproliferative activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Antimicrobial Evaluation, and Computational Investigation of Substituted Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives

Dagli

Karakurt

et al. 2020

ChemistrySelect

View full text Add to dashboard Cite

In this study, a novel series of 2,6-disubstituted and 2,5,6trisubstituted imidazo[2,1-b][1,3,4]thiadiazole derivatives were synthesized starting from 2-amino-1,3,4-thiadiazole derivatives. Structures of the synthesized compounds were characterized using various analysis techniques. Then, in vitro biological activity tests were carried out for all synthesized compounds and they were found to show moderate to good activity against all bacteria and fungi tested. Next, molecular docking simulations were performed to observe the inhibition effect of the synthesized compounds on the 3R9C receptor and support their biological activity results. Finally, the pharmacokinetic, ADME and toxicity properties of all compounds were examined using FAF-Drugs and ProTox webservers and it was concluded that they had acceptable toxicity and ADME properties.

show abstract

“…In this sense, another metal‐free and suitable methodology promoted by iodine to access 2‐arylselenoimidazoles of formula 123 in good to excellent reaction yield has been reported. This transformation is presented in Scheme 28 [139] …”

Section: Chemistrymentioning

confidence: 99%

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Sonego,

de Diego,

Szajnman

et al. 2023

Chemistry A European J

View full text Add to dashboard Cite

Selenium, originally described as a toxin, turns out to be a crucial trace element for life that appears as selenocysteine and its dimer, selenocystine. From the point of view of drug developments, selenium‐containing drugs are isosteres of sulfur and oxygen with the advantage that the presence of the selenium atom confers antioxidant properties and high lipophilicity, which would increase cell membrane permeation leading to better oral bioavailability. In this article, we have focused on the relevant features of the selenium atom, above all, the corresponding synthetic approaches to access a variety of organoselenium molecules along with the proposed reaction mechanisms. The preparation and biological properties of selenosugars, including selenoglycosides, selenonucleosides, selenopeptides, and other selenium‐containing compounds will be treated. We have attempted to condense the most important aspects and interesting examples of the chemistry of selenium into a single article.

show abstract

Iodine-promoted direct thiolation (selenylation) of imidazole with disulfides (diselenide): A convenient and metal-free protocol for the synthesis of 2-arylthio(seleno)imidazole

Cited by 18 publications

References 59 publications

Synthesis, structural characterization, biological activity, and theoretical studies of some novel thioether‐bridged 2,6‐disubstituted imidazothiadiazole analogues

Synthesis, structural characterization, biological activity, and theoretical studies of some novel thioether‐bridged 2,6‐disubstituted imidazothiadiazole analogues

Synthesis, Characterization, Antimicrobial Evaluation, and Computational Investigation of Substituted Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Contact Info

Product

Resources

About