Methods for substitution of the thioxo group with the oxo group in imidazolidine-2-thione derivatives

Kuptsova, A. O.; Vinogradova, Ekaterina E.; Кравченко, Ангелина Н.; Газиева, Галина А.

doi:10.1007/s11172-022-3488-0

Cited by 12 publications

(2 citation statements)

References 71 publications

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“…From a synthetic point of view, the conversion of thione group into the corresponding oxo analog has been reported by several efficient approaches [10].…”

Section: Introductionmentioning

confidence: 99%

3a-(4-Chlorophenyl)-1-thioxo-2,3,3a,4-tetrahydroimidazo[1,5-a]quinazolin-5(1H)-one

Defant,

Innocenti,

Mancini

2024

Preprint

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With the aim to produce new heterocycle molecules, the previously reported 2-(aminomethyl)-2-(4-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one was converted efficiently by reacting with N,N’-dithiocarbonyldiimidazole (DTCI), to produce the substituted imidazolidine-2-thione moiety inserted in a three fused ring scaffold of the title compound. The molecular composition was confirmed by a high-resolution MS experiment, and its structure was elucidated by 1H, 13CNMR, and IR analyses. The thioacetamide form of the product was supported by density functional theory (DFT)-NMR analysis where 13C chemical shifts of thioacetamide form and of its iminothiol tautomer were calculated in chloroform at the BP86 /Jgauss-TZP2 level of theory. The very good linear correlation between 13C chemical shifts by experiment and by calculation for the NHC=S form confirmed the structure.

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“…From a synthetic point of view, the conversion of thione group into the corresponding oxo analog has been reported by several efficient approaches [10].…”

Section: Introductionmentioning

confidence: 99%

3a-(4-Chlorophenyl)-1-thioxo-2,3,3a,4-tetrahydroimidazo[1,5-a]quinazolin-5(1H)-one

Defant,

Innocenti,

Mancini

2024

Preprint

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“…Imidazole and benzimidazole cores are widely found in natural products and biologically active compounds [ 8 , 9 , 10 , 11 , 12 , 13 , 14 ]. 2-Thioderivatives of imidazole were found to possess antifungal activity [ 15 , 16 , 17 , 18 , 19 , 20 , 21 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation on the Fungicidal Activity of S-Alkyl Substituted Thioglycolurils

Vinogradova

Alekseenko

Попков

et al. 2023

IJMS

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A series of S-alkyl substituted thioglycolurils was prepared through the alkylation of corresponding thioglycolurils with halogenoalkanes and tested for their fungicidal activity against six phytopathogenic fungi from different taxonomic classes: Venturia inaequalis, Rhizoctonia solani, Fusarium oxysporum, Fusarium moniliforme, Bipolaris sorokiniana, and Sclerotinia sclerotiorum, and two pathogenic yeasts: Candida albicans and Cryptococcus neoformans var. grubii. A number of S-alkyl substituted thioglycolurils exhibited high activity against Venturia inaequalis and Rhizoctonia solani (85–100% mycelium growth inhibition), and moderate activity against other phytopathogens. S-Ethyl substituted thioglycolurils possessed a high activity against Candida albicans. Additionally, the hemolytic and cytotoxic properties of promising derivatives were determined using human red blood cells and human embryonic kidney cells, respectively. Two S-ethyl derivatives possessed both low cytotoxicity against normal human cells and high fungicidal activity against Candida albicans.

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Synthesis and antiplatelet activity of 2-substituted imidazolines

et al. 2023

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Methods for substitution of the thioxo group with the oxo group in imidazolidine-2-thione derivatives

Cited by 12 publications

References 71 publications

3a-(4-Chlorophenyl)-1-thioxo-2,3,3a,4-tetrahydroimidazo[1,5-a]quinazolin-5(1H)-one

3a-(4-Chlorophenyl)-1-thioxo-2,3,3a,4-tetrahydroimidazo[1,5-a]quinazolin-5(1H)-one

Synthesis and Evaluation on the Fungicidal Activity of S-Alkyl Substituted Thioglycolurils

Synthesis and antiplatelet activity of 2-substituted imidazolines

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