Experimental and Theoretical Spectroscopic Study of Thione-Thiol Tautomerism of New Hybrides 1,3,4-Oxadiazole-2-thion with Acridine-9(10H)-one

Karpenko, Yu. V.; Omelyanchik, L. O.; Panasenko, T. G.

doi:10.23939/chcht12.04.419

Cited by 4 publications

(3 citation statements)

References 39 publications

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“…For example, iLOGP takes Gibbs energy into account and is calculated using GB/SA in water and n-octanol. According to studies, MLOGP should be less than 4.15, XLOGP3 should be in the range of -0.7 to +5.0 [15,16], and WLOGP should be less than 5.88 [13]. The majority of compounds from the virtual library correspond to these lipophilicity criteria (Table 2).…”

Section: Discussionmentioning

confidence: 99%

“…An important factor for parenterally administered drugs is their solubility in water (expressed in log S values), which determines the amount of active substance that can be administered in a small therapeutic dose (Table 3). The solubility class is usually evaluated on a log S scale, where "insoluble" < -10 < "poorly soluble" < -6 < "moderately soluble" < -4 < "soluble" < -2 < "well soluble" < 0 < "highly soluble" [13]. According to the ESOL model, the expected values of log S should not exceed -6.…”

Section: Discussionmentioning

confidence: 99%

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Synthesis and properties of 6-(2,6-dichlorophenyl)-3- (3-methyl-1H-pyrazol-5-yl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b] [1,3,4]thiadiazine-7-carboxylic acid and its salts

Fedotov

Gotsulya

2023

АП

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Carboxylic acids and their derivatives are an important component of many biological processes. For example, they can be used to create new medicines that can be useful in the fight against various diseases. Additionally, compounds containing a thiazole moiety may possess beneficial properties in practical pharmacy. The incorporation of this heterocyclic structure in molecules can positively impact several biological characteristics, such as anti-inflammatory, antiviral, and antifungal activities. Consequently, exploring novel compounds that combine a thiazole fragment with a carboxyl group holds promise for the advancement of new drugs and diagnostic tools that can contribute significantly to the battle against numerous diseases. The aim of the work was to create a number of organic and inorganic salts of 6-(2,6-dichlorophenyl)-3-(3-methyl-1H-pyrazol-5-yl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine-7-carboxylic acid and study of their properties, as well as selective determination of the biological potential of these compounds. Materials and methods. The synthetic part of the study involved the sequential synthesis of the original compound 4-amino-5-(3-methyl-1H-pyrazol-5-yl)-1,2,4-triazole-3-thiol using a well-established method described in previous articles. The next stage involved the reaction of thiol with 2,3-dichlorobenzaldehyde in a medium of glacial acetic acid. The resulting Schiff base was subsequently reacted with 2-chloroethanoic acid in tetrahydrofuran in the presence of an equimolar amount of sodium hydride. Salts of the corresponding acid were formed during the reaction of 6-(2,6-dichlorophenyl)-3-(3-methyl-1H-pyrazol-5-yl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine-7-carboxylic acid with both organic and inorganic bases in an aqueous-alcohol medium. The structures of all synthesized compounds were determined using 1H NMR spectroscopy and elemental analysis. Additionally, the individuality of each compound was confirmed using high-performance liquid chromatography-mass spectrometry. Results. The study determined the optimal conditions for the formation of both organic and inorganic salts of 6-(2,6-dichlorophenyl)-3-(3-methyl-1H-pyrazol-5-yl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine-7-carboxylic acid. The analysis of pharmacokinetic parameters and physicochemical properties using ADME (absorption, distribution, metabolism, and excretion) allowed for the identification of promising synthesized compounds and the selection of more optimal compounds for further investigation. Conclusions. The structure of 12 compounds was synthesized and confirmed. Physical-chemical and pharmacokinetic analysis of ADME parameters was carried out and promising compounds were selected for more in-depth research.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Synthesis and properties of 6-(2,6-dichlorophenyl)-3- (3-methyl-1H-pyrazol-5-yl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b] [1,3,4]thiadiazine-7-carboxylic acid and its salts

Fedotov

Gotsulya

2023

АП

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“…44 Heteroaromatic thiol which remain equilibrium between tautomeric thione and thiol changes the reactivity pattern of thiol group compared to simple heteroaryl or aryl thiols. 45 The only report wherein both heteroaromatic thiols and thiones engaged in C-3 sulfenylation of imidazo[1,2-a]pyridine used I2 as catalyst and DMSO as oxidant (Scheme 1; entry 3). 46 To the best of our knowledge, sulfenylation of imidazo[1,2-a]pyridine using using 1,3,4-oxadiazole-2-thiol has not been reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel imidazopyridine-oxadiazole molecular hybrids by a regioselective sulfenylation of imidazo[1,2-a]pyridines with 1,3,4-oxadiazole-2-thiols using I2-FeCl3 catalytic system and O2/air as co-oxidant

Ghosh¹,

Dutta²,

Kushwah³

et al. 2022

Arkivoc

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Imidazo[1,2-a]pyridine and 1,3,4-oxadiazole are privileged scaffolds in medicinal chemistry owing to their diverse biological as well as pharmacological properties. They also have wide applications in material chemistry due to their interesting photophysical properties. Combining these two scaffolds through a thioether linkage leads to novel imidazopyridine-oxadiazole hybrids. This has been achieved by a regioselective C-3 sulfenylation of imidazo[1,2-a]pyridines with 1,3,4-oxadiazole-2-thiols using I2-FeCl3 as an efficient catalytic system and aerial oxygen as co-oxidant. This protocol provides a general, mild, efficient and atom-economic method for C-3 sulfenylation of imidazo[1,2-a]pyridines with 1,3,4-oxadiazole-2-thiols, a class of heterocyclic thiols not being used in such reactions.

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Solvent promoted tautomerism in thione-containing tetraazatricyclics: evidence from 1H NMR spectroscopy and transition state studies

2022

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Experimental and Theoretical Spectroscopic Study of Thione-Thiol Tautomerism of New Hybrides 1,3,4-Oxadiazole-2-thion with Acridine-9(10H)-one

Cited by 4 publications

References 39 publications

Synthesis and properties of 6-(2,6-dichlorophenyl)-3- (3-methyl-1H-pyrazol-5-yl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b] [1,3,4]thiadiazine-7-carboxylic acid and its salts

Synthesis and properties of 6-(2,6-dichlorophenyl)-3- (3-methyl-1H-pyrazol-5-yl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b] [1,3,4]thiadiazine-7-carboxylic acid and its salts

Synthesis of novel imidazopyridine-oxadiazole molecular hybrids by a regioselective sulfenylation of imidazo[1,2-a]pyridines with 1,3,4-oxadiazole-2-thiols using I2-FeCl3 catalytic system and O2/air as co-oxidant

Solvent promoted tautomerism in thione-containing tetraazatricyclics: evidence from 1H NMR spectroscopy and transition state studies

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