Synthesis of spiro derivatives of 1,2,3-triazolo[5,1-b][1,3,4]thiadiazines and biological activity thereof

Калинина, Т. А.; Bystrykh, Olga A.; Поздина, Варвара А.; Глухарева, Т. В.; Улитко, М. В.; Morzherin, Yu. Yu.

doi:10.1007/s10593-015-1742-1

Cited by 12 publications

(4 citation statements)

References 19 publications

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“…A Dimroth rearrangement of 1,2,3-thiadiazolylhydrazones 97 give in situ 1,2,3-triazole-4-thiolates 97A , was reacted with α -bromoacetophenones in ethanol with triethylamine; it produced cis and trans -isomers of ethyl-5-aroyl-6-aryl-6,7-dihydro-5 H -[ 1 , 2 , 3 ]triazolo[5,1- b ][1,3,4]thiadiazine-3-carboxylats 98a–g in a 1:4 ratio [ 69 ]. Similarly, spirocyclic 1,2,3-triazolo[5,1- b ]1,3,4-thiadiazines 98h–k was synthesized from the corresponding 3-cyclopentylidene(cyclohexylidene)amino-triazole-4-thiolates [ 70 ] ( Scheme 42 ). The crystal structures of 98h–k were determined using single crystal X-ray diffraction [ 71 ].…”

Section: Synthesis Of Triazolo[51- B ]Thiadiazinesmentioning

confidence: 99%

Synthetic Methods and Pharmacological Potentials of Triazolothiadiazines: A Review

Mostafa,

Radini,

El-Rahman

et al. 2024

Molecules

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This review article examines the synthetic pathways for triazolothiadiazine derivatives, such as triazolo[3,4-b]thiadiazines, triazolo[5,1-b]thiadiazines, and triazolo[4,3-c]thiadiazines, originating from triazole derivatives, thiadiazine derivatives, or thiocarbohydrazide. The triazolothiadiazine derivatives exhibit several biological actions, including antibacterial, anticancer, antiviral, antiproliferative, analgesic, anti-inflammatory, and antioxidant properties. The review article aims to assist researchers in creating new biologically active compounds for designing target-oriented triazolothiadiazine-based medicines to treat multifunctional disorders.

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Section: Synthesis Of Triazolo[51- B ]Thiadiazinesmentioning

confidence: 99%

Synthetic Methods and Pharmacological Potentials of Triazolothiadiazines: A Review

Mostafa,

Radini,

El-Rahman

et al. 2024

Molecules

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“…[1,2,3]Triazolo [5,1-b] [1,3,4]thiadiazines (III)-(V) and (VII) were synthesized according to published procedures (Kalinina et al, 2015(Kalinina et al, , 2017c. Crystals suitable for X-ray diffraction (XRD) analysis were grown by slow evaporation of a solution of the corresponding compound in dimethyl sulfoxide (DMSO) at room temperature.…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

“…Interestingly, many studies have been devoted to s-triazolo [3,4-b][1,3,4]thiadiazines, which have been shown to have a wide spectrum of biological activity, including anticancer (LaPorte et al, 2016;Zhang et al, 2015;Hassan et al, 2018;Kamel & Megally Abdo, 2014;Khan et al, 2014), antimicrobial (Haggam, 2016;Almajan et al, 2010;Karthikeyan et al, 2008;Ghattas et al, 2012;El-Sayed & Asghar, 2014;Ghorab et al, 2000;Hassanien, 2003;Aggarwal et al, 2011;Ö zil et al, 2015) and anti-inflammatory (El Shehry et al, 2010;El-Serwy et al, 2013), while information on the biological profile of isomeric as-triazolo [5,1-b] [1,3,4]thiadiazine is limited. Some recent research has shown that spiro derivatives of as-triazolo [5,1-b] [1,3,4]thiadiazine can inhibit the growth of rhabdomyosarcoma (RD) tumour cells (Kalinina et al, 2015) and some compounds had a stimulating effect on the growth and development of plant seeds (Kalinina et al, 2018;Vysokova et al, 2019) and animal cells (Kalinina et al, 2015). However, the mode of the effect of as-triazolo[5,1-b][1,3,4]-thiadiazines has not been studied so far.…”

Section: Introductionmentioning

confidence: 99%

The different modes of chiral [1,2,3]triazolo[5,1-b][1,3,4]thiadiazines: crystal packing, conformation investigation and cellular activity

Обыденнов

Калинина

Vysokova

et al. 2020

Acta Crystallogr C Struct Chem

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The crystal structures of four new chiral [1,2,3]triazolo[5,1-b][1,3,4]thiadiazines are described, namely, ethyl 5′-benzoyl-5′H,7′H-spiro[cyclohexane-1,6′-[1,2,3]triazolo[5,1-b][1,3,4]thiadiazine]-3′-carboxylate, C19H22N4O3S, ethyl 5′-(4-methoxybenzoyl)-5′H,7′H-spiro[cyclohexane-1,6′-[1,2,3]triazolo[5,1-b][1,3,4]thiadiazine]-3′-carboxylate, C20H24N4O4S, ethyl 6,6-dimethyl-5-(4-methylbenzoyl)-6,7-dihydro-5H-[1,2,3]triazolo[5,1-b][1,3,4]thiadiazine-3-carboxylate, C17H20N4O3S, and ethyl 5-benzoyl-6-(4-methoxyphenyl)-6,7-dihydro-5H-[1,2,3]triazolo[5,1-b][1,3,4]thiadiazine-3-carboxylate, C21H20N4O4S. The crystallographic data and cell activities of these four compounds and of the structures of three previously reported similar compounds, namely, ethyl 5′-(4-methylbenzoyl)-5′H,7′H-spiro[cyclopentane-1,6′-[1,2,3]triazolo[5,1-b][1,3,4]thiadiazine]-3′-carboxylate, C19H22N4O3S, ethyl 5′-(4-methoxybenzoyl)-5′H,7′H-spiro[cyclopentane-1,6′-[1,2,3]triazolo[5,1-b][1,3,4]thiadiazine]-3′-carboxylate, C19H22N4O4S, and ethyl 6-methyl-5-(4-methylbenzoyl)-6-phenyl-6,7-dihydro-5H-[1,2,3]triazolo[5,1-b][1,3,4]thiadiazine-3-carboxylate, C22H22N4O3S, are contrasted and compared. For both crystallization and an MTT assay, racemic mixtures of the corresponding [1,2,3]triazolo[5,1-b][1,3,4]thiadiazines were used. The main manner of molecular packing in these compounds is the organization of either enantiomeric pairs or dimers. In both cases, the formation of two three-centre hydrogen bonds can be detected resulting from intramolecular N—H...O and intermolecular N—H...O or N—H...N interactions. Molecules of different enantiomeric forms can also form chains through N—H...O hydrogen bonds or form layers between which only weak hydrophobic contacts exist. Unlike other [1,2,3]triazolo[5,1-b][1,3,4]thiadiazines, ethyl 5′-benzoyl-5′H,7′H-spiro[cyclohexane-1,6′-[1,2,3]triazolo[5,1-b][1,3,4]thiadiazine]-3′-carboxylate contains molecules of only the (R)-enantiomer; moreover, the N—H group does not participate in any significant intermolecular interactions. Molecular mechanics methods (force field OPLS3e) and the DFT B3LYP/6-31G+(d,p) method show that the compound forming enantiomeric pairs via weak N—H...N hydrogen bonds is subject to greater distortion of the geometry under the influence of the intermolecular interactions in the crystal. For intramolecular N—H...O and S...O interactions, an analysis of the noncovalent interactions (NCIs) was carried out. The cellular activities of the compounds were tested by evaluating their antiproliferative effect against two normal human cell lines and two cancer cell lines in terms of half-maximum inhibitory concentration (IC50). Some derivatives have been found to be very effective in inhibiting the growth of Hela cells at nanomolar and submicromolar concentrations with minimal cytotoxicity in relation to normal cells.

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“…Previously, compounds that selectively accelerate the proliferation of human skin fibroblasts in vitro were discovered ( 10 ). It was found that ethyl 5-(4-ethoxybenzoyl)-5,7-dihydrospiro[[1,2,3]triazolo[5,1- b ][1,3,4]thiadiazine-6,1'-cyclopentane]-3-carboxylate (STT) stimulates skin regeneration ( 5 11 ).…”

Section: Introductionmentioning

confidence: 99%

Spiroconjugated 1,2,3-triazolo[5,1-b]1,3,4-thiadiazine stimulates functional activity of fibroblasts under skin injury regeneration

Petrova,

Chebanova,

Khatsko

et al. 2024

Research in Pharmaceutical Sciences

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Background and purpose: One of the most important mechanisms of tissue regeneration is the high functional activity of cells, including proliferation. Currently, there are practically no effective skin cell activators on the pharmaceutical market. The purpose of this work was to demonstrate the stimulating effect of spiroconjugated 1,2,3-triazolo[5,1-b]1,3,4-thiadiazine (STT) on the functional activity of fibroblasts. Experimental approach: STT containing ointment for dermal application was made. To assess in vivo effect of the STT a linear wound model in rats was tested. A combination of histological techniques and mechanical testing was employed to estimate the stimulating effect of STT on the functional activity of fibroblasts. Findings/Results: The STT significantly increased the number of fibroblasts as well as the density and order of produced collagen fibers in the dermis during the wound healing process. As a result, a tissue was formed at the site of damage with the structure corresponding to normal skin. In addition, skin functions were restored, in particular mechanically. Conclusion and implications: The results suggested the stimulating effect of the STT on fibroblast activity and demonstrated its potential for skin regeneration.

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Synthesis of spiro derivatives of 1,2,3-triazolo[5,1-b][1,3,4]thiadiazines and biological activity thereof

Cited by 12 publications

References 19 publications

Synthetic Methods and Pharmacological Potentials of Triazolothiadiazines: A Review

Synthetic Methods and Pharmacological Potentials of Triazolothiadiazines: A Review

The different modes of chiral [1,2,3]triazolo[5,1-b][1,3,4]thiadiazines: crystal packing, conformation investigation and cellular activity

Spiroconjugated 1,2,3-triazolo[5,1-b]1,3,4-thiadiazine stimulates functional activity of fibroblasts under skin injury regeneration

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