Comparative in vitro study of the growth regulative activity of potato microplants under the influence of derivatives 1,2,3-triazolo-1,3,4-thiadiazines

Vysokova, O. A.; Калинина, Т. А.; Kanwugu, Osman N.; Cherepanova, Olga A; Kochubei, A. A.; Koksharova, M. K.; Глухарева, Т. В.

doi:10.1063/1.5087397

Cited by 2 publications

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“…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.…”

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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

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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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