Macroheterocyclic Compound of ABBB-Type Containing 2N-Alkyl Substituted 1,2,4-Thiadiazoline Fragment: Synthesis and Acid-Base Properties

Butina, Yu. V.; Данилова, Е. А.; Kudayarova, T. V.; Malyasova, A. S.

doi:10.6060/mhc180166d

Cited by 3 publications

(5 citation statements)

References 10 publications

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“…[29] Though the yield of the Mcs obtained was low because of the difficulty of their purification they had very interesting properties of molecular chameleons, [30] which is an unique ability for postsynthetic modification of the molecular optic properties. [31] The UV-Vis spectra of compounds 5-8, 16-18, 24-28 were similar to each other. [24,28,31] There were two absorption bands at 263-283 nm and at 473-532 nm.…”

Section: Abbb-type Mcs With Various Heterocyclic Fragmentsmentioning

confidence: 57%

“…[31] The UV-Vis spectra of compounds 5-8, 16-18, 24-28 were similar to each other. [24,28,31] There were two absorption bands at 263-283 nm and at 473-532 nm. The first band (263-283 nm) indicates the presence of the heterocyclic fragment.…”

Section: Abbb-type Mcs With Various Heterocyclic Fragmentsmentioning

confidence: 57%

“…[28] and 1,3,4-thiadiazole-containing (5-8) [24] Mcs corresponded to the resonance of protons at intracyclic nitrogen atom of isoindole moieties. In 1 H NMR spectra of 1,2,4-thiadiazole-containing Mcs (24-28) [31] the similar signals are not observed. Mcs (24)(25)(26)(27)(28) were revealed to be protonated both at the absence of protons and the presence of nitrogen atoms in the intracyclic cavity.…”

Section: Abbb-type Mcs With Various Heterocyclic Fragmentsmentioning

confidence: 87%

“…The phenomenon was studied by us both experimentally in two systems: CH 2 Cl 2 -CF 3 COOH and C 2 H 5 OH-H 2 SO 4 and theoretically by DFT method with B3LYP hybrid functional and the 6-31G (d,p) basic set. [31] According to spectrophotometric titration, one acid molecule participated in protonation at the first stage. Quantum chemistry calculation demonstrated that the most energetically favor-able configuration was the one in which the proton addition takes place at the intracyclic nitrogen atom of the isoindole residue located opposite the thiadiazole ring.…”

Section: Abbb-type Mcs With Various Heterocyclic Fragmentsmentioning

confidence: 99%

See 3 more Smart Citations

Triazole- and Thiadiazolecontaining Macroheterocycles: Review of Main Achievements for Last Decade

Suvorova¹,

Kustova²,

Данилова³

et al. 2020

MHC

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Section: Abbb-type Mcs With Various Heterocyclic Fragmentsmentioning

confidence: 57%

Section: Abbb-type Mcs With Various Heterocyclic Fragmentsmentioning

confidence: 57%

Section: Abbb-type Mcs With Various Heterocyclic Fragmentsmentioning

confidence: 87%

Section: Abbb-type Mcs With Various Heterocyclic Fragmentsmentioning

confidence: 99%

See 2 more Smart Citations

Triazole- and Thiadiazolecontaining Macroheterocycles: Review of Main Achievements for Last Decade

Suvorova¹,

Kustova²,

Данилова³

et al. 2020

MHC

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“…Макрогетероциклические соединения (Мс) проявляют нелинейно-оптические, люминесцентные, жидкокристаллические, противоопухолевые, антибактериальные свойства, которые позволяют широко использовать подобные молекулы в технике и медицине [1][2][3][4][5][6][7][8]. Все большее значение приобретают Мс с расширенной π-электронной системой и координационной полостью, которая способна вмещать один атом металла большого радиуса или несколько атомов меньшего радиуса.…”

Section: Introductionunclassified

Synthesis and Properties of Bisthiadiazoles with Ethyl and Butyl Spacers

Suvorova¹,

Petukhova²,

Данилова³

et al. 2020

Liq. Cryst. and their Appl.

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This article is devoted to a selection of the most effective preparative method for the synthesis of bis(5-amino-1,3,4-thiadiazole-2-yl)alkanes. These compounds are binuclear diamines consisting of symmetrical 1,3,4-thiadiazole fragments connected by alkyl spacers of various lengths. The structures of the obtained compounds were determined by IR spectroscopy, mass-spectrometry and elemental analysis. The possibility of using these molecules as precursors for the synthesis of macroheterocyclic compounds with expended coordination cavity consisting of six small cycles was demonstrated. Optimal synthesis conditions of bis(5-amino-1,3,4-thiadiazole-2-yl)ethane and bis(5-amino-1,3,4-thiadiazole-2-yl)butane were found by variation of reaction time and temperature. Virtual screening of the obtained compounds was carried out in order to predict antibacterial and biological activities as well as toxic properties of the targeted products. On the basis of the known literature data on polynuclear diamines, the exhibition of the liquid crystal properties of the synthesized molecules is supposed.

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The prediction of the spectrum of biological activity and antimicrobial properties of diaminoazoles

et al. 2019

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The work is devoted to predicting and studying biological properties of N-substituted analogs of 3,5-diamino-1,2,4-thiadiazole, which, in their turn, include in the composition of many drugs that exhibit a wide range of pharmacological actions. For searching of new alternative drugs with an antibacterial activity, but lacking resistance of microorganism strains to them, a computer screening of 2N-alkyl-substituted 5-amino-3-imino-1,2,4-thiadiazolines previously synthesized by us was carried out. The prediction of the spectrum of biological activity, as well as the determination of the probable toxicity of these compounds, was performed using the freely available computer programs PASS, Anti-Bac-Pred, and GUSAR. The study of the antibacterial activity in vitro against gram-positive (Staphylococcus aureus, Staphylococcus saprophyticus, Staphylococcus epidermidis) and gram-negative (Escherichia coli, Pseudomonas aeruginosae) bacterial strains was performed by the disco-diffusion method. Experimental data roughly correspond to the predictions.

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Macroheterocyclic Compound of ABBB-Type Containing 2N-Alkyl Substituted 1,2,4-Thiadiazoline Fragment: Synthesis and Acid-Base Properties

Cited by 3 publications

References 10 publications

Triazole- and Thiadiazolecontaining Macroheterocycles: Review of Main Achievements for Last Decade

Triazole- and Thiadiazolecontaining Macroheterocycles: Review of Main Achievements for Last Decade

Synthesis and Properties of Bisthiadiazoles with Ethyl and Butyl Spacers

The prediction of the spectrum of biological activity and antimicrobial properties of diaminoazoles

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