Synthesis and characterization of 2,5-dibutylthio-2,3-dihydro-2-formyl-4H-pyran thiosemicarbazones and their copper complexes

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Abstract

Previously unknown derivatives of thiosemicarbazide were obtained in high yields by the condensation reaction of 2,5-dibutylthio-2,3-dihydro-2-formyl-4H-pyran with 4-phenylthiosemicarbazide or thiosemicarbazide when boiling in EtOH. The reaction products are represented by colored oils. Cu(II) complexes based on 2,5-dibutylthio-2,3-dihydro-2-formyl-4H-pyran carbazones were synthesized by their interaction with copper (II) chloride. All these complexes are soluble in dimethylformamide (DMF) and dimethyl sulfoxide (DMSO) and, according to elemental analysis, have a 1:1 metal-ligand stoichiometry. The obtained compounds were studied using IR and 1H, 13C, 15N NMR spectroscopy, as well as elemental analysis. The obtained copper-containing complexes with thiosemicarbazones are of particular interest due to their pronounced biological activity. The thiosemicarbazone 2,5-dibutylthio-2,3-dihydro-2-formyl-4H-pyran compound was subjected to primary screening for acute toxicity. The obtained results showed that, when taken intragastricaly, the studied compound can be characterized as a substance with a low risk of acute toxicity. According to the DL50 parameter, the compound belongs to the V hazard class (DL50>2000 mg/kg).

About the authors

E. A. Verochkina

A. E. Favorsky Irkutsk Institute of Chemistry SB RAS

Email: kleptsova84@mail.ru

N. V. Vchislo

A. E. Favorsky Irkutsk Institute of Chemistry SB RAS

Email: vchislo@bk.ru

L. I. Larina

A. E. Favorsky Irkutsk Institute of Chemistry SB RAS

Email: larina@irioch.irk.ru

E. A. Titov

A. E. Favorsky Irkutsk Institute of Chemistry SB RAS; East-Siberian Institute of Medical and Ecological Research

Email: g57097@yandex.ru

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