Biological Activity of Some Heterocyclic Compounds Based on Polyol Acetals and their Derivatives

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Pharmaceutical Chemistry Journal, Vol. 54, No. 9, December, 2020 (Russian Original Vol. 54, No. 9, September, 2020)

BIOLOGICAL ACTIVITY OF SOME HETEROCYCLIC COMPOUNDS BASED ON POLYOL ACETALS AND THEIR DERIVATIVES G. Z. Raskil’dina,1,* U. Sh. Kuz’mina,2 Yu. G. Borisova,1 Yu. V. Vakhitova,2 and S. S. Zlotskii1 Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 54, No. 9, pp. 27 – 31, September, 2020.

Original article submitted June 2, 2020. The biological activity of cyclic acetals (penta- and dipentaerythritol, ethriol, and diglycerol) and 5-ethyl-5-hydroxymethyl-1,3-dioxane esters was studied in vitro. The cytotoxic properties of 5-ethyl-5hydroxymethyl-1,3-dioxane esters were established on HEK293 and SH-SY5Y cell lines. Potential antioxidant properties of 7,11,18,21-tetraoxaspiro-5,2,2,5-heneicosane, 2-[(5-ethyl-5-hydroxymethyl)-1,3-dioxan-2-yl]phenol, 4.4-[oxydi(methylene)]-bis-2-diisopropyl-1,3-dioxolane, 4,4¢-[oxydi(methylene)]-bis-1,3-dioxolane, (5-ethyl-1,3-dioxan-5-yl)methyl-2-methyl acrylate, and bis(5-ethyl-1,3-dioxan-5-yl)methyl maleate were established in vitro using an oxidative stress model. Keywords: acetals, polyols, esters, cytotoxicity in vitro, antioxidant activity in vitro.

Derivatives of 2,2-dimethyl-1,3-dioxolane, 1,3-dioxolanes, and acetals of pentaerythritol and dipentaerythritol are used as additives for oils and polymers and starting materials to synthesize various plasticizers, solvents, stabilizers, alkyd and epoxide resins, corrosion inhibitors, etc. [1 – 3]. Furthermore, these compounds are attractive because of their potential applications in medicine. Compounds of this class are known to possess rather broad spectra of biological activity and have demonstrated cytotoxic, antioxidant, antimicrobial, and antiviral properties [4 – 8]. The goal of the present work was to synthesize new cyclic acetals of penta- and dipentaerythritol, ethriol, and diglycerol and esters of 5-ethyl-5-hydroxymethyl-1,3-dioxane and to study their cytotoxic and antioxidant properties in vitro.

30 mL/min, column length 25 m, programmed heating from 50 to 280°C at 8°C/min). NMR spectra were recorded in CDCl3 on a Bruker Avance-500 spectrometer (500.13 MHz). Acetals 9 – 14 were prepared as before [9]. 3,9-Diisopropyl-2,4,8,10-tetraoxaspiro-5,5-undecane (9). Mp 43 – 44 °C. PMR spectrum, d, ppm: 0.82 (s, 12H, 4 CH3), 1.96 – 2.02 (m, 2H, 2 CH), 3.54 – 3.69 (m, 8H, 4 CH2), 4.69 (d, 2H, 2 CH, J 2.9 Hz). 7,11,18,21-Tetraoxaspiro-5,2,2,5-heneicosane (10). Mp 51 – 52 °C. PMR spectrum, d, ppm: 1.93 – 2.01 (m, 20H, 10 CH2), 2.98 – 3.41 (m, 8H, 4 CH2). Oxy-bis(methylene-1,5-dioxaspiro-5,5-undecane-3,3diyl)dimethanol (11). Mp 58 – 59 °C. PMR spectrum, d, ppm: 1.51 – 1.29 (m, 20H, 10 CH2), 2.66 (d, 4H, 4 CHa, J 3.1 Hz), 2.96 (d, 4H, 4 CHb, J 3.0 Hz), 3.62 (s, 4H, 2 CH2), 4.12 (s, 4H, 2 CH2). 2-[(5-Ethyl-5-hydroxymethyl)-1, 3-dioxan-2-yl]phenol (12). Viscous colorless liquid. PMR spectrum, d, ppm: 0.85 (s, 3H, CH3), 1.20 (t, 2H, CH2, J 5.0, 11.0 Hz), 3.08 (s, 2H, CH2), 3.56 – 3.60 (m, 4H, 2 CH2), 4.90 (d, 1H, CH, J 2.7

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