DOI 10.1007/s11094-020-02295-8
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-5-
hydroxymethyl-1,3-dioxane esters were established on HEK293 and SH-SY5Y cell lines. Potential antioxi-
dant properties of 7,11,18,21-tetraoxaspiro-5,2,2,5-heneicosane, 2-[(5-ethyl-5-hydroxymethyl)-1,3-diox-
an-2-yl]phenol, 4.4-[oxydi(methylene)]-bis-2-diisopropyl-1,3-dioxolane, 4,4¢-[oxydi(methylene)]-bis-1,3-di-
oxolane, (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-dioxola-
nes, 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]. Further-
more, these compounds are attractive because of their poten-
tial 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 dipenta-
erythritol, ethriol, and diglycerol and esters of 5-ethyl-5-hyd-
roxymethyl-1,3-dioxane and to study their cytotoxic and an-
tioxidant 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
CDCl on a Bruker Avance-500 spectrometer (500.13 MHz).
3
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
CH ), 1.96 – 2.02 (m, 2H, 2 CH), 3.54 – 3.69 (m, 8H, 4
3
CH ), 4.69 (d, 2H, 2 CH, J 2.9 Hz).
2
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
CH ), 2.98 – 3.41 (m, 8H, 4 CH ).
2
2
Oxy-bis(methylene-1,5-dioxaspiro-5,5-undecane-3,3-
diyl)dimethanol (11). Mp 58 – 59 °C. PMR spectrum, d ,
ppm: 1.51 – 1.29 (m, 20H, 10 CH ), 2.66 (d, 4H, 4 CH , J
2
a
3.1 Hz), 2.96 (d, 4H, 4 CH , J 3.0 Hz), 3.62 (s, 4H, 2 CH ),
EXPERIMENTAL CHEMICAL PART
b
2
4.12 (s, 4H, 2 CH ).
2
Chromatographic analysis of the reaction products used
an HRGC 5300 Mega Series Carlo Erba chromatograph with
a flame-ionization detector (He carrier gas, flow rate
2-[(5-Ethyl-5-hydroxymethyl)-1, 3-dioxan-2-yl]phenol
(12). Viscous colorless liquid. PMR spectrum, d , ppm: 0.85
(s, 3H, CH ), 1.20 (t, 2H, CH , J 5.0, 11.0 Hz), 3.08 (s, 2H,
3
2
CH ), 3.56 – 3.60 (m, 4H, 2 CH ), 4.90 (d, 1H, CH, J
1
2
2
Ufa State Petroleum Technical University, 1 Kosmonavtov St., Ufa,
2.7 Hz), 6.90 – 7.12 (m, 5H, Ph).
Bashkortostan, 450064 Russia.
2
Institute of Biochemistry and Genetics, Ufa Scientific Center of the Rus-
4,4¢-[Oxydi(methylene)]-bis-2-diisopropyl-1,3-dioxo-
lane (13). Viscous colorless liquid. PMR spectrum, d , ppm:
sian Academy of Sciences, 71 – 1E Prosp. Oktyabrya, Ufa, Bashkorto-
stan, 450054 Russia.
*
e-mail: graskildina444@mail.ru
1.52 – 1.58 (m, 2H, 2 CH), 1.85 (s, 12H, 4 CH ), 3.70 (d, 4H,
3
909
0091-150X/20/5409-0909 © 2020 Springer Science+Business Media, LLC