Synthesis of 4,4′-substituted 2,2′-[ethane-1,2-diylbis(selanediyl)]bis(1H-imidazol-5(4H)-ones)

Article abstract of DOI:10.1007/s11172-021-3108-4

Synthesis of new bis(seleno-imidazolone) derivatives bearing the alkyl and aryl moieties at the N(1) atom of the five-membered ring was developed. Cytotoxicity of the synthesized compounds against A549, VA-13, MCF-7, and HEK293T cell lines was evaluated.

Full text of DOI:10.1007/s11172-021-3108-4

Russian Chemical Bulletin, International Edition, Vol. 70, No. 3, pp. 457—462, March, 2021
457
Synthesis of 4,4´-substituted
2,2´-[ethane-1,2-diylbis(selanediyl)]bis(1H-imidazol-5(4H)-ones)
A. V. Finko,a A. I. Sokolov,a L. A. Vasilyeva,a D. A. Skvortsov,a A. S. H. Al-Khazraji,b
E. N. Ofitserov,b N. V. Zyk,a A. G. Majouga,a,b and E. K. Beloglazkinaa
aDepartment of Chemistry, Lomonosov Moscow State University,
1 Leninskie Gory, 119991 Moscow, Russian Federation.
E-mail: finko.alexander@gmail.com
bDmitry Mendeleev University of Chemical Technology of Russia,
9 Miusskaya pl., 125047 Moscow, Russian Federation
Synthesis of new bis(seleno-imidazolone) derivatives bearing the alkyl and aryl moieties at
the N(1) atom of the five-membered ring was developed. Cytotoxicity of the synthesized com-
pounds against A549, VA-13, MCF-7, and HEK293T cell lines was evaluated.
Key words: imidazolone, 2-selenohydantoine, bis(seleno) derivatives, organoselenium
compounds, alkylation, cytotoxicity, MTT test, in vitro.
Bis-thioimidazolone derivatives
To date, a wide variety of the organoselenium deriva-
tives have been described that show antioxidant,1—6 anti-
tumor,7 antiviral,8 antimicrobial,9 antithyroid10 effects
and other biological activities.11 Interest in organosele-
nium chemistry increased significantly after finding that
selenium is present in glutathione peroxidase, the mam-
malian enzyme that regulates the concentration of the
reactive oxygen species in cells.12 Lysova and coworkers13
have reported the synthesis of metal-organic frameworks
R = Alk, Ar, HetAr
based on N-donor Se-containing ligand; luminescence of
X = CH, N
the synthesized structures was found to be due to intra-
ligand transitions.
Bis-selenoimidazolone derivatives
Bis-thioimidazolone derivatives14,15 were used as the
ligands to obtain complexes of different metals (Cu+1
,
Cu+2, Co+2 16—22
compounds with potential antifungal activity.23
)
and some of them were developed as
Bis-selenoimidazolone derivatives and their biological
properties are less studied. Synthesis of complex com-
pounds of selenoimidazolones with Co+2, Ni+2, Cu+2
,
and Cu+1 and their electrochemical properties (oxidation
and reduction potentials) were first reported in 2012.24
Biological activities of 3-aryl-5-arylidene-2-selenohy-
dantoins were studied.25 It was found that in the pairs
of 2-thiohydantoin and 2-selenohydantoin derivatives
with the same substituents, the Se-containing com-
pounds are more active.
The aim of the present work is to synthesize 4-al-
kylidene- and 4-arylidene-substituted derivatives of
2-selenohydantoin dimers and study their antitumor
activity in vitro. It should be noted that dispiro deriva-
tives of 2-selenohydantoin with promising antioxidant
and cytotoxic activities were recently synthesized.26
R1, R2 = Alk, Ar
Results and Discussion
Compound 1 used as the starting material in the syn-
thesis of 4-alkylidene- and 4-arylidene-substituted de-
rivatives was synthesized as earlier described.25 Seleno-
ureas 2a—c and 2-selenohydantoins 3a—f were prepared
as shown in Scheme 1 following the known procedures.27,28
Previously,24 compound 3d was synthesized in 25%
yield; while the method reported in the present work
provides the target compounds in the yields above 55%.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 457—462, March, 2021.
1066-5285/21/7003-0457 © 2021 Springer Science+Business Media LLC

Finko et al.
458
Russ. Chem. Bull., Int. Ed., Vol. 70, No. 3, March, 2021
Scheme 1
Reagents and conditions: i. R1NH2, DMAP (1 mol.%) or base-free, Et2O; ii. 1) R2CHO, KOH (2%), EtOH; 2) NH4Cl/H2O.
Com-
pound
R1
R2
Yield
(%)
Com-
pound
R1
R2
Yield
(%)
2a
2b
—
—
97
3c
98
Ph
41
3d
3e
Ph
Ph
Ph
58
76
2c
—
82
3a
3b
69
91
3f
55
Ph
The intermediate selenohydantoins of type 3 are capable
of undergoing selenol-selenone tautomerism and, there-
fore, show high SeH acidity (cf. pKa (Me—SeH)29 = 5.2;
pKa (Ph—SeH)30 = 5.9). These compounds are readily
deprotonated on treatment with inorganic bases in polar
aprotic solvents (DMSO, DMF).
When compounds 3a—f were treated with excess
K2CO3 in DMF, the color of the reaction mixture changed
to red due to the selenolate formation. To the obtained
solution of selenolate, 1,2-dibromoethane was added
portionwise at –10 °C. 1,2-Dibromoethane reacted with
selenolate to form an ethylene bridge between two seleno-
hydantoin moieties. The full conversion was achieved
within 8—9 h (Scheme 2). The reaction conditions for the
synthesis of compounds 4a—f were optimized with respect
of the base (Cs2CO3, K2CO3) and solvent (DMSO, DMF).
It was found that both Cs2CO3 and K2CO3 provide nearly
the same yields of the target products, therefore, less
expensive K2CO3 was preferred. In DMSO, the content
of monoalkylation products was higher and prolongation
of the reaction time led to resinification of the reaction
mixture.
Thus, we synthesized a series of 2-selenohydantoin
dimers 4a—f bearing aliphatic and aromatic substituents
at N(1).
Cytotoxicity of the synthesized compounds 4a—f was
evaluated in vitro (Table 1) against MCF-7 (metastatic
breast cancer), A549 (lung adenocarcinoma), VA-13
(slow-growing human lang fibroblasts), and HEK293T
(easily transducable human embryonic kidney 293 cells
expressing a mutant variant of SV40 large T antigen) cell
lines using standard MTT assay.31 Enzalutamide (antian-
drogen)32,33 and Nutlin-3a (inhibitor of the p53/MDM2
interaction)34,35 were used as the reference drugs.
Table 1. Cytotoxicity (CC50) of the synthesized compounds 4a—f
Compound
CC50/μmol L–1
VA-13
A549
MCF-7
HEK293T
4a
4b
4c
4d
4e
4f
3.3 0.5
7.5 1.4
13.9 3.1
16.9 3.2
1.9 0.3
14.4 1.1
—
2.7 0.4
25.0 5.8
8.0 0.7
17.5 2.3
52.7 16
32.7 5.5
131.8 46.4
4.8 0.5
33.5 5.1
8.3
9.9 0.7
54.1 12.5
4.7 0.7
3.1 0.9
4.5 0.3
12.5 0.8
—
4.6 1
1.7 0.1
11.6 0.9
15.1
Nutlin-3a
Enzalutamide
63.4
21.2
>100
5.1 0.3

New bis(seleno-imidazolone) derivatives
Russ. Chem. Bull., Int. Ed., Vol. 70, No. 3, March, 2021
459
Scheme 2
Reagents and conditions: 1,2-dibromoethane (0.5 equiv.), K2CO3 (1.5 equiv.), DMF, –10 °C.
using precoated plates Merck Silicagel 60 F254
.
1H NMR and
All studied compounds exhibited high nonspecific
cytotoxicity against the test cell lines. Compounds 4c and
4d showed selective cytotoxic effect against HEK293T and
A549 cells as compared to the non-cancerous cell line
VA-13. Compound 4e occurred most cytotoxic; its CC50
value is almost an order of magnitude higher than that of
the reference compounds and compounds 4a and 4f bear-
ing the isopropylidene substituents at the position 5 of the
imidazolone ring. For more detailed evaluation of the
cytotoxicity effect of the synthesized compounds, a broader
array of the cell lines is required as well as additional stud-
ies of the mechanism of cytotoxicity, for instance, the
studies of binding of the compounds with bovine serum
albumin, their ability to intercalate into the DNA duplex,
proteasome inhibitory activity, etc.
13H NMR spectra were recorded on Bruker Avance 400 instru-
ment in CDCl3 and DMSO-d6. IR spectra were recorded with
a UR-20 IR spectrometer in Nujol and a Termo Nicolet IR200
FT-IR spectrometer at a resolution of 4 cm–1. The reactions
were monitored by LC/MS using Thermo Dionex Ultimate 3000
and ABSciex 3200 Qtrap instruments equipped with a quadruple
detector and a Thermo Scientific Acclaim RSLC 120 C18 3 μm
column (150×4.6 mm). High-resolution electrospray ionization
mass spectrometry was performed with a Bruker microTOF II
instrument. Melting points of the synthesized compounds were
measured with an OptiMelt MPA100 automated melting point
system with the heating rate from 0.1 to 20 °deg min–1 (maximum
temperature of 400 °C, accuracy of 0.1 °C).
Synthesis of ethyl 2-[3-alkyl(aryl)selenoureido]acetates (2a—c)
was described in detail in our previous publication.27 To a solu-
tion of amine (1 equiv.) in anhydrous diethyl ether, ethyl 2-iso-
selenocyanoacetate 1 (1.1 equiv.) was added dropwise. The reaction
mixture was stirred for 30 min and DMAP (1 mol.%) was added.
Stirring was continued for 2—12 h. The precipitated selenoureas
2a—c were collected by filtration using filtration funnels with
glass sintered disc, washed with small amount of chilled diethyl
ether, and dried under vacuum of the water jet pump.
Experimental
All starting reagents are commercially available and were
used as purchased. The reaction course was monitored by TLC

Finko et al.
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Russ. Chem. Bull., Int. Ed., Vol. 70, No. 3, March, 2021
Synthesis of 2-selenohydantoins 3a—f (general procedure).27,28
(4Z,4´Z)-2,2´-[Ethane-1,2-diylbis(selanediyl)]bis[1-cyclo-
propyl-4-(2-methylpropylidene)-1H-imidazol-5(4H)-one] (4a)
was prepared from (Z)-3-cyclopropyl-5-(2-methylpropylidene)-
2-selenoxoimidazolidin-4-one (3a) (90 mg) and 1,2-dibromo-
ethane (33 mg). Yield 67 mg (71%). White crystals. M.p.
Selenoureas 2 (1 equiv.) were added to 2% solution of KOH in
EtOH (10 mL) under vigorous stirring. After 5 min, the mixture
acquired a deep violet color. Then the appropriate aldehyde
(1.2 equiv.) was added. The reaction mixture was stirred at 20 °C
for 2 h, neutralized to pH 4.5 with a saturated aqueous ammo-
nium hydrochloride solution, and extracted with dichlorometh-
ane (3×50 mL). The combined organic layers were dried with
Na2SO4 and the solvent was removed in vacuo. The residue
was subjected to flash column chromatography (elution with
dichloromethane). The eluates containing the target product
were concentrated in vacuo to dryness. The obtained solid was
recrystallized from glacial AcOH to give pure Z isomers of com-
pounds 3a—f.
1
172—173 °C. H NMR (400 MHz, CDCl3), δ: 0.96 (ddd, 8 H,
4 CH2Cycl; J = 6.5 Hz, J = 3.8 Hz, J = 2.5 Hz); 1.11 (d, 12 H,
4 Me, J = 6.7 Hz); 2.57 (dq, 2 H, 2 CHCycl, J = 6.5 Hz,
J = 4.2 Hz); 3.18 (qd, 2 H, 2 CHiobut, J = 13.3 Hz, J = 6.6 Hz);
3.72 (s, 4 H, 2 CH2); 6.14 (d, 2 H, 2 CH, J = 9.6 Hz). 13C NMR
(101 MHz, CDCl3), δ: 6.5 (4 C), 22.4 (4 C), 22.5 (2 C), 26.6
(2 C), 27.5 (2 C), 138.0 (2 C), 139.8 (2 C), 160.9 (2 C), 169.0
(2 C). IR (diamond), ν/cm–1: 577, 662, 712, 755, 826, 934, 971,
1032, 1100, 1114, 1131, 1180, 1229, 1286, 1370, 1397, 1455,
1509, 1663, 1719, 1728, 2866, 2963, 3015. HRMS (FTMS + cESI):
found 543.0766 [M + H]+; calculated for C22H30N4O2Se2
543.0772.
(4Z,4´Z)-2,2´-[Ethane-1,2-diylbis(selanediyl)]bis[4-benzyl-
idene-1-cyclopropyl-1H-imidazol-5(4H)-one] (4b) was prepared
from (Z)-5-benzylidene-3-cyclopropyl-2-selenoxoimidazolidin-
4-one (3b) (80 mg) and 1,2-dibromoethane (22 mg). Yield 56 mg
(67%). Yellow crystals. M.p. 236—237 °C. 1H NMR (400 MHz,
CDCl3), δ: 1.02—1.07 (m, 8 H, 4 CH2Cycl); 2.64—2.70 (m, 2 H,
2 CHCycl); 3.91 (s, 4 H, 2 CH2); 6.87 (s, 2 H, 2 CH); 7.37—7.41
(m, 6 H, HAr); 8.10—8.12 (m, 4 H, HAr). 13C NMR (101 MHz,
CDCl3), δ: 6.5 (4 C), 22.6 (2 C), 26.7 (2 C), 124.5 (2 C), 128.7
(4 C), 130.1 (2 C), 132.0 (4 C), 134.5 (2 C), 139.0 (2 C), 163.4
(2 C), 169.9 (2 C). IR (diamond), ν/cm–1: 539, 552, 581,
617, 656, 693, 727, 783, 765, 829, 873, 938, 954, 1007, 1029,
1107, 1153, 1179, 1196, 1212, 1288, 1315, 1329, 1237, 1374,
1351, 1399, 1427, 1449, 1570, 1491, 1636, 1717, 3047. HRMS
(FTMS + cESI): found m/z 611.0450 [M + H]+; calculated for
C28H26N4O2Se2 611.0459.
Physicochemical and spectral data of compounds 3a,c,d,f
coincide with those published earlier.27,28
(Z)-5-Benzylidene-3-cyclopropyl-2-selenoxoimidazolidin-4-
one (3b) was prepared from ethyl 2-(3-cyclopropylselenoureido)
acetate (2a) (0.25 g) and benzaldehyde (0.115 mL). Yield 0.28 g
(91%). Orange crystals. M.p. 155—156 °C. 1H NMR (400 MHz,
DMSO-d6), δ: 0.95—1.01 (m, 4 H, CH2Cyclo); 2.86 (ddd, 1 H,
CHCyclo, J = 11.1 Hz, J = 7.3 Hz, J = 4.1 Hz); 6.65 (s, 1 H, CH);
7.41—7.45 (m, 3 H, HAr); 7.78—7.80 (m, 2 H, HAr); 12.80 (s, 1 H,
NH). 13C NMR (101 MHz, DMSO-d6), δ: 6.7 (2 C), 25.4, 113.2,
126.7, 128.8 (2 C), 129.5, 130.3 (2 C), 132.4, 164.0, 180.6.
IR (KBr), ν/cm–1: 451, 554, 579, 690, 724, 760, 821, 874,
958, 925, 1027, 1054, 1088, 1169, 1206, 1236, 1313, 1266, 1326,
1435, 1497, 1461, 1651, 1728, 1740, 3011, 3058, 3200. HRMS
(FTMS + cESI): found m/z 293.0188 [M + H]+; calculated for
C13H12N2OSe 293.0188.
(Z)-5-(2-Methylpropylidene)-3-phenyl-2-selenoxoimidazol-
idin-4-one (3e) was prepared from ethyl 2-(3-phenylselenoure-
ido)acetate (2b) (035 g) and isobutyraldehyde (125 mL). Yield
0.274 g (76%). Yellow crystals. M.p. 202—203 °C. 1H NMR
(400 MHz, DMSO-d6), δ: 1.07 (d, 6 H, 2 Me, J = 6.5 Hz); 3.01
(qd, 1 H, CH, J = 13.0 Hz, J = 6.6 Hz); 5.84 (d, 1 H, CH,
J = 10.5 Hz); 7.34 (d, 2 H, HAr, J = 7.1 Hz); 7.47 (m, 3 H, HAr);
12.95 (s, 1 H, NH). 13C NMR (75 MHz, DMSO-d6), δ: 21.6
(2 C), 26.5, 125.7, 128.2, 128.7 (2 C), 128.8, 128.9 (2 C), 134.0,
162.2, 177.8. IR (KBr), ν/cm–1: 409, 440, 501, 522, 607, 627,
668, 687, 734, 754, 860, 880, 903, 943, 968, 989, 1015, 1056,
1084, 1123, 1145, 1156, 1171, 1211, 1242, 1272, 1308, 1369,
1382, 1433, 1452, 1471, 1483, 1576, 1645, 1700, 2937, 3222.
HRMS (FTMS + cESI): found m/z 293.0196 [M – H]–; calcu-
lated for C13H14N2OSe 293.0198.
Synthesis of 4,4´-substituted 2,2´-[ethane-1,2-diylbis(selanyl-
diyl)]bis[1H-imidazol-5(4H)-ones] (4a—f) (general procedure).
To a solution of (Z)-3-substituted 5-[(alkyl/aryl)idene]-2-
selenoxoimidazolidin-4-one 3 (1 equiv.) in DMF, K2CO3
(1.5 equiv.) was added. The obtained mixture was stirred for
10 min, cooled to –10 °C, and treated portionwise with 1,2-di-
bromoethane (0.5 equiv.). After 3—4 h, the reaction mixture
was warmed to ~20 °C, this resulted in the change in the color
of the reaction mixture from red to yellow. After the reaction
completion (TLC monitoring), the mixture was diluted with
water, the precipitate obtained was collected by filtration using
filtration funnels with glass sintered disc, and successively washed
with EtOH and diethyl ether. The obtained dry powder was
subjected to column chromatography. The eluates containing
the target products were concentrated in vacuo and recrystallized
from dichloromethane—petroleum ether to give pure products 4.
(4Z,4´Z)-2,2´-[Ethane-1,2-diylbis(selanediyl)bis[1-cyclopro-
pyl-4-(4-ethoxybenzylidene)-1H-imidazol-5(4H)-one] (4c) was
prepared from (Z)-3-cyclopropyl-5-(4-ethoxybenzylidene)-2-
selenoxoimidazolidin-4-one (3c) (73 mg) and 1,2-dibromoethane
(18 mg). Yield 51 mg (68%). Yellow crystals. M.p. 231—232 °C.
1H NMR (400 MHz, CDCl3), δ: 1.01 (s, 8 H, 4 CH2Cycl);
1.42—1.45 (t, 6 H, 2 OCH2CH3, J = 6.2 Hz); 2.63—2.69 (s, 2 H,
2 CHCycl); 3.90 (s, 4 H, 2 CH2); 4.07 (q, 4 H, 2 OCH2CH3,
J = 11.8 Hz, J = 6.0 Hz); 6.85 (s, 2 H, 2 CH), 6.89 (d, 4 H, HAr
,
J = 7.4 Hz); 8.07 (d, 4 H, HAr, J = 7.2 Hz). 13C NMR (101 MHz,
CDCl3), δ: 6.52 (4 C), 14.9 (2 C), 22.6 (2 C), 26.7 (2 C), 63.7
(2 C), 114.8 (4 C), 124.8 (2 C), 127.2 (2 C), 133.9 (4 C), 137.2
(2 C), 160.6 (2 C), 161.4 (2 C), 170.0 (2 C). IR (diamond),
ν/cm–1: 488, 540, 560, 581, 660, 724, 757, 811, 834, 873, 893,
923, 954, 1003, 1031, 1042, 1085, 1109, 1148, 1175, 1211, 1240,
1306, 1348, 1253, 1369, 1396, 1423, 1443, 1495, 1565, 1508,
1630, 1599, 1710, 2925, 2982, 3083. HRMS: (FTMS + cESI):
found m/z 699.0974 [M + H]+; calculated for C32H34N4O4Se2
699.0984.
(4Z,4´Z)-2,2´-[Ethane-1,2-diylbis(selanediyl)]bis[4-benzyl-
idene-1-phenyl-1H-imidazol-5(4H)-one] (4d) was prepared from
(Z)-5-benzylidene-3-phenyl-2-selenoxoimidazolidin-4-one (3d)
(100 mg) and 1,2-dibromoethane (28 mg). Yield 86 mg (83%).
Yellow crystals. M.p. 245—246 °C. 1H NMR (400 MHz, CDCl3),
δ: 3.94 (s, 4 H, 2 CH2); 7.00 (s, 2 H, CH); 7.33—7.38 (m, 10 H,
HAr); 7.47—7.55 (m, 6 H, HAr); 8.14 (d, 4 H, HAr, J = 4.1 Hz).
13C NMR (101 MHz, CDCl3), δ: 26.9 (2 C), 125.5 (2 C),
127.2 (4 C), 128.8 (4 C), 129.5 (2 C), 129.8 (4 C), 130.3 (2 C),

New bis(seleno-imidazolone) derivatives
Russ. Chem. Bull., Int. Ed., Vol. 70, No. 3, March, 2021
461
132.2 (4 C), 133.0 (2 C), 134.4 (2 C), 138.3 (2 C), 160.9 (2 C),
168.7 (2 C). IR (diamond), ν/cm–1: 559, 639, 658, 689, 717,
760, 727, 774, 891, 925, 946, 1026, 1063, 1107, 1152, 1206, 1228,
1284, 1304, 1320, 1349, 1361, 1398, 1448, 1488, 1571, 1595,
1634, 1728, 3021, 3423. HRMS (FTMS + cESI): found m/z
683.0470 [M + H]+; calculated for C34H26N4O2Se2 683.0459.
(4Z,4´Z)-2,2´-[Ethane-1,2-diylbis(selanediyl)]bis[4-(2-meth-
ylpropylidene)-1-phenyl-1H-imidazol-5(4H)-one] (4e) was pre-
pared from (Z)-5-(2-methylpropylidene)-3-phenyl-2-selen-
oxoimidazolidin-4-one (3e) (80 mg) and 1,2-dibromoethane
(26 mg). Yield 42 mg (60%). White crystals. M.p. 166—167 °C.
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1H NMR (400 MHz, CDCl3), δ: 1.14 (d, 12 H, 4 Meisobut
,
J = 6.7 Hz); 3.24 (qd, 2 H, 2 CHisobut, J = 13.5 Hz, J = 6.7 Hz);
3.74 (s, 4 H, 2 CH2); 6.30 (d, 2 H, 2 CH, J = 9.7 Hz); 7.26—7.30
(m, 4 H, HAr); 7.43—7.50 (m, 6 H, HAr). 13C NMR (101 MHz,
CDCl3), δ: 22.3 (4 C), 26.9 (2 C), 27.7 (2 C), 127.2 (4 C), 127.3
(2 C), 129.4 (2 C), 129.7 (4 C), 129.82 (2 C), 129.84 (2 C), 133.0
(2 C), 139.2 (2 C). IR (diamond), ν/cm–1: 422, 506, 585,
613, 631, 660, 707, 750, 721, 842, 767, 881, 921, 943, 971, 1026,
1055, 1073, 1112, 1129, 1173, 1211, 1285, 1356, 1383, 1397,
1452, 1596, 1513, 1662, 1733, 2869, 2928, 2965, 3052. HRMS
(FTMS + cESI): found m/z 615.0764 [M + H]+; calculated for
C28H30N4O2Se2 615.0772.
(4Z,4´Z)-2,2´-[Ethane-1,2-diylbis(selanediyl)]bis[1-(4-meth-
oxyphenyl)-4-(2-methylpropylidene)-1H-imidazol-5(4H)-one]
(4f) was prepared from (Z)-3-(4-methoxyphenyl)-5-(2-methyl-
propylidene)-2-selenoxoimidazolidin-4-one (3f) (70 mg) and
1,2-dibromoethane (21 mg). Yield 61 mg (84%). White crystals.
M.p. 119—120 °C. 1H NMR (400 MHz, CDCl3), δ: 1.13 (d, 12 H,
4 Meisobut, J = 6.7 Hz); 3.18—3.27 (m, 2 H, 2 CHisobut); 3.72
(s, 4 H, 2 CH2); 3.83 (s, 6 H, 2 OMe); 6.28 (d, 2 H, 2 CH,
J = 9.7 Hz); 6.97 (d, 4 H, HAr, J = 8.8 Hz); 7.19 (d, 4 H, HAr
,
17. E. K. Beloglazkina, A. G. Majouga, R. B. Romashkina, A. A.
Moiseeva, N. V. Zyk, Polyhedron, 2007, 26, 797; DOI:
10.1016/j.poly.2006.09.012.
18. A. G. Majouga, E. K. Beloglazkina, O. V. Shilova, A. A.
Moiseeva, N. V. Zyk, Russ. Chem. Bull., 2009, 58, 1392; DOI:
10.1007/s11172-009-0185-1.
19. E. K. Beloglazkina, A. G. Majouga, A. V. Mironov, A. V.
Yudina, O. Yu. Kuznetsova, N. V. Zyk, Polyhedron, 2014, 76,
45; DOI: 10.1016/j.poly.2014.03.045.
J = 8.7 Hz). 13C NMR (101 MHz, CDCl3), δ: 22.3 (4 C), 26.7
(2 C), 27.7 (2 C), 55.7 (2 C), 114.9 (4 C), 125.4 (2 C), 128.7
(4 C), 128.8 (2 C), 138.9 (2 C), 139.3 (2 C), 160.3 (2 C), 168.0
(2 C). IR (diamond), ν/cm–1: 534, 593, 734, 745, 754, 834, 936,
947, 1024, 1108, 1131, 1172, 1185, 1211, 1299, 1283, 1259, 1360,
1446, 1454, 1506, 1514, 1606, 1655, 1729, 2864, 2961. HRMS
(FTMS + cESI): found m/z 675.0976 [M + H]+; calculated for
C30H34N4O4Se2 675.0983.
20. A. Majouga, M. Zvereva, M. Rubtsova, D. Skvortsov,
A. Mironov, D. Azhibek, O. Krasnovskaya, V. Gerasimov,
A. Udina, N. Vorozhtsov, E. Beloglazkina, L. Agron,
L. Mikhina, A. Tretyakova, N. Zyk, N. Zefirov, A. Kabanov,
O. Dontsova, J. Med. Chem., 2014, 57, 6252; DOI: 10.1021/
jm500154f.
21. E. K. Beloglazkina, O. O. Krasnovskaya, D. A. Guk, V. A.
Tafeenko, A. A. Moiseeva, N. V. Zyk, A. G. Majouga, Poly-
hedron, 2018, 148, 129; DOI: 10.1016/j.poly.2018.04.005.
22. O. O. Krasnovskaya, D. A. Guk, A. E. Naumov, V. N.
Nikitina, A. S. Semkina, K. Yu. Vlasova, V. Pokrovsky, O. O.
Ryabaya, S. S. Karshieva, D. A. Skvortsov, I. V. Zhirkina,
R. R. Shafikov, P. V. Gorelkin, A. N. Vaneev, A. S. Erofeev,
D. M. Mazur, V. A. Tafeenko, V. I. Pergushov, M. Ya.
Melnikov, M. A. Soldatov, V. V. Shapovalov, A. V. Soldatov,
R. A. Akasov, V. M. Gerasimov, D. A. Sakharov, A. A.
Moiseeva, N. V. Zyk, E. K. Beloglazkina, A. G. Majouga,
J. Med. Chem., 2020, 63, 13031; DOI: 10.1021/acs.
jmedchem.0c01196.
This work was performed within the framework of the
State assignment of Lomonosov Moscow State University
using the equipment of Center of the collective usage of MSU.
This paper does not contain descriptions of studies on
animals or humans.
The authors declare no competing interests.
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Received November 23, 2020;
in revised form December 9, 2020;
accepted December 28, 2020