Synthesis and Evaluation of Antibacterial Activity of 1,2,4-Oxadiazole-Containing Biphenylcarboxylic Acids

Article abstract of DOI:10.1134/S1070363220090042

Abstract: A one-pot method for the synthesis of biphenylcarboxylic acids containing 1,2,4-oxadiazole ring in the NaOH–DMSO system was developed. The results of in vitro experiments showed that the synthesized compounds exhibit antibacterial activity against susceptible strains of E. coli and S. aureus.

Full text of DOI:10.1134/S1070363220090042

ISSN 1070-3632, Russian Journal of General Chemistry, 2020, Vol. 90, No. 9, pp. 1611–1619. © Pleiades Publishing, Ltd., 2020.
Russian Text © The Author(s), 2020, published in Zhurnal Obshchei Khimii, 2020, Vol. 90, No. 9, pp. 1349–1357.
Synthesis and Evaluation of Antibacterial Activity
of 1,2,4-Oxadiazole-Containing Biphenylcarboxylic Acids
a,
a
b
a
M. V. Tarasenko *, S. I. Presnukhina , S. V. Baikov , and A. A. Shetnev
a
M.V. Dorogov Center for Transfer of Pharmaceutical Technologies,
K.D. Ushinsky Yaroslavl State Pedagogical University, Yaroslavl, 150000 Russia
b
St. Petersburg State University, St. Petersburg, 199034 Russia
*
e-mail: mkarunnaya@mail.ru
Received April 21, 2020; revised April 21, 2020; accepted April 30, 2020
Abstract—Aone-pot method for the synthesis of biphenylcarboxylic acids containing 1,2,4-oxadiazole ring in the
NaOH–DMSO system was developed. The results of in vitro experiments showed that the synthesized compounds
exhibit antibacterial activity against susceptible strains of E. coli and S. aureus.
Keywords: heterocycles, dicarboxylic acid anhydrides, basic catalysis, antimicrobial activity, amidoximes
DOI: 10.1134/S1070363220090042
1
,2,4-Oxadiazole derivatives have recently attracted
containing a carboxyl group in a step-economic way under
mild conditions [40]. In particular, the 1,2,4-oxadiazole
derivative with 2,2′-biphenylcarboxylic acid was obtained
for the first time (Scheme 1).
much attention of researchers due to the wide use of
these heterocycles both in medicinal chemistry and in
materials science [1–5]. For example, 1,2,4-oxadizole-
containing drugs such as Ataluren (Duchenne’s
disease) [6], Azilsartan (treatment of hypertension) [7],
Opikapon (Parkinson’s disease) [8], Oxolamine (a cough
suppressant) [9], Amenamivir (HIV therapy) [10], and
Naldemidine (pain reliever) [11] are successfully used
in medical practice.
Since 2,2′-biphenyldicarboxylic acids and their
derivatives are of interest as potential antimicrobial agents
[41–43], we studied the reactions of various aromatic and
heterocyclic amidoximes with diphenic anhydrides, and
also evaluated antibacterial activity of the resulting hybrid
structures against Staphylococcus aureus and Escherichia
coli strains, which are examples of important pathogenic
microorganisms.
One of the priority areas of medical application of
1
,2,4-oxadiazoles is the search for new antibacterial
agents, primarily against resistant bacterial strains [12–
0]. This is due to the fact that the growth of resistance
of pathogenic microorganisms to antibacterial drugs is a
global threat of the XXI century [21–26].
Amidoximes 2a–2h were obtained by reacting
commercially available nitriles 1a–1h with an alcoholic
solution of hydroxylamine (Scheme 2) in accordance with
the procedure described in [44].
2
Earlier, we have developed an efficient method for the
synthesis of 1,2,4-oxadiazoles with different functional
peripheries based on the condensation of amidoximes
with carboxylic acids [27] or their derivatives [28–31].
Subsequently, this approach was successfully applied to
obtain biologically active derivatives of 1,2,4-oxadiazole
2,2′-Biphenyldicarboxylic acids 4a–4c were syn-
thesized from anthranilic acids 3a–3c, which were first
converted to diazonium salts and then subjected to copper-
catalyzed coupling (Scheme 3) according to the method
described in [45].
Diphenic anhydrides 5a–5c were obtained by
dehydrationofthecorresponding2,2′-biphenyldicarboxylic
acids 4a–4c under the action of trifluoroacetic acid
anhydride (TFAA) [46] and reacted in situ with
amidoximes 2a–2h (Scheme 3). This reaction occurs in
two stages: the first is the O-acylation of amidoxime 2
with the formation of intermediate 6, which undergoes
[
32–36] (including those with antimicrobial activity [37])
and synthetic building blocks valuable for drug design
38, 39].
Previously, we have reported the reaction of
[
amidoximes with dicarboxylic acid anhydrides, which
makes it possible to obtain 1,2,4-oxadiazole systems
1
611

1612
TARASENKO et al.
Scheme 1.
Scheme 2.
then cyclization to 1,2,4-oxadiazole 7 [40]. The second
stage of this process is sensitive to the medium pH
and can be catalyzed by both acids and bases [47–49];
however, methods using the base catalysis are much more
widespread. In our work, for the synthesis of the target
recommendations [60]. The results are presented in
Table 1. A number of compounds 7b–7f did not affect
the growth of bacterial cells at concentrations up to
200 μg/mL. Compounds 7g and 7h had a bacteriostatic
effect at the highest concentration (200 μg/mL). The
best results were shown by the acids containing a
1
,2,4-oxadiazoles we used the NaOH–DMSO system,
since its effectiveness has been previously proved by the
example of reactions of amidoximes with a wide range
of carbonyl compounds. Thus, a series of oxadiazole-
biphenyl hybrids 7a–7j was obtained in 30–92% yields
by the reaction of amidoximes 2a–2h with diphenic
anhydrides 5a–5c (Scheme 3).
4-chlorophenyl substituent at position 3 of the oxadiazole
ring. Their bacteriostatic effect was comparable with
that of clinically significant antibacterial drugs of the
nitrofurans and sulfonamides series (12.5 μg/mL), but
significantly lower than the MIC values for the control
antibiotic pefloxacin. These compounds (7a, 7i, 7j) can
be recommended as lead compounds for further medicinal
chemistry optimization in order to develop a prototype
of a new class of antibacterial agents.
Antibacterial activity was evaluated by the method
of double serial dilutions in accordance with the
Table 1. Antibacterial activity of 1,2,4-oxadiazole derivatives
7
a–7j
EXPERIMENTAL
MIC, ꢀg/mL
Nitriles, substituted anthranilic acids, organic and
inorganic reagents and solvents, unless otherwise
specified, were obtained from commercial sources
Compound
Staphylococcus aureus Escherichia coli
(
АТСС-25923)
(С600)
50
7
a
50
(
Merck) and were used without further purification.
7
7
b
c
>200
>200
>200
>200
>200
200
>200
>200
>200
>200
>200
200
Samples of S. aureus reference strains (ATCC-25923)
were obtained from the American Type Culture
Collection (ATCC); E. coli strain (C600) was provided
by the Laboratory of Molecular Biology of the
G.K. Skryabin Institute of Biochemistry and Physiology of
Microorganisms of RAS. For cultivation microorganisms,
the nutrient media LB Broth (Lennox) and LB Agar
produced by DIA-M (Obninsk) were used.
7
d
7
e
7
f
7
g
7
h
200
200
7
7
i
j
>200
50
<0.5
12.5
12.5
<0.5
1
13
19
H, C, F NMR spectra were recorded on a Bruker
AVANCE DRX-400 spectrometer with operating
Pefloxacin
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 90 No. 9 2020

SYNTHESIS AND EVALUATION OF ANTIBACTERIAL ACTIVITY
1613
Scheme 3.
frequencies of 400, 376 and 101 MHz for H, 19F, and
1
N′-Hydroxyisonicotinimidamide (2c) [51]. Yield
1.13 g (88%), white powder, mp 198–200°С. H NMR
13
1
C, respectively, using DMSO-d or CDCl as a solvent.
6
3
High-resolution mass spectra were recorded on a Bruker
Daltonics MicrOTOF-II instrument, ionization method
was electrospray (ESI), ionization source temperature
was 180°С, eluent was methanol. Melting points
were determined on an Electrothermal IA 9300 Series
apparatus. The reaction progress was monitored by TLC
on Silufol-254 plates (visualization of chromatograms by
UV irradiation at 254 nm).
spectrum, δ, ppm: 6.00 br. s (2H, NH ), 7.60–7.69 m (2H,
Ar), 8.63–8.52 m (2H, Ar), 10.04 s (1H, OH).
2
N′-Hydroxy-4-methoxybenzimidamide (2d) [52].
1
Yield 0.97 g (78%), white powder, mp 107–109°С. H
NMR spectrum, δ, ppm: 3.76 s (3Н, ОСН ), 5.67 br. s
3
(
2H, NH ), 6.92 d (2Н, Ar, J = 7.5 Hz), 7.08 d (2Н, Ar,
2
J = 7.5 Hz), 9.43 s (1Н, ОН).
N′-Hydroxy-4-methylbenzimidamide (2e) [53].
Amidoximes 2a–2h were obtained as described in
1
Yield 1.44 g (96%), white powder, mp 141–143°С. H
[44].
NMR spectrum, δ, ppm: 2.32 s (3Н, СН ), 5.57 br. s (2H,
3
N′-Hydroxy-4-chlorobenzimidamide (2a) [44].
NH ), 7.15 d (2Н, Ar, J = 7.0 Hz), 7.56 d (2Н, Ar, J =
1
2
Yield 1.51 g (89%), white powder, mp 128–130°С. H
7
.0 Hz), 9.45 s (1Н, ОН).
NMR spectrum, δ, ppm: 5.85 br. s (2H, NH ), 7.43 d
2
N′-Hydroxynicotinimidamide (2f) [54]. Yield 1.13 g
(
(
2Н, Ar, J = 8.6 Hz), 7.66 d (2Н, Ar, J = 8.6 Hz), 9.71 s
1Н, ОН).
1
(
86%), white powder, mp 107–109°С. H NMR spectrum,
δ, ppm: 5.99 br. s (2H, NH ), 7.33–7.49 m (1H, Ar),
2
N′-Hydroxy-4-bromobenzimidamide (2b) [50].
1
7.81–7.92 m (1Н,Ar), 8.40–8.61 m (1Н,Ar), 8.85 d (1Н,
Ar, J = 1.9 Hz), 9.85 s (1H, ОН).
Yield 1.93 g (90%), beige powder, mp 141–143 °С. H
NMR spectrum, δ, ppm: 5.83 br. s (2H, NH ), 7.55 d
2
(
2Н, Ar, J = 8.7 Hz), 7.61 d (2H, Ar, J = 8.7 Hz), 9.70 s
N′-Hydroxy-4-nitrobenzimidamide (2g) [55]. Yield
1.20 g (98%), yellow powder, mp 188–190°С. H NMR
1
(1H, OH).
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 90 No. 9 2020

1614
TARASENKO et al.
1
spectrum, δ, ppm: 5.94 br. s (2H, NH ), 7.95 d (2Н,Ar, J =
white powder, mp 160–161°C. Н NMR spectrum, δ,
2
8
.5 Hz), 8.2 d (2Н, Ar, J = 8.5 Hz), 10.07 s (1Н, ОН).
ppm: 7.29 d (1H, Ar, J = 7.5 Hz), 7.39 d (1H, Ar, J =
7
.5 Hz), 7.48–7.67 m (5H, Ar), 7.72 t (1H, Ar, J =
N′-Hydroxy-3-nitrobenzimidamide (2h) [56]. Yield
.57 g (87%), yellow powder, mp 170–172°С. H NMR
1
7.4 Hz), 7.87 d (2H, Ar, J = 8.2 Hz), 7.94–8.01 m (1H,
Ar), 8.19 d (1H, Ar, J = 7.7 Hz), 12.54 c (1H, COOH).
1
spectrum, δ, ppm: 6.11 br. s (2H, NH ), 7.69 t (1H, Ar,
2
1
3
С NMR spectrum, δ , ppm: 122.8 (Ar), 125.4 (Ar),
J = 8.0 Hz), 8.13 d. t (1Н,Ar, J = 8.0, 1.0 Hz), 8.23 d. d. d
C
1
28.3 (Ar), 128.4 (Ar), 129.1 (2C, Ar), 129.7 (Ar), 129.8
(
9
1H, Ar, J = 8.0, 2.0, 1.0 Hz), 8.52 t (1H, Ar, J = 2.0 Hz),
.99 s (1H, OH).
1,1′-Biphenyl]-2,2′-dicarboxylic acids 4a–4c were
synthesized according to the procedure [45].
1,1′-Biphenyl]-2,2′-dicarboxylic acid (4a) [57].
(2С, Ar), 130.2 (Ar), 131.2 (2С, Ar), 131.2 (Ar), 132.0
(
Ar), 132.8 (Ar), 136.8 (Ar), 141.5 (Ar), 143.0 (Ar),
[
1
67.2 (oxadiazole), 168.1 (COOH), 176.6 (oxadiazole).
+
Mass spectrum, m/z: 399.0519 [M + Na] (calcd.
C H ClN O Na: 399.0507).
[
2
1
13
2
3
Yield 7.14 g (84%), beige powder, mp 226–228°C.
2
′-[3-(4-Bromophenyl)-1,2,4-oxadiazol-5-yl]bi-
1
Н NMR spectrum, δ, ppm (DMSO-d ): 7.13–7.16 m
6
phenyl-2-carboxylic acid (7b). Yield 0.99 g (92%),
white powder, mp 150–151°C. Н NMR spectrum, δ,
ppm: 7.29 d. d (1H, Ar, J = 7.6, 1.4 Hz), 7.40 d. d (1H,
Ar, J = 7.6, 1.4 Hz), 7.55 t. d (1H, Ar, J = 7.6, 1.4 Hz),
7
(
7
2H, Ar), 7.41–7.45 m (2H, Ar), 7.51–7.53 m (2H, Ar),
.86–7.89 m (2H, Ar), 12.33 br. s (2H, COOH).
,6′-Dimethyl-[1,1′-biphenyl]-2,2′-dicarboxylic
acid (4b) [58]. Yield 1.79 g (97%), beige powder, mp
1
6
.63 t. t (2H, Ar, J = 7.6, 1.4 Hz), 7.70–7.82 m (5H, Ar),
1
2
(
7
22–227°C. Н NMR spectrum, δ, ppm (CDCl ): 2.41 s
3
7.96 d. d (1H, Ar, J = 7.6, 1.4 Hz), 8.19 d. d (1H, Ar, J =
7.6, 1.4 Hz), 12.56 s (1H, COOH). С NMR spectrum,
6H, CH ), 7.16–7.21 m (2H, Ar), 7.34–7.38 m (2H, Ar),
13
3
.68–7.71 m (2H, Ar), 11.08 s (2H, COOH).
,5′-Difluoro-[1,1′-biphenyl]-2,2′-dicarboxylic acid
4c) [59]. Yield 1.50 g (84%), beige powder, mp 245–
δC, ppm: 122.8 (Ar), 125.6 (Ar), 125.8 (Ar), 128.3 (Ar),
128.4 (Ar), 129.3 (2С, Ar), 129.8(Ar), 130.2 (Ar), 131.2
(3С, Ar), 132.0 (Ar), 132.8 (2С, Ar), 132.8 (Ar), 141.5
(Ar), 143.0 (Ar), 167.3 (oxadiazole), 168.1 (COOH),
176.6 (oxadiazole). Mass spectrum, m/z: 421.0191 [M +
5
(
2
(
1
1
46°C. Н NMR spectrum, δ, ppm (CDCl ): 7.14–7.20 m
3
2H, Ar), 7.39–7.46 m (2H, Ar), 7.64–7.71 m (2H, Ar),
0.56 br. s (2H, COOH).
+
H] (calcd. C H BrN O : 421.0182).
2
1
14
2
3
General procedure for the preparation of (1,2,4-
2′-[3-(Pyridin-4-yl)-1,2,4-oxadiazol-5-yl]biphenyl-
2-carboxylic acid (7c). Yield 0.35 g (40%), white
powder, mp 206–207°C. Н NMR spectrum, δ, ppm:
oxadiazol-5-yl)biphenyl-2-carboxylic acids 7a–7j.
A solution of trifluoroacetic anhydride (5 mmol) was
added with stirring to a suspension of [1,1′-biphenyl]-
,2′-dicarboxylic acid 4 (2.5 mmol) in anhydrous ethyl
acetate (20 mL). The reaction mixture was stirred for
4 h, after which the starting material completely
dissolved. The resulting solution was concentrated
under reduced pressure until a solid residue was formed,
which was washed with cold hexane (30 mL) and dried
in vacuum. The resulting anhydride was dissolved in
DMSO (3 mL) and amidoxime 2 (2.5 mmol) was added.
The reaction mixture was stirred at room temperature
for 2 h, then powdered sodium hydroxide (5 mmol)
was added, and the resulting mixture was stirred for
another 1 h. The reaction mixture was diluted with water
1
7.30 d. d (1Н, Ar, J = 7.6, 1.4 Hz), 7.41 d. d (1Н, Ar, J =
7.6, 1.4 Hz), 7.57 t. d (1Н, Ar, J = 7.6, 1.4 Hz), 7.65 t. d
(2Н, Ar, J = 8.1, 1.4 Hz), 7.72–7.76 m (1H, Ar), 7.76–
7.83 m (2H, Ar), 7.97 d. d (1Н, Ar, J = 7.6, 1.4 Hz),
8.21 d. d (1Н,Ar, J = 8.1, 1.4 Hz), 8.81 s (2H,Ar), 12.56 s
2
2
1
3
(1H, COOH). С NMR spectrum, δ , ppm: 122.6 (Ar),
C
128.3 (Ar), 128.5 (Ar), 128.6 (Ar), 129.8 (Ar), 130.2
(Ar), 131.2 (Ar), 131.9 (Ar), 132.1 (2С, Ar), 132.1 (Ar)
132.8 (Ar), 133.0 (Ar), 133.8 (Ar), 141.4 (Ar), 143.1
(Ar), 151.4 (2С,Ar), 166.7 (oxadiazole), 168.1 (COOH),
177.1 (oxadiazole). Mass spectrum, m/z: 344.1029 [M +
+
H] (calcd. C H N O : 344.1030).
2
0
14
3
3
2
′-[3-(4-Methoxyphenyl)-1,2,4-oxadiazol-5-yl]bi-
(
30 mL) and acidified with concentrated hydrochloric acid
phenyl-2-carboxylic acid (7d). Yield 0.78 g (82%), white
to pH = 1 (for compounds 7a, 7b, 7d, 7e, 7g–7j), or
with acetic acid to pH = 5 (for compounds 7c, 7f). The
precipitate was filtered off, washed with water (25 mL)
and dried in air.
1
powder, mp 170–171°C. Н NMR spectrum, δ, ppm:
3
.82 s (3H,CH ), 7.03–7.12 m (2H, Ar), 7.28 d. d (1H,
3
Ar, J = 7.6, 1.4 Hz), 7.38 d. d (1H, Ar, J = 7.6, 1.4 Hz),
.55 t. d (1H, Ar, J = 7.6, 1.4 Hz), 7.62 t. d (2H, Ar, J =
7
2
′-[3-(4-Chlorophenyl)-1,2,4-oxadiazol-5-yl]-
7.6, 1.4 Hz), 7.71 t. d (1H, Ar, J = 7.6, 1.4 Hz), 7.75–
7.83 m (2H, Ar), 7.97 d. d (1H, Ar, J = 7.8, 1.5 Hz),
biphenyl-2-carboxylic acid (7a). Yield 0.58 g (61%),
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SYNTHESIS AND EVALUATION OF ANTIBACTERIAL ACTIVITY
1615
8
.18 d. d (1H, Ar, J = 7.8, 1.5 Hz), 12.49 s (1H, COOH).
С NMR spectrum, δ , ppm: 55.9 (ОCH ), 115.1 (2С,
141.4 (Ar), 143.1 (Ar), 149.7 (Ar), 166.7 (oxadiazole),
13
168.1 (COOH), 177.1 (oxadiazole). Mass spectrum, m/z:
C
3
+
Ar), 118.9 (Ar), 123.0 (Ar), 128.2 (Ar), 128.3 (Ar), 129.0
2С, Ar), 129.6 (Ar), 130.2 (Ar), 131.1 (Ar), 131.2 (2С,
Ar), 132.0 (Ar), 132.6 (Ar), 141.7 (Ar), 143.0 (Ar),
62.2 (Ar), 167.7 (oxadiazole), 168.1 (COOH), 176.0
388.0926 [M + H] (calcd. C H N O : 388.0928).
2
1
14
3
5
(
2
′-[3-(3-Nitrophenyl)-1,2,4-oxadiazol-5-yl]bi-
phenyl-2-carboxylic acid (7h). Yield 0.34 g (34%), beige
1
1
powder, mp 150–151°C. Н NMR spectrum, δ, ppm:
+
(oxadiazole). Mass spectrum, m/z: 373.1175 [M + H]
7.31 d (1H, Ar, J = 7.6 Hz), 7.42 d (1H, Ar, J = 7.6 Hz),
7.57 t (1H, Ar, J = 7.6 Hz), 7.65 t (2H, Ar, J = 7.6 Hz),
7.74 t (1H, Ar, J = 7.6 Hz), 7.84 t (1H, Ar, J = 8.0 Hz),
7.98 d. d (1H, Ar, J = 7.8, 1.4 Hz), 8.22 d. d (1H, Ar, J =
7.8, 1.4 Hz), 8.28 d. t (1H, Ar, J = 7.8, 1.4 Hz), 8.41 d. d
(calcd. C H N O : 373.1183).
22
17
2
4
2
′-[3-(4-Methylphenyl)-1,2,4-oxadiazol-5-yl]bi-
phenyl-2-carboxylic acid (7e). Yield 0.79 g (87%), white
powder, mp 146–147°C. Н NMR spectrum, δ, ppm:
1
2
7
1
7
.36 s (3H, CH ), 7.28 d. d (1H, Ar, J = 7.6, 1.4 Hz),
3
(1H, Ar, J = 8.0, 1.0 Hz), 8.53 t (1H, Ar, J = 2.0 Hz),
.33 d (2H, Ar, J = 7.9 Hz), 7.39 d. d (1H, Ar, J = 7.6,
.4 Hz), 7.54–7.58 m (1H, Ar), 7.62 t. d (2H, Ar, J =
.6, 1.4 Hz), 7.71 t. d (1H, Ar, J = 7.6, 1.4 Hz), 7.76 d
13
1
1
2.58 s (1H, COOH). С NMR spectrum, δ , ppm:
C
22.0 (Ar), 122.6 (Ar), 126.6 (Ar), 128.0 (Ar), 128.3
(Ar), 128.4 (Ar), 129.8 (Ar), 130.2 (Ar), 131.2 (2C, Ar),
(2H, Ar, J = 7.8 Hz), 7.97 d. d (1H, Ar, J = 7.6, 1.5 Hz),
1
1
1
3
31.3 (Ar), 131.6 (Ar), 132.1 (Ar), 133.0 (Ar), 133.3 (Ar),
41.5 (Ar), 143.1 (Ar), 148.7 (Ar), 166.6 (oxadiazole),
68.1 (COOH), 176.9 (oxadiazole). Mass spectrum, m/z:
8
.19 d. d (1H, Ar, J = 7.8, 1.4 Hz), 12.62 s (1H, COOH).
С NMR spectrum, δ , ppm: 21.5 (CH ), 123.0 (Ar),
1
3
C
3
1
23.8 (Ar), 127.3 (2С, Ar), 128.2 (Ar), 128.3 (Ar), 129.7
+
88.0921 [M + H] (calcd. C H N O : 388.0928).
2
1
14
3
5
(
Ar), 130.2 (2С, Ar), 130.2 (Ar), 131.1 (Ar), 131.2 (2С,
Ar), 132.0 (Ar), 132.6 (Ar), 141.6 (Ar), 141.9 (Ar),
43.0 (Ar), 167.9 (oxadiazole), 168.1 (COOH), 176.2
2
′-[3-(4-Chlorophenyl)-1,2,4-oxadiazol-5-yl]-6,6′-
dimethyl-[1,1′-biphenyl]-2-carboxylic acid (7i). Yield
1
1
+
0.84 g (81%), white powder, mp 98–100°C. Н NMR
(oxadiazole). Mass spectrum, m/z: 379.1056 [M + Na]
spectrum, δ, ppm: 2.40 s (3H, CH ), 2.49 s (3H, CH ),
3
3
(calcd. C H N O Na: 379.1053).
22
16
2
3
7
.30 t (1H, Ar, J = 7.6 Hz), 7.43–7.59 m (3H, Ar),
.61–7.65 m (3H, Ar), 7.94 d (1H, Ar, J = 7.7 Hz), 8.11 d
2′-[3-(Pyridin-3-yl)-1,2,4-oxadiazol-5-yl]biphenyl-
7
2-carboxylic acid (7f). Yield 0.27 g (30%), white powder,
(
2H, Ar, J = 8.2 Hz), 12.91 s (1H, СООН). 13С NMR
1
mp 205–206°C. Н NMR spectrum, δ, ppm: 7.30 d. d (1H,
Ar, J = 7.6, 1.4 Hz), 7.41 d. d (1H, Ar, J = 7.6, 1.4 Hz),
spectrum, δ , ppm: 20.3 (CH ), 20.5 (CH ), 123.9 (Ar),
C
3
3
125.5 (Ar), 127.0 (Ar), 127.8 (Ar), 128.0 (Ar), 129.4 (2С,
7
7
8
.55–7.66 m (4H, Ar), 7.74 t. d (1H, Ar, J = 7.6, 1.4 Hz),
.98 d. d (1H, Ar, J = 7.7, 1.5 Hz), 8.17–8.27 m (2H, Ar),
.92 d (2H, Ar, J = 8.6 Hz), 12.57 s (1H, COOH). С
Ar), 129.9 (2С, Ar), 130.2 (Ar), 131.4 (Ar), 132.9 (Ar),
133.5 (Ar), 135.6 (Ar), 137.0 (Ar), 137.4 (Ar), 137.5 (Ar),
1
3
1
38.6 (Ar), 167.6 (oxadiazole), 167.8 (COOH), 175.2
NMR spectrum, δ , ppm: 122.6 (Ar), 127.7 (Ar), 128.3
C
+
(oxadiazole). Mass spectrum, m/z: 427.0811 [M + Na]
calcd. C H СlN O Na: 427.0820).
(Ar), 128.4 (Ar), 129.8 (Ar), 130.2 (Ar), 131.2 (Ar), 131.3
(
2
3
18
2
3
(Ar), 131.3 (Ar), 132.1 (Ar), 132.9 (2С, Ar), 134.8 (Ar),
1
41.5 (Ar), 143.1 (Ar), 148.2 (Ar), 152.8 (Ar), 166.3
2′-[3-(4-Chlorophenyl)-1,2,4-oxadiazol-5-yl]-5,5′-
(
oxadiazole), 168.1 (COOH), 176.7 (oxadiazole). Mass
difluoro-[1,1′-biphenyl]-2-carboxylic acid (7j). Yield
0.75 g (72%), white powder, mp 157–158°C. Н NMR
+
1
spectrum, m/z: 344.1026 [M + H] (calcd. C H N O :
2
0
14
3
3
3
44.1030).
spectrum, δ, ppm: 7.36–7.39 m (1H, Ar), 7.43–7.56 m
(
2
2H,Ar), 7.58–7.63 m (3H,Ar), 7.72 d. d (1H,Ar, J = 9.5,
2
′-[3-(4-Nitrophenyl)-1,2,4-oxadiazol-5-yl]bi-
.8 Hz), 7.87 d (2H, Ar, J = 8.3 Hz), 7.99 d. d (1H, Ar,
phenyl-2-carboxylic acid (7g). Yield 0.35 g (35%),
beige powder, mp 202–203°C. Н NMR spectrum, δ,
ppm: 7.26–7.34 m (1H, Ar), 7.41 d (1H, Ar, J = 7.6 Hz),
.57 d (1H, Ar, J = 7.7 Hz), 7.64 t (2H, Ar, J = 7.6 Hz),
.74 t (1H, Ar, J = 7.6 Hz), 7.97 d (1H, Ar, J = 7.8 Hz),
.11 d (2H, Ar, J = 8.5 Hz), 8.21 d (1H, Ar, J = 7.8 Hz),
.35–8.40 m (2H, Ar), 12.62 s (1H, СООН). C NMR
spectrum, δ , ppm: 122.7 (Ar), 124.9 (2С,Ar), 128.3 (Ar),
13
1
J = 9.5, 2.8 Hz), 12.97 s (1H, СООН). С NMR spectrum,
δC, ppm: 116.3 d (J = 24.9 Hz, Ar), 116.8 d (J = 23.2 Hz,
Ar), 119.1 d (J = 21.2 Hz, Ar), 119.8 d (J = 21.1 Hz,
Ar), 124.5 (Ar), 124.6 (Ar), 125.1 (Ar), 129.1 (2С, Ar),
129.9 (2С, Ar), 133.5 d (J = 7.3 Hz, Ar), 133.7 d (2С, J =
8.0 Hz, Ar), 136.8 d (J = 3.3 Hz, Ar), 137.0 (Ar), 138.3 d
(J = 3.4 Hz, Ar), 162.7 d (J = 245.3 Hz, Ar), 163.1 d (J =
245.7 Hz, Ar), 166.8 d (J = 2.0 Hz, oxadiazole), 1.67.3
(COOH), 175.3 d (J = 2.8 Hz, oxadiazole). 19F NMR
7
7
8
8
1
3
C
1
(
28.5 (Ar), 128.7 (2С, Ar), 129.9 (Ar), 130.2 (Ar), 131.2
2С, Ar), 131.3 (Ar), 132.1 (Ar), 132.3 (Ar), 133.0 (Ar),
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 90 No. 9 2020

1616
TARASENKO et al.
spectrum, δ , ppm: –114.08, –113.68. Mass spectrum, m/z:
density data was used to plot the dependence of optical
density on drug concentration. The minimum inhibitory
concentration (MIC) was considered the concentration of
the drug at which the average light transmittance of the
suspension (based on the results of three experiments)
did not significantly exceed 1% of the average value
of the growth control and/or the point where the curve
reached a plateau.
F
+
4
13.0498 [M + H] (calcd. C H СlF N O : 413.0499).
2
1
12
2
2
3
Antibacterial activity was evaluated by the double
serial dilutions procedure using the turbidimetric method
for monitoring the microorganisms growth in accordance
with the recommendations [60]. The change in the
intensity of light transmission under the influence of
solutions of the test substances in the concentration range
of 0–200 μg/mL was carried out using a 512 UV/VIS
Bibby Scientific Jenway 6715 spectrophotometer.
Pefloxacin mesylate (CAS 70458-95-6, Jin Jinle
Chemical Co., China) was used as a reference.
FUNDING
This work was financially supported by the Russian
Foundation for Basic Research (project no. 19-33-60064) using
the equipment of the Resource Centers “Chemical Analysis
and Materials Research Center” and “Magnetic Resonance
Research Center” of the Research Park of St. Petersburg State
University.
Preparation of solutions. The studied drug (5.0 mg)
was dissolved in 100 μL of dimethyl sulfoxide, then
1
0 μL of the resulting solution was taken, and the
concentration of the drug was adjusted to 200 μg/mL
with sterile LB broth. The formation of a homogeneous
solution was observed. A solution of the test compound
was introduced into cuvettes (V = 4 mL) and a sequential
two-fold dilution was made. The resulting dilutions of the
drug was as follows: 0.8, 1.6, 3.1, 6.2, 12.5, 25, 50, 100,
CONFLICT OF INTEREST
No conflict of interest was declared by the authors.
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