Design, synthesis, antifungal activity, and molecular docking of novel trifluoromethyl pyrimidine derivatives containing 1,3,4‐oxadiazole and thioether moieties as potential succinate dehydrogenase inhibitors
Nianjian Pan,
Ruirui Wu,
Chang Yan
и другие.
Journal of Heterocyclic Chemistry,
Год журнала:
2023,
Номер
60(10), С. 1768 - 1777
Опубликована: Июль 31, 2023
Abstract
Succinate
dehydrogenase
(SDH),
a
pivotal
enzyme
linking
the
respiratory
electron
transport
chain
and
tricarboxylic
acid
(TCA)
cycle,
has
been
identified
as
an
ideal
target
for
developing
effective
fungicides.
In
this
study,
20
novel
trifluoromethyl
pyrimidine
derivatives
containing
1,3,4‐oxadiazole
thioether
moieties
were
prepared
characterized
their
structures
by
1
H
NMR,
13
C
HRMS.
Bioassay
results
showed
that
some
of
compounds
revealed
moderate
to
good
in
vitro
antifungal
activities
toward
Rhizoctonia
solani
(
R.
),
Botryosphaeria
dothidea
B.
Phomopsis
sp.,
Botrytis
cinerea
Fusarium
oxysporum
F.
Sclerotinia
sclerotiorum
S.
Phytophthora
infestans
P.
Magnaporthe
oryzae
M.
).
particular,
6g
6i
had
better
activity
against
,
with
EC
50
values
19.43
28.22
μg/mL,
respectively,
than
Pyrimethanil
(57.30
μg/mL).
As
well,
compound
6r
exhibited
value
3.61
which
lower
Boscalid
(0.40
addition,
t
he
molecular
docking
simulation
interacted
GLN‐150,
ASP‐153,
LYS‐151,
GLY‐154,
GLY‐228
SDH
through
hydrogen
bond,
could
explain
probable
mechanism
action
between
SDH.
This
is
first
report
on
potential
inhibitors.
Язык: Английский
Synthesis, crystal structure, Hirshfeld surface analysis, energy frameworks, molecular docking and DFT calculation of new pyrazole-4-carboxamide compound as antifungal agent
Journal of Molecular Structure,
Год журнала:
2024,
Номер
1317, С. 139145 - 139145
Опубликована: Июнь 30, 2024
Язык: Английский
Recent advances in the synthesis of 3(5)-trifluoromethylpyrazoles
Synthetic Communications,
Год журнала:
2023,
Номер
54(2), С. 87 - 110
Опубликована: Ноя. 29, 2023
This
review
mainly
focused
on
the
synthesis
of
3(5)-trifluoromethylpyrazoles
via
condensation
trifluoromethyl-β-diketones
with
hydrazines.
Also,
a
special
emphasis
is
led
biological
potential
fluorine
containing
compounds
and
pyrazoles
in
introduction
section.
We
have
covered
all
literature
reported
reactions
Язык: Английский
Design, Synthesis, and Fungicidal Activities of Novel Strobilurin Derivatives Containing a Substituted 1,3,4‐Oxadiazole Moiety
Journal of Heterocyclic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Дек. 25, 2024
ABSTRACT
To
explore
novel
structures
of
strobilurin
fungicides,
a
series
derivatives
featuring
substituted
1,3,4‐oxadiazole
in
the
side
chain
were
synthesized
using
an
intermediate
derivatization
method
and
characterized
by
nuclear
magnetic
resonance
spectroscopy
(NMR)
high‐resolution
mass
spectrometry
(HRMS).
The
reactions
involved
synthesis
process
include
hydrazine
hydrolysis,
cyclization,
nucleophilic
substitution
reactions.
raw
materials
required
for
these
are
readily
available,
procedures
reaction
straightforward.
fungicidal
activities
compounds
tested
inhibition
zone
method.
rate
compound
5f
on
Magnaporthe
oryzae
was
81.8%
at
concentration
3.125
mg/L,
EC
50
value
(0.3045
mg/L)
better
than
superior
to
that
kresoxim‐methyl
(0.5247
mg/L).
Язык: Английский