Research Square (Research Square),
Год журнала:
2023,
Номер
unknown
Опубликована: Июль 13, 2023
Abstract
A
novel
four-component
diastereoselective
synthesis
of
pyridinium
salts
piperidin-2-ones
is
reported.
The
Michael–Mannich
cascade
was
conducted
using
Michael
acceptors,
ylides,
aromatic
aldehydes
and
ammonium
acetate
in
methanol.
It
a
convenient
approach
to
the
1-((3
SR
,4
RS
,6
)-5,5-dicyano-2-oxo-4,6-diarylpiperidin-3-yl)pyridin-1-ium
halogenides
with
three
stereocenters
48–84%
or
1-((
3SR,4RS,5RS,6SR
)-5-cyano-5-(methoxycarbonyl)-2-oxo-4,6-diarylpiperidin-3-yl)pyridin-1-ium
halogenide
four
44–74%.
This
reaction
highly
stereoselective.
Only
one
diastereomer
formed.
Ammonium
plays
dual
role,
acting
as
base
nitrogen
source.
Structures
synthesized
compounds
were
confirmed
by
1
H
NMR,
13
C
IR
mass
spectra.
formation
single
singe-crystal
X-ray
diffraction
studies.
Advanced Materials Interfaces,
Год журнала:
2024,
Номер
11(17)
Опубликована: Май 1, 2024
Abstract
Quaternary
ammonium
compounds
(QACs)
are
well‐known
for
their
antimicrobial
properties,
but
widespread
use
is
limited
due
to
suboptimal
efficiency
and
safety
concerns.
Recent
progress
in
materials
science
has
paved
the
way
development
of
QAC‐based
composites
(QACCs).
QACCs
with
diverse
compositions
have
shown
enhanced
effectiveness
biosafety
various
applications,
such
as
food
packaging,
capacitive
deionization,
household
antimicrobials.
This
review
provides
a
comprehensive
summary
synthesis
approaches
different
types
QACCs.
Moreover,
this
examines
taking
underlying
structure‐activity
relationship
into
consideration.
In
addition,
perspectives
presented
on
remaining
challenges
future
research
directions
further
It
expected
that
will
provide
valuable
reference
design
next
generation
QACC‐based
agents.
Biomolecules,
Год журнала:
2024,
Номер
14(8), С. 957 - 957
Опубликована: Авг. 7, 2024
The
adherence
of
pathogenic
microorganisms
to
surfaces
and
their
association
form
antibiotic-resistant
biofilms
threatens
public
health
affects
several
industrial
sectors
with
significant
economic
losses.
For
this
reason,
the
medical,
pharmaceutical
materials
science
communities
are
exploring
more
effective
anti-fouling
approaches.
This
review
focuses
on
properties,
structure-activity
relationships
environmental
toxicity
quaternary
ammonium
salts
(QAS)
and,
as
a
subclass,
ionic
liquid
compounds.
Greener
alternatives
such
QAS-based
antimicrobial
polymers
biocide
release,
non-fouling
(i.e.,
PEG,
zwitterions),
fouling
release
poly(dimethylsiloxanes),
fluorocarbon)
contact
killing
properties
highlighted.
We
also
report
dual-functional
stimuli-responsive
materials.
Given
impacts
in
submerged
surfaces,
we
emphasize
importance
less
explored
approaches
marine
industry
developing
efficient
membranes
for
water
treatment
systems.
International Journal of Molecular Sciences,
Год журнала:
2024,
Номер
25(5), С. 2761 - 2761
Опубликована: Фев. 27, 2024
Organic
ammonium
and
phosphonium
salts
exert
excellent
antimicrobial
effects
by
interacting
lethally
with
bacterial
membranes.
Particularly,
quaternary
lipids
have
demonstrated
efficiency
both
as
gene
vectors
antibacterial
agents.
Here,
aiming
at
finding
new
devices
belonging
to
classes,
we
prepared
a
water-soluble
lipid
(6)
salt
(1)
designing
synthetic
path
where
1
would
be
an
intermediate
achieve
6.
All
synthesized
compounds
were
characterized
Fourier-transform
infrared
spectroscopy
Nuclear
Magnetic
Resonance.
Additionally,
potentiometric
titrations
of
NH3+
groups
6
performed
further
confirm
their
structure
determining
experimental
molecular
weight.
The
activities
assessed
first
against
selection
multi-drug-resistant
clinical
isolates
Gram-positive
Gram-negative
species,
observing
remarkable
activity
Enterococcus
Staphylococcus
genus.
Further
investigations
on
wider
variety
strains
these
species
confirmed
the
(MICs
=
4–16
4–64
µg/mL,
respectively),
while
24
h-time-killing
experiments
carried
out
different
S.
aureus
evidenced
bacteriostatic
behavior.
Moreover,
6,
lower
MIC
concentration,
did
not
show
significant
cytotoxic
when
exposed
HepG2
human
hepatic
cell
lines,
paving
way
for
potential
application.
Journal of Molecular Liquids,
Год журнала:
2024,
Номер
401, С. 124616 - 124616
Опубликована: Март 30, 2024
Antimicrobial
resistance
(AMR)
poses
a
global
threat
to
human
health,
as
exemplified
by
the
devastating
impact
of
ESKAPE
pathogens,
reducing
treatment
options,
increasing
disease
burden,
and
elevating
death
rates
due
failure.
This
looming
health
has
rekindled
interest
in
development
new
antimicrobial
therapies.
In
this
study,
library
49
structurally
related
quaternary
heteronium
salts
(QHSs),
such
ammonium
phosphonium
compounds,
was
screened
at
concentration
32
µg/mL
against
five
pathogens
(methicillin-resistant
Staphylococcus
aureus
(MRSA),
Klebsiella
pneumoniae,
Acinetobacter
baumannii,
Pseudomonas
aeruginosa,
Escherichia
coli),
well
yeast-like
fungus
Candida
albicans.
The
preliminary
high-throughput
screening
(HTS)
data
revealed
that
QHSs
with
longer
alkyl
chain
lengths
(≥12
carbons)
exhibited
broad-spectrum
activity,
C14–C16
homologous
demonstrating
highest
potency.
alkyl-triphenylphosphonium
1a–g
most
significant
activity
among
all
tested
compound
series.
compounds
identified
active
initial
HTS
underwent
confirmation
assays
determine
minimum
inhibitory
(MIC)
cytotoxicity,
following
established
protocols.
Confirmatory
33
hits
(MIC
≤
16
µg/mL),
78
%
effective
low
micromolar
concentrations
(≤0.25
µg/mL).
Seven
showed
safety
profiles
HEK-293
cells
red
blood
below
Based
on
comparative
analysis
their
potency
pathogenic
microorganisms
cell
toxicity,
triphenylphosphonium
quinolinium
linear
C8
hydrocarbon
substituents
(compounds
1b
5b,
respectively),
isoquinolinium,
methylpyridinium
triethylammonium
C18
3g,
4g,
7g,
respectively)
have
emerged
promising
candidates
for
microbial
growth
control.
International Journal of Molecular Sciences,
Год журнала:
2024,
Номер
25(22), С. 12264 - 12264
Опубликована: Ноя. 15, 2024
Antibacterial
coatings
based
on
quaternary
ammonium
compounds
(QACs)
have
been
widely
investigated
in
controlled
release
applications.
Quaternary
are
low-cost
and
easily
accessible
disinfectants
that
extensively
used,
especially
after
the
COVID-19
outbreak.
There
has
a
growing
interest
developing
clearer
understanding
of
various
aspects
need
to
be
taken
into
account
for
design
used
biomedical
field.
In
this
contribution,
we
outline
mechanism
action
those
materials
as
well
key
parameters
associated
with
their
structure
antibacterial
activity.
Moreover,
emphasis
placed
type
QACs
applications
A
brief
outlook
future
research
guidelines
development
dual-function
is
also
discussed.
ACS Infectious Diseases,
Год журнала:
2024,
Номер
10(4), С. 1080 - 1096
Опубликована: Март 28, 2024
The
global
surge
in
bacterial
infections,
compounded
by
the
alarming
escalation
of
drug-resistant
strains,
has
evolved
into
a
critical
public
health
crisis.
Among
challenges
posed,
biofilms
stand
out
due
to
their
formidable
resistance
conventional
antibiotics.
This
review
delves
burgeoning
potential
pillar[n]arenes,
distinctive
macrocyclic
host
molecules,
as
promising
anti-biofilm
agents.
is
structured
two
main
sections,
each
dedicated
exploring
distinct
facets
pillar[n]arene
applications.
first
section
scrutinizes
functionalized
pillar[n]arenes
with
particular
emphasis
on
cationic
derivatives.
analysis
reveals
significant
efficacy
inhibiting
biofilm
formation,
underscoring
pivotal
role
specific
chemical
attributes
combating
microbial
communities.
second
shifts
its
focus
inclusion
complexes,
elucidating
how
serve
encapsulation
platforms
for
enhances
stability
antibiotics
and
enables
controlled
release,
thereby
amplifying
antibacterial
activity.
examination
complexes
provides
valuable
insights
synergy
between
traditional
antibiotics,
offering
novel
avenue
overcoming
resistance.
comprehensive
highlights
escalating
threat
infections
urgent
need
innovative
strategies
counteract
biofilms.
unique
properties
both
molecules
complex
hosts,
position
them
candidates
quest
effective
exploration
mechanisms
opens
new
avenues
research
development
ongoing
battle
against
biofilm-related
challenges.
