Brønsted Acid-Catalyzed Diastereoselective Synthesis of Spiroisoindolinones from Enamides
Organic Letters,
Год журнала:
2024,
Номер
26(11), С. 2321 - 2325
Опубликована: Март 11, 2024
A
highly
diastereoselective
synthesis
of
spiroisoindolinones
from
enamides
and
3-hydroxy-isoindolinones
is
reported.
The
reaction
proceeds
rapidly
in
the
presence
p-toluenesulfonic
acid
as
a
Brønsted
catalyst
affords
variety
densely
substituted
with
three
contiguous
stereogenic
centers
high
yields
(≤98%)
diastereoselectivities
(up
to
dr
>98:<2:0:0).
Язык: Английский
Synthesis of amide derivatives containing the imidazole moiety and evaluation of their anti‐cardiac fibrosis activity
Archiv der Pharmazie,
Год журнала:
2024,
Номер
357(8)
Опубликована: Апрель 28, 2024
Abstract
Three
series
of
N
‐{[4‐([1,2,4]triazolo[1,5‐
α
]pyridin‐6‐yl)‐5‐(6‐methylpyridin‐2‐yl)‐1
H
‐imidazol‐2‐yl]methyl}acetamides
(
14a
–
d
,
15a
n
and
16a
f
)
were
synthesized
evaluated
for
activin
receptor‐like
kinase
5
(ALK5)
inhibitory
activities
in
an
enzymatic
assay.
The
target
compounds
showed
high
ALK5
activity
selectivity.
half
maximal
concentration
(IC
50
phosphorylation
16f
(9.1
nM),
the
most
potent
compound,
was
2.7
times
that
clinical
candidate
EW‐7197
(vactosertib)
14
LY‐2157299.
selectivity
index
against
p38α
mitogen‐activated
protein
>109,
which
much
higher
than
positive
controls
(EW‐7197:
>41,
LY‐2157299:
4).
Furthermore,
a
molecular
docking
study
provided
interaction
modes
between
ALK5.
Compounds
14c
14d
effectively
inhibited
expression
α‐smooth
muscle
actin
(α‐SMA),
collagen
I,
tissue
inhibitor
metalloproteinase
1
(TIMP‐1)/matrix
13
(MMP‐13)
transforming
growth
factor‐β‐induced
human
umbilical
vein
endothelial
cells.
especially
at
low
concentrations,
suggests
these
could
inhibit
myocardial
cell
fibrosis.
are
potential
preclinical
candidates
treatment
cardiac
Язык: Английский
Stereoselective Synthesis of 2‐Oxyenamides**
Sara‐Cathrin Krieg,
Jennifer Grimmer,
Annika Maria Pick
и другие.
European Journal of Organic Chemistry,
Год журнала:
2022,
Номер
2022(31)
Опубликована: Июль 18, 2022
Abstract
An
improved
route
for
the
highly
stereoselective
synthesis
of
(
Z
)‐2‐oxyenamides
is
reported.
The
desired
products
can
be
accessed
in
only
three
steps
from
aminoacetaldehyde
dimethyl
acetal
as
common,
readily
available
building
block
a
modular
fashion.
procedure
has
been
applied
to
various
acylated
and
sufonylated
oxyenamides.
Mechanistic
theoretical
studies
provide
conclusive
rationale
observed
stereoselectivities.
Язык: Английский