A
rewired
Yonemitsu
multicomponent
reaction
was
designed
to
readily
synthesize
a
family
of
6-substituted
indolocarbazoles.
In
this
approach,
indole
2-carboxaldehyde
and
nucleophilic
species
directly
yield
the
final
adducts
through
domino
reaction.
The
scope
new
process
analyzed,
range
aldehydes
nucleophiles
established.
Comparative
studies
with
analogous
compounds
reveal
important
details
on
mechanism.
Experimental
computational
address
conformational
behavior
representative
adducts,
determining
their
potential
chirality.
These
novel
structures
are
potent
activating
ligands
human
aryl
hydrocarbon
receptor,
importantly
being
non-toxic.
Furthermore,
scaffold
may
be
included
in
2-step
synthesis
(homo)-PROTACs
that
efficiently
specifically
degrade
receptor.
Our
approach
allows
control
target
biomedicine
chemistry.
Frontiers in Chemistry,
Год журнала:
2024,
Номер
12
Опубликована: Сен. 18, 2024
Since
Strecker’s
discovery
of
multicomponent
reactions
(MCRs)
in
1850,
the
strategy
applying
an
MCR
approach
has
been
use
for
over
a
century.
Due
to
their
ability
quickly
develop
molecular
diversity
and
structural
complexity
interest,
MCRs
are
considered
efficient
organic
synthesis.
Although
such
as
Ugi,
Passerini,
Biginelli,
Hantzsch
widely
studied,
this
review
emphasizes
significance
selective
elegantly
produce
compounds
potential
medicinal
chemistry
industrial
material
science
applications,
well
sustainable
methods.
During
synthesis,
provide
advantages
atom
economy,
recyclable
catalysts,
moderate
conditions,
preventing
waste,
avoiding
solvent
use.
also
reduce
number
sequential
multiple
one
step.
ACS Central Science,
Год журнала:
2025,
Номер
unknown
Опубликована: Апрель 10, 2025
A
multidisciplinary
platform
is
presented
to
address
aryl
hydrocarbon
receptor
(AhR)
modulation.
rewired
Yonemitsu
multicomponent
reaction
with
indole
2-carboxaldehydes
and
nucleophilic
species
was
designed
access
a
family
of
6-substituted
indolocarbazoles.
The
conformational
behavior
these
compounds
examined
rationalize
their
axial
chirality.
In
silico
docking
molecular
simulations
highlighted
key
features
implicated
in
binding
AhR.
Furthermore,
the
synthesis
linkable
derivatives
allowed
direct
development
conjugated
entities.
Reporter
gene
target
expression
analyses
identified
novel
structures
as
potent
noncytotoxic
activating
AhR
ligands,
that
can
be
extended
bifunctional
molecules.
anti-inflammatory
properties
agonists
were
assessed
interleukin-13
treated
keratinocytes.
Altogether,
synergistic
research
synthetic
computational
chemistry
integrated
biological
studies
opens
avenues
toward
understanding
roles
targeted
therapeutics.
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(15), С. 10773 - 10784
Опубликована: Июль 17, 2024
This
study
showcases
successfully
switchable
approaches
to
accomplish
the
C3-aryl
methylation
and
C3-
amino
of
privileged
nitrogen-containing
pharmaceutical
compounds
"imidazopyridines"
with
distinct
amines,
which
surmounts
long-standing
requirement
for
a
superfluous
directing
group.
These
two
transformations
manifest
pronounced
regio-
chemo-divergent
behavior,
demonstrating
unprecedented
multicomponent
"abnormal
Mannich
Mannich-type"
reactions.
The
remarkable
environmentally
benign
protocol
has
been
efficiently
extended
concise
synthesis
late-stage
derivatization.
RSC Advances,
Год журнала:
2024,
Номер
14(42), С. 31072 - 31116
Опубликована: Янв. 1, 2024
This
article
describes
recent
advances
in
one-pot
chemoselective
reactions
and
their
mechanism
insights.
Here,
the
substrate,
catalyst,
solvent,
temperature
play
a
vital
role
modulating
chemoselectivity.
Organic Chemistry Frontiers,
Год журнала:
2022,
Номер
9(22), С. 6179 - 6186
Опубликована: Янв. 1, 2022
A
mild
and
highly
efficient
Ugi-3CR
using
a
novel
Cu-COOH@MOF-6
as
the
catalyst
has
been
developed,
which
provides
facile
access
to
α-amino
amides.
The
recycling
test
XRD
images
showed
that
catalytic
system
good
stability
recyclability.
Chemistry - A European Journal,
Год журнала:
2023,
Номер
29(45)
Опубликована: Май 19, 2023
Cyclopentadienyliron
dicarbonyl-based
complexes
present
opportunities
for
underexplored
disconnections
in
synthesis.
Access
to
challenging
dihydropyrrolone
products
is
achieved
by
propargylic
C-H
functionalization
of
alkynes
the
formation
cyclic
organoiron
species.
Excellent
regioselectivity
unsymmetrical
observed
many
cases.
Notably,
under
these
stoichiometric
conditions
diverges
from
those
previously
catalysis,
occurring
at
more-substituted
terminus
alkyne,
allowing
methine
and
quaternary
centers.
Divergent
demetallation
intermediate
gives
access
chemically
diverse
which
are
amenable
further
functionalization.
Future Medicinal Chemistry,
Год журнала:
2022,
Номер
14(21), С. 1583 - 1606
Опубликована: Окт. 20, 2022
Among
neurodegenerative
pathologies
affecting
the
older
population,
Alzheimer's
disease
is
most
common
type
of
dementia
and
leads
to
neurocognitive
behavioral
disorders.
It
a
complex
progressive
age-related
multifactorial
characterized
by
series
highly
interconnected
pathophysiological
processes.
Within
last
decade,
multitarget-directed
ligand
strategy
has
emerged
as
viable
approach
developing
molecules
that
exhibit
several
pharmacophores
which
can
target
different
enzymes
receptors
involved
in
pathogenesis
disease.
Herein,
we
focus
on
using
multicomponent
reactions
such
Hantzsch,
Biginelli
Ugi
develop
these
biologically
active
multitopic
ligands.
Current Organic Chemistry,
Год журнала:
2024,
Номер
28(9), С. 725 - 732
Опубликована: Апрель 17, 2024
Abstract:
Organocatalyst
1,4-diazabicyclo
[2.2.2]octane
(DABCO)
has
proven
to
be
an
efficient
and
environmentally
friendly
catalyst
in
the
multicomponent
reaction
involving
aldehydes,
ethylenediamine,
thioglycolic
acid
under
microwave
conditions.
DABCO
stands
out
among
other
organic
catalysts
due
its
cost-effectiveness,
non-toxic
nature,
conscious
profile.
The
method
employed
this
study
exhibited
exceptional
attributes,
such
as
high
yields,
swift
times,
atom
economy,
reusability,
minimal
loading.
Additionally,
there
were
excellent
yields
of
products
(90-94%).
melting
points,
UV-Vis,
IR,
1HNMR,
13CNMR,
used
analyze
produced
compounds.
invitro
antibacterial
activity
synthesized
compounds
was
investigated
against
pathogenic
strains
E.
coli
Bacillus
supstalis,
results
obtained
further
explained
with
help
DFT
molecular
orbital
calculations.
Moreover,
compound
4b
found
most
potent
agent
amongst
all
tested
