The
continuous
development
of
click
reactions
with
new
connecting
linkage
is
crucial
for
advancing
the
frontiers
chemistry.
Selenium-nitrogen
exchange
(SeNEx)
chemistry,
a
versatile
chemistry
in
represents
an
all-encompassing
term
nucleophilic
substitution
events
that
replace
nitrogen
at
electrophilic
selenium(II)
center,
enabling
flexible
and
efficient
assembly
linkages
around
Se(II)
core.
Several
SeNEx
chemistries
have
been
developed
inspired
by
biochemical
reaction
between
Ebselen
cysteine
residue,
demonstrated
significant
potential
on-plate
nanomole-scale
parallel
synthesis,
selenium-containing
DNA-encoded
library
(SeDEL)
as
well
peptide
protein
bioconjugation.
This
concept
aims
to
present
origins,
advancements,
applications
selenium(II)-nitrogen
while
also
outlining
directions
future
research
this
field.
Acta Pharmaceutica Sinica B,
Год журнала:
2023,
Номер
14(2), С. 492 - 516
Опубликована: Окт. 11, 2023
DNA-encoded
chemical
library
(DEL)
links
the
power
of
amplifiable
genetics
and
non-self-replicating
phenotypes,
generating
a
diverse
world.
In
analogy
with
biological
world,
DEL
world
can
evolve
by
using
central
dogma,
wherein
DNA
replicates
PCR
reactions
to
amplify
genetic
codes,
sequencing
transcripts
information,
DNA-compatible
synthesis
translates
into
phenotypes.
Importantly,
is
key
expanding
space.
Besides,
evolution-driven
selection
system
pushes
chemicals
under
selective
pressure,
i.e.,
desired
strategies.
this
perspective,
we
summarized
recent
advances
in
synthetic
toolbox
panning
strategies,
which
will
shed
light
on
drug
discovery
harnessing
vitro
evolution
via
DEL.
Abstract
The
chemical
and
biological
interest
in
this
element
the
molecules
bearing
selenium
has
been
exponentially
growing
over
years.
Selenium,
formerly
designated
as
a
toxin,
becomes
vital
trace
for
life
that
appears
selenocysteine
its
dimeric
form,
selenocystine,
active
sites
of
selenoproteins,
which
catalyze
wide
variety
reactions,
including
detoxification
reactive
oxygen
species
modulation
redox
activities.
From
point
view
drug
developments,
organoselenium
drugs
are
isosteres
sulfur‐containing
oxygen‐containing
with
advantage
presence
atom
confers
antioxidant
properties
high
lipophilicity,
would
increase
cell
membrane
permeation
leading
to
better
oral
bioavailability.
This
statement
is
paramount
relevance
considering
big
number
clinically
employed
compounds
sulfur
or
atoms
their
structures
nucleosides
carbohydrates.
Thus,
article
we
have
focused
on
relevant
features
application
medicinal
chemistry.
With
increasing
chemistry,
attempted
highlight
most
significant
published
data
subject,
mainly
concentrating
analysis
last
In
consequence,
recent
advances
pharmacological
discussed.
Angewandte Chemie International Edition,
Год журнала:
2024,
Номер
63(15)
Опубликована: Фев. 12, 2024
Abstract
Click
chemistry
is
a
powerful
molecular
assembly
strategy
for
rapid
functional
discovery.
The
development
of
click
reactions
with
new
connecting
linkage
great
importance
expanding
the
toolbox.
We
report
first
selenium‐nitrogen
exchange
(SeNEx)
reaction
between
benzoselenazolones
and
terminal
alkynes
(Se−N
to
Se−C),
which
inspired
by
biochemical
SeNEx
Ebselen
cysteine
(Cys)
residue
Se−S).
formed
selenoalkyne
connection
readily
elaborated,
thus
endowing
this
multidimensional
diversity.
Besides,
modular,
predictable,
high‐yielding,
features
fast
kinetics
(k2≥14.43
M
−1
s
),
excellent
group
compatibility,
works
well
at
miniaturization
(nanomole‐scale),
opening
up
many
interesting
opportunities
organo‐Se
synthesis
bioconjugation,
as
exemplified
sequential
(coupled
ruthenium‐catalyzed
azide‐alkyne
cycloaddition
(RuAAC)
sulfur‐fluoride
(SuFEx)),
selenomacrocycle
synthesis,
nanomole‐scale
Se‐containing
natural
product
library
DNA‐encoded
(DEL),
late‐stage
peptide
modification
ligation,
multiple
functionalization
proteins.
These
results
indicated
that
useful
developments,
established
will
serve
transformative
platform
in
multidisciplinary
fields
such
synthetic
chemistry,
material
science,
chemical
biology,
medical
drug
The Journal of Organic Chemistry,
Год журнала:
2023,
Номер
88(9), С. 5572 - 5585
Опубликована: Апрель 21, 2023
Organoselenium
compounds
are
important
scaffolds
in
pharmaceutical
molecules.
Herein,
we
report
metal-free,
electrochemical,
highly
chemo-
and
regioselective
synthesis
of
gem-diselenides
through
the
coupling
α-keto
sulfoxonium
ylides
with
diselenides.
The
versatility
electrochemical
manifold
enabled
selenylation
ample
scope
broad
functional
group
tolerance,
as
well
setting
stage
for
modification
complex
bioactive
Detailed
mechanistic
studies
revealed
that
key
C-Se
bond
was
constructed
using
n-Bu4NI
an
electrolyte
catalyst
electrosynthetic
protocol.
Finally,
desired
showed
excellent
antimicrobial
activity
against
Candida
albicans,
which
can
be
identified
lead
further
exploration.
European Journal of Medicinal Chemistry Reports,
Год журнала:
2023,
Номер
9, С. 100113 - 100113
Опубликована: Сен. 7, 2023
Natural
products
play
a
key
role
in
the
history
of
human
drug
discovery,
and
especially
for
anticancer
agents.
Copper(I)-catalyzed
alkyne-azide
[3+2]
cycloaddition
(CuAAC)
reaction
is
perhaps
most
powerful
method
efficient
modification
complex
natural
products,
enabling
direct
incorporation
various
functional
groups
accompanied
by
formation
multifunctional
1,2,3-triazole
motif,
which
could
not
only
serve
as
an
basic
hydrophilic
connecting
group
but
also
bioisosteres
5-
or
6-membered
heterocycles
amide
group,
thus
facilitating
improvement
activities
and/or
drug-like
properties.
This
contribution
extensively
summarizes
state-of-the-art
application
activity.
The
aim
to
gain
deep
understanding
fruitful
achievements
well
limitations
CuAAC
click
chemistry
product
activity,
provide
perspectives
directions
regarding
future
studies
medicinal
chemistry.
Abstract
An
ideal
DNA‐encoded
library
(DEL)
selection
requires
the
to
consist
of
diverse
core
skeletons
and
cover
chemical
space
as
much
possible.
However,
lack
efficient
on‐DNA
synthetic
approaches
toward
has
greatly
restricted
diversity
DEL.
To
mitigate
this
issue,
work
disclosed
a
“Mask
&
Release”
strategy
streamline
challenging
skeleton
synthesis.
N
‐phenoxyacetamide
is
used
masked
phenol
versatile
directing
group
mediate
diversified
DNA‐compatible
C‐H
functionalization,
introducing
1st‐dimensional
at
defined
site,
simultaneously
releasing
functionality,
which
can
facilitate
introduction
2nd
diversity.
This
not
only
provides
set
syntheses
DNA‐conjugated
drug‐like
such
ortho
‐alkenyl/sulfiliminyl/cyclopropyl
phenol,
benzofuran,
dihydrobenzofuran
but
also
paradigm
for
method
development.
Bioconjugate Chemistry,
Год журнала:
2023,
Номер
34(8), С. 1459 - 1466
Опубликована: Июль 14, 2023
The
DNA-encoded
chemical
library
(DEL)
is
a
powerful
hit
selection
technique
in
either
basic
science
or
innovative
drug
discovery.
With
the
aim
to
circumvent
issue
concerning
DNA
barcode
damage
conventional
on-DNA
copper-catalyzed
azide–alkyne
cycloaddition
reaction
(CuAAC),
we
have
successfully
developed
first
DNA-compatible
enolate–azide
[3
+
2]
reaction.
merits
of
this
DEL
chemistry
include
metal-free
and
high
fidelity,
conversions
easy
operation,
broad
substrate
scope,
ready
access
highly
substituted
1,4,5-trisubstituted
triazoles.
Thus,
it
will
not
only
further
enrich
toolbox
but
also
great
potential
practical
synthesis.
ACS Medicinal Chemistry Letters,
Год журнала:
2024,
Номер
15(9), С. 1591 - 1597
Опубликована: Авг. 23, 2024
DNA-encoded
library
(DEL)
is
a
powerful
hit
selection
technique
in
both
basic
science
and
innovative
drug
discovery.
In
this
study,
we
report
robust
straightforward
DNA-compatible
diazo-transfer
reaction
utilizing
FSO
