Angewandte Chemie,
Journal Year:
2024,
Volume and Issue:
136(15)
Published: Feb. 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
Angewandte Chemie International Edition,
Journal Year:
2020,
Volume and Issue:
60(4), P. 1959 - 1966
Published: Oct. 6, 2020
Using
gem-difluoromethylene
alkynes
as
effectors,
unprecedented
diverse
C-H
activation/[4+2]
annulations
of
simple
benzoic
acids
are
reported.
The
chemodivergent
reaction
outcomes
well-tuned
by
Rh/Ir-catalyzed
system;
in
the
RhIII
catalysis,
3-alkenyl-1H-isochromen-1-one
and
3,4-dialkylideneisochroman-1-one
skeletons
afforded
a
solvent-dependent
manner
whereas
difluoromethylene-substituted
1H-isochromen-1-ones
generated
under
IrIII
-catalyzed
system.
Mechanistic
studies
revealed
that
unusually
double
β-F
eliminations
fluorine
effect-induced
regioselective
reductive
elimination
independently
involved
to
enable
distinct
modes
for
divergent
product
formations.
Besides,
synthetic
application
both
derivatization
obtained
diene
products
on-DNA
synthesis
DNA-tagged
difluorinated
isocoumarin
have
been
demonstrated,
which
manifested
great
potential
utility
developed
protocols.
Angewandte Chemie International Edition,
Journal Year:
2024,
Volume and Issue:
63(15)
Published: Feb. 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
Angewandte Chemie International Edition,
Journal Year:
2022,
Volume and Issue:
61(35)
Published: May 17, 2022
Abstract
Click
chemistry
is
a
concept
wherein
modular
synthesis
used
for
rapid
functional
discovery.
To
this
end,
continuous
discovery
of
clickable
chemical
transformations
the
pillar
to
support
development
field.
This
report
details
C3‐H
selenylation
indole
that
suitable
on‐plate
parallel
and
DNA‐encoded
library
(
Se
DEL)
via
bioinspired
LUMO
activation
strategy.
reaction
modular,
robust
highly
site‐selective,
it
features
simple
mild
system
(catalyzed
by
nonmetallic
B(C
6
F
5
)
3
at
room
temperature),
high
yields
excellent
group
compatibility.
Using
method,
1350
indole‐selenides
was
synthesized
in
an
efficient
practical
manner,
enabling
identification
ai
as
promising
compound
with
nanomolar
antiproliferative
activity
cancer
cells
situ
phenotypic
screening.
These
results
indicate
great
potential
new
high‐throughput
medicinal
biology.
iScience,
Journal Year:
2020,
Volume and Issue:
23(6), P. 101197 - 101197
Published: May 23, 2020
Although
insulin
is
a
life-saving
medicine,
administration
by
daily
injection
remains
problematic.
Our
goal
was
to
exploit
the
power
of
DNA-encoded
libraries
identify
molecules
with
insulin-like
activity
but
potential
be
developed
as
oral
drugs.
strategy
involved
using
104-member
library
containing
160
Traditional
Chinese
Medicines
(nDEL)
that
bind
and
activate
receptor.
Importantly,
we
used
natural
ligand,
insulin,
liberate
bound
molecules.
Using
this
selection
method
on
our
relatively
small,
highly
diverse,
nDEL
yielded
molecule
capable
both
binding
activating
Chemical
analysis
showed
polycyclic
analog
guanidine
metformin,
known
drug
treat
diabetes.
By
protocol
other,
even
larger,
DELs
can
expect
additional
organic
Angewandte Chemie International Edition,
Journal Year:
2021,
Volume and Issue:
61(7)
Published: Dec. 14, 2021
The
use
of
a
proper
encoding
methodology
is
one
the
most
important
aspects
when
practicing
DEL
technology.
A
"headpiece"-based
double-stranded
method
currently
widely
used
for
productive
DEL.
However,
robustness
construction
conflicts
with
versatility
presented
by
single-stranded
applications.
We
here
report
novel
method,
which
based
on
"reversible
covalent
headpiece
(RCHP)".
RCHP
allows
reversible
interconversion
between
double-
and
DNA
formats,
providing
an
avenue
to
robust
synthesis
allowing
applications
in
distinct
setups.
have
validated
this
encoded
self-assembled
chemical
library
DNA-encoded
dynamic
Notably,
RCHP-settled
construction,
unique
"ternary
complex"
mediating
ligand
isolation
against
non-immobilized
targets
was
developed.
ChemMedChem,
Journal Year:
2022,
Volume and Issue:
17(17)
Published: July 27, 2022
Selenium
(Se)
is
an
emerging
versatile
player
in
medicinal
chemistry.
The
incorporation
of
Se
into
small
molecules
and
natural
products
could
have
multiple
benefits.
However,
the
lack
efficient
methods
for
synthesis
Se-containing
chemical
library
has
greatly
hindered
development
seleno-medicinal
With
aim
to
address
this
issue,
we
proposed
"clickable
selenylation"
reactions,
which
can
be
used
situ
DNA-encoded
(SeDEL),
thereby
quickly
producing
ultra-large
collections
compounds
boosting
This
research
paradigm
concluded
as
selenylation
chemistry
development→in
construction/SeDEL
synthesis→phenotype-
or
target-based
screening→seleno-hit
compound".
Chemistry - A European Journal,
Journal Year:
2021,
Volume and Issue:
27(71), P. 17952 - 17959
Published: Oct. 28, 2021
Isoselenazolone
derivatives
have
attracted
significant
research
interest
because
of
their
potent
therapeutic
activities
and
indispensable
applications
in
organic
synthesis.
Efficient
construction
functionalized
isoselenazolone
scaffolds
is
still
challenging,
thus
new
synthetic
approaches
with
improved
operational
simplicity
been
particular
interest.
In
this
manuscript,
we
introduce
a
rhodium-catalyzed
direct
selenium
annulation
by
using
stable
tractable
elemental
selenium.
A
series
benzamides
as
well
acrylamides
were
successfully
coupled
under
mild
reaction
conditions,
the
obtained
isoselenazolones
could
be
pivotal
precursors
for
several
organoselenium
compounds.
Based
on
designed
control
experiments
X-ray
absorption
spectroscopy
measurements,
propose
an
unprecedented
selenation
mechanism
involving
highly
electrophilic
Se(IV)
species
reactive
donor.
The
was
further
verified
computational
study.
The Journal of Organic Chemistry,
Journal Year:
2023,
Volume and Issue:
88(7), P. 4554 - 4568
Published: March 22, 2023
An
efficient
method
for
pharmaceutically
useful
selenoflavones
via
a
ruthenium-catalyzed
selenylation
reaction
is
demonstrated.
The
was
applied
to
synthesize
diverse
alkenyl
selenides
from
simple
unsaturated
acids/amides
and
diaryl
diselenides.
A
wide
range
of
differently
substituted
diselenides
can
be
in
this
protocol
with
good
functional
group
excellent
stereo-
regioselectivity.
Angewandte Chemie,
Journal Year:
2022,
Volume and Issue:
134(35)
Published: May 17, 2022
Abstract
Click
chemistry
is
a
concept
wherein
modular
synthesis
used
for
rapid
functional
discovery.
To
this
end,
continuous
discovery
of
clickable
chemical
transformations
the
pillar
to
support
development
field.
This
report
details
C3‐H
selenylation
indole
that
suitable
on‐plate
parallel
and
DNA‐encoded
library
(
Se
DEL)
via
bioinspired
LUMO
activation
strategy.
reaction
modular,
robust
highly
site‐selective,
it
features
simple
mild
system
(catalyzed
by
nonmetallic
B(C
6
F
5
)
3
at
room
temperature),
high
yields
excellent
group
compatibility.
Using
method,
1350
indole‐selenides
was
synthesized
in
an
efficient
practical
manner,
enabling
identification
ai
as
promising
compound
with
nanomolar
antiproliferative
activity
cancer
cells
situ
phenotypic
screening.
These
results
indicate
great
potential
new
high‐throughput
medicinal
biology.
Advanced Synthesis & Catalysis,
Journal Year:
2022,
Volume and Issue:
364(20), P. 3544 - 3550
Published: Sept. 2, 2022
Abstract
A
palladium‐catalyzed
remote
δ
‐C−H
selenylation
of
arylethylamide
derivatives
with
readily
available
diselenides
has
been
reported.
This
protocol
relies
on
the
use
a
removable
picolinamide
directing
group
to
access
unsymmetrical
diaryl
selenides
in
45–98%
yields.
Furthermore,
inactivated
‐C(alkenyl)−H
bond
was
also
compatible
this
reaction
and
afforded
thermo‐dynamically
unfavorable
Z
‐selective‐alkenyl
complete
control
site‐
stereoselectivity.
magnified
image
