Annulated Heterocyclic[g]Coumarin Composites: Synthetic Approaches and Bioactive Profiling
Chemistry & Biodiversity,
Год журнала:
2023,
Номер
21(3)
Опубликована: Дек. 25, 2023
Abstract
Coumarins,
widely
abundant
natural
heterocyclic
compounds,
are
extensively
employed
in
creating
various
biologically
and
pharmacologically
potent
substances.
The
hybridization
of
heterocycles
presents
a
key
opportunity
to
craft
innovative
multicyclic
compounds
with
enhanced
biological
activity.
Fusing
different
rings
the
coumarin
structure
an
intriguing
method
for
crafting
fresh
hybrid
possessing
remarkable
effects.
In
pursuit
heterocyclic‐fused
coumarins,
wide
range
annulated
heterocyclic[
g
]coumarin
composites
has
been
introduced,
displaying
impressive
potency.
influence
linear
attachment
on
performance
resulting
investigated.
This
review
centers
synthetic
methodologies,
structural
activity
relationship
investigation,
potentials
composites.
We
conducted
searches
across
several
databases,
including
Web
Science,
Google
Scholar,
PubMed,
Scopus.
After
sieving,
we
ultimately
identified
included
71
pertinent
studies
published
between
2000
middle
2023.
will
provide
valuable
perspectives
medicinal
chemists
prospective
design
synthesis
lead
significant
therapeutic
effects,
centered
around
heterocycle‐fused
frameworks.
Язык: Английский
A One-Pot Synthesis of Substituted Pyrrolo[2,1-a]isoquinolines via an Oxidation/Annulation Sequence of 2-(3,4-Dihydroisoquinolin-2(1H)-yl)malononitriles
The Journal of Organic Chemistry,
Год журнала:
2025,
Номер
unknown
Опубликована: Май 15, 2025
A
highly
effective
oxidation/annulation
reaction
between
2-isocyanoacetates
and
2-(3,4-dihydroisoquinolin-2(1H)-yl)malononitriles
has
been
successfully
developed
to
give
substituted
pyrrolo[2,1-a]isoquinoline
derivatives
with
moderate
good
yields
in
a
one-pot
manner.
Язык: Английский
Chromenone‐Fused Pyrrolizines and Pyrrolizine Analogues of Lamellarins: Expanding the Lamellarin Family
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(6)
Опубликована: Янв. 9, 2024
Abstract
Several
N
‐ethoxycarbonylmethyl
enaminones,
prepared
by
Eschenmoser
sulfide
contraction
between
‐(ethoxycarbonylmethyl)pyrrolidine‐2‐thione
and
various
ortho
‐oxygenated
phenacyl
halides,
underwent
cyclisation
to
give
ethyl
6‐aryl‐2,3‐dihydro‐1
H
‐pyrrolizine‐5‐carboxylates
upon
microwave
heating
with
silica
gel
in
xylene.
With
enaminones
made
from
‐hydroxyphenacyl
not
only
did
dihydropyrrolizine
formation
take
place,
but
spontaneous
lactonisation
also
occurred
9,10‐dihydrochromeno[4,3‐
b
]pyrrolizin‐6(8
)‐ones.
Bromination
Suzuki‐Miyaura
arylation
of
these
chromenopyrrolizines
at
the
free
C−H
site
on
pyrrole
ring
afforded
four
analogues
lamellarin
alkaloids
which
a
pyrrolidine
replaces
isoquinoline
system
fused
polycyclic
core.
The
product
11‐(3,4‐dimethoxyphenyl)‐2,3‐dimethoxy‐9,10‐dihydrochromeno[4,3‐
)‐one,
particular,
is
congener
well‐known
G
trimethyl
ether.
Preliminary
results
pertaining
an
extension
chromenone‐fused
indolizines
are
reported.
Язык: Английский
Cascade Synthesis of Pyrrolo[1,2-a]quinolines and Pyrrolo[2,1-a]isoquinolines via Formal [3 + 2]-Cycloaddition of Push–Pull Nitro Heterocycles with Carbonyl-Stabilized Quinolinium/Isoquinolinium Ylides
The Journal of Organic Chemistry,
Год журнала:
2024,
Номер
89(14), С. 9816 - 9829
Опубликована: Июнь 25, 2024
Various
substituted
pyrrolo[1,2-
Язык: Английский
A Comprehensive Review of Synthetic Approaches Toward Lamellarin D and its Analogous
Pooja Sivaganesan,
Subiksha VL,
Arupratan Sahoo
и другие.
ChemistrySelect,
Год журнала:
2024,
Номер
9(37)
Опубликована: Окт. 1, 2024
Abstract
Lamellarin
D,
a
naturally
occurring
molecule,
isolated
from
marine
molluscs,
it
exhibits
potent
pharmacological
activities,
such
as
topoisomerase
I
inhibition,
antiproliferation,
antiviral,
insecticidal,
antimetastatic
and
anticancer
effects,
making
promising
candidate
for
drug
development.
This
review
explores
the
synthesis
of
D
employing
various
methodologies.
These
synthetic
approaches
have
enabled
researchers
to
access
its
analogous
efficiently,
facilitating
further
investigation
into
their
biological
properties.
Our
study
summarizes
major
contributions
these
efforts
larger
community,
primarily
focusing
on
general
techniques
toward
counterpart
since
isolation
in
1997
present.
Язык: Английский
Synthesis of imidazole-fused pentacyclic pyrrolo[3,4-c]coumarins via base-promoted rearrangement of coumarin-substituted N-heterocyclic carbene precursors
New Journal of Chemistry,
Год журнала:
2024,
Номер
48(38), С. 16676 - 16682
Опубликована: Янв. 1, 2024
The
stoichiometric
reaction
between
coumarin-substituted
N-heterocyclic
carbene
(NHC)
precursors
and
Pd(OAc)
2
,
in
the
presence
of
an
external
base,
yielded
imidazole-fused
pentacyclic
pyrrolo[3,4-
c
]coumarin
derivatives.
Язык: Английский
Synthesis of Natural Product‐like Indeno[2,1‐b]indole/Shikimic Acid Hybrid Analogues with Anti‐osteoclastogenic Activity via Photo‐Nazarov Reaction
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
unknown
Опубликована: Сен. 24, 2024
Abstract
Indeno[2,1‐
b
]indole
and
shikimic
acid‐like
structures
are
natural
privileged
scaffolds
in
several
bioactive
NPs.
In
this
work,
we
developed
a
high‐efficient
diastereoselective
synthetic
approach
to
construct
novel
indeno[2,1‐
]indole/shikimic
acid
hybrid
analogues
via
photo‐Nazarov
reaction.
The
protocol
is
the
first
case
of
excited‐state
cyclization
indole‐2‐yl
vinyl
ketone
]indole.
(6a
S
,
10a
R
)‐products
were
afforded
moderate
good
yields
(37–92
%)
for
most
substrates
(91
%
model
substrate
1
aa
)
after
condition
optimization.
Even
more
attractive,
synthesized
(
2
t
3
c
d
exhibited
potent
RANKL‐induced
osteoclastogenesis
inhibitory
activities
(inhibitory
rate
>50
at
5
μ
M),
which
suggested
promising
prospect
tetracyclic
scaffold
anti‐osteoporosis
drug
development.
Язык: Английский
Visible Light Mediated Iron‐Catalyzed One‐Pot Synthesis of Chromenopyrroles from Benzyl Alcohols, 2‐Hydroxyacetophenones and Methyl/Ethyl Isocyanoacetate at Room Temperature
ChemistrySelect,
Год журнала:
2024,
Номер
9(37)
Опубликована: Сен. 30, 2024
Abstract
An
effective,
facile,
trivial,
and
one‐pot
procedure
for
the
synthesis
of
chromenopyrroles
from
benzyl
alcohols,
2‐hydroxyacetophenones,
methyl/ethyl
isocyanoacetate
at
room
temperature
in
presence
visible
light
has
been
developed.
The
Ag
salt
plays
an
important
role
activation
cyclization
step.
Air‐stable
low‐cost
Knölker
iron
complex
utilized
dehydrogenation
primary
alcohols
that
would
typically
require
a
higher
temperature.
established
protocol
is
scalable
extensive
functional
group
tolerance,
generating
good
to
excellent
yields
Язык: Английский