Loading…
Synthesis and inhibitory activity against MurA and MurZ enzymes of 4-pyrano[2,3-]pyrimidine-1-1,2,3-triazole hybrid compounds having piperidine and morpholine rings
A series of d -glucose-conjugated 4 H -pyrano[2,3- d ]pyrimidine-1 H -1,2,3-triazole hybrid compounds 12a-g and 13a-g having piperidine and morpholine rings were synthesized by click chemistry between corresponding propargyl derivatives and azide of d -glucose using CuI@montmorillonite as a catalyst...
Saved in:
Published in: | New journal of chemistry 2023-06, Vol.47 (25), p.118-11821 |
---|---|
Main Authors: | , , , , , , , |
Format: | Article |
Language: | |
Online Access: | Get full text |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
Summary: | A series of
d
-glucose-conjugated 4
H
-pyrano[2,3-
d
]pyrimidine-1
H
-1,2,3-triazole hybrid compounds
12a-g
and
13a-g
having piperidine and morpholine rings were synthesized by click chemistry between corresponding propargyl derivatives and azide of
d
-glucose using CuI@montmorillonite as a catalyst. Their inhibitory activities against
E. coli
MurA and
S. aureus
MurA and MurZ enzymes were examined. The morpholine ring at position 3 along with the ethoxy group at position 4 on the benzene nucleus made 1,2,3-triazole
13b
become the most potent inhibitor in this series against all three enzymes,
E. coli
MurA as well as
S. aureus
MurA and MurZ with IC
50
values of 0.15 ± 0.05, 1.02 ± 0.05, and 1.21 ± 0.05 μM, respectively. This compound also exhibited a strong bacterial growth inhibitory activity against
E. coli
and
S. aureus
with MIC values of 0.78 and 1.56 μg mL
−1
, respectively. Induced fit docking and molecular dynamics simulations were carried out on enzyme
1UAE
in order to elucidate the inhibition potential of
13b
against corresponding tested enzyme UDP-
N
-acetylglucosamine enolpyruvyl transferase MurA.
A series of 1
H
-1,2,3-triazoles
12a-g
and
13a-g
having 4
H
-pyrano[2,3-
d
]pyrimidine and
d
-glucose rings was synthesized by click chemistry and their inhibitory activity against UDP-
N
-acetylglucosamine enolpyruvyl transferases (MurA & MurZ) was examined. |
---|---|
ISSN: | 1144-0546 1369-9261 |
DOI: | 10.1039/d3nj01718d |