Synthesis of 2-acetylpyridine--substituted thiosemicarbazonates of copper() with high antimicrobial activity against methicillin resistant , 1 and
The basic interest in the present study pertains to developing metal based antimicrobial agents, as several microorganisms have built resistance to the conventional drugs. In this respect, reactions of 2-acetylpyridine- N 1 -substituted thiosemicarbazones, {(C 5 H 4 N 4 )-(CH 3 )C 2 &z.dbd;N 3 -...
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Published in | New journal of chemistry Vol. 43; no. 29; pp. 11727 - 11742 |
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Main Authors | , , , , , , , |
Format | Journal Article |
Published |
23.07.2019
|
Online Access | Get full text |
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Summary: | The basic interest in the present study pertains to developing metal based antimicrobial agents, as several microorganisms have built resistance to the conventional drugs. In this respect, reactions of 2-acetylpyridine-
N
1
-substituted thiosemicarbazones, {(C
5
H
4
N
4
)-(CH
3
)C
2
&z.dbd;N
3
-N
2
(H)-C
1
(&z.dbd;S)-N
1
HR} (abbrev. HL
3R
: R = H, Me, Et, and Ph), with copper(
i
) halides in equimolar ratios have been carried out and consequently mononuclear copper(
ii
) complexes, [Cu
II
X(N
4
,N
3
,S-L
3R
)] (R = H, Me, Et, and Ph; X = Cl, 1-4; Br, 5-8; I, 9-12), have been isolated. The formation of these complexes with Cu
II
-halogen bonds, especially with iodide anions, occurred
via
a proton coupled electron transfer mechanism (PCET), which involved the simultaneous release of electrons from Cu
I
to combine with protons derived from the N
2
H moiety, and the metal itself converting to Cu
II
. The analytical data, spectroscopy (IR, ESR, UV-visible, and ESI-mass) and X-ray crystallography confirmed their molecular structures. These pseudo square planar copper(
ii
) complexes have been tested for their antimicrobial activity against methicillin resistant
Staphylococcus aureus
(MRSA) bacteria,
Staphylococcus aureus
(MTCC740),
Klebisella pneumoniae
1 (MTCC-109),
Salmonella typhimurium
2 (MTCC1251) and
Candida albicans
(MTCC 227). In particular, the antimicrobial activity against MRSA,
Klebisella pneumoniae
1 (MTCC-109) and
Candida albicans
(MTCC 227) is comparable to or better than that of the reference compounds gentamicin and amphotericin B. Significantly, several complexes have shown
in vitro
high cell viability (88-92%) determined using MTT assay {MTT = 3-[(4,5-dimethylthiazol-2-yl)-2,5-diphenyl]tetrazolium bromide}.
The basic interest in the present study pertains to developing metal based antimicrobial agents, as several microorganisms have built resistance to the conventional drugs. |
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Bibliography: | Electronic supplementary information (ESI) available. CCDC 11 ( 1895667 ) 1895668 1895663 1895664 1895665 1895666 For ESI and crystallographic data in CIF or other electronic format see DOI 1895662 4 5 6 and 7 10.1039/c9nj01459d 9 10 |
ISSN: | 1144-0546 1369-9261 |
DOI: | 10.1039/c9nj01459d |