Metallation of some new imines and evaluation of their antimicrobial and anticancer activity

Article abstract of DOI:10.1080/15533174.2012.754761

Metallation of new imines 2-(4-(Dimethylamino)benzylidene- amino)benzenethiol (1) and 2-(4-nitrobenzylideneamino)-benz- enethiol(5) with Hg(II), Ni(II) acetate, and palladium chloride afforded metallated products (2), (3), and (4) in the form of monomercu

Full text of DOI:10.1080/15533174.2012.754761

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Metallation of Some New Imines and Evaluation of
Their Antimicrobial and Anticancer Activity
Emtithal A. El-Sawi a & Tahany M. Sayed a
a Department of Chemistry, Faculty of Women for Arts, Science and Education, Ain Shams
University, Heliopolis, Cairo, Egypt
Accepted author version posted online: 11 Feb 2013.Published online: 13 Mar 2013.
To cite this article: Emtithal A. El-Sawi & Tahany M. Sayed (2013): Metallation of Some New Imines and Evaluation of Their
Antimicrobial and Anticancer Activity, Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 43:6,
722-727
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Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 43:722–727, 2013
Copyright ꢀ Taylor & Francis Group, LLC
C
ISSN: 1553-3174 print / 1553-3182 online
DOI: 10.1080/15533174.2012.754761
Metallation of Some New Imines and Evaluation of Their
Antimicrobial and Anticancer Activity
Emtithal A. El-Sawi and Tahany M. Sayed
Department of Chemistry, Faculty of Women for Arts, Science and Education, Ain Shams University,
Heliopolis, Cairo, Egypt
Schiff bases have been synthesized from different aldehyde and
diamine using P2O5/SiO2 as catalyst by crushing in a mortar at
room temperature under free solvent conditions.[8] Some met-
allated Schiff bases with Ni(II), Co(II), and Cu(II) exhibited
potential effect as killing agents for Biomphalaria alexandrina
snails without affecting the surrounding environment.[9] Schiff
base 2-(4-methoxybenzylidene amino) benzene-thiol, its metal-
lation with mercury(II), nickel(II), palladium(II), and phospho-
rylation gave compounds exhibited antimicrobial and anticancer
activity.[10] Organopalladium and organomercury compounds
via metallation of some new Schiff bases were also synthe-
sized.[11,12] Screening of organopalladium of the acetone Schiff
bases of S-methyl-and S-benzyldithiocarbazate compounds for
their cytotoxicities against T-lymphoblastic leukemia cancer
cells shows that they exhibit strong cytotoxicities against this
cancer; their activities being more than that of the standard
anticancer drug tamoxifen.[13] Biological studies of some palla-
dium(II) and platinum(II) compounds derived from biologically
active sulfur donor ligands 1-H-indol-2,3-dione benzothiazo-
line and 5-nitro-1-H-indol-2,3-dione benzothiazoline have been
noted that the growth-inhibiting potential of the compounds is
greater than the parent benzothiazolines toward a variety of fun-
gal and bacterial strains.[14] Environmentally benign studies of
bivalent transition metal complexes with Co2+, Ni2+, and Zn2+
of tridentate Schiff base ligands were evaluated for their in vitro
antimicrobial activity,[15] in continuation to our previous works
on Schiff bases and their metallation. This work planned to syn-
thesize new imines containing electron-attracting and electron-
repelling groups followed by metallation with some metal salts
such as Hg(II), Ni(II) acetates, and Pd(II) chloride to study their
effect on orientation in each case and screening the antimicrobial
and anticancer activity.
Metallation of new imines 2-(4-(Dimethylamino)benzylidene-
amino)benzenethiol (1) and 2-(4-nitrobenzylideneamino)-benz-
enethiol(5) with Hg(II), Ni(II) acetate, and palladium chloride
afforded metallated products (2), (3), and (4) in the form of
monomercurated, dinickel nickel bis-, monopalladated products
and monometallated products of Hg++ and Ni++ (6) and (7), and
monopalladated cyclized product (8), respectively. Compounds (1)
and (5) were prepared from the reaction of o-aminothiophenol
with N,N-dimethylaminobenzaldehyde and p-nitrobenzaldehyde
in ethyl alcohol. Elemental analyses, IR, 1HNMR, and mass spec-
tral elucidated the structures. All the newly synthesized compounds
have been evaluated for their antimicrobial activity against gram
positive and gram negative bacteria and fungi. Compounds (4) and
(8) exhibited in vitro anticancer activity toward breast cancer.
Keywords anticancer activity, antimicrobial, imines, metallation
INTRODUCTION
Schiff bases derived from aromatic amines and aromatic
aldehydes have a wide variety of applications in many fields
(e.g., biological, inorganic, and analytical chemistry).[1,2]
A
series of Schiff bases have been synthesized from the con-
densation of (4.4ꢁ-diaminodiphenylsulphone) with various aro-
matic or heterocyclic aldehydes and the new compounds
were evaluated for their in vitro activity against several mi-
crobes.[3,4] Schiff base derivatives of 4-methylpyridin-2-amine
have been screened for their antimicrobial activities.[5] Some
Schiff bases of [4-(amino)-5-phenyl-4H-1,2,4-triazole-3-thiol]
were screened for their antianxietic activity.[6] Schiff bases
derived from 2-amino 4,6- dimethyl benzothiazole and pyri-
dine/pyrrole 2-carboxyaldehyde and their complexes were also
screened for the antimicrobial activity, antibacterial activity
against bacteria such as S. aureus, E. coli, and antifungal ac-
tivity against A. niger and A. flavus.[7] Mild and significant
EXPERIMENTAL
Melting points were measured by a Gallen Kamp melt-
ing point apparatus. Thin-layer chromatography was performed
with fluorescent silica gel plates HF254 (Merck), and plates were
viewed under UV light at 254 and 265 nm. The elemental anal-
yses for C, H, and N were determined by a Perkin-Elmer an-
alyzer 2440 (Micro Analytical Center, Cairo University Giza,
Received 19 May 2012; accepted 28 November 2012.
Address correspondence to Emtithal A. El-Sawi, Department of
Chemistry, Faculty of Women for Arts, Science and Education,
Ain Shams University, Heliopolis, Cairo, Egypt. E-mail: elsawi e@
yahoo.com.
722

IMINES, METALLATION, ANTIMICROBIAL, ANTICANCER
723
Egypt). Infrared spectra (λ-cm−1) were recorded on Bruker Vec-
tor (Germany) and on Mattson FT-IR 1000 (Cairo University
Giza, Egypt), using KBr disks. Mass spectra were measured on
GCQ Finnigan MAT (Cairo University Giza, Egypt). 1H-NMR
spectra were recorded on Gemini 200 MHZ NMR spectrometer,
in DMSO-d6 solution with TMS as internal standard in the Mi-
cro Analytical Center, Cairo University, Giza, Egypt. Analyses
of mercury were carried out by thiocyanate method[16] using fer-
ric alum as indicator as well as by mercurometry using diphenyl
carbazone-bromothymol blue as indicator.[17] The antibacterial
activity was determined in a laboratory belongs to the Micro
Analytical Center, Cairo University, and anticancer activity was
checked in the National Cancer Institute, Cancer Biology De-
partment, Pharmacology, Cairo University, Egypt.
MS spectrum m/z (%): the base beak at 253(100). Anal. Calcd.
for C15H15N2SPdCl: C 45.39,H 3.78, N 7.06, Pd 26.73. Found:
C 45.22, H 3.76, N 7.00, Pd 26.62.
Preparation of Imine (5) 2-(4-nitrobenzylideneamino)
benzenethiol
A mixture of 2-aminothiophenol (0.125 g, 1 mmol) and p-
nitrobenzaldhyde (0.151 g, 1 mmol) in 20 mL ethanol was re-
fluxed for 1 h; the formed precipitate was collected by filtration,
dried, and crystallized from ethanol. Compound (5): yellow
crystals, Yield: 92%; m.p: 189–190◦C. IR cm−1 (ν): 3040 (ArC-
H), 2978–2845 (Aliph. C-H str.), 2552 (SH), 1631(C N), 1600
(Ar. C C), 1426 (Aliph. CH bend.), 1512, 1360 (conjugated
NO2). MS spectrum m/z (%): 257 (0.3) for M–1+, the base peak
at 240 (100). Anal. Calcd. for C13H10N2 O2S: C 60.46, H 3.87,
N 10.85. Found: C 60.49, H 3.88, N 11.00.
Preparation of imine(1) 2-(4-(dimethylamino)
benzylideneamino)benzenethiol
Metallation of (5) to give (6),(7) (general procedure)
A mixture of (1 mmol) of (1) and (1 mmol) of metal acetate in
30 mL toluene and few drops of acetic acid was refluxed for 3 h,
the precipitated product was filtered, dried, and crystallized from
acetic acid. Metallated compound (6): gray crystals, 89% yield;
m.p. d. 280–281◦C. IR cm−1 (ν): 3072 (ArC-H), 2944–2856
(Aliph. C-H str.), 2550 (SH), 1649 (C N), 1600 (Ar. C C),
1471 (Aliph. CH bend.), 1515, 1362 (conjugated NO2), 797–630
(Arom. out of plane+bend.), 510 (Hg-C). MS spectrum m/z
(%): 519 (0.2) M+2 , base peak at 93(100). Anal. Calcd. for
C15H12HgN2O4S: C 34.88, H 2.32, N 5.42, Hg 38.87. Found
(%): C 43.65, H 2.32, N 7.99, Hg 38.80.
2-aminothiophenol (0.125 g,
1 mmol) in 20 mL
ethyl alcohol was added to (0.149 g, 1mmol) of N,N-
dimethylaminobenzaldhyde in 20 mL ethyl alcohol and the
mixture was refluxed for 4 h then left to cool. The precipitated
product was filtered, dried, and crystallized from ethyl alcohol to
give compound (1): white crystals from ethyl alcohol, m.p. 125-
√
126◦C, 39% yield, IR cm−1 ( ): 2986–2888 (C-H, aliph. Str.),
1
2548 (SH), 1470 (C-H, aliph. bend.), 1608 (C N). HNMR
showed δ 8.01 ppm (1H, HC N), δ7.53–7 ppm (8H, arom.),
δ3.2 ppm (1H, SH), and δ2.9 ppm(6H, 2CH3). Anal. Calcd. for
C15H16N2S: C 70.31, H 6.25, N 10.93. Found: C 70.52, H 6.28,
N 10.95.
Metallated compound (7): green crystals, 85% yield, m.p
above 350◦C. IR cm−1 (ν): 3048 (ArC-H), 2954–2850 (Aliph.
C-H str.), 2550 (SH), 1682 (C O), 1649 (C N), 1600 (Ar.
C C), 1418 (Aliph. CH bend.), 1560, 1315 (conjugated NO2),
831–628 (Arom. out of plane bend.), 552 Ni-C. MS spectrum
m/z (%): 448 (1) M+1 +, base peak at 51(100). Anal. Calcd.
for C15H12N2NiO4S.4H2O: C 40.29, H 4.47, N 6.26, Ni 13.19.
Found (%): C 40.16, H 4.58, N 6.88, Ni 13.00.
Metallation of (1) to Give (2), (3), and (4) (General
Procedure)
A mixture of (0.256 g, 1 mmol) of Schiff base (1) and
(1 mmol) of mercuric acetate or nickel acetate in 30 mL toluene
and 2 mL acetic acid or palladium chloride in methanol with
few drops of HCl was refluxed for 3 h, left to cool where crys-
talline products (2), (3), or (4) were precipitated after cooling,
filtered, and dried and crystallized from acetic acid to give (2)
or (3) and from methanol to give compound (4): violet crys-
Metallation of Compound (5) to Give Compound (8)
A mixture of (0.258 g, 1 mmol) of compound 1 and (0.177 g,
1 mmol) of palladium chloride in 30 mL methanol and 2 mL
conc. HCl was refluxed for 3 h, and the crystalline product was
formed, filtered, dried, and crystallized from methyl alcohol.
Metallated compound (8): brown crystals, Yield: %, m.p above
300◦C. IR cm−1 (ν): 3040 (ArC-H), 2853 (Aliph. C-H str.), 1650
(C N), 1600 (Ar. C C), 1418 (Aliph. CH bend.), 1512, 1360
(conjugated NO2), 798–684 (Arom. out of plane bend.), 537
(Pd-C). MS spectrum m/z (%): 401 (4.38) M+2+, base peak
at 183(100). Anal. Calcd. for C13H8N2O2PdS.HCl: C 39.09, H
2.25, N 7.01, Pd 26.59. Found: C 40.12, H 2.20, N 7.04, Pd
26.50.
tals from acetic acid, m.p. 320–321◦C, 42% yield, IR cm−1
√
( ): 3210 (NH) and at 510 (C-Hg).[18] MS spectrum m/z (%):
the molecular ion peak at 554(2.5), the base peak at 93(100),
259(1) HgOCOCH3+, 256 (12) M-HgOCOCH3+, 200(22) Hg+.
Anal. Calcd. for C17H18N2SO2Hg.2/3CH3 COOH: C 39.66, H
3.72, N 5.04, Hg 36.17. Found: C 39.50, H 3.50, N 4.98.
Compound (3): Green crystals from acetic acid, m.p.
√
335–336◦C, IR cm−1 ( ): 3243 (NH), at 552 (Ni-C) and absence
√
√
of
and
N. The MS spectrum m/z (%): the molecular
SH
C
ion peak at 905(0.7), the base peak at 51(100). Anal. Calcd. for
C34H32N4SO4Ni3.10 H2 O: C 43.03, H 5.48, N 5.90, Ni 18.57.
Found: C 42.92, H 5.46, N 5.88, Ni 18.52.
Compound (4): Orange crystals from methyl alcohol, m.p.
√
1
260–261◦C, IR cm−1 ( ):537 (C-Pd). The HNMR spectrum
RESULTS AND DISCUSSION
showed signals at δ7.8–6.9 ppm (aromatic protons), δ 4.6 ppm
N,N-dimethylaminobenzaldehyde
reacted
with
o-
(NH) and δ 2.8 ppm (2CH3) protons and absence of δ 8.1 ppm. aminothiophenol in ethyl alcohol to give new product (1).

724
E. A. EL-SAWI AND T. M. SAYED
HS
N
H3C
H3C
H
C
N
2-(4-(dimethylamino)benzylideneamino)benzenethiol
(1)
Hg(OAc)2
PdCl2
Ni(OAc)2
NiOCOCH3
H
N
S
H3C
H3C
H3C
N
CH
Pd
S
N
C
N
H
S
H3C
H3C
H3C
(2)
N
C
HgOCOCH3
Ni
S
N
H3C
H3C
H
Cl
C
N
N
(4)
H
NiOCOCH3
(3)
SCH. 1.
√
and
√
Ni-C
N. The MS spectrum
The reaction was done also under microwave irradiation, and
by fusion with two times yield. Metallation of the product
with mercuric acetate, nickel acetate and palladium chloride
afforded compounds (2), (3), and (4) (Scheme 1).
spectrum showed new bands for
at 3243 cm−1
,
at
NH
√
√
552 cm−1, and absence of
SH
C
showed the molecular ion peak at m/z 905 (0.7%). The base peak
at m/z 51 (100%) can be attributed to C4 H3+. The fragment
at m/z 371 (2.1%), 255 (8.1%), 227 (17.6), 228 (53.9%), 93
(12.8%), and 78 (66.8%) is due to
The structure of product (1) was confirmed by IR, 1H-NMR,
elemental analysis, and chemical tests. The IR spectrum showed
√
√
√
CH aliphatic stretching at 2986–2888 cm−1
,
SH at 2548 cm−1
,
√
bending at 1470 cm−1, and
at 1608 cm−1. 1HNMR
+
H3C
S
H3C
S
CH
C
N
+
+
S
C
N
H3C
N
H3C
,
showed δ8.01 ppm (1H, HC N), δ7.53–7 ppm (8H, arom.),
δ3.2 ppm (1H, SH), and δ2.9 ppm (6H, 2CH3). It gave negative
azo dye and this proved that condensation occurred via NH2 and
the aldehydic carbonyl, also it gave positive spot test[19] for –SH
as well as its solubility in sodium hydroxide
H2N
,
C
N
N
H
N
H
H
NiOCOCH3
+
.
+
+
S
.
,
H2N
&
CH
H2N
N
H
Action of Mercuric Acetate on Compound (1)
Mercuric acetate reacted with compound (1) in toluene under
reflux to afford monomercurated product (2) via coordination to
nitrogen followed by electrophilic substitution of the aromatic
moiety.
Action of Palladium Chloride on Compound (1)
Reaction of palladium chloride with compound 1 in methanol
with drops of conc. HCl gave mono palladated compound (4).
The structure was consistent with the data obtained from ele-
mental analysis, IR, and MS spectra. The IR spectrum showed
√
S
new absorption band at 537 cm−1 due to C-Pd. The HNMR
H3C
1
HS
N
H3C
-AcOH
H
N
CH
Hg(OAc)2
N
C
N
H
spectrum showed signals at δ7. 8–6.9 ppm (aromatic protons),
δ4.6 ppm (NH) and δ2.8 ppm (6H, 2CH3) protons and absence
of(1H, HC N) at δ 8.1 ppm. The MS spectra did not show the
molecular ion peak, the base beak at m/z 253 (100%) due to
H3C
H3C
(2)
HgOCOCH3
Elucidation of the structure was based on elemental analysis,
IR, and MS spectra. The IR spectrum showed the absence of SH
√
group and the presence of the new absorption bands of
at
NH
√
+
H2C
3210 cm−1 and C-Hg at 510 cm
.
−1 [18] The MS spectrum showed
S
N
C
the molecular ion peak at m/z 554 (2.5%), the base peak at m/z 93
(100%) PhNH+2 and fragments at m/z’s 259 (1%) HgOCOCH3
256 (12%) M-HgOCOCH3+, and 200 (22%) Hg+.
,
+
N
H3C
the fragments at m/z’s 255, 240, 227, and 118 can be attributed
to p-Nitrobenzaldhyde reacted with o-aminothiophenol in ethyl
Action of Nickel Acetate on Compound (1)
The metallated product (3) was synthesized via the reaction
of compound 1 with nickel acetate, where it gave dinickelated-
nickel bis-compound (3). The data obtained from elemental
analysis, IR, and MS spectra confirmed its structure. The IR
S
S
S
H3C
Pd
.
C N
,
,
N
CH
H2N
CH
H2N
H3C
N
N
N
and
m/z 118(18.8%)
m/z 227(21.9%)
m/z 240(37.5%)
m/z 255(31.3%)

IMINES, METALLATION, ANTIMICROBIAL, ANTICANCER
725
alcohol under reflux for 3 h to give 2-(4-nitrobenzylideneamino) substitution in the m-position followed by elimination of HCl
benzenethiol (5). The reaction may proceeds via condensation with the formation of ArC-Pd-S-. The IR for compound (8)
√
reaction.
showed the absence of S-H (confirmed also by spot test[19]), and
new band for Pd-C at 539. The 1H NMR spectrum showed signal
at δ 8.4 ppm ( N CH Ar proton) and signals at δ8.2–6.9 ppm
(aromatic protons) (Scheme 2).
NO2
SH
Measurement of Potential Cytotoxicity of Compound 4 by
SRB Assay
CH
N
Potential cytotoxicity of the compound was tested using the
method of Skehan.[20] Cells were plated in 96-multiwell plate
(104 cells/well) for 24 h before treatment with the compound
to allow attachment of cells to the wall of the plate. Different
concentrations of the compound under test (0, 5, 12.5, 25,
50 μg/mL) were prepared for each individual dose. Monolayer
cells were inocubated with the compound for 48 h at 37◦C and
in an atmosphere of 5% CO. After 48 h they were fixed, washed,
and stained with sulfo-rhodamine-B stain. Excess stain was
washed with acetic acid and attached stain was recovered with
Tris base. Color intensity is measured in an ELIZA reader. The
relation between surviving fraction and drug conc. is plotted
(Figure 1) and (Figure 2) to get the survival curve of each tumor
cell line after the specified compound. The antitumor activity
result indicated that compounds (4) and (8) showed antitumor
activity against the tested human breast carcinoma cell line
MCF7 (in vitro) with varying intensities in comparison to the
known anticancer drugs doxorubicin. Moreover compound
(4) showed cytotoxic activity (IC50 = 4.04 μg/mL) while
(5)
Considering the data of IR, MS spectroscopy, and elemental
analysis, the structure of (5) was investigated and gave negative
azo dye; it also gave a positive spot test[19] for SH as well as its
√
solubility in sodium hydroxide. The IR spectrum showed
SH
√
√
2552,
1649, and NO2 1515, 1362 (conjugated NO2).
N
C
The metallation of compound (5) with mercuric acetate, nickel
acetate, and palladium chloride takes place in good yield and
the reaction may take place via substitution reaction in the m
position with respect to the nitro group. The structures were
confirmed by elemental analyses, IR, 1H NMR, and MS spectra.
√
The IR showed
for compounds (6) and (7) and showed
S-H
new bands for Hg-C at 512 cm−1 and N i-C at 552 cm−1. The MS
showed m/z 519 (0.2%) M+2+, m/z 448 (1%) M+1+, and base
peak at 93 (100%) and m/z 51 (100%), respectively. The reaction
took place in the case of palladium chloride via electrophilic
NO2
SH
CH
N
(5)
Hg(OCOCH3)2
Ni(OCOCH3)2
toluene +
drops of AcOH
PdCl2
CH3OH +
drops of HCl
toluene +
drops of AcOH
4H2O
NO2
NO2
NO2
.HCl
H3COCONi
H3COCOHg
SH
Pd
SH
S
CH
CH
HC
N
N
N
(6)
(8)
(7)
SCH. 2.

726
E. A. EL-SAWI AND T. M. SAYED
TABLE 1
Antimicrobial activity of the products toward some types of bacteria and fungus
Inhibition zone diameter (mm/mg) sample
Pseudomonas
Escherichia
aeruginosa
Staphylococcus Streptococcus
Aspergillus
Candida albicans
Sample
coli (G−)
(G−)
aureus (G+)
faecalis (G+) flavus (Fungus)
(Fungus)
Control: DMSO
Tetracycline
Amphotericin B
00
27
0
17
26
19
22
7
00
19
0
13
30
22
15
12
14
9
00
26
0
22
25
28
18
7
00
29
0
00
0
18
17
00
0.0
35
0.0
00
0
19
13
00
22
25
0.0
11
0.0
23
(1)
(2)
(3)
(4)
(5)
(6)
(7)
(8)
15
29
16
19
19
22
27
11
21
11
22
29
11
22
9
0.0
12
32
FIG. 2. Drug cytotoxicity of product (8) and and doxorubicin.
FIG. 1. Drug Cytotoxicity of Product (4) and doxorubicin.

IMINES, METALLATION, ANTIMICROBIAL, ANTICANCER
727
doxorubicin IC50 = 3.13 μg/mL and compound (8) showed product (8). All the newly synthesized compounds exhibited
IC50 = 18 μg/mL while doxorubicin IC50 = 4.20 μg/mL.
antibacterial and antifungal activities. Compound (4) and (8)
exhibited in vitro anticancer activity toward breast cancer.
Antimicrobial Investigation
For these investigation the filter paper disc method was ap-
plied with nutrient broth (NB).The seeded NB (1 cm3) was REFERENCES
homogenized in the tubes with 9 cm3 of melted (45◦C) nutrient
agar (NA).The homogeneous suspensions were poured into Petri
dishes. The discs of filter paper (diameter 5 mm) were ranged
on the cool medium. After cooling on the formed solid medium,
2 × 10−5dm3 of the investigated compounds were applied us-
ing a micropipette. After incubation for 24 h in a thermostat at
25–27◦C, the inhibition (sterile) zone diameters (including disc)
were measured and expressed in mm. An inhibition zone diam-
eter over 8 mm indicates that the tested compounds are active
against some of bacteria and fungi under investigation.[21–24]
The antibacterial activities of the investigated compounds were
tested against E. coli, Pseudomonas aeruginosa, Staphylococ-
cus aureus, Streptococcus faecalis, and some kinds of fungi;
Streptococcus faecalis and Candida albican. In the same time
with the antibacterial and antifungal investigations of the new
compounds were also tested as well as the pure solvent. The
concentration of each solution was 1.0 × 10−3 mol dm3. Com-
mercial DMSO was employed to dissolve the tested samples.
The results of antibacterial and antifungal activities in vitro are
shown in Table 1. It was found that compound (2) exhibited
greater activity than the standard toward Escherichia coli and
compound (8) exhibited greater activity than the standard to-
ward Pseudomonas aeruginosa, compound (6) the more active
toward Staphylococcus aurous (G+), compound (2) the more
active toward Streptococcus faecalis (G+), while compound (4)
exhibited greater activity than the standard toward Aspergillus
flavus (fungus), and compound (4) exhibited greater activity than
the standard toward Candida albicans (fungus) with respect to
the standard.
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CONCLUSION
2-(4-(Dimethylamino)benzylideneamino)benzenethiol (1)
and
2-(4-nitrobenzylidene-amino)-benzenethiol(5)
were
synthesized and metallated with Hg(II), Ni(II) acetate, and
palladium chloride to afford metallated products (2), (3),
and (4) in the form of monomercurated, dinickel nickel bis-,
and monopalladated products and monometallated products
of Hg++ & Ni++ (6), (7), and monopalladated cyclized
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