Facile, three-component synthesis of dithiocarbamate derivatives with potent antimicrobial activity

Article abstract of DOI:10.1080/10426500903453300

A one-pot three component synthesis of alkyl/aryl-dithiocarbamic acid-3-oxo-3-(phenoxathiin-2-yl)-1-phenyl/(4-chlorophenyl)propyl esters (3a-n) was achieved from the reaction of 3-phenyl/(4-chlorophenyl)-1-(phenoxathiin-2- yl)propenones (1a,b), amine, and carbon disulfide. The antimicrobial activities of some compounds were also screened against some selected bacteria and fungi. Copyright Taylor & Francis Group, LLC.

Full text of DOI:10.1080/10426500903453300

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Phosphorus, Sulfur, and Silicon and the
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Facile, Three-Component Synthesis of
Dithiocarbamate Derivatives With Potent
Antimicrobial Activity
M. S. Behalo a & A. A. Aly a
a Chemistry Department, Faculty of Science, Benha University,
Benha, Egypt
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To cite this article: M. S. Behalo & A. A. Aly (2010): Facile, Three-Component Synthesis of
Dithiocarbamate Derivatives With Potent Antimicrobial Activity, Phosphorus, Sulfur, and Silicon and
the Related Elements, 185:11, 2194-2200
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Phosphorus, Sulfur, and Silicon, 185:2194–2200, 2010
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500903453300
FACILE, THREE-COMPONENT SYNTHESIS
OF DITHIOCARBAMATE DERIVATIVES WITH POTENT
ANTIMICROBIAL ACTIVITY
M. S. Behalo and A. A. Aly
Chemistry Department, Faculty of Science, Benha University, Benha, Egypt
A
one-pot three component synthesis of alkyl/aryl-dithiocarbamic acid-3-oxo-3-
(phenoxathiin-2-yl)-1-phenyl/(4-chlorophenyl)propyl esters (3a–n) was achieved from the
reaction of 3-phenyl/(4-chlorophenyl)-1-(phenoxathiin-2-yl)propenones (1a,b), amine,
and carbon disulfide. The antimicrobial activities of some compounds were also screened
against some selected bacteria and fungi.
Supplemental materials are available for this article. Go to the publisher’s online edition of
Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental
file.
Keywords Antimicrobial activity; dithiocarbamates; phenoxathiin
INTRODUCTION
The chemistry of dithiocarbamates has attracted the interest of many researchers
in the last several years. There are a few general approaches involving amines, carbon
disulfide, and alkyl halide, epoxide or Michael acceptors to afford dithiocarbamates,1–6
which have demonstrated a broad spectrum of applications including in the agrochemical,
medicinal, and rubber industries.7–10
On the other hand, phenoxathiin derivatives were found to be active as potential
antihypertensive,11 antimicrobial,12, 13 antitumor,14 and anti-inflammatory agents15 and have
promising fluorescent properties.16, 17 Several phenoxathiin pyridinium derivatives were
prepared and have acted as effective antifungal agents against Aspergillus and Candida.18
In previous work, we reported three components synthesis of dithiocarbamates and
heterocycles from azoalkene systems, carbon disulfide, and primary amine.19 In our ongoing
research program that aims at the synthesis of biologically active compounds,20–22 we report
here the one-pot synthesis of dithiocarbmates having bulky phenoxathiin moiety substituted
at position-2 utilizing carbon disulfide, amine, and phenoxathiinylchalcones as Michael
acceptors in order to enhance their biological and pharmacological activities.
Received 30 July 2009; accepted 28 October 2009.
All strains were kindly supplied from Botany Department, Faculty of Science, Benha University, Benha,
Egypt.
Address correspondence to M. S. Behalo, Chemistry Department, Faculty of Science, Benha University,
P. O. Box 13518, Benha, Egypt. E-mail: mohamedbehalo@hotmail.com
2194

SYNTHESIS OF DITHIOCARBAMATE DERIVATIVES
2195
RESULTS AND DISCUSSION
The starting chalcones, 3-phenyl/(4-chlorophenyl)-1-(phenoxathiin-2-yl)propenones
(1a,b), were prepared by the reaction of 2-acetylphenoxathiin and aromatic aldehydes,
namely benzaldehyde and 4-chlorobenzaldehyde.23
The reaction of 3-phenyl-1-(phenoxathiin-2-yl)propenone (1a) (1 mmol), carbon
disulfide (3 mmole), and n-propylamine (2a) (1.5 mmol) in THF at room temperature af-
forded propyl-dithiocarbamic acid-3-oxo-3-(phenoxathiin-2-yl)-1-phenylpropyl ester (3a)
in good yield (Scheme 1). The structure of compound 3a was assigned on the basis of the
elemental analysis and spectroscopic data (1HNMR, 13CNMR, MS, and IR).
SCSNH
O
O
CS2, THF
r.t., 2h
+
Ar
Ph
Ar
Ph
NH2
1a
2a
3a
S
Ar =
O
Scheme 1
From these results, and in order to generalize this three-component synthesis, chal-
cones 1a,b were allowed to react with different amines, viz. benzylamine, cyclohexylamine,
1-amino-2-acetaldahyde diethylacetal, diethylamine, and carbon disulide under the same
reaction conditions. It was found that the reaction afforded the corresponding dithiocar-
bamate derivatives 3a–n (Scheme 2). The spectral data and the elemental analysis of the
products are all consistent with the assigned structures.
O
R1 R2
O
SCSN
CS2, THF
r.t., 2h
Ar
+
R1 R2 NH
Ar
X
1a,b
2
3a-n
X
1a, X = H
1b, X = Cl
Scheme 2
The reaction was also carried out in different organic solvents such as ethanol, ace-
tonitrile, dimethylformamide, diethyl ether, and finally solvent-free conditions. In these
solvents, the reaction proceeded from low to high yield to give the corresponding dithio-
carbamates (Table I).
On the other hand, aromatic amines such as aniline and p-toluidine did not participate
well in the reaction due to isolation of low yield.

2196
M. S. BEHALO AND A. A. ALY
Table I Reaction of chalcones 1a,b with carbon disulfide and amines
Entry
1
Chalcone 1
Amine, R1R2NH 2
Product 3
a
Yield% Mp ◦C
1a
85
182–184
2
b
91
177–179
3
4
c
88
196–198
d
68
206–208
5
6
e
f
83
212–214
45
194–196
7
g
49
202–204
8
9
1b
h
i
82
195–197
83
186–188
10
11
j
82
214–216
k
75
183–185
12
13
l
74
206–208
m
39
180–182
14
n
46
191–193

SYNTHESIS OF DITHIOCARBAMATE DERIVATIVES
2197
CONCLUSION
The objectives of the present study were to synthesize and investigate the biological
activities of new phenoxathiin-containing compounds. This aim has been verified by an ef-
ficient three-component synthesis of dithiocarbamate derivatives 3a–n at room temperature
from the reaction of phenoxathiinylchalcones 1a,b, carbon disulfide, and amines.
BIOLOGICAL ACTIVITIES
Some of the newly synthesized target compounds were evaluated in vitro for their
antibacterial activity against Bacillus Subtilis and Rhadococcus equii as Gram-positive
bacteria and Pseudomonas aeruginosa and Escherichia coli as Gram-negative bacteria24
(see the Supplemental Materials, available online).
EXPERIMENTAL
All reactions were monitored by thin layer chromatography (TLC) using Merck
Platen Kieselgel 60 F 25G. Chromatographic purifications were performed on columns
packed with Merck silica gel 60, and melting points are uncorrected. IR spectra in KBr
were recorded using a Perkin-Elmer 298 spectrophotometer. Mass spectra were obtained
using a Shimadzu GCMS-QP 1000 EX mass spectrometer. 1H and 13C NMR spectra were
obtained using 400 MHz and 100 MHz, respectively, in the Institute of Organic Chemistry,
Faculty of Science and Technology, University of Urbino, Italy.
General Procedure for the Synthesis of Dithiocarbmates 3a–n
To a stirred solution of amine 2 (1.5 mmol) in THF (20 mL), CS2 (3 mmol) was
added. The chalcone 1 (1 mmol) was added, and the reaction mixture was stirred at room
temperature for 2 h. Excess carbon disulfide was removed, and the crude product was
purified by column chromatography on silica gel and ethyl acetate/cyclohexane as eluent.
3-Oxo-3-(phenoxathiin-2-yl)-1-phenylpropylpropyldithiocarbamate (3a).
1H NMR (DMSO-d6), δ ppm = 1.07–1.11 (t, 3H, CH3), 2.03 (m, 2H, CH2), 3.32–3.37(t,
2H, CH2N), 3.46–3.49(d, 2H, CH2CO), 4.85–4.93(dd, 1H, CHS), 6.97–7.53(m, 12H, Ar-
H), 12.60 (s, 1H, NH, exchangeable); 13C NMR 14.0 (CH3), 22.2 (CH2), 39.9 (CHS), 47.6
(CH2CO), 52.4 (CH2N), 117.2, 117.4, 117.9, 125.0, 126.6, 126.7, 127.2, 128.2, 129.0,
130.1, 131.1, 135.2, 151.9, 156.9 (phenoxathiin and phenyl carbons), 191.1 (CO), 199.1
(CS); IR, 1680 (CO), 3187 (NH), 2923, 2854 (CH2), 1218 (CS) cm−1; MS: m/z: 465 (M+);
Anal. calcd. for C25H23NO2S3 (465.65): C, 64.49; H, 4.98; N, 3.01%. Found: C, 64.66; H,
5.12; N, 3.21%.
3-Oxo-3-(phenoxathiin-2-yl)-1-phenylpropylcyclohexyldithiocarbamate
1
(3b). H NMR (DMSO-d6), δ ppm = 1.53 (m, 6H, 3CH2), 2.14 (m, 4H, 2CH2), 3.82 (m,
1H, CHN), 4.19–4.28 (d, 2H, CH2CO), 5.06 (dd, 1H, CHS), 6.78–8.05(m, 12H, Ar-H),
11.10 (s, 1H, NH, exchangeable); 13C NMR 22.2, 28.9, 32.3 (5CH2), 39.8 (CHS), 42.7
(CH2CO), 52.3 (CHN), 117.6, 118.3, 125.2, 125.9, 126.4, 127.0, 127.6, 128.3, 129.3,
131.5, 133.5, 144.9, 151.0, 159.0 (phenoxathiin and phenyl carbons), 193.4 (CO), 196.2
(CS); IR, 1681 (CO), 3350 (NH), 2925, 2850 (CH2), 1216 (CS) cm−1; MS: m/z: 505
(M+); Anal. calcd. for C28H27NO2S3 (505.71): C, 66.50; H, 5.38; N, 2.77%. Found: C,
66.82; H, 5.47; N, 2.68%.

2198
M. S. BEHALO AND A. A. ALY
3-Oxo-3-(phenoxathiin-2-yl)-1-phenylpropyl diethyldithiocarbamate (3c).
1H NMR (DMSO-d6), δ ppm = 1.13–1.24 (2t, 6H, 2CH3), 3.66–3.69 (d, 2H, CH2CO),
4.01–4.17 (2q, 4H, 2CH2), 5.82 (dd, 1H, CHS), 6.72–7.98 (m, 12H, Ar-H), 10.47 (s, 1H,
NH, exchangeable); 13C NMR 11.3 (2CH3), 45.7 (CHS), 47.2 (2CH2), 47.9 (CH2CO),
117.9, 118.1, 118.8, 121.6, 122.4, 122.9, 125.1, 128.3, 128.5, 131.1, 134.2, 136.2, 154.8,
156.9 (phenoxathiin and phenyl carbons), 191.2 (CO), 195.2 (CS); IR, 1704 (CO),
3378 (NH), 2980, 2844 (CH2), 1232 (CS) cm−1; MS: m/z: 479 (M+); Anal. calcd. for
C26H25NO2S3 (479.68): C, 65.10; H, 5.25; N, 2.92%. Found: C, 65.27; H, 5.39; N,
2.88%.
3-Oxo-3-(phenoxathiin-2-yl)-1-phenylpropyl (2,2-diethoxyethyl)dithio-
1
carbamate (3d). H NMR (DMSO-d6), δ ppm = 1.24–135 (2t, 6H, 2CH3), 2.25–2.26
(d, 2H, CH2N), 4.05 (d, 2H, CH2CO), 4.07 (dd, 1H, CHS), 4.15–4.31 (2q, 4H, 2CH2), 5.06
(m, 1H, OCH), 7.20–7.95 (m, 12H, Ar-H), 8.75 (s, 1H, NH, exchangeable); 13C NMR 14.2
(2CH3), 42.2 (CHS), 48.1 (CH2CO), 51.5 (CH2NH), 53.5 (2CH2O), 95.4 (CHO), 115.5,
116.3, 116.9, 119.6, 121.4, 122.5, 124.2, 126.5, 128.1, 130.7, 132.5, 138.2, 151.6, 155.4
(phenoxathiin and phenyl carbons), 193.4 (CO), 198.8 (CS); IR, 1688 (CO), 3345 (NH),
2935, 2820 (CH2), 1315 (CS) cm−1; MS: m/z: 539 (M+); Anal. calcd. for C28H29NO4S3
(539.72): C, 62.31; H, 5.42; N, 2.60%. Found: C, 62.45; H, 5.53; N, 2.49%.
3-Oxo-3-(phenoxathiin-2-yl)-1-phenylpropylbenzyldithiocarbamate (3e).
1H NMR (DMSO-d6), δ ppm = 3.72 (s, 2H, CH2), 3.78–3.82 (d, 2H, CH2CO), 4.69 (m, 1H,
CH), 6.93–7.88 (m, 17H, Ar-H), 9.38 (s, 1H, NH, exchangeable); 13C NMR 43.5 (CHS),
48.7 (CH2 CO), 51.2 (CH2NH), 115.9, 117.3, 118.4, 121.4, 121.9, 123.1, 123.7, 125.2,
127.4, 128.3, 130.3, 131.4, 131.8, 133..1, 133.5, 141.2, 153.7, 158.4 (phenoxathiin and
phenyl carbons), 188.9 (CO), 197.2 (CS); IR, 1685 (CO), 3335 (NH), 2945, 2830 (CH2),
1240 (CS) cm−1; MS: m/z: 513 (M+); Anal. calcd. for C29H23NO2S3 (513.68): C, 67.81;
H, 4.51; N, 2.73%. Found: C, 68.11; H, 4.72; N, 2.63%.
3-Oxo-3-(phenoxathiin-2-yl)-1-phenylpropyl phenyldithiocarbamate (3f).
1H NMR (CDCl3), δ ppm = 3.35–3.38 (d, 2H, CH2), 4.67 (m, 1H, CH), 7.01–7.98 (m,
17H, Ar H), 10.22 (s, 1H, NH, exchangeable); IR, 1684 (CO), 2930, 2845 (CH2), 1252
(CS) cm−1; Anal. calcd. for C28H21NO2S3 (499.67): C, 67.30; H, 4.24; N, 2.80%. Found:
C, 67.13; H, 4.15; N, 2.72%.
3-Oxo-3-(phenoxathiin-2-yl)-1-phenylpropyl p-tolyldithiocarbamate (3g).
1H NMR (DMSO-d6), δ ppm = 2.25 (s, 3H, CH3), 4.12 (d, 2H, CH2), 4.87 (m, 1H, CH),
6.92–7.50 (m, 12H, Ar-H), 10.98 (s, 1H, NH, exchangeable); 13C NMR 23.2 (CH3), 48.3
(CHS), 51.2 (CH2 C O), 115.2, 118.2, 118.7, 120.1, 121.4, 121.4, 123.6, 125.7, 128.4,
128.5, 129.1, 131.3, 133.5, 133.8, 135.6, 144.6, 152.4, 154.8 (phenoxathiin and phenyl
carbons), 192.5 (CO), 196.3 (CS); IR, 1690 (CO), 3364 (NH), 2930, 2825 (CH2), 1282
(CS) cm−1; MS: m/z: 513 M+); Anal. calcd. for C29H23NO2S3 (513.68): C, 67.81; H,
(
4.51; N, 2.73%. Found: C, 68.05; H, 4.75; N, 2.67%.
1-(4-Chlorophenyl)-3-oxo-3-(phenoxathiin-2-yl)propylpropyldithiocar-
1
bamate (3h). H NMR (DMSO-d6), δ ppm = 1.12–1.15 (t, 3H, CH3), 2.06 (m, 2H,
CH2), 3.25–3.28 (t, 2H, CH2N), 3.41–3.45 (d, 2H, CH2CO), 5.12–5.18 (dd, 1H, CH),
7.07–7.98 (m, 11H, Ar-H), 11.35 (s, 1H, NH, exchangeable); IR, 1695 (CO), 3325 (NH),
2933, 2840 146 (CH2), 1310 (CS) cm−1; Anal. calcd. for C25H22NO2S3Cl (500.10): C,
60.04; H, 4.43; N, 2.80%. Found: C, 59.82; H, 4.30; N, 2.86%.
1-(4-Chlorophenyl)-3-oxo-3-(phenoxathiin-2-yl)propylcyclohexyldithio-
1
carbamate (3i). H NMR (DMSO-d6), δ ppm = 1.80 (m, 6H, 3CH2), 2.44 (m, 4H,
2CH2), 3.07–3.09 (d, 2H, CH2CO), 3.78 (m, 1H, CHN), 5.38–5.48 (dd, 1H, CHS),

SYNTHESIS OF DITHIOCARBAMATE DERIVATIVES
2199
7.08–8.01 (m, 12H, Ar-H), 11.55 (s, 1H, NH, exchangeable); 13C NMR 22.0, 29.2, 31.8
(5CH2), 39.92 (CHS), 44.2 (CH2C O), 50.17 (CHN), 118.2, 118.5, 123.8, 125.6, 126.6,
127.2, 127.7, 128.8, 130.5, 131.6, 132.8, 142.8, 152.2, 157.9 (phenoxathiin and phenyl
carbons), 188.7, (CO), 193.84 (CS); IR, 1680 (CO), 3400 (NH), 2920, 2850 (CH2),
1250(CS); MS: m/z: 540 (M+); Anal. calcd. for C28H26NO2S3Cl (540.16): C, 62.26; H,
4.85; N, 2.59%. Found: C, 62.45; H, 4.97; N, 2.66%.
1-(4-Chlorophenyl)-3-oxo-3-(phenoxathiin-2-yl)propyl diethyldithiocar-
1
bamate (3j). H NMR (DMSO-d6), δ ppm = 1.09–1.14 (2t, 6H, 2CH3), 3.45–3.49 (d,
2H, CH2 CO), 4.22–4.29 (2q, 4H, 2CH2), 4.91 (1H, CHS), 6.94–8.01 (m, 11H, Ar H),
9.58 (s, 1H, NH, exchangeable); IR,1687(CO), 2930, 2835 (CH2), 1245(CS); Anal. calcd.
for C26H24NO2S3Cl (514.12): C, 60.74; H, 4.71; N, 2.72%. Found: C, 60.94; H, 4.88; N,
2.78%.
1-(4-Chlorophenyl)-3-oxo-3-(phenoxathiin-2-yl)propyl(2,2-diethoxyethyl)
1
dithiocarbamate (3k). H NMR (CDCl3), δ ppm = 1.15–1.28 (2t, 6H, 2CH3), 2.18–2.22
(d, 2H, CH2N), 3.84–3.88 (d, 2H, CH2CO), 4.12 (t, 1H, CHS), 4.14–4.27 (2q, 4H, 2CH2),
5.11–5.16 (m, 1H, OCH), 6.92–8.06 (m, 11H, Ar-H), 9.84 (s, 1H, NH, exchangeable);
IR, 1692 (CO), 3270 (NH), 2936, 2845 (CH2), 1260 (CS) cm −1;Anal. calcd. for
C28H28NO4S3Cl (574.17): C, 58.52; H, 4.91; N, 2.44%. Found: C, 58.42; H, 4.80; N,
2.48%.
1-(4-Chlorophenyl)-3-oxo-3-(phenoxathiin-2-yl)propylbenzyldithiocar-
1
bamate (3l). H NMR (DMSO-d6), δ ppm = 3.46 (s, 2H, CH2), 3.85–3.89 (d, 2H,
CH2CO), 5.33 (m, 1H, CH), 6.77–7.92 (m, 16H, Ar-H), 9.85 (s, 1H, NH, exchangeable);
IR, 1700 (CO), 2938, 2840 (CH2), 1270 (CS) cm −1; Anal. calcd. for C29H22NO2S3Cl
(548.14): C, 63.55; H, 4.05; N, 2.56%. Found: C, 63.72; H, 4.13; N, 2.63%.
1-(4-Chlorophenyl)-3-oxo-3-(phenoxathiin-2-yl)propylphenyldithiocar-
1
bamate (3m). H NMR (DMSO-d6), δ ppm = 3.23–3.27 (d, 2H, CH2), 4.85 (m, 1H,
CH), 6.97–8.01 (m, 16H, Ar-H), 9.23 (s, 1H, NH, exchangeable); IR, 1680 (CO), 2945,
2825 (CH2), 1312 (CS); Anal. calcd. for C28H20NO2S3Cl (534.11): C, 62.97; H, 3.77; N,
2.62%. Found: C, 63.11; H, 3.85; N, 2.68%.
1-(4-Chlorophenyl)-3-oxo-3-(phenoxathiin-2-yl)propylp-tolyldithiocar-
1
bamate (3n). H NMR (DMSO-d6), δ ppm = 2.38 (s, 3H, CH3), 4.32–4.36 (d, 2H, CH2),
5.16 (m, 1H, CH), 6.79–7.95 (m, 15H, Ar-H), 9.87 (s, 1H, NH, exchangeable); IR, 1705
(CO), 3385 (NH), 2925, 2838 (CH2), 1310 (CS) cm−1; Anal. calcd. for C29H22NO2S3Cl
(548.14): C, 63.55; H, 4.05; N, 2.56%. Found: C, 63.68; H, 4.12; N, 2.62%.
REFERENCES
1. C. M. Buess, J. Am. Chem. Soc., 77, 6613 (1955).
2. R. N. Salvatore, S. Sahaba, and K. W. Junga, Tetrahedron Lett., 42, 2055 (2001).
3. A. Ziyaei-Halimjani and M. R. Saidi, J. Sulfur Chem., 26, 149 (2005).
4. F. Busque, P. D. March, M. Fegueredo, J. Font, and L. Gonzales, Eur. J. Org. Chem., 1492 (2004).
5. N. Azizi, F. Aryanasab, L. Torkiyan, A. Ziyaei, and M. R. Saidi, J. Org. Chem., 71, 3634 (2006).
6. N. Azizi, B. Pourhasan, F. Aryanasab, and M. R. Saidi, Synlett, 1239 (2007).
7. C. Rafin, E. Veignie, M. Sancholle, D. Postal, C. Len, P. Villa, and G. Ronco, J. Agric. Food
Chem., 48, 5283 (2001).
8. P. J. Nieuwenhizen, A. W. Ehlers, J. G. Haasnoot, S. R. Janse, J. Reedijk, and E. J. Baerends, J.
Am. Chem. Soc., 121, 163 (1999).

2200
M. S. BEHALO AND A. A. ALY
9. L. Ronconi, C. Marzano, P. Zanello, M. Corsini, G. Miolo, C. Macca, A. Trevisan, and D.
Fregona, J. Med. Chem., 49, 1648 (2006).
10. M. R. Wood, D. J. Duncalf, S. P. Rannard, and S. Perrier, Org. Lett., 8, 553 (2006).
11. J. J. Tegeler, H. H. Ong, and J. A. Profitt, J. Heterocyclic Chem., 20, 867 (1983).
12. Y. M. Al-Hiari and B. A. Sweileh, Asian J. Chem., 18(3), 2285 (2006).
13. O. Maior, D. Gavriliu, and S. Stoia, South. Braz. J. Chem., 3, 79 (1995).
14. G. W. Rewcastle, G. J. Atwell, B. D. Palmer, P. D. Boyd, B. C. Baguley, and W. A. Denny, J.
Med. Chem., 34(2), 491 (1991).
15. Y. Girard, P. Hamel, and D. Delorme, US Patent 5036067 (1990); Chem. Abstr., 115, 232258
(1991).
16. S. Ionescua, D. Gavriliu, O. Maior, and M. Hillebrand, J. Photochem. Photobiol. A, 124, 67
(1999).
17. T. Constantinescu, A. Mischie, O. Maior, F. Badea, M. Vasilescu, M. T. Caproiu, R. Socoteanu,
and D. Nourescu, Rev. Roum. Chim., 45, 1009 (2000).
18. C. T. Supuran, A. Scozzafava, F. Briganti, G. Loloiu, and O. Maior, J. Enzyme Inhib., 31(4), 291
(1998); Chem. Abstr., 130, 49076 (1999).
19. O. A. Attanasi, L. D. Crescentini, G. Favi, P. Filippone, G. Giorgi, F. Mantellini, G. Moscatelli,
and M. S. Behalo, Org. Lett., 11(11), 2265 (2009).
20. Y. A. Issac, I. G. El-Karim, S. G. Donia, and M. S. Behalo, Sulf. Lett., 25(4), 183 (2002).
21. Y. A. Issac, I. G. El-Karim, M. S. Behalo, A. A. Aly, and S. G. Donia, Olaj, Szappan, Kozmetika,
57(4), 128 (2008).
22. M. S. Behalo, Phosphorus, Sulfur, and Silicon, 184(1), 206 (2009).
23. E. Lescot, N. P. Buu-Hoi, and N. D. Xuong, J. Chem. Soc., 2408 (1956).
24. C. Leifert, S. Chidbouree, S. Hampson, S. Workman, D. Sigee, H. A. S. Epton, and A. Harbour,
J. Appl. Bact., 78, 97 (1995).