Microwave-assisted synthesis of some novel and potent antibacterial and antifungal compounds with biological screening

Article abstract of DOI:10.1007/s00044-011-9611-7

Hydantoins have widely been used as antiarrythmic, anticonvulsant and antitumor agents but recent research has shown a different and novel cytotoxic activity of hydantoins and its derivatives, i.e. anti HIV, antibacterial and antifungal. The following research article deals with the synthesis of hydantoins and their derivatives by Mannich reaction viz., 3-(substituted)-5,5- diphenylimidazolidine-2,4-dione and 1-(substituted)-3,5,5- triphenylimidazolidine-2,4-dione. The synthesised compounds are novel and some of the compounds showed good antibacterial and antifungal activity equivalent to the standards used. All synthetic procedures were carried out in a microwave and not by conventional methods, which led to speedy process and high yield for the same. Springer Science+Business Media, LLC 2011.

Full text of DOI:10.1007/s00044-011-9611-7

MEDICINAL
CHEMISTRY
RESEARCH
Med Chem Res (2012) 21:1098–1106
DOI 10.1007/s00044-011-9611-7
ORIGINAL RESEARCH
Microwave-assisted synthesis of some novel and potent
antibacterial and antifungal compounds with biological screening
•
Mayank Bapna Bharat Parashar
•
•
Vinod K. Sharma Lalit S. Chouhan
Received: 22 January 2010 / Accepted: 21 February 2011 / Published online: 27 March 2011
Ó Springer Science+Business Media, LLC 2011
Abstract Hydantoins have widely been used as anti-
arrythmic, anticonvulsant and antitumor agents but recent
research has shown a different and novel cytotoxic activity
of hydantoins and its derivatives, i.e. anti HIV, antibacte-
rial and antifungal. The following research article deals
with the synthesis of hydantoins and their derivatives by
Mannich reaction viz., 3-(substituted)-5,5-diphenylimida-
zolidine-2,4-dione and 1-(substituted)-3,5,5-triphenylimi-
dazolidine-2,4-dione. The synthesised compounds are
novel and some of the compounds showed good antibac-
terial and antifungal activity equivalent to the standards
used. All synthetic procedures were carried out in a
microwave and not by conventional methods, which led to
speedy process and high yield for the same.
Introduction
Human beings have always thrived to do something new in
their scientific approach. Pharmaceutical Chemistry is one
such branch where this particular idea is being fulfilled and
continuing with this idea of search for a new compound
with therapeutic effects was being effected. Microorgan-
isms have the ability to mutate and produce a new strain
which is resistant to the existing drugs. Be it a human error
or environmental factors, every decade there are new stains
of viruses, bacteria and to an extent fungi.
The aim is to generate a new compound having potent
antifungal and antibacterial property and which, in future
gives protection against wide range of microorganisms
including HIV.
Keywords Microwave ꢀ Hydantoins ꢀ Mannich bases ꢀ
Antibacterial and antifungal
Rational design
A lot of synthetic research and biological activity deter-
mination was carried out on substituted isatin heterocyclic
derivatives, when tested for activity; it was found that they
were cytotoxic (Islam et al., 2001a, b; Lingcon et al.,
2001). This gave a pathway for synthesis of isatin like
compounds viz. hydantoins and thiohydantoins (Muccioli
and Pupaert, 2003). The imidazoline-2,4-dione or hydan-
toin nucleus is a common 5-membered ring containing a
reactive cyclic urea core. The heterocyclic is present in a
wide range of biologically active compounds including
antiarrythmic, anticonvulsant and antitumor agents.
M. Bapna (&)
Smriti College of Pharmaceutical Education and Research,
308-B, Scheme No. 71, Gumastha Nagar,
Indore 452009, Madhya Pradesh, India
e-mail: mayankbapna@rediffmail.com
B. Parashar
Geetanjali College of Pharmaceutical Studies, Manwa Khera,
Udaipur, Rajasthan, India
V. K. Sharma
Hydantoins and thiohydantoins posseses antiarrythmic,
anticonvulsant and antitumor activity but recent research
has shown a different and novel cytotoxic activity for both
these compounds, i.e. anti HIV, antibacterial and anti-
fungal (Kashemliton and Islam, 2006; Patel et al., 2006).
Microwave Chemistry Laboratory, Department of Chemistry,
University College of Science, M.L. Sukhadia University,
Udaipur, Rajasthan, India
L. S. Chouhan
B.N. Girls PG College of Pharmacy, Udaipur, India
123

Med Chem Res (2012) 21:1098–1106
1099
The basic requirement for any medicinal substance is that it
should be potent. For this purpose, N-Mannich bases of
hydantoins were synthesized which were supposed to
posses antifungal and antibacterial property. To improve
the efficiency of the synthetic procedure microwave was
used in place of conventional apparatus (Wen-Ben et al.,
2003; Bausera et al., 1998; Keiko et al., 2007).
Experimental
Step-1: general procedure for synthesis of 5,5-
diphenylimidazolidine-2,4-dione (1a) and 3,5,5-
triphenylimidazolidine-2,4-dione (1b)
Benzil and urea were taken in molar ratio of 1:2, and were
dissolved in sufficient quantity of DMSO. To this solu-
tion, 10 g of potassium hydroxide solution was added so
that the solution becomes basic. Following a 90 s 750 W
pulse, the mixture was stirred for 5 min, cooled and then
30 s pulse were applied at 6, 9, 12, 15, 18, 24 and 30 min.
It was then poured into cold water acidified with HCl and
the precipitate so obtained was filtered, dried and washed
with water. The product was then recrystallized with
ethanol.
O
NH
O
HN
O
N
H
O
ISATIN
HYDANTOIN
Chemistry
Synthesis of 5,5-diphenylimidazolidine-2,4-dione and 3,5,5-
triphenylimidazolidine-2,4-dione is a base catalyzed con-
densation of benzil, urea or monophenyl urea in DMSO. The
formation of theses products follows pinacol–pinacoline
type rearrangement. Synthesis of N-Mannich bases involves
reaction of 5,5-diphenylhydantoin having active hydrogen
atom attached to nitrogen, undergoing amino-methylation
reaction in microwave oven in presence of formaldehyde,
secondary amines as well as primary amines such as mor-
pholine, 1-methylpiperazine, 1H-benzo[d]imidazole, 1H-
benzo[d][1,2,3]triazole, diethylamine and 2-aminothiazole.
The different substituted products have been successfully
synthesized in domestic microwave oven. The amino
methylated products have been tested for antibacterial
and antifungal activity. The structure of these synthesized
compounds has been elucidated on the basis of their ele-
mental analysis and spectral data. The synthetic scheme is
given in Scheme 1.
Step-2: general procedure for synthesis of
3-(substituted)-5,5-diphenylimidazolidine-2,4-dione
(3a–j) and 1-(substituted)-3,5,5-triphenylimidazolidine-
2,4-dione (4a–j)
Previously synthesized derivative of hydantoin and form-
aldehyde were dissolved in DMF and to it substituted
amine was added. The mixture was then activated by two
pulses of 15 s each at 20% power. The mixture was
then stirred for 5 min and cooled. The whole mixture was
then microwaved with a pulse of 15 s for a total of 3–5 min
with some stirring and cooling time in between each
pulse. It was then poured into cold water and ice mixture,
acidified with HCl and the precipitate so obtained was
filtered, dried and washed with water. The product
was then recrystallized with methanol Structures (3a–j and
4a–j).
Scheme 1 Synthesis of
3-(substituted)-5,5-
diphenylimidazolidine-2,4-
dione and 1-(substituted)-3,5,5-
triphenylimidazolidine-2,4-
dione
O
O
O
,
DMSO
NaOH
H2N
+
NHR
Microwave
HN
N-R
O
O
1a-b
O
O
R
NH
R1
H
R
N
O
N-R
H
DMF
Microwave
N
R1
3a-j and 4a-j
123

1100
Med Chem Res (2012) 21:1098–1106
(3a) 3-(Morpholinomethyl)-5,5-diphenylimidazolidine-
2,4-dione
(3b) 3-((4-Methylpiperazin-1-yl) methyl)-5,5-
diphenylimidazolidine-2,4-dione
Yield 80%, Mp 230°C, IR (KBr) cm-1: 3270 (–NH,
amide), 3030 (CH, str., aromatic), 2325 (CH2, str.) 1750,
Yield 88%, Mp 210°C, IR (KBr) cm-1: 3280 (–NH amide),
3035 (CH, str., aromatic), 2325 (CH2, str.), 1755, 1743
(C=O, str.), 1278 (3°N, amine). 1H NMR (d ppm) (CDCl3):
7.0–7.60 (m, 10H, Ar–H), 7.70 (s, 1H, NH), 4.28 (m, 2H,
CH2), 2.90–3.10 (8H, piperzine), 2.30 (s, 3H, N–CH3).
Anal. Calcd for C21H24N4O2: C, 69.21; H, 6.64; N, 15.37;
Found C, 69.52; H, 6.20; N, 14.90. LCMS: m/z [M]?
364.3.
1
1740 (C=O, str.), 1280 (3°N, amine). H NMR (d ppm)
(CDCl3): 7.0–7.50 (m, 10H, Ar–H), 8.801 (s, 1H, NH),
4.15 (m, 2H, CH2), 2.80–3.68 (m, 8H, morpholine ring).
Anal. Calcd for C20H21N3O3: C, 68.36; H, 11.02; N, 11.96.
Found C, 68.66; H, 11.58; N, 1154. LCMS: m/z [M?1]?
352.4.
Structure 1
O
O
O
NH
N
NH
N
NH
N
N
O
N
O
N
N
O
O
N
N
(3b)
(3a)
(3c)
CH3
O
O
O
NH
N
NH
N
NH
N
N
N
N
N
O
O
O
O
O
N
(3e)
(3f)
(3d)
O
O
O
NH
NH
N
N
NH
N
HN
HS
HN
NH
O
O
N
O
N
S
N
(3g)
(3i)
(3h)
O
NH
N
NH
N
O
(3j)
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Med Chem Res (2012) 21:1098–1106
1101
Structure 2
O
O
O
N
N
N
N
N
N
N
O
O
N
O
O
N
N
N
N
(4a)
(4c)
(4b)
CH3
O
O
O
N
N
N
N
N
N
N
O
O
O
O
N
N
N
O
N
(4f)
(4e)
(4d)
O
O
O
N
N
N
N
N
N
HN
HS
HN
N
O
O
O
N
S
N
(4h)
(4i)
(4g)
O
N
N
N
O
(4j)
(3c) 3-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-5,5-
diphenylimidazolidine-2,4-dione
(3d) 3-((1H-imidazol-1-yl) methyl)-5,5-
diphenylimidazolidine-2,4-dione
Yield 82%, Mp 221°C, IR (KBr) cm-1: 3265 (NH, amide),
3122 (CH str., aromatic), 2310 (CH2, str.), 1736, 1743
(C=O, str.), 1265 (3°N, amine). 1H NMR (d ppm) (CDCl3):
7.10–8.10 (m, 14H, Ar–H, –C=C–Ar and benzotrizol 5H),
6.50 (s, 1H, NH), 5.70 (s, 2H, N–CH2–N). Anal. Calcd for
C22H17N5O2: C, 68.92; H, 4.47; N, 18.27. Found C, 67.22;
H, 4.78; N, 18.50. LCMS: m/z [M-1]? 382.4.
Yield 79%, Mp 195°C, IR (KBr) cm-1: 3278 (NH, amide),
3100 (CH str., aromatic), 2315 (CH2, str.), 1748, 1755
(C=O, str.), 1282 (3°N, amine). 1H NMR (d ppm) (CDCl3):
6.70–7.60(m, 13H, Ar–H, –C=C–Ar and imidazole 3H),
6.70 (s, 1H, NH), 5.80 (s, 2H, N–CH2–N). Anal. Calcd for
C19H16N4O2: C, 68.66; H, 4.84; N, 16.89. Found C, 68.43;
H, 5.14; N, 17.10. LCMS: m/z [M?1]? 333.4.
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Med Chem Res (2012) 21:1098–1106
(C=O, str.), 1235 (3°N, amine). 1H NMR (d ppm) (CDCl3):
7.10–7.60(m, 10H, Ar–H, –C=C–Ar), 6.00(s, 1H, N–H.),
4.38 (s, 2H, N–CH2–N), 2.40 (s, 4H, CH2, CH2), 1.20(s,
6H, dimethyl group). Anal. Calcd for C20H23N3O2:
C,71.19; H, 6.87; N, 12.45. Found C, 69.90; H, 7.02; N,
12.45. LCMS: m/z [M]? 352.4.
(3e) 3-((1H-benzo[d]imidazol-1-yl)methyl)-5,5-
diphenylimidazolidine-2,4-dione
Yield 88%, Mp 205°C, IR (KBr) cm-1: 3260 (NH, amide),
3127 (CH str., aromatic), 2300 (CH2, str.), 1746, 1763
(C=O, str.), 1275 (3°N, amine). 1H NMR (d ppm) (CDCl3):
7.10–8.30 (m, 15H, Ar–H, –C=C–Ar and benzimidazole
5H), 6.70 (s, 1H, NH), 5.60 (s, 2H, N–CH2–N). Anal. Calcd
for C23H18N4O2: C, 72.24; H,4.74; N, 14.65. Found
C,72.24; H, 5.08; N, 5.05. LCMS: m/z [M]? 382.4.
(3j) 3-((Dimethyl amino)methyl)-5,5-
diphenylimidazolidine-2,4-dione
Yield 81%, Mp 218°C, IR (KBr) cm-1: 3230 (NH, amide),
3130 (CH str., aromatic), 2325 (CH2, str.), 1742, 1760
(C=O, str.), 1245 (3°N, amine). 1H NMR (d ppm) (CDCl3):
7.06–8.30 (m, 10H, Ar–H, –C=C–Ar), 6.00 (s, 1H, NH),
4.38 (s, 2H, N–CH2–N), 2.30 (s, 6H, dimethyl). Anal.
Calcd for C18H19N3O2: C, 69.88; H, 6.19; N, 13.58. Found
C, 70.09; H, 6.40; N, 13.20. LCMS: m/z [M?1]? 325.2.
(3f) 2-((2,5-Dioxo-4,4-diphenylimidazolidin-1-
yl)methyl)isoindoline-1,3-dione
Yield 80%, Mp 212°C, IR (KBr) cm-1: 3255 (NH, amide),
3132 (CH str., aromatic), 2320 (CH2, str.), 1736, 1743,
1
1720, 1680 (C=O, str.), 1255(3°N, amine). H NMR (d
ppm) (CDCl3): 7.06–8.10 (m, 19H, Ar–H, –C=C–Ar and
phthalamide 4H), 6.15 (s, 1H, NH), 5.60 (s, 2H, N–CH2–
N–). Anal. Calcd for C24H17N3O4: C,70.07; H, 4.16; N,
10.21. Found C, 70.34; H, 4.50; N, 10.42. LCMS: m/z [M-
1]? 410.2.
(4a) 1-(Morpholinomethyl)-3,5,5-triphenylimidazolidine-
2,4-dione
Yield 88%, Mp 230°C, IR (KBr) cm-1: 3100 (CH str.,
aromatic), 2315 (CH2, str.), 1746, 1756 (C=O, str.), 1288
(3°N, amine). 1H NMR (d ppm) (CDCl3): 7.00–7.50
(m, 15H, Ar–H, –C=C–Ar), 4.20 (m, 2H,–CH2–), and
2.8–3.56 (m, 8H, morpholine ring). Anal. Calcd for
C26H25N3O3: C, 73.05; H, 5.89; N, 9.83. Found C, 73.46;
H, 6.23; N, 10.20. LCMS: m/z [M-1]? 426.6.
(3g) 3-((Benzo[d]thiazol-2-yl amino)methyl)-5,5-
diphenylimidazolidine-2,4-dione
Yield 85%, Mp 222°C, IR (KBr) cm-1: 3240, 3130 (NH,
amide), 3132 (CH str., aromatic), 2320 (CH2, str.), 1742,
1
1760 (C=O, str.), 1225 (3°N, amine). H NMR (d ppm)
(CDCl3): 7.06–8.30(m, 14H, Ar–H, –C=C–Ar and ben-
othiozole), 6.10(s, 1H, HN–COCPh2), 4.92 (s, 2H, N–CH2–
N–), 4.20(s, 1H, NH). Anal. Calcd for C23H18N4O2S: C,
66.65; H, 4.38; N, 13.52. Found C, 67.02; H, 4.68; N,
13.10. LCMS: m/z [M-1]? 413.5.
(4b) 1-((4-Methylpiperazin-1-yl)methyl)-3,5,5-
triphenylimidazolidine-2,4-dione
Yield 80%, Mp 235°C, IR (KBr) cm-1: 3065 (CH str.,
aromatic), 2335 (CH2, str.) 1745, 1733 (C=O, str.), 1268
(3°N, amine). 1H NMR (d ppm) (CDCl3): 7–7.60 (m, 15H,
Ar–H, –C=C–Ar), 4.23 (m, 2H, –CH2–) and 2.50–2.80 (m,
8H, piperzine), 2.28 (s, 3H, –NCH3). Anal. Calcd for
C27H28N4O2: C, 73.30; H, 6.41; N, 12.72. Found C, 72.02;
H, 6.63; N, 13.05. LCMS: m/z [M?1]? 441.6.
(3h) 5,5-Diphenyl-3-((thiazol-2-yl
amino)methyl)imidazolidine-2,4-dione
Yield 79%, Mp 208°C, IR (KBr) cm-1: 3255, 3120(NH,
amide), 3132 (CH str., aromatic), 2310(CH2, str.), 1730,
1
1743 (C=O, str.), 1235 (3°N, amine). H NMR (d ppm)
(CDCl3): 7.06–8.10(m, 12H, Ar–H, –C=C–Ar and amin-
othiozole), 6.15(s, 1H, N–COCPh2), 4.80 (s, 2H, N–CH2–
N–), 4.10 (s, 1H, NH). Anal. Calcd for: C19H16N4O2S: C,
63.02; H, 4.64; N, 15.67. Found C, 62.62; H, 4.43; N,
15.37. LCMS: m/z [M?1]? 367.3.
(4c) 1-((1H-benzo[d][1,2,3] triazol-1-yl)methyl)-3,5,5-
triphenylimidazolidine-2,4-dione
Yield 78%, Mp 248°C, IR (KBr) cm-1: 3105 (CH str., aro-
matic), 2300 (CH2, str.) 1723, 1737 (C=O, str.), 1255 (3°N,
amine). 1H NMR (d ppm) (CDCl3): 7.08–8.10 (m, 19H, Ar–
H, –C=C–Ar and benzotriazole 5H), 5.65 (s, 2H, N–CH2–N).
Anal. Calcd for C28H21N5O2: C, 73.19; H, 4.61; N, 15.24.
Found C, 73.40; H, 4.42; N, 15.02. LCMS: m/z [M]? 459.6.
(3i) 3-((Diethyl amino)methyl)-5,5-diphenylimidazolidine-
2,4-dione
Yield 80%, Mp 217°C, IR (KBr) cm-1: 3220 (NH, amide),
3120 (CH, str., aromatic), 2330 (CH2, str.), 1732, 1750
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Med Chem Res (2012) 21:1098–1106
1103
(4d) 1-((1H-imidazol-1-yl)methyl)-3,5,5-
triphenylimidazolidine-2,4-dione
(4i) 1-((Diethyl amino)methyl)-3,5,5-
triphenylimidazolidine-2,4-dione
Yield 82%, Mp 228°C, IR (KBr) cm-1: 3110 (CH str., aro-
matic), 2325 (CH2, str.), 1738, 1743 (C=O, str.), 1272 (3°N,
amine). 1H NMR (dppm)(CDCl3):6.70–7.60 (m, 18H, Ar–H,
–C=C–Ar and imidazole 3H), 5.68 (s, 2H, N–CH2–N). Anal.
Calcd for C25H20N4O2: C, 73.51; H, 4.94; N, 13.72. Found C,
73.20; H, 5.21; N, 13.52. LCMS: m/z [M-1]? 407.4.
Yield 78%, Mp 252°C, IR (KBr) cm-1: 3125 (CH str.,
aromatic), 2315 (CH2 str.), 1730, 1747 (C=O, str.), 1222
1
(3°N, amine). H NMR (d ppm) (CDCl3): 7.10–7.60 (m,
15H, Ar–H, –C=C–Ar), 4.28 (s, 2H, N–CH2–N), 2.35 (s,
4H, CH2), 1.10(s, 6H, –dimethyl group). Anal. Calcd for:
C26H27N3O2: C, 75.52; H, 6.58; N, 10.16. Found C, 75.70;
H, 6.32; N, 10.34. LCMS: m/z [M?1]? 429.4.
(4e) 1-((1H-benzo[d] imidazol-1-yl) methyl)-3,5,5-
triphenylimidazolidine-2,4-dione
(4j) 1-((Dimethyl amino)methyl)-3,5,5-
triphenylimidazolidine-2,4-dione
Yield 87%, Mp 252°C, IR (KBr) cm-1: 3127 (CH str.,
aromatic), 2280 (CH2, str.), 1730, 1746 (C=O, str.), 1265
Yield 80%, Mp 202°C, IR (KBr) cm-1: 3130 (CH str., aro-
matic), 2320(CH2, str.), 1732, 1750, (C=O, str.), 1240 (3°N,
amine). 1H NMR (d ppm) (CDCl3): 7.06–7.60(m, 15H, Ar–H,
–C=C–Ar), 4.28 (s, 2H, N–CH2–N), 2.25 (s, 6H, dimethyl).
Anal. Calcd for: C24H23N3O2: C, 74.78; H, 6.01; N, 10.90.
Found C, 75.08; H, 6.31; N, 11.20. LCMS: m/z [M-1]? 399.4.
1
(3°N, amine). H NMR (d ppm) (CDCl3): 7.00–8.10 (m,
20H, Ar–H, –C=C–Ar and benzimidazole 6H), 5.52 (s, 2H,
N–CH2–N). Anal. Calcd for C29H22N4O2: C, 75.97; H,
4.84; N, 12.22. Found C, 76.60; H, 5.02; N, 12.02. LCMS:
m/z [M?1]? 459.6.
(4f) 2-((2,5-Dioxo-3,4,4-triphenylimidazolidin-1-
yl)methyl)isoindoline-1,3-dione
Antibacterial and antifungal studies
Yield 78%, Mp 242°C, IR (KBr) cm-1: 3126 (CH str.,
aromatic), 2314(CH2, str.) 1730, 1740, 1715, 1675 (C=O,
str.), 1245 (3°N, amine). 1H NMR (d ppm) (CDCl3):
7.06–8.15 (m, 19H, Ar–H, –C=C–Ar and phthalmide 4H),
5.50 (s, 2H, N–CH2–N). Anal. Calcd for C30H21N3O4:
C,73.91; H, 4.34; N, 8.62. Found C, 74.23; H, 4.02; N 8.90.
LCMS: m/z [M-1]? 486.5.
All the synthesized compounds were evaluated for bio-
logical activity, i.e. antimicrobial and antifungal. Anti-
bacterial activities of some selected compounds were
determined against four different strains of two gram-
positive bacteria (Bacillus subtitis and Staphylococcus
aureus) and two gram-negative (Pseudomonas aeruginosa
and Escherichia coli) bacteria. The inhibition of growth of
bacteria was compared with the standard drug ampicillin.
Synthesized compounds were also tested for their anti-
fungal activity against Candida albicans and Aspergillus
niger using Griseofulvin as a standard. Disc diffusion
method was used for determining the biological activity
using nutrient agar and potato dextrose agar to culture the
bacteria and fungus, respectively. The plate was incubated
for 24 h at 35°C for the bacteria and 48 h at 28°C for
fungus to record the diameter of anti-bacterial and anti-
fungal activity.
(4g) 1-((Benzo[d]thiazol-2-ylamino)methyl)-3,5,5-
triphenylimidazolidine-2,4-dione
Yield 76%, Mp 252°C, IR (KBr) cm-1: 3130 (N–H amide),
3132 (CH str., aromatic), 2310(CH2, str.) 1736, 1756 (C=O,
str,), 1222 (3°N, amine). 1H NMR (d ppm) (CDCl3):
7.06–8.10 (m, 19H, Ar–H, –C=C–Ar and benothiozol 4H),
4.98 (s, 2H, N–CH2–N), 4.10(s, 1H, N–H). Anal. Calcd for:
C29H22N4O2S: C, 71.00; H, 4.52; N,11.42. Found C, 70.82;
H, 4.62; N, 11.12. LCMS: m/z [M-1]? 489.6.
(4h) 3,5,5-Triphenyl-1-((thiazol-2-yl
amino)methyl)imidazolidine-2,4-dione
Procedure
The synthesized compounds were dissolved in DMF and
screened for their antibacterial and antifungal activity at
concentrations of 1000 and 500 lg/ml, respectively. A blank
test was conducted to check the antimicrobial activity of
DMF. The results are recorded in the form of primary
screening. The synthesized compounds found active in the
primary screening were further tested in a second set of
dilution against all microorganisms for secondary screening.
Yield 80%, Mp 234°C, IR (KBr) cm-1: 3128 (CH str.,
aromatic), 2308 (–CH2, str.) 1728, 1740, (C=O, str.), 1230,
1
(3°N, amine). H NMR (d ppm) (CDCl3): 7.06–8.10 (m,
17H, Ar–H, –C=C–Ar and aminothiozol 2H), 4.60 (s, 2H,
N–CH2–N), 4.05 (s, 1H, NH). Anal. Calcd for
C25H20N4O2S: C, 68.16; H, 4.58; N, 12.72. Found C,
68.42; H, 4.22; N, 12.54. LCMS: m/z [M]? 442.4.
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1105
Table 3 Antifungal activity of compound 3(a-j)
Antifungal activity (zone of inhibition in mm)
C. no.
C. albicans
A. niger
50 lg/ml
100 lg/ml
200 lg/ml
50 lg/ml
100 lg/ml
200 lg/ml
3a
10
12
11
17
16
15
17
11
09
16
18
12
13
12
24
24
16
18
12
10
18
25
15
13
13
30
32
20
32
13
11
19
40
10
11
11
15
16
12
16
11
08
16
21
11
12
11
17
19
15
19
11
10
18
24
12
12
11
19
32
16
31
11
12
18
40
3b
3c
3d
3e
3f
3g
3h
3i
3j
Griseofulvin
Table 4 Antifungal activity of compounds 4(a–j)
Antifungal activity (zone of inhibition in mm)
C. no.
C. albicans
A. niger
50 lg/ml
100 lg/ml
200 lg/ml
50 lg/ml
100 lg/ml
200 lg/ml
4a
10
12
11
10
16
15
13
11
09
16
18
12
13
12
11
24
16
15
12
10
18
25
15
13
13
13
32
20
20
13
11
19
40
10
11
11
10
16
12
16
11
08
16
21
11
12
11
12
19
15
16
11
10
18
24
12
12
11
13
32
16
20
11
12
18
40
4b
4c
4d
4e
4f
4g
4h
4i
4j
Griseofulvin
The active compounds were diluted to 200, 100 and 50 lg/ml
concentrations. The results revealed that all the newly syn-
thesized compounds exhibited promising antibacterial and
antifungal activity against the test organisms. The data for all
the compounds is reported in Tables 1, 2, 3, 4.
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Most of the synthesized compounds were found to possess
mild to moderate antibacterial and antifungal activity
except a couple of compounds which showed excellent
activity, almost equivalent to the given standards. In future,
further processing of the compounds will take place which
may lead to a potentially improved compound.
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