An efficient ultrasound promoted one-pot three-component synthesis and antibacterial activities of novel pyrimido[4,5-b]quinoline- 4,6(3H,5H,7H,10H)- dione derivatives

Article abstract of DOI:10.2174/157017812803521207

A series of novel pyrimido[4,5-b]quinoline-4,6(3H,5H,7H,10H)-dione derivatives was synthesized by one-pot three-component reaction of the appropriate aldehyde, dimedone or cyclohexanedione and 6-aminothiouracil in ethanol under ultrasonic irradiation at 50 oC in short reaction times (1.5-3 min) and excellent yields (94-99%). The antibacterial activities of the synthesized compounds were evaluated on M. leuteus, B. subtilis, E. coli and Ps. aeruginosa. All the synthesized products showed good antibacterial activities.

Full text of DOI:10.2174/157017812803521207

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664
Letters in Organic Chemistry, 2012, 9, 664-670
An Efficient Ultrasound Promoted One-Pot Three-Component Synthesis
and Antibacterial Activities of Novel Pyrimido[4,5-b]quinoline-
4,6(3H,5H,7H,10H)-dione Derivatives
Maryam S. Jourshari1, Manouchehr Mamaghani1*, Khalil Tabatabaeian1, Farhad Shirini1,
Mehdi Rassa2 and Hadiss Langhari1
1Department of Chemistry, Faculty of Sciences, University of Guilan, P.O. Box 41335-1914, Rasht, Iran
2Department of Biology, Faculty of Sciences, University of Guilan, P.O. Box 41335-1914, Rasht, Iran
Received December 03, 2011: Revised August 27, 2012: Accepted August 27, 2012
Abstract: A series of novel pyrimido[4,5-b]quinoline-4,6(3H,5H,7H,10H)-dione derivatives was synthesized by one-pot
three-component reaction of the appropriate aldehyde, dimedone or cyclohexanedione and 6-aminothiouracil in ethanol
o
under ultrasonic irradiation at 50 C in short reaction times (1.5-3 min) and excellent yields (94-99%). The antibacterial
activities of the synthesized compounds were evaluated on M. leuteus, B. subtilis, E. coli and Ps. aeruginosa. All the syn-
thesized products showed good antibacterial activities.
Keywords: 6-aminothiouracil, antibacterial, MCR, one-pot, pyrimido[4,5-b]quinolone, pyridopyrimidine, pyrazole, ultrasound.
INTRODUCTION
tetrahydro-1,3-dimethyl-2,4-dioxopyrimidin-5-yl)-3-oxo-pr-
opanenitrile with aromatic aldehydes [30]. However, some
of these methods are limited because of slow reaction rate,
poor yields, side products, tedious workup, and the use of
toxic solvents or expensive catalysts. Therefore, there still
remain many challenges in the synthesis of these biologically
important compounds.
Due to their significant roles in drug discovery, research
on the synthesis of polyfunctinalized heterocyclic com-
pounds, in particular compounds incorporating nitrogen het-
erocycles, has received much interest in recent years [1-5].
Fused heterocyclic systems containing pyrimidine struc-
tural units, such as pyrimidopyrimidines, pyrazoloquinolines,
pyrazolopyridopyrimidines, and pyridopyrimidines have
been reported to display a wide range of pharmacological
activities [6-10]. Indeed, structures containing the
pyrido[2,3-d]primidine moiety have shown strong biological
activities such as, analgesic, anti-inflammatory [11], anti-
convulsive [12,13], antipyretic [14], cardiotonic [15,16],
antitumoral [17], bactericidal [18], antihistaminic [19], diu-
retic [20] and bronchiodilator [21] activities. Consequently,
preparation of these compounds has attracted considerable
attention in recent years and numerous methods have been
reported for their synthesis. For example, a three-component
reaction, catalyzed by KF-Al2O3 [22], a solvent-free meth-
odology employing barbituric acids [23], one-pot reaction of
isatin, barbituric acids and 1H-pyrazole-5-amines [10], a
two-step convergent strategy [24], reaction of isoxazoles
with 2,6-diaminopyridinone [25], a double annulation strat-
egy using ꢀ-alkenoyl-ꢀ-carbamoylketene-(S,S)-acetals [26],
ring transformation of isoxazolo[3,4-d]pyrimidine [27], reac-
tion between 6-aminouracils with cyano olefins [28], in-
tramolecular hetero Diels–Alder reactions involving 1-oxa-
1,3-butadienes [29] and reaction of 3-(6-amino-1,2,3,4-
On the other hand, functionally substituted 1,3-
diarylpyrazole derivatives have received considerable atten-
tion due to their wide range of useful biological properties,
which include antimicrobial, anti-inflammatory (COX-2 in-
hibitor and ulcerogenic activity), antitubercular, antitumor,
antiangiogenesis, anti-parasitic and antiviral activities [31-
36]. Therefore, it would be beneficial to design a system
which combines bio-labile nuclei such as pyrazole, pyridine
and pyrimidine in a molecular framework and to evaluate
their additive microbial effects. Thus, we report herein the
synthesis of some new heteroaryl substituted pyrimido[4,5-
b]quinoline-4,6(3H,5H,7H,10H)-dione derivatives via a fast
and multi-component reaction under ultrasonic irradiation, as
a clean source of energy.
The resistance of common pathogens to standard drugs
plays an important role in treatment failure [37]. Therefore,
searching for new antimicrobial agents with specific activity
is a prime objective of medicinal and synthetic chemists.
In our ongoing research for new synthetic methods for
the development of efficient and environmentally friendly
protocols for the synthesis of biologically important hetero-
cyclic products [38], several novel derivatives of
pyrimido[4,5-b]quinoline-4,6(3H,5H,7H,10H)-dione (6a-i)
have been synthesized by one-pot three-component cyclo-
condensation reaction of dimedone or cyclohexanedione (1),
*Address correspondence to this author at the Department of Chemistry,
Faculty of Sciences, University of Guilan, P.O. Box 41335-1914,
Rasht, Iran; Fax: (+98) 1313233262; E-mails: m-chem41@guilan.ac.ir,
mchem41@gmail.com
1875-6255/12 $58.00+.00
© 2012 Bentham Science Publishers

An Efficient Ultrasound Promoted One-Pot Three-Component
Letters in Organic Chemistry, 2012, Vol. 9, No. 9
665
O
O
Ar
O
O
NH
NH
US
Ethanol
50 oC
+
+
ArCHO
R
H2N
N
SCH3
R
N
H
N
SCH3
O
R
R
1
2
3
4a-i
R = H, CH3
Scheme 1. An Efficient Synthesis of Pyrimido [4,5-b] quinoline-4, 6(3H,5H,7H,10H)-diones Under Ultrasonic Irradiations.
an appropriate aldehyde (2) and 6-aminothiouracil (3) at 50
oC, under ultrasonic irradiation (40 kHz) (Scheme 1). This
simple protocol furnished the desired products in short reac-
tion times (1.5-3 min) and excellent yields (94–99%) (Table
1). The structure of all the synthesized compounds was es-
tablished by spectroscopic (IR, 1H-NMR, 13C-NMR) and
elemental analyses [39]. H-NMR spectroscopy of the prod-
ucts (6a-i) clearly showed the dihydropyridine ring protons
H-5 and H-10 as singlet at the range of 4.93-5.61 and 12.07-
13.36 ppm respectively. The effect of different solvents was
also examined on the efficiency of the reaction using prepa-
ration of 4a as a model reaction (Table 2). Of the solvents
tested in the screening, ethanol was the solvent of choice. All
the reactions described in this report were therefore carried
out under optimized conditions (EtOH, 50 oC).
1
All the newly synthesized compounds were also screened
for their antibacterial activities (Table 3).
Table 1. Synthesis of Pyrimido[4,5-b]quinoline-4,6(3H,5H,7H,10H)-dione (4a-i).
Entry
4a
Product
Time (min)
Yield (%)a,b
N
N
3 (240)c
96 (83)c
O
O
NH
N
H
N
SCH3
Cl
N
N
O
O
4b
4c
4d
4e
2
3
2
2
97
94
97
98
NH
N
N
SCH3
H
H3CO
O2N
O2N
N
N
O
O
N
NH
N
SCH3
H
N
N
O
O
NH
N
N
SCH3
H
N
N
O
O
N
NH
N
SCH3
H

666 Letters in Organic Chemistry, 2012, Vol. 9, No. 9
Saffari Jourshari et al.
Table 1. contd…
Entry
Product
Time (min)
Yield (%)a,b
H3CO
N
N
O
O
N
4f
3
96
NH
N
SCH3
H
Br
N
N
O
O
N
4g
2
96
NH
N
SCH3
H
N
O
O
N
4h
1.5
1.5
99
99
NH
N
H
SCH3
S
O
O
N
4i
NH
N
H
SCH3
aIsolated yield. bIdentified by spectroscopic (IR, 1H NMR, 13C NMR) and elemental analyses. CClassical reaction was carried out using cyclohexa-1,3-dione (1 mmol), arylaldehyde
(2a) (1 mmol) and 6-amino-2-(methylthio)pyrimidin-4(3H)-one (1mmol) in ethanol (10 mL) under reflux condition which provided 4a in 83% yield after 240 min.
Table 2. Synthesis of 4a in Different Solvents in Ultrasonic Condition.
Entry
Solvent
Time (min)
Yield (%)a
1
Ethanol
H2O
3
5
96
65
88
85
92
88
66
2
3
THF
8
4
Ethanol/H2Ob
Methanol
Acetonitrile
Chloroform
5
5
3
6
5
7
10
aIsolated yield. bA 1:1 mixture.
Quantitative screening of antibacterial activity is given in
Table 3. Although all the compounds exhibited some anti-
bacterial activity, it seems those pyrazole substituted prod-
ucts that carried a more polar group or were capable of form-
ing hydrogen bonds (except 4c) were more active; specifi-
cally, compounds 4b, 4d, 4e, 4f and thienyl substituted 4i
showed higher levels of antibacterial activity. Compounds
4a, 4c, 4g and 4h, overall, seem to have been least effective.
ANTIBACTERIAL SCREENING
The purified products were screened for their antibacte-
rial activity by using spectrophotometric (turbidimetric)
analysis. Absorbance values were measured at 600 nm and
converted to percentage antibacterial activity (AA %). It was
calculated using the following formula: % Reduction in Ab-
sorbance
=
100-[{(Abssample-Absblank)/Abs
} ꢀ100].
control

An Efficient Ultrasound Promoted One-Pot Three-Component
Letters in Organic Chemistry, 2012, Vol. 9, No. 9
667
Table 3. Quantitative Screening of Antibacterial Activity.
Absorbance at 600 nm
Z
Compound
Absorbance
Bacillus
subtilis
Micrococcus
leuteus
Pseudomonas
aeruginosa
Escherichia
coli
1
2
Control
(Abs control
(Abs sample – Abs blank
% Reduction in Absorbance (AA %)
(Abs sample – Abs blank
% Reduction in Absorbance (AA %)
(Abs sample – Abs blank
% Reduction in Absorbance (AA %)
(Abs sample – Abs blank
% Reduction in Absorbance (AA %)
(Abs sample – Abs blank
% Reduction in Absorbance (AA %)
(Abs sample – Abs blank
% Reduction in Absorbance (AA %)
(Abs sample – Abs blank
% Reduction in Absorbance (AA %)
(Abs sample – Abs blank
% Reduction in Absorbance (AA %)
(Abs sample – Abs blank
% Reduction in Absorbance (AA %)
)
0.220
0.189
14.1
0.529
0.340
35.72
0.101
80.90
0.385
27.22
0.124
76.55
0.047
91.11
0.101
80.9
0.338
0.239
29.28
0.105
68.93
0.220
34.91
0.159
52.95
0.074
78.1
0.374
0.297
20.58
0.053
85.82
0.350
6.41
)
4a
)
0.043
80.45
0.116
47.27
0.076
75
3
4
4b
4c
4d
4e
4f
)
)
0.108
71.12
0.120
67.91
0.141
62.29
0.166
55.61
0.304
18.71
0.194
48.12
5
)
0.050
77.27
0.043
80.45
0.217
1.36
6
)
0.124
63.31
0.104
69.23
0.225
33.43
0.109
67.75
7
)
0.430
18.71
0.260
50.85
0.088
83.36
8
4g
4h
4i
)
0.203
7.72
9
)
0.099
55
10
In conclusion, a new series of substituted pyrimido[4,5-
b]quinoline-4,6(3H,5H,7H,10H)-dione derivatives 4a-i has
been synthesized via an MCR approach and was character-
ized by spectral and elemental analyses. This synthetic strat-
egy allows the construction of relatively complicated nitro-
gen containing fused heterocyclic systems in short reaction
times and excellent yields using a green protocol. All the
derivatives of newly synthesized compounds, pyrimido[4,5-
b]quinoline-4,6(3H,5H,7H,10H)-dione derivatives (4a-4i),
were screened for their antibacterial activities. Antibacterial
activities of the synthesized compounds are given in Table 3.
Compounds 4b, 4d, 4e, 4f, 4i showed good antibacterial ac-
tivities in the case of all microorganism. Other products
showed weakness to average antibacterial activities. In gen-
eral introducing a more polar pyrazole moiety, except in the
case of 4c, increases the antibacterial activities of the synthe-
sized pyrimido[4,5-b]quinoline-4,6-dione derivatives. More
verification of the structure activity relation of these hetrocy-
cles is underway.
solute ethanol was irradiated in an ultrasonic cleaning unit
(Elmasonic S 40H) at 50 C for 1.5-3 minutes. The resultant
precipitate was filtered and recrystallized from ethanol to
furnish the desired pure products (4a-j) in 94-99% yields.
o
Product Characterization Data
4a: White solid; M.p. 306–309 °C; Found: C, 67.21; H,
4.68; N, 14.33 C27H23N5O2S requires C, 67.34; H, 4.81; N,
14.54%; FT-IR (KBr): 3220, 3180, 3080, 2950, 2880, 1640,
1620, 1590, 1520, 1483, 1360, 1265, 1230, 1180, 1140, 950,
ꢀ
1
1
760, 690 cm ; H-NMR (400 MHz, DMSO-d6): ꢁH 1.82,
1.90 (m, 2H), 2.08-2.16 (m, 2H), 2.43-2.49 (m, 2H), 2.50 (s,
3H), 5.10 (s, 1H), 7.26 (t, 1H, J = 7.2 Hz), 7.34-7.47 (m,
5H), 7.82 (d, 2H, J = 8.0 Hz), 7.89 (d, 2H, J = 6.8 Hz,), 8.15
(s, 1H), 9.70 (s, NH), 12.1 (s, NH) ppm. 13C-NMR (100
MHz, DMSO-d6): ꢁC 13.2, 21.1, 27.0, 29.2, 37.2, 98.8, 111.6,
118.4, 126.2, 127.6, 128.0, 128.1, 129, 129.2, 129.8, 135.1,
140.0, 151.5, 152.7, 158.2, 160.1, 162.2, 194.7.
4b: White solid; M.p. 220-221 °C; Found: C, 62.98; H,
4.05; N, 13.43 C27H22ClN5O2S requires C, 62.84; H, 4.30; N,
13.57%; FT-IR (KBr) 3400, 3220, 3180, 3080, 2925, 2870,
1645, 1620, 1590, 1540, 1493, 1442, 1358, 1265, 1224,
1180, 1138, 1082, 1058, 1020, 958, 883, 835, 750, 722, 685
Typical Procedure for Preparation of pyrimido[4,5-
b]quinoline-4,6(3H,5H,7H,10H)-diones (4a-j)
A mixture of 1,3- cyclohexanedione or dimedone (1) (1
mmol), appropriate aldehyde (2) (1mmol), and 6-amino-2-
(methylthio)pyrimidin-4(3H)-one (3) (1mmol) in 10 mL ab-
ꢀ
1
1
cm ; H- NMR (400 MHz, DMSO-d6): ꢁH 1.79-1.86 (m,

668 Letters in Organic Chemistry, 2012, Vol. 9, No. 9
Saffari Jourshari et al.
2H), 2.11-2.16 (m, 2H), 2.50 (s, 2H), 2.51 (s, 3H), 5.06 (s,
1H), 7.26 (t, 1H, J = 7.2 Hz), 7.42-7.49 (m, 4H), 8.09 (d, 8.4
Hz), 8.16 (s, 1H), 9.76 (s, 1H), 12.20 (s, 1H); 13C-NMR (100
MHz, DMSO-d6): ꢀC 13.2, 21.2, 25.1, 27.0, 37.2, 98.9,
111.8, 118.5, 126.3, 128.2, 129.5, 129.8, 130.9, 132.5, 134.1,
139.9, 150.2, 151.8, 152.7, 160.5, 162.0, 194.9.
114.8, 118.1, 120.1, 126.0, 126.6, 127.0, 129.3, 130.0, 140.0,
151.4, 158.9, 159.1, 161.7, 164.2, 198.7.
4g: White solid; M.p. 276-278 °C; Found: C, 59.33; H,
4.36; N, 11.82 C29H26BrN5O2S requires C, 59.18; H, 4.45; N,
11.90%; FT-IR (KBr) 3250, 3180, 3100, 3070, 2950, 1640,
1600, 1540, 1500, 1450, 1360, 1270, 1222, 1168, 1070,
ꢁ
1
1
4c: White solid; M.p. 260- 262 °C; Found: C, 65.87; H,
4.99; N, 13.53 C28H25N5O3S requires C, 65.74; H, 4.93; N,
13.69%; FT-IR (KBr) 3400, 3320, 3220, 3180, 3050, 3000,
2920, 2800, 2780, 1650, 1640, 1558, 1520, 1500, 1445,
1361, 1280, 1240, 1185, 1052, 1018, 1000, 950, 900, 830,
1005, 960, 840, 830, 755, 735, 690 cm ; H-NMR (400
MHz, DMSO-d6): ꢀ 0.93 (s, 3H), 1.0 (s, 3H), 1.97-2.3 (m,
4H), 2.42 (s, 3H), 5.01 (s, 1H), 7.26 (t, 1H, J = 7.4 Hz), 7.45
(t, 2H, J = 7.8), 7.61 (d, 2H, J = 8.4), 7.79 (d, 2H, J = 7.6),
8.01 (d, 2H, J = 8.4), 8.13 (s, 1H), 9.72 (s, 1H), 12.08 (s,
1H); 13C-NMR (100 MHz, DMSO-d6): ꢀ 13.2, 25.2, 27.7,
29.0, 31.2, 32.6, 50.7, 99.0, 110.6, 118.4, 121.2, 126.4,
128.1, 129.6, 129.9, 131.1, 131.2, 134.4, 139.8, 150.2, 150.7,
156.4, 160.0, 162.9, 194.6.
ꢁ
1
790, 750, 690 cm ; 1H-NMR (400 MHz, DMSO-d6): ꢀ 1.72-
1.83 (m, 2H), 2.09-2.20 (m, 2H), 2.43 (m, 2H), 2.51 (s, 3H),
3.82 (s, 3H), 5.07 (s, 1H), 6.96 (d, 2H, J = 8.0 Hz), 7.25 (t,
1H, J = 6.4 Hz), 7.44 (t, 2H, J = 7.0 Hz), 7.80 (t, 4H, J = 6.6
Hz), 8.10 (s, 1H), 9.69 (s, 1H), 12.08 (s, 1H); 13C-NMR (100
MHz, DMSO-d6): ꢀ 13.2, 21.1, 25.1, 27.0, 37.2, 55.5, 81.6,
98.8, 111.7, 113.5, 118.3, 126.1, 127.6, 127.8, 128.9, 129.8,
130.4, 140.0, 151.3, 152.6, 159.1, 161.0, 163.9, 194.7.
4h: White solid; M.p. 230-232 °C; Found: C, 59.70; H,
4.95; N, 16.21 C17H16N4O2S requires C, 59.98; H, 4.74; N,
16.46 %; FT-IR (KBr) 3400, 3280, 3050, 2920, 2850, 2800,
2620, 1718, 1680, 1640, 1605, 1558, 1486, 1460, 1420,
1365, 1320, 1305, 1280, 1258, 1230, 1180, 1138, 1110,
1058, 1020, 1005, 990, 960, 935, 890, 880, 865, 820, 760,
4d: Pale yellow solid; M.p. 276-277 °C; Found: C, 61.34;
H, 4.11; N, 15.80 C27H22N6O4S requires C, 61.59; H, 4.21;
N, 15.96%; FT-IR (KBr) 3320, 3200, 3050, 3005, 2910,
2800, 2750, 1645, 1620, 1598, 1540, 1500, 1450, 1332,
1280, 1223, 1180, 1100, 1060, 1000, 960, 900, 860, 820,
ꢁ
1
750, 720, 690 cm ; 1H-NMR (400 MHz, DMSO-d6): ꢀ 1.75-
1.95 (m, 2H), 2.15-2.35 (m, 2H), 2.51 (s, 3H), 2.52-2.66 (m,
2H), 4.94 (s, 1H), 7.20 (m, 2H), 8.40 (m, 2H), 9.96 (s, 1H),
12.43 (s, 1H); 13C-NMR (100 MHz, DMSO-d6): ꢀ 13.2,
21.2, 26.9, 33.8, 37.1, 97.0, 109.7, 123.3, 149.0, 150.6,
152.7, 154.3, 161.3, 162.0, 194.8.
ꢁ
1
750, 710, 690 cm ; 1H-NMR (400 MHz, DMSO-d6): ꢀ 1.86-
2.16 (m, 4H), 2.43, (s, 2H), 2.50 (s, 3H), 5.08 (s, 1H), 7.30
(t, 1H, J = 7.0 Hz), 7.47 (t, 2H, J = 7.6 Hz), 7.86 (d, 2H, J =
8.0 Hz), 8.22 (s, 1H), 8.31 (s, 4H), 9.79 (s, 1H), 12.14 (s,
1H); 13C-NMR (100 MHz, DMSO-d6): ꢀ 13.2, 21.2, 25.3,
26.9, 37.1, 81.6, 111.7, 118.7, 123.5, 126.7, 128.8, 129.9,
130.1, 130.3, 139.7, 142.2, 147.0, 149.3, 152.8, 156.4, 160.8,
162.2, 195.0.
4i: White solid; M.p. 308-310 °C; Found: C, 55.84; H,
4.49; N, 12.28 C16H15N3O2S2 requires C, 55.65; H, 4.38; N,
12.16 %; FT-IR (KBr) 3220, 3120, 3080, 3020, 2950, 2860,
1655, 1610, 1545, 1478, 1445, 1360, 1262, 1222, 1180,
ꢁ
1
1
1140, 1078, 1000, 960, 880, 845, 785, 700 cm ; H-NMR
(400 MHz, DMSO-d6): ꢀ 1.86-1.95 (m, 2H), 2.29 (m, 2H),
2.51 (s, 3H), 2.59 (m, 2H), 5.25 (s, 1H), 6.72 (s, br., 1H),
6.82 (s, br., 1H), 7.18 (s, br., 1H), 9.97 (s, 1H), 12.49 (s, 1H);
13C-NMR (100 MHz, DMSO-d6): ꢀ 13.2, 21.3, 26.9, 28.6,
37.2, 97.9, 110.6, 123.4, 123.9, 127.0, 151.1, 152.4, 153.5,
161.0, 162.0, 194.7.
4e: Yellow solid; M.p. 262-264 °C; Found: C, 62.65; H,
4.91; N, 15.02 C29H26N6O4S requires C, 62.80; H, 4.73; N,
15.15%; FT-IR (KBr) 3500, 3460, 3300, 3200, 3000, 2920,
2750, 1660, 1620, 1580, 1540, 1442, 1295, 1240, 1222,
ꢁ
1
1
1180, 1145, 1050, 975, 900, 860, 795, 740, 690 cm ; H-
NMR (400 MHz, DMSO-d6): ꢀ 0.92 (s, 3H), 0.99 (s, 3H),
2.15-2.24 (m, 3H), 2.36 (s, 3H), 2.44 (d, 1H, J = 16.8 Hz),
5.62 (s, 1H), 7.33 (t, 1H, J = 6.8 Hz), 7.52 (t, 1H, J = 7.0
Hz), 7.60 (d, 2H, J = 8.0 Hz), 7.84 (d, 2H, J = 7.2 Hz), 7.97
(s, 1H), 8.1 (d, 2H, J = 8.0 Hz), 11.99 (s, 1H), 13.32 (s, 1H);
13C-NMR (100 MHz, DMSO-d6): ꢀ 13.0, 25.6, 28.1, 28.5,
31.7, 44.3, 50.0, 95.8, 114.6, 118.5, 121.5, 122.8, 124.1,
126.7, 127.6, 129.1, 129.3, 130.1, 139.8, 141.1, 146.6, 149.7,
159.4, 161.7, 163.9, 198.8.
Determination of Antimicrobial Activity
Antibacterial activity was determined against Eschrechia
coli, Bacillus subtilis, Pseudomonas aeruginosa and Micro-
coccus leuteus. The synthesized molecule, dissolved in
DMSO, was added to 3 mL of nutrient broth (Merck) to ob-
tain a final concentration of 125 ꢂg/mL. The bacteria were
inoculated into this mixture and allowed to grow for 18 h at
4f: Milky solid; M.p. 266- 268 °C; Found: C, 66.53; H,
5.35; N, 16.12 C30H29N5O3S requires C, 66.77; H, 5.42; N,
12.98%; FT-IR (KBr) 3500, 3480, 3300, 3200, 3000, 2920,
2730, 1640, 1615, 1580, 1445, 1295, 1242, 1220, 1015, 980,
o
37 C. Control samples were prepared by adding only the
bacteria and DMSO, the DMSO alone, and the synthesized
molecule alone. Degree of growth was determined spectro-
photometerically by measuring absorbance at 600 nm, and
corrections made using the controls.
ꢁ
1
1
900, 795 cm ; H-NMR (400 MHz,DMSO-d6): ꢀ 0.91 (s,
3H), 0.96 (s, 3H), 2.16 (m, 3H), 2.34 (d, 1H, J = 17.2 Hz)
2.42 (s, 3H), 3.75 (s, 3H), 5.52 (s, 1H), 6.81 (d, 2H, J = 8.4
Hz), 7.24 (d, 2H, J = 8.4 Hz), 7.28 (t, 1H, J = 7.2), 7.49 (t,
2H, J = 7.8 Hz), 7.78 (d, 2H, J = 8.0 Hz), 7.89 (s, 1H), 12.07
(s, 1H), 13.36 (s, 1H); 13C-NMR (100 MHz, DMSO-d6): ꢀ
13.0, 25.6, 28.1, 28.5, 44.2, 50.0, 55.6, 56.5, 95.8, 113.3,
CONFLICT OF INTEREST
The author(s) confirm that this article content has no con-
flicts of interest.

An Efficient Ultrasound Promoted One-Pot Three-Component
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