Synthesis and antimicrobial activity of newer indole semicarbazones

Article abstract of DOI:10.1007/s00044-010-9502-3

A series of 1-(2-Oxo-2-phenyl-ethyl)-2-phenyl- 1H-indole-3yl)methylene) semicarbazone derivatives (4a-g and 6a-c) were synthesized by the condensation of derivatives of 1-(2-Oxo-2-phenyl-ethyl)-2-phenyl-1Hindole- 3-carbaldehyde and semicarbazide in ethanol under microwave irradiation procedure. Both conventional and microwave-irradiated syntheses have been carried out to compare their yields and reaction time. The structures of the synthesized compounds were confirmed by spectral data. The antimicrobial activities of the synthesized compounds were screened using broth dilution method. Among all the screened compounds some of the compounds exerted good antifungal activity against C. albicans and C. rugosa. All the compounds exhibited moderate activity against bacteria such as B. subtilis, S. aureus, S. epidermidis, E. coli, P. aeoginosa, and K. pneumoniae. Springer Science+Business Media, LLC 2010.

Full text of DOI:10.1007/s00044-010-9502-3

MEDICINAL
CHEMISTRY
RESEARCH
Med Chem Res (2012) 21:85–90
DOI 10.1007/s00044-010-9502-3
ORIGINAL RESEARCH
Synthesis and antimicrobial activity of newer indole
semicarbazones
•
S. Vijaya Laxmi B. Rajitha
Received: 28 September 2010 / Accepted: 3 November 2010 / Published online: 26 November 2010
Ó Springer Science+Business Media, LLC 2010
Abstract A series of 1-(2-Oxo-2-phenyl-ethyl)-2-phenyl-
1H-indole-3yl)methylene) semicarbazone derivatives
(4a–g and 6a–c) were synthesized by the condensation
of derivatives of 1-(2-Oxo-2-phenyl-ethyl)-2-phenyl-1H-
indole-3-carbaldehyde and semicarbazide in ethanol under
microwave irradiation procedure. Both conventional and
microwave-irradiated syntheses have been carried out to
compare their yields and reaction time. The structures of
the synthesized compounds were confirmed by spectral
data. The antimicrobial activities of the synthesized com-
pounds were screened using broth dilution method. Among
all the screened compounds some of the compounds
exerted good antifungal activity against C. albicans and
C. rugosa. All the compounds exhibited moderate activity
against bacteria such as B. subtilis, S. aureus, S. epide-
rmidis, E. coli, P. aeoginosa, and K. pneumoniae.
chemists to search potential new antimicrobial agents to
cure microbial infections effectively (Nagai et al., 2002;
Joan et al., 2002; Nagano et al. 2000; John et al., 2000).
2-Phenyl indole-3-carbaldehyde is a versatile heterocyclic
identified as strong antimitotic agent (Susanne et al., 2008).
2-Aryl indole derivatives also displayed diverse biological
activities such as antiestrogen (Ismail et al., 1997; Fung-
Tomc et al., 2002) antiinflammatory (Von Angerer et al.,
1900; BibergerandVonAngerer, 1998) cytotoxic (Stevenson
et al., 2000) and antimitotic (Doris Kaufmann et al., 2007;
Mahboobi et al., 2005) activities. Semicarbazones also pos-
sessed various therapeutic activities (Dimmock and Baker,
1994; Jenny et al., 2002. Fedorova et al., 1998). Microwave
irradiation presents a powerful tool toward organic reactions
which offers several advantages including shorter reaction
time, cleaner reaction profiles, and simple experimental
product isolation procedures (Loupy, 2002). In continuation
to our research on biologically important heterocyclics in our
laboratory (Suresh Kuarm et al., 2010; Venumadhav et al.,
2009;Rajitha etal., 2005), wehavesynthesizednew2-phenyl
indole semicarbazones under conventional and microwave
irradiation conditions and investigated their antimicrobial
activity. All the new compounds were characterized and
identified by IR, 1H-NMR, 13C-NMR.
Keywords 2-phenyl-1H-indole-3-carbaldehyde Á
Semicarbazide Á Antimicrobial activity
Introduction
In the recent past, bacterial infections have increased at an
alarming rate causing deadly diseases and wide spread
epidemics in humans. All types of bacterial diseases have
taken a high toll on humanity (Todar’s Online Text book of
Biotechnology, http://www.textbookofbiotechnology.net/).
The resistance of antibiotics to control emerging and
pre-emerging bacterial pathogens focused the medicinal
Results and discussion
The aim of this study is to investigate presence of anti-
microbial activities of N-substituted-2-phenyl indole
semicarbazone moieties (4a–g, 6a–c). The synthesis of
these compounds is outlined in Schemes 1 and 2. The
alkylation and arylation of compound 1 (2-phenyl-1H-
indole-3-carbaldehyde) is carried out under microwave
(MW) irradiation, conventional, and at room temperature
S. Vijaya Laxmi Á B. Rajitha (&)
Department of Chemistry, National Institute of Technology,
Warangal 506004, India
e-mail: rajitabhargavi@yahoo.com
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Med Chem Res (2012) 21:85–90
Scheme 1 Synthesis of target
compounds 4a-g
(RT) in the presence of K2CO3 and Tetra-n-butylammo-
nium bromide (TBAB) in N,N-dimethylformamide (DMF).
A comparative study of the above three methods has been
critically conducted to evaluate the yields of the products,
the time taken for the completion of the reaction, and
conditions favorable for the smooth conduct of the reac-
tions. The data is presented in Table 1.
Table 1 Results of the synthesized compounds 3a–f and 5a–c
Entry
Product
Mw 2–5 min
D 2–3 h
Rt 6–8 h
1
2
3a
3b
3c
3d
3e
3f
85
88
87
75
75
86
82
77
74
73
70
72
75
63
64
70
73
65
64
60
58
56
60
50
50
60
54
60
49
55
3
4
Further, compounds 3a–g and 5a–c are condensed with
semicarbazide in microwave and conventional methods in
ethanol furnished (4a–g and 6a–c).Good yields were
observed within minutes only under microwave irradiation
condition, results are depicted in Table 2. Formation of the
semicarbazones (4a–g and 6a–c) is confirmed due to the
absence of aldehydic signal at d 9.93. The signals at d ppm
8.3, 6.2, and 9.8 confirm C=C–H, NH2, and NH protons of
semicarbazone, respectively. Further, C=O signal of semi-
carbazone is confirmed by 13C-NMR at 156.6–156.7-ppm
range. And IR signal of both C=O and NH2 was observed at
1687, 3434 cm-1, respectively. EIMS of the given com-
pounds displayed the molecular ion (m?1) which confirmed
5
6
7
3g
5a
5b
5c
8
9
10
Table 2 Results of the synthesized compounds 4a–g and 6a–c
Entry
Product
Mw 1–2 min
D 1–3 h
1
2
3
4
5
6
7
8
9
10
4a
4b
4c
4d
4e
4f
82
86
86
72
75
82
74
72
75
72
77
72
73
76
77
70
73
66
59
60
1
their molecular weights. Spectral data H-NMR, IR, 13C-
NMR of the synthesized compounds were in full agreement
with the proposed structures.
4g
6a
6b
6c
Antimicrobial activity
All the prepared compounds were evaluated in vitro for
their antifungal and antibacterial activities (Villanova,
1982; Linday, 1962).
Scheme 2 Synthesis of target compounds 6a-c
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Med Chem Res (2012) 21:85–90
87
Antibacterial activity
fluconazole (30 lg/ml). The treated and the control solu-
tions were kept at 27°C for 48 h. Zones of inhibition were
measured and the diameter was measured in millimeter.
Three to four replicates were maintained for each
treatment.
Determination of minimum inhibitory concentration
(MIC) of synthetic compounds
The MIC was measured by broth dilution method (Villa-
nova, 1982). A set of sterile test tubes with nutrient broth
media was capped with cotton plugs (test tube numbers
1–9). The test compound was dissolved in dimethyl sulf-
oxide (DMSO) and concentration of 100 lg/ml of the test
compound was added to the first tube, which was serially
diluted from 1 to 9. A fixed volume of 0.5 ml overnight
culture is added in all the test tubes and incubated at 37°C
for 24 h. After incubation period, the tubes were measured
for turbidity with spectrophotometer.
Antibacterial activity
Antibacterial activities were evaluated against B. subtilis,
S. aureus, S. epidermidis, E. coli, P. aeoginosa, and
K. pneumoniae. The MICs (lg/ml) of tested compounds
against bacteria are shown in Table 3. From the data, the
MIC values indicate that all the compounds exhibited a
varied range (37.5–150 lg/ml) of antibacterial activity
against all the tested bacterial strains.
It is observed that the antibacterial activity in the series
decreased with the introduction of alkyl substituents
(6b, 6c). When compared, the phenacyl moiety enhanced
the antibacterial activity. Among the all compounds,
4f displayed promising activity on P. aeoginosa and
K. pneumoniae bacteria at 75 and 37.5 lg/ml (MIC),
respectively, due to the introduction of NO2 group at para
position. The electron-withdrawing nature of nitro group
might be responsible for the enhanced activity in the series.
Hence, we propose that 4f can be considered as a lead
analog for subsequent optimization in the ongoing search
for novel antibacterial agents.
Antifungal activity
The ready-made Potato Dextrose Agar (PDA) medium
(Himedia, 39 g) was suspended in distilled water
(1000 ml) and heated to boiling until completely dissolved.
The medium and petri dishes were autoclaved at pressure
of 15 lb/inc2 for 20 min. Agar cup bioassay was employed
for testing antifungal activity. The medium was poured into
sterile petri dishes under aseptic conditions in a laminar
flow chamber. When the medium in the plates solidified,
0.5 ml of (1 week old) culture of test organism was inoc-
ulated and uniformly spread over the agar surface with a
sterile L-shaped rod. Solutions were prepared by dissolving
the compound in methanol and different concentrations
were made (30 and 100 lg/ml). After inoculation, cups
were scooped out with 6-mm sterile cork borer and the lids
of the dishes were replaced. To each cup different con-
centrations of test solutions (30,100 lg/ml) were added.
Control solutions were maintained with methanol and
Antifungal activity
The in vitro antifungal activities of the novel compounds
were examined against two fungal strains C. albicans and
C. rugosa. Here, amphotericin B was used as standard
drug. No zone of inhibition was observed for the
Table 3 In vitro antibacterial activity (MIC) values for compounds 4a–g and 6a–c
Compounds
MIC (lg/ml)
B. subtilis
S. aureus
S. epidermidis
E. coli
P. aeroginosa
K. pneumoniae
4a
125
110
130
130
125
130
110
125
110
125
125
[150
25
110
140
130
125
130
110
130
115
135
[150
22
100
125
120
130
140
130
120
120
140
[150
20
100
115
115
120
4b
4c
105
135
130
4d
[150
140
[150
145
[150
120
4e
4f
120
75
37.5
135
4g
[150
140
105
6a
125
[150
110
6b
[150
125
120
6c
[150
12.5
110
Ciprofloxacin
24
25
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Med Chem Res (2012) 21:85–90
was monitored by TLC. After completion of the reaction, the
reaction mixture was cooled to room temperature and then
treated with water. The precipitate was filtered and recrys-
tallized from ethanol which furnished the compounds
Table 4 In vitro antifungal activity (MIC) values for compounds
4a–f and 6a–c
Compounds
Zone of inhibition in mm
C. albicans
C. rugosa
1
3a–g and 5a–c. The H-NMR data of compounds 3a–g,
5a–c are given below.
100 lg
150 lg
100 lg
150 lg
4a
0
4
8
10
10
10
14
15
12
13
0
5
8
12
10
10
14
12
10
15
1-(2-Oxo-2-phenyl-ethyl)-2-phenyl-1H-indole-3-carbalde-
1
hyde (3a) m.p.:185–190°C; H-NMR (DMSO, d, ppm):
5.87 (s, 2H), 7.32–8.27 (m, 14H), 9.60 (s, 1H). MS EIMS:
70 eV (m?1) 340 (100%). For the M.F C23H17NO2, M.Wt
339.
4b
4d
7
7
4e
8
8
4f
9
10
7
6a
10
9
6b
9
1-[2-(4-Chloro-phenyl)-2-oxo-ethyl]-2-phenyl-1H-indole-3-
1
carbaldehyde (3b) m.p.: 150–155°C; H-NMR (DMSO,
d, ppm): 5.86 (s, 2H), 7.33–8.25 (m, 13H), 9.62 (s, 1H). MS
EIMS: 70 eV (m?1) 374. For the M.F C23H16ClNO2, M.Wt
373.
6c
8
10
21
Amphotericin B (50 lg)
23.5
compounds 4c and 4g. Remaining compounds exhibited
zone of inhibition range from 4 to 15 mm. In both 4a–g and
6a–c series, alkyl-substituted compounds 6a–c have shown
significant activity when compared with aryl substituents.
The zone of inhibition (mm) and concentration (lg/ml) of
the tested compounds are illustrated in Table 4
1-[2-(4-Bromo-phenyl)-2-oxo-ethyl]-2-phenyl-1H-indole-3-
1
carbaldehyde (3c) m.p.: 160–163°C; H-NMR (DMSO,
d, ppm): 5.87 (s, 2H), 7.36–8.29 (m, 13H), 9.65 (s, 1H).
1-(2-Oxo-2-p-tolyl-ethyl)-2-phenyl-1H-indole-3-carbalde-
1
hyde (3d) m.p.: 180–183°C; H-NMR (DMSO, d, ppm):
5.8 (s, 2H), 2.3 (s, 3H), 7.33–8.25 (m, 13H), 9.60 (s, 1H).
Experimental protocols
1-[2-(4-Methoxy-phenyl)-2-oxo-ethyl]-2-phenyl-1H-indole-
3-carbaldehyde (3e) m.p.: 190–194°C; 1H-NMR (DMSO,
d, ppm): 5.86 (s, 2H), 3.8(s, 3H), 7.35–8.27 (m, 13H), 9.61
(s, 1H).
Chemistry
Chemicals were purchased from Merck (purity 98%). All
melting points were determined with Quimis apparatus
(Model Q-340 s 13) and were uncorrected. TLC was per-
formed on 2.0 9 6.0 cm aluminum sheets covered with
silica gel (Sorbent, with 200 lm thickness) under ultravi-
olet radiation. Ethyl acetate:hexane (2:8) is used as a
mobile phase. Infrared (IR) spectra were obtained with
ABB spectro photometer (Model: FTLA 2000-100) using
KBr pellets. 1H-NMR, was measured on Brucker 300-MHz
spectrometer using DMSO as a solvent and TMS as
internal standard. Mass spectra were recorded on a Jeol
JMSD-300 spectrometer.
1-[2-(4-Nitro-phenyl)-2-oxo-ethyl]-2-phenyl-1H-indole-3-
1
carbaldehyde (3f) m.p.: 200–205°C; H-NMR (DMSO,
d, ppm): 5.88 (s, 2H), 7.3–8.25 (m, 14H), 9.64 (s, 1H).
1-[2-Biphenyl-4-yl-2-oxo-ethyl)-2-phenyl-1H-indole-3-carb-
aldehyde (3g) m.p.: 167–170°C; 1H-NMR (DMSO, d,
ppm): 5.86 (s, 2H), 7.2–8.25 (m, 18H), 9.62 (s, 1H).
1-Allyl-2-phenyl-1H-indole-3-carbaldehyde (5a) m.p.:
1
150–153°C; H-NMR (DMSO, d, ppm): 4.6 (d, 2H), 5.04,
5.06 (d, 2H), 5.89 (m, 1H), 7.2–8.2(9H, m), 9.64 (s, 1H).
Synthesis procedure for the derivatives of 1-(2-Oxo-2-
phenyl-ethyl)-2-phenyl-1H-indole-3-carbaldehyde (3a–g)
and derivatives of 1-alkyl-2-phenyl-1H-indole-3-
carbaldehyde (5a–c)
1-Butyl-2-phenyl-1H-indole-3-carbaldehyde (5b) m.p.:
1
230–235°C; H-NMR (DMSO, d, ppm): 0.98 (t, 3H), 1.44
(m, 2H), 1.78 (m, 2H), 3.5(t, 2H), 7.20–8.1(m, 9H) 9.61 (s,
1H).
A mixture of 2-phenyl-1H-indole-3-carbaldehyde (1 mmol),
derivatives of four substituted phenacylbromide (1 mmol) or
alkyl bromides (1 mmol), K2CO3 and TBAB were dissolved
in DMF and irradiated the reaction mixture for 2–3 min at
300 W in domestic microwave oven. Progress of the reaction
2-Phenyl-1-(propyl-2-ynyl)-1H-indole-3-carbaldehyde (5c)
1
m.p.: 220–225°C; H-NMR (DMSO, d, ppm): 1.9 (s, 1H),
4.61 (s, 2H), 7.20–8.1 (m, 9H), 9.63 (s, 1H).
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Med Chem Res (2012) 21:85–90
89
13H), 8.34 (s, 1H C=C–H) 9.82 (s, 1NH). 13C-NMR
(DMSO, d, ppm): 20.1, 50.5, 109.9, 110.3, 121.2, 122.2,
123, 124.3, 128.3, 128.7, 129.1, 129.4, 130, 130.4, 131.9,
133.2, 137.4, 137.6, 142.9, 156.7, 193.6.
Synthesis procedure for the derivatives of 1-(2-Oxo-2-
phenyl-ethyl)-2-phenyl-1H-indole-3yl)methylene)
semicarbazone (4a–g) and derivatives of 1-alkyl-2-phenyl-
1H-indole-3yl) methylene)semicarbazone (6a–c)
Derivatives of 1-(2-Oxo-2-phenyl-ethyl)-2-phenyl-1H-
indole-3-carbaldehyde (3a–g) or derivatives of 1-alkyl-2-
phenyl-1H-indole-3-carbaldehyde (5a–c) (1.0 mmol) was
dissolved in absolute ethanol. An equal molar amount of
semicarbazide was added to it and the mixture was irra-
diated under microwave for 1–2 min. On cooling the solid
was found to separate. The precipitate was filtered and
washed with rectified spirit. This procedure often resulted
in a pure product without the need for further purification.
The characterization data of compounds 4a–g, 6a–c are
given below.
1-[2-(4-Methoxy-phenyl)-2-oxo-ethyl]-2-phenyl-1H-indole-
3yl)methylene)semicarbazone (4e) m.p.: 160–165°C; IR
(KBr) (cm-1): 3434 (N–H), 2923, 1687 (C=O), 1579,
1425, 1228, 1120 (C–O), 1098, 986, 749, 1H-NMR
(DMSO, d, ppm): 3.84 (s, 3H, OCH3) 5.7 (s, 2H), 6.23 (s,
2H NH2), 7.20–8.25 (m, 13H), 8.27 (s, 1H C=C–H) 9.88 (s,
1NH). 13C-NMR (DMSO, d, ppm): 50.1, 55.6, 109.7,
110.2, 111.3, 114.1, 121.1, 122.1, 122.8, 124.2, 127.1,
128.6, 128.8, 129, 130.4, 137.3, 137.6, 140.2, 156.6, 192.3.
1-[2-(4-Nitro-phenyl)-2-oxo-ethyl]-2-phenyl-1H-indole-3yl)
methylene)semicarbazone (4f) m.p.: 150–155°C; IR
(KBr) (cm-1): 3434 (N–H), 2923, 1687 (C=O), 1579, 1525
1-(2-Oxo-2-phenyl-ethyl)-2-phenyl-1H-indole-3yl)methylene)
semicarbazone (4a) m.p.: 217–220°C; IR (KBr) (cm-1):
3434 (N–H), 2923, 1687 (C=O), 1579, 1463, 1446, 1425,
1228, 1098, 986, 749, 691, 566; 1H-NMR (DMSO, d,
ppm): 5.73 (s, 2H), 6.22 (s, 2H, NH2), 7.21–8.32 (m, 14H),
8.34 (s, 1H, C=C–H) 9.81 (s, 1NH). MS EIMS:70 eV
(m ? 1) 397(100%). For the M.F C24H20N4O2, M.Wt 396.
13C-NMR (DMSO, d, ppm): 50.5, 109.7, 110.2, 121.2,
122.2, 124.2, 128.7, 128.6, 129, 129.1, 129.4, 129.9, 130.4,
132.8, 137.3, 137.6, 139, 142.7, 156.6, 192.4.
1
(N–O), 1463, 1446, 1425, 1228, 1098, 986, 750. H-NMR
(DMSO, d, ppm): 5.69 (s, 2H), 6.29 (s, 2H NH2), 7.20–8.4
(m, 13H), 8.36 (s, 1H C=C–H) 9.82 (s, 1NH)). 13C-NMR
(DMSO, d, ppm): 50.1, 109.7, 110.2, 111.3, 114.1, 121.1,
122.1, 122.8, 123.4, 123.4, 124.2, 127.1, 129, 137.3, 137.6,
140.2, 142.7, 148.3, 156.6, 192.3.
1-[2-Biphenyl-4-yl-2-oxo-ethyl)-2-phenyl-1H-indole-3yl)
methylene)semicarbazone (4g) m.p.: 170–173°C; IR
(KBr) (cm-1): 3434 (N–H), 2923, 1687 (C=O), 1579,
1-[2-(4-Chloro-phenyl)-2-oxo-ethyl]-2-phenyl-1H-indole-
3yl)methylene)semicarbazone (4b) m.p.: 205–210°C; IR
(KBr) (cm-1): 3434(N–H), 2923, 1687 (C=O), 1579, 1463,
1
1463, 1446, 1425, 1228, 1098, 986, 749, 691, 566; H-
NMR (DMSO, d, ppm): 5.86 (s, 2H), 6.3(s, 2H, NH2)
7.2–8.3 (m, 18H), 8.37 (s, 1H C=CH) 9.82 (s, 1NH). 13C-
NMR (DMSO, d, ppm): 50.1, 109.7, 110.2, 111.3, 114.1,
121.1, 122.1, 122.8, 123.4, 123.4, 124.2, 126.2,
127.2127.3, 128, 129, 137.3, 137.6, 140.2, 142.7, 148.3,
156.6, 192.3.
1
1446, 1425, 1228, 1098, 986, 749, 695. H-NMR (DMSO,
d, ppm): 5.7 (s, 2H), 6.3 (s, 2H, NH2), 7.23–8.32 (m, 13H),
8.33(s, 1H, C=C–H), 9.82 (s, 1NH). 13C-NMR (DMSO, d,
ppm): 50.5, 109.9, 110.3, 121.2, 122.2, 124.2, 128.7, 129,
129.1, 129.4, 129.9, 130.4, 132.8, 137.3, 137.5, 139, 142.8,
156.6, 193.4.
1-Allyl-2-phenyl-1H-indole-3yl)methylene)semicarbazone
(6a) m.p.: 205–210°C; IR (KBr) (cm-1): 3434 (N–H),
3080 (C=C–H of allyl) 2923, 1687 (C=O), 1640 (C=C of
1-[2-(4-Bromo-phenyl)-2-oxo-ethyl]-2-phenyl-1H-indole-3yl)
methylene)semicarbazone (4c) m.p.: 210–215°C; IR (KBr)
(cm-1): 3434 (N–H), 2923, 1687 (C=O), 1579, 1463, 1446,
1425, 1228, 1098, 986, 749, 691. 1H-NMR (DMSO, d,
ppm): 5.7 (s, 2H), 6.3 (s, NH2), 7.20–8.32 (m, 13H), 8.34
(s, 1H C=C–H) 9.82 (s, 1NH). 13C-NMR (DMSO, d, ppm):
50.5, 109.9, 110.3, 121.2, 122.2, 123, 124.3, 128.3, 128.7,
129.1, 129.4, 130, 130.4, 131.9, 133.2, 137.4, 137.6, 142.9,
156.7, 193.6.
1
allyl) 1579, 1463, 1446, 1425, 1228, 1098, 986, 749; H-
NMR (DMSO, d, ppm): 4.6 (d, 2H), 5.04, 5.06 (d, 2H),
5.89 (m, 1H), 6.18 (s, 2H, NH2), 7.17–8.27(m, 9H), 8.28 (s,
1H C=CH) 9.78 (s, 1NH). 13C-NMR (DMSO, d, ppm):
40.2, 109.3, 110.3, 115, 120.9, 122.2, 122.7, 124.2, 128.6,
128.9, 129, 129.9, 130, 130.7, 136.4, 137.4, 142.5, 156.7.
1-Butyl-2-phenyl-1H-indole-3yl)methylene)semicarbazone
(6b) m.p.: 210–212°C; IR (KBr) (cm-1): 3434 (N–H),
2970 (CH3, C–H stre), 2923, 1687 (C=O), 1579, 1463,
1-(2-Oxo-2-p-tolyl-ethyl)-2-phenyl-1H-indole-3yl)methylene)
semicarbazone (4d) m.p.: 190–200°C; IR (KBr) (cm-1):
3434 (N–H), 3010 (C–H), 2923, 1687 (C=O), 1579, 1463,
1
1446, 1425, 1228, 1098, 986, 749, H-NMR (DMSO, d,
ppm): 0.98 (t, 3H), 1.44 (m, 2H), 1.78 (m, 2H), 3.5(t, 2H),
1
1446, 1228, 1098, 986, 749. H-NMR (DMSO, d, ppm):
2.3 (s, 3H CH3) 5.7 (s, 2H), 6.3 (s, 2H, NH2), 7.20–8.32 (m,
6.2 (s, 2NH) 7.20-8.1(m, 9H) 8.3 (s, 1H C=CH) 9.8 (s,
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Med Chem Res (2012) 21:85–90
1NH). 13C-NMR (DMSO, d, ppm): 13.2, 19.1, 31.2, 42.8,
109.3, 110.3, 120.9, 122.2, 122.7, 124.2, 128.6, 128.9, 129,
129.9, 130.7, 136.4, 137.4, 142.5, 156.6.
´
Kaufmann D, Pojarova M, Vogel S, Liebl R, Gastpar R, Gross D,
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2-Phenyl-1-(propyl-2-ynyl)-1H-indole-3yl)methylene)semi-
carbazone (6c) m.p.: 215–217°C; IR (KBr) (cm-1): 3433
(N–H), 3305(sp hybridized C–H), 2923, 1686 (C=O), 1579,
1463, 1446, 1425, 1228, 1098, 986, 748. 1H-NMR (DMSO,
d, ppm): 1.9 (s, 1H), 4.61 (s, 2H), 6.2 (s, 2H, NH2)
7.20–8.1(m, 9H), 8.3 (s, 1H C=C–H) 9.8 (s, 1NH). 13C-
NMR (DMSO, d, ppm): 30.7, 60.7, 70.5, 109.3, 110.3,
120.9, 122.3, 122.9, 124.2, 128.4, 128.9, 129, 129.9, 130.7,
136.4, 137.4, 142.5, 156.6.
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amino acid alterations in penicillin-binding proteins (PBPs) 1a,
2b, and 2x on PBP affinities of penicillin, ampicillin, amoxicil-
lin, cefditoren, cefuroxime, cefprozil, and cefaclor in 18 clinical
isolates of penicillin-susceptible, intermediate, and resistant
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Acknowledgments The authors wish to thank Dr. U.S.N. Murthy,
Head, Biology division, Indian Institute of Chemical Technology,
Hyderabad for screening the antimicrobial activity of the synthesized
compounds. We also wish to thank the Ministry of Human Resource
Development for granting the research fellowship to SV.
disubstituted
pyrrolidinylthio-1b-methylcarbapenems
with
potent activities against methicillin-resistant Staphylococcus
aureus and Pseudomonas aeruginosa. Antimicrob Agents Che-
mother 44:489–495
Rajitha B, Thirupathi Reddy Y, Narasimha Reddy P (2005) Sulfamic
acid a novel and efficient catalyst for the synthesis of aryl-14-H-
dibenzo[a, f]Xanthenes in conventional heating and microwave
irradiation. Tetrahedron Lett 46:8691–8693
Conflicts of interest The author reports no conflicts of interest.
Stevenson GI, Smith AL, Lewis S, Michie SG, Neduvelil JG, Patel S,
Marwood R, Castro JL (2000) Solid-phase synthesis of 2,3-
disubstituted indoles: discovery of a novel, high-affinity, selec-
tive h5-HT2A antagonist. Bioorg Med Chem Lett 10:2697–2699
Suresh Kuarm B, Venu Madhav J, Vijaya Laxmi S, Rajitha B,
Thirupathi Reddy Y, Narsimha Reddy P, Crooks PA (2010)
Expeditious pechmann condensation by using biodegradable
cellulose sulfuric acid as a solid acid catalyst. Synth Commun
40:3358–3364
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