Synthesis of some new indolo[2,3-c]isoquinolinyl pyrazoles, -1,3,4-oxadiazoles and their biological activities

Article abstract of DOI:10.1007/s00044-012-0366-6

A new series of novel compounds [10-substituted 6H, 7H-indolo[2,3-c] isoquinolin-5-one-6-yl]carbohydrazides (3a-c), 1-[10-substituted 6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]fomyl-, -3′,5′- dimethylpyrazoles (4a-c), -3′,5′-diphenylpyrazoles (5a-c), -3′-methylpyrazol-5′-ones (6a-c) and -1′,3′,4′- oxidiazole-2′-thiones (7a-c) linked to indoloisoquinoline at position-6 through formyl bridge was prepared. The structures of these newly synthesized compounds were confirmed by their spectral studies and elemental analysis. These compounds have been screened for their antimicrobial and antioxidant activities. Compounds 4a, 4b, 5a, 5b, 5c, 6b, 7a, and 7c exhibited the maximum zone of inhibition against A. niger, A. flavus, and A. fumigatus. Compounds 4a, 5a, 5c, 6b, 6c, 7a, and 7b showed good antibacterial activity. Compounds 4b, 4c, 5b, 5c, 6a, 6b, 7a, 7b, and 7c showed good radical scavenging activity compared with standards.

Full text of DOI:10.1007/s00044-012-0366-6

MEDICINAL
CHEMISTRY
RESEARCH
Med Chem Res (2013) 22:3787–3793
DOI 10.1007/s00044-012-0366-6
ORIGINAL RESEARCH
Synthesis of some new indolo[2,3-c]isoquinolinyl pyrazoles, -1,3,4-
oxadiazoles and their biological activities
•
Anand R. Saundane Vaijinath A. Verma
•
Katkar Vijaykumar
Received: 19 March 2012 / Accepted: 13 November 2012 / Published online: 9 December 2012
Ó Springer Science+Business Media New York 2012
Abstract A new series of novel compounds [10-substi-
tuted 6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]carbo-
hydrazides (3a–c), 1-[10-substituted 6H, 7H-indolo[2,
3-c]isoquinolin-5-one-6-yl]fomyl-, -30,50-dimethylpyrazoles
(4a–c), -30,50-diphenylpyrazoles (5a–c), -30-methylpyrazol-
50-ones (6a–c) and -10,30,40-oxidiazole-20-thiones (7a–c)
linked to indoloisoquinoline at position-6 through formyl
bridge was prepared. The structures of these newly synthe-
sized compounds were confirmed by their spectral studies
and elemental analysis. These compounds have been
screened for their antimicrobial and antioxidant activities.
Compounds 4a, 4b, 5a, 5b, 5c, 6b, 7a, and 7c exhibited the
maximum zone of inhibition against A. niger, A. flavus, and
A. fumigatus. Compounds 4a, 5a, 5c, 6b, 6c, 7a, and 7b
showed good antibacterial activity. Compounds 4b, 4c, 5b,
5c, 6a, 6b, 7a, 7b, and 7c showed good radical scavenging
activity compared with standards.
Introduction
Pyridoindoles (Carbolines) are known for their wide
spectrum of biological activities, viz., anticoagulant
(Cohen and Cattanach, 1967), anticonvulsant (Saxena
et al., 1969), antidepressant (Garmaise and Parks, 1973),
anti-inflammatory, antibacterial (Winter et al., 1979),
antitumor (Ishizumi and Katsube, 1980; Sumitomo, 1983),
and antihistaminic (Kosuge et al., 1973). However, there
are few reports on the antimicrobial activities of a-carb-
olines (Azimvand, 2012; Thakur et al., 2010), and
recently we have reported the antioxidant and antimicro-
bial activities (Saundane et al., 2012) of compounds
containing this system. Apart from this, pyrazole and its
derivatives have been found to exhibit antimicrobial,
anthelmintic, oxytocic (Hiremath et al., 1993; 1995;
1997), anti-inflammatory, analgesic (Saundane et al.,
1998a), ulcerogenic, and lipid peroxidation (Amir and
Kumar 2005) activities. Some of the pyrazole analogs
were reported as antimicrobial (Sridhar et al., 2004;
Bondock et al. 2010), fungicides (Chen et al., 2000;
Vicentini et al., 2007), and antioxidant (Burgute et al.,
2007) activities. In addition, 1,3,4-oxadiazoles are also
known for their biologic importance, viz., anticancer
(Rajyalakshmi et al., 2011), antifungal (Abdel-Rahman,
2004), antibacterial (Padmavathi et al., 2009), and anti-
oxidant (Padmavathi et al., 2010) activities. The aim of
the present study was both to explore the effect of the
synthesized compounds on the tested pathogens and to
find lead compounds having potent antimicrobial and/or
antioxidant activity. Hence, in the continuation of our
work on the synthesis of biologically important a-carbo-
lines, we are reporting the synthesis, antimicrobial and
antioxidant activities of the title compounds in the present
communication.
Keywords Indolo[23-c]isoquinoline ꢀ Pyrazole ꢀ
Pyrazolone ꢀ Oxadizole ꢀ Antimicrobial ꢀ Antioxidant
Electronic supplementary material The online version of this
article (doi:10.1007/s00044-012-0366-6) contains supplementary
material, which is available to authorized users.
A. R. Saundane (&) ꢀ K. Vijaykumar
Department of Post-Graduate Studies and Research in
Chemistry, Gulbarga University, Gulbarga 585 106,
Karnataka, India
e-mail: arsaundane@rediff.com
V. A. Verma
Shri Prabhu Arts, Science & J. M. Bohra Commerce College,
Shorapur 585 224, India
123

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Med Chem Res (2013) 22:3787–3793
Results and discussion
Biological activities
The reaction sequence employed for the synthesis of
title compounds is illustrated in Scheme 1. The starting
compounds 10-substituted 6H, 7H-indolo[2,3-c]isoquinolin-
5-ones (1a–c), ethyl[10-substituted 6H, 7H-indolo[2,3-c]iso-
quinolin-5-one-6-yl]formates (2a–c) and [10-substituted 6H,
7H-indolo[2,3-c]isoquinolin-5-one-6-yl]carbohydrazides
(3a–c) were prepared according to the reported method
(Hiremath et al.,1995). The hydrazide (3a) were subjected
to cyclocondensation with acetyl acetone or dibenzoyl
methane or ethyl acetoacetate in dry methanol containing
catalytic amount of conc. hydrochloric acid under reflux
temperature to yield 10-[10-chloro-6H, 7H-indolo[2,3-c]
isoquinolin-5-one-6-yl]formyl-, -30,50-dimethylpyrazole (4a),
-30,50-diphenylpyrazole (5a) and -30-methylpyrazol-50-one
(6a), respectively.
Literature survey reveals that most of the synthesized
compounds contain the biologically active pharmacophores
–N–CO–N–, –N–CO–N–CO– and oxdiazoles which
exhibited the wide range of activities such as, antimicrobial
(Dhansay et al., 2010; Jaiswal et al., 2012; Latthe et al.,
2006; Patel et al., 2007; Aanandhi et al., 2011), antioxidant
(George et al., 2008; Aanandhi et al., 2010; Amornraksa
et al., 2009), anti-inflammatory (Amir Mohd et al., 2007),
and anticancer (Aboraia et al., 2006), etc. Therefore, based
on these observations, the synthesized compounds have been
screened for their antimicrobial and antioxidant activities.
Antimicrobial activity
Compound (3a) on reaction with carbon disulfide and
potassium hydroxide in dry methanol under reflux condi-
tions afforded 50-[10-chloro-6H, 7H-indolo[2, 3-c]iso-
quinolin-5-one- 6-yl]-10, 30, 40-oxidiazol-20-thione (7a).
Similarly, other derivatives in the series were prepared and
structures of these compounds were confirmed by their
spectral studies and elemental analysis.
The newly synthesized compounds (4–7) were screened for
their antimicrobial activity by Cup-plate method (Indian
pharmacopoeia, 1985; Saundane et al., 1998b). Escherichia
coli, Bacillus subtilis, and Pseudomonas putida were used
for antibacterial activity. Antifungal activity was evaluated
against Asperigillus niger, Asperigillus flavus, and Asper-
igillus fumigatus. For the screening, nutrient agar medium
Scheme 1 Schematic pathway
for the synthesis of compounds
4–7
R
R
ClCOOC2H5
N
N
O
N
N O
H
H
H
O
OC2H5
1a-c
2a-c
N2H4.H2O
R
N
N
O
H
O
NHNH2
3a-c
O
R
O
O
O
O
O
CS2/ KOH
OC2H5
R
R
R
N
N O
N
N O
N
N
O
N N O
H
H
H
H
O
S
O
N
N
O
N
N
O
N
N
N
NH
CH3
C6H5
O
6a-c
C6H5
5a-c
CH3
H3C
7a-c
4a-c
a
b
c
R=
Cl CH3 OCH3
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Med Chem Res (2013) 22:3787–3793
3789
by antioxidant. The RSA of the newly synthesized com-
pounds (4–7) was carried out by following literature pro-
cedure (Hatano et al., 1988) using ascorbic acid (AA),
2-tert-butyl-4-methoxy phenol (butylated hydroxy anisole,
BHA), and 2-(1,1-dimethylethyl)-1,4-benzenediol (tertiary
butylated hydroquinone, TBHQ) as standards. The RSA of
test compounds in methanolic solution at 25, 50, 75, and
100 lg/ml concentrations containing freshly prepared
DPPH solution (0.004 % w/v) was carried out and com-
pared with those of standards AA, BHA, and TBHQ. All
the test analyses were performed on three replicates and
results were averaged. The results in percentage were
expressed as the ratio of absorption decrease in the pres-
ence of test compounds and absorption of DPPH solution in
the absence of test compounds at 517 nm on Elico SL 171
Mini Spec spectrophotometer. The results are shown in the
Figs. 1 and 2.
Table 1 Antimicrobial activity of synthesized compounds (4–7)
Compd. Antibacterial activity
no
Antifungal activity
(zone of inhibition in mm)
(zone of inhibition in mm)
E. coli B. subtilis P. putida A. niger A. flavus A. fumigatus
4a
4b
4c
5a
5b
5c
6a
6b
6c
7a
7b
7c
S1
S2
09
13
11
10
05
11
07
10
17
18
11
13
19
–
11
11
08
13
09
11
10
08
10
19
11
10
20
–
19
10
10
18
13
17
15
18
10
20
19
07
22
–
16
08
10
04
15
09
06
12
09
17
08
10
–
11
16
08
09
13
17
09
14
07
16
13
10
–
15
11
04
15
04
15
13
15
04
17
10
15
–
18
19
18
The analysis of results indicated that compounds 5b, 5c,
6a, 6b, 7a, 7b, and 7c exhibited good radical scavenging
activity (56.21, 60.05, 67.45, 57.98, 68.35, 57.69, and
60.75 %) at 25 lg/ml concentration, respectively. Com-
pounds 5b, 6b, 7a, 7b, and 7c showed radical scaveng-
ing ability (56.86, 64.20, 69.82, 65.38, and 67.75 %) at
50 lg/ml concentration, respectively. While compounds
4c, 6b, and 7a showed radical scavenging ability (53.84,
Where, S1 Streptomycin (Standard), S2 Fluconazole (Standard)
and potato dextrose agar medium were used for antibacterial
and antifungal activity. The compounds were tested at
1 mg/ml concentration. Streptomycin and fluconazole were
used as standards for antibacterial and antifungal activities,
respectively. The results are reported in (Table 1).
The investigation of antibacterial screening revealed
that compounds 6c and 7a exhibited maximum zone of
inhibition against E. coli. Compound 7a exhibited maxi-
mum inhibitory zone against B. subtilis. Whereas, com-
pounds 5a, 5c, 6b, 7a, and 7b exhibited maximum zone of
inhibition against P. putida.
In the case of antifungal activity, compounds 4a, 5b, and
7a showed maximum zone of inhibition against A. niger.
Compounds 4b, 5c, and 7a exhibited good activity against
A. flavus. Compounds 4a, 5a, 5c, 6b, 7a, and 7c showed good
activity against A. fumigatus. Rest of the compounds showed
either lower activity or inactive against the organisms tested.
From the results of antimicrobial activities, it could be
assumed that the majority of synthesized compounds having
chloro and methoxy substituents exhibited better activity.
Fig. 1 Antioxidant activity of compounds (4–5)
Antioxidant activity
1, 1-Diphenyl-2-picryl hydrazyl (DPPH) radical
scavenging activity (RSA)
DPPH has an odd electron and has strong absorption band
at 517 nm. The reduction capability of DPPH radical was
determined by decrease in its absorption at 517 nm induced
Fig. 2 Antioxidant activity of compounds (6–7)
123

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Med Chem Res (2013) 22:3787–3793
56.50, and 57.98) at 75 lg/ml concentration, respectively.
The compounds 4b and 7a exhibited RSA (64.74 and
68.93 %) at 100 lg/ml concentration, respectively. Com-
pound 7a showed maximum RSA may be due to presence
of chloro and methoxy group. However, none of the
compounds exhibited better RSA than the standards.
off under reduced pressure and the residue was cooled to
room temperature. The separated solid was filtered off,
washed with cold methanol (5-7 mL), dried, and recrys-
tallized from ethanol to furnish pure 4a–c, 5a–c and 6a–c.
10-[10-chloro-6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]
formyl-30,50-dimethylpyrazole (4a) Yield: 72 %, mp [
300 °C; Rf, 0.65 ethyl acetate:acetone (6:4) mixture; FTIR
(KBr) cm-1: 3,278 (Indole NH); 1,654 (C=O); 1,630
1
Conclusion
(C=O); 1,620 (C=N); H NMR (DMSO-d6, d, ppm), 10.90
(s, 1H, indole NH); 7.20–8.40 (m, 7H, Ar–H); 6.10 (s, 1H,
Pyrazole-H); 3.50 (s, 3H, CH3); 2.33 (s, 3H, CH3);
13C-NMR (DMSO-d6, 125 MHz, d), 162.8, 161.0, 145.5,
139.1, 138.8, 136.1, 134.6, 132.9, 132.4, 130.9, 130.7,
130.2 129.7, 128.6, 126.1, 125.4, 122.0, 120.9, 120.3, 22.8,
20.6; MS (EI) m/z 390 (M?); 392 (M??2). Anal. %
C21H15N4O2Cl: C, 64.54; H, 3.87; N, 14.34. Found: C,
64.41; H, 3.82; N, 14.29.
The present study revealed that the compounds having
chloro and methoxy substituents exhibited good antimi-
crobial and antioxidant activities.
Experimental procedure
Chemistry
10-[10-methyl-6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]
formyl-30,50-dimethylpyrazole (4b) Yield: 68 %, mp [
300 °C; Rf, 0.71 ethyl acetate:acetone (6:4) mixture; FTIR
(KBr) cm-1: 3,388 (Indole NH); 1,700 (C=O); 1,658
Materials and methods
1
All the reagents were obtained commercially and used by
further purification. Melting points were determined by an
open capillary method and are uncorrected. Purity of the
compounds was checked by TLC using silica gel-G coated
alumininum plates (Merck) and spots were visualized by
exposing the dry plates in iodine vapors. The IR (KBr)
spectra were recorded using a Perkin-Elmer Spectrum on
FT-IR spectrometer. The 1H NMR (DMSO) spectra
recorded using Marcy Plus (Varian 400 MHz) and the
chemical shifts were expressed in ppm (d scale) and 13C
NMR (125 MHz, DMSO) spectra recorded on Bruker
NMR. Mass spectra were recorded using a ILS-CHU-C-41-
VBV4 MS mass spectrometer.
(C=O); 1,623 (C=N); H NMR (DMSO-d6, d, ppm) 11.09
(s, 1H, indole NH); 7.00–8.06 (m, 7H, Ar–H); 6.10 (s, 1H,
Pyrazole-H); 2.58 (s, 3H, CH3); 2.52 (s, 3H, CH3); 2.21 (s,
3H, CH3); Anal. % C22H18N4O2: C, 71.34; H, 4.90; N,
15.13. Found: C, 71.31; H, 4.82; N, 15.29.
10-[10-methoxy-6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]
formyl-30,50-dimethylpyrazole (4c) Yield: 70 %, mp [
300 °C; Rf, 0.45 ethyl acetate:acetone (6:4) mixture; FTIR
(KBr) cm-1: 3,300 (Indole NH); 1,684 (C=O); 1,650 (C=O);
1
1,630 (C=N); H NMR (DMSO-d6, d, ppm) 11.82 (s, 1H,
indole NH); 7.10–8.23 (m, 7H, Ar–H); 6.22 (s, 1H, Pyrazole-
H); 3.67 (s, 3H, OCH3); 2.35 (s, 3H, CH3); 2.25 (s, 3H, CH3);
Anal. % C22H18N4O3: C, 68.38; H, 4.70; N, 14.50. Found: C,
68.41; H, 4.82; N, 14.39.
General procedure for the synthesis of 10-substituted
6H, 7H-indolo[2,3-c]isoquinolin-5-ones (1a–c), ethyl [10-
substituted 6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]
formates (2a–c) and [10-substituted 6H, 7H-indolo[2,3-c]
10-[10-chloro-6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]
formyl-30,50-diphenylpyrazole (5a) Yield: 72 %, mp [
300 °C; Rf, 0.65 ethyl acetate:acetone (6:4) mixture; FTIR
(KBr) cm-1: 3,214 (indole-NH); 1,739 (C=O); 1,700
isoquinolin-5-one-6-yl]carbohydrazides (3a–c). These
compounds were prepared by reported literature methods
(Hiremath et al., 1995).
1
(C=O); 1,630 (C=N); H NMR (DMSO-d6, d, ppm), 11.00
General procedure for the synthesis of 10-[10-substituted
6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]formyl-, -30,50-
dimethylpyrazoles (4a–c), -30,50-diphenylpyrazoles (5a–c)
and -30-methylpyrazole-50-ones (6a–c). A mixture of
hydrazides (3a–c) (0.001 mol) and acetyl acetone or
dibenzoyl methane or ethyl acetoacetate (0.001 mol) in dry
methanol containing 4–5 drops of conc. HCl was refluxed
for 4 h on steam bath. The excess of solvent was distilled
(s, 1H, indole NH); 7.05–8.21 (m, 17H, Ar–H); 6.10 (s, 1H,
Pyrazole-H); 13C-NMR (DMSO-d6, 125 MHz, d), 163.0,
160.8, 146.3, 140.4, 135.8, 135.3, 135.1, 134.3, 133.9,
131.3, 129.8, 129.3, 129.2, 129.1, 128.8, 128.7, 128.3,
128.5, 128.2, 127.4, 127.3, 127.2, 127.1, 126.4, 126.3,
126.2, 126.1, 126.0, 121.8, 121.4, 121.3; MS (EI) m/z 514
(M?); 516 (M??2). Anal. % C31H19N4O2Cl: C, 72.30; H,
3.72; N, 10.88. Found: C, 72.21; H, 3.82; N, 10.71.
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Med Chem Res (2013) 22:3787–3793
3791
10-[10-methyl-6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]
formyl-30,50-diphenylpyrazole (5b) Yield: 72 %, mp
298–99 °C; Rf, 0.72 ethyl acetate:acetone (6:4) mixture;
FTIR (KBr) cm-1: 3,385 (indole-NH); 1,721 (C=O); 1,700
(C=O); 1,628 (C=N); 1H NMR (DMSO-d6, d, ppm), 11.82 (s,
1H, indole NH); 7.19–8.08 (m, 17H, Ar–H); 6.24 (s, 1H,
Pyrazole-H); 2.48 (s, 3H, CH3); Anal. % C32H22N4O2: C,
77.72; H, 4.48; N, 11.33. Found: C, 77.75; H, 3.78; N, 10.68.
General procedure for the synthesis of 50-[10-substituted 6H,
7H-indolo[2,3-c]isoquinolin-5-one-6-yl]-10,30,40-oxidiaz-
ole-20-thiones (7a–c). A mixture of hydrazides (3a–c)
(0.005 mol), KOH (0.005 mol), and CS2 (5 ml) in metha-
nol (50 ml) was refluxed on a steam bath until the evolu-
tion of H2S ceased (45–48 h). The solvent was then
evaporated and residue dissolved in ice-cold water. The
resulting clear solution was filtered and the filtrate was
acidified with dilute HCl. The separated solid was filtered,
washed with water, dried, and recrystallized from ethanol
to furnish pure 7a–c.
10-[10-methoxy-6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]
formyl-30,50-diphenylpyrazole (5c) Yield: 72 %, mp
265-66 °C; Rf, 0.52 ethyl acetate:acetone (6:4) mixture;
FTIR (KBr) cm-1: 3,306 (indole-NH); 1,725 (C=O); 1,700
(C=O); 1,630 (C=N); 1H NMR (DMSO-d6, d, ppm), 11.82 (s,
1H, indole NH); 7.19-8.08 (m, 17H, Ar–H); 6.38 (s, 1H,
Pyrazole-H); 3.46 (s, 3H, OCH3); Anal. % C32H22N4O3: C,
75.28; H, 4.34; N, 10.97. Found: C, 75.20; H, 4.28; N, 11.25.
50-[10-chloro-6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]
-10,30,40-oxidiazole-20-thione (7a) Yield: 62 %, mp [
300 °C; Rf, 0.62 ethyl acetate:methanol (9:1) mixture;
FTIR (KBr) cm-1: 3,283 (indole-NH); 3,154 (NH); 1,658
1
(C=O); 1,201 (C=S); H NMR (DMSO-d6, d, ppm) 11.32
(s, 1H, indole NH); 9.21 (s, 1H, NH); 7.23–8.12 (m, 7H,
Ar–H); 13C-NMR (DMSO-d6, 125 MHz, d), 176.2, 163.5,
158.1, 148.3, 139.2, 137.1, 136.7, 136.1, 129.8, 129.1,
128.9, 128.5, 127.3, 127.1, 121.4, 121.2, 120.9; MS (EI)
m/z 368 (M?); 370 (M??2). Anal. % C17H9N4O2SCl: C,
55.36; H, 2.46; N, 15.19. Found: C, 55.41; H, 2.40; N,
15.11.
10-[10-chloro-6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]
formyl-30-methylpyrazole-50-one (6a) Yield: 66 %, mp [
300 °C; Rf, 0.70 ethyl acetate:methanol (9:1) mixture;
FTIR (KBr) cm-1: 3,290 (indole-NH); 1,700 (C=O); 1,660
1
(C=O); 1,655 (C=O); H NMR (DMSO-d6, d, ppm), 11.00
(s, 1H, indole NH); 7.41–8.40 (m, 7H, Ar–H); 3.09 (s, 2H,
CH2); 2.21 (s, 3H, CH3); 13C-NMR (DMSO-d6, 125 MHz,
d), 163.3, 160.4, 158.0, 148.1, 139.8, 139.1, 135.8, 133.1,
132.4, 131.9, 130.1, 129.8, 129.1, 128.9, 126.3, 125.8,
122.5, 120.9, 120.1, 39.50, 19.6; MS (EI) m/z 392 (M?);
394 (M??2). Anal. % C20H13N4O3Cl: C, 61.16; H, 3.34;
N, 14.26. Found: C, 62.00; H, 3.22; N, 14.18.
50-[10-methyl-6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]
-10,30,40-oxidiazole-20-thione (7b) Yield: 60 %, mp
244–45 °C; Rf, 0.52 ethyl acetate:methanol (9:1) mixture;
FTIR (KBr) cm-1: 3,333 (indole-NH); 3,282 (NH); 1,700
1
(C=O); 1,213 (C=S); H NMR (DMSO-d6, d, ppm), 11.74
(s, 1H, indole NH); 9.00 (s, 1H, NH); 7.03–8.00 (m, 7H,
Ar–H); 2.18 (s, 3H, CH3); Anal. % C18H12N4O2S: C,
62.06; H, 3.47; N, 16.08. Found: C, 61.86; H, 3.40; N,
16.11.
10-[10-methyl-6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]
formyl-30-methylpyrazole-50-one (6b) Yield: 82 %, mp
288–89 °C; Rf, 0.52 ethyl acetate:methanol (9:1) mixture;
FTIR (KBr) cm-1: 3,330 (indole-NH); 1,700 (C=O); 1,682
1
(C=O); 1,664 (C=O); H NMR (DMSO-d6, d, ppm), 11.84
50-[10-methoxy-6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]
-10,30,40-oxidiazole-20-thione (7c) Yield: 56 %, mp 295–
96 °C; Rf, 0.45 ethyl acetate:methanol (9:1) mixture; FTIR
(KBr) cm-1: 3,315 (indole-NH); 3,245 (NH); 1,701 (C=O);
(s, 1H, indole NH); 7.00–8.25 (m, 7H, Ar–H); 3.10 (s, 2H,
CH2); 2.58 (s, 3H, CH3); 2.18 (s, 3H, CH3); Anal. %
C21H16N4O3: C, 67.73; H, 4.33; N, 15.05. Found: C, 67.82;
H, 4.28; N, 15.18.
1
1,210 (C=S); H NMR (DMSO-d6, d, ppm), 11.59 (s, 1H,
indole NH); 8.75 (s, 1H, NH); 7.00–8.12 (m, 7H, Ar–H);
3.68 (s, 3H, OCH3); Anal. % C18H12N4O3S: C, 59.33; H,
3.32; N, 15.38. Found: C, 60.06; H, 3.40; N, 15.31.
10-[10-methoxy-6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]
formyl-30-methylpyrazole-50-one (6c) Yield: 58 %, mp [
300 °C; Rf, 0.63 ethyl acetate:methanol (9:1) mixture; FTIR
(KBr) cm-1: 3,300 (indole-NH); 1,713 (C=O); 1,700 (C=O);
Acknowledgments The authors are thankful to the Chairman,
Department of Chemistry, Gulbarga University, Gulbarga, for pro-
viding laboratory facilities and Chairman, Department of Microbiol-
ogy, Gulbarga University, Gulbarga, for providing facilities to carry
out antimicrobial activity. We are also thankful to Director, Indian
Institute of Technology, Madras, Chennai, for providing spectral data.
1
1,682 (C=O); H NMR (DMSO-d6, d, ppm), 11.68 (s, 1H,
indole NH); 7.10–8.20 (m, 7H, Ar–H); 3.25 (s, 2H, CH2); 3.58
(s, 3H, OCH3); 2.18 (s, 3H, CH3); Anal. % C21H16N4O4: C,
64.94; H, 4.15; N, 14.43. Found: C, 65.11; H, 4.28; N, 14.38.
123

3792
Med Chem Res (2013) 22:3787–3793
5-one-6-yl]acetyl-3, 5-disubstituted-pyrazoles/pyrazolones and
5-[10-substituted 6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]
methyl-1,3,4-oxadiazole-2-thiones. J Indian Chem Soc 72(10):
735–738
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