Synthesis and in vitro microbial activities of amides of pyridoquinolone

Article abstract of DOI:10.1007/s00044-010-9443-x

Abstract In this study, we report the antimicrobial evaluation of newly synthesized amides of pyridoquinolones from substituted aniline, substituted phenyl thioureas and 4-amino-N-(substitutedphenyl)benzenesulfonamide. Structures of selected compounds hav

Full text of DOI:10.1007/s00044-010-9443-x

MEDICINAL
CHEMISTRY
RESEARCH
Med Chem Res (2011) 20:1054–1067
DOI 10.1007/s00044-010-9443-x
ORIGINAL RESEARCH
Synthesis and in vitro microbial activities of amides
of pyridoquinolone
•
Navin B. Patel Sarvil D. Patel Hiren I. Chauhan
•
Received: 23 November 2009 / Accepted: 17 September 2010 / Published online: 2 October 2010
Ó Springer Science+Business Media, LLC 2010
Abstract In this study, we report the antimicrobial eval-
uation of newly synthesized amides of pyridoquinolones
from substituted aniline, substituted phenyl thioureas and
4-amino-N-(substitutedphenyl)benzenesulfonamide. Struc-
tures of selected compounds have been established by IR
and 1H NMR spectra and elemental analysis. The structure–
activity releationships have been studied by screening of
antimicrobial activity over S. aureus, B. subtilis, E. coli,
P. aeruginosa, and C. albicans using cup–plate method.
antagonist (Bromidge et al., 2002), antitubercular (Kamal
et al., 2007) and antifungal (Briganti et al., 1997) etc.
Pyridoquinolones were synthesized and evaluated for
antimicrobial activity (Lee et al., 1992; Lee and Chang,
1994, 1996), in which pyridine ring was fused with qui-
nazoline ring, and generally known as phenanthroline. The
structure–activity relationships of fluoroquinolone have
been studied in some reviews (Mitscher, 2005; Bhanot
et al., 2001); consideration of the above facts and the
presence of fused pyrido ring in nalidixic acid urged us to
synthesize structurally similar compounds to fluoroquino-
lone by replacing fluoro group with chloro and hydroxy
groups at C–6 possition with fused pyrido ring; the car-
boxylic acid group was further converted to amides for
enhanced antimicrobial activity.
Keywords Pyridoquinolone Á Phenyl thioureas Á
Sulfonamides Á Antimicrobial activity
Introduction
Discovery of nalidixic acid gave an important class of
antibacterial known as fluoroquinolones. They can inhibit
DNA gyrase and topoisomerase IV enzymes, essential for
DNA supercoiling. Phenyl thiourea derivatives possess
significant pharmacological importance, e.g., antiviral
(Yan et al., 2009), antimicrobial (Turan-Zitouni et al.,
2002), antidiabetic (Maruyama et al., 2009), antitubercular
(Sycheva et al., 1966) etc. Sulfonamides demonstrated
bacteriostatic activity by inhibiting the bio-synthesis of
folic acid (Brown, 1962). Its derivatives possess versatile
activity, e.g., carbonic anhydrase inhibitors (Supuran et al.,
1998), anticancer (Reddy et al., 2004), anti-inflammatory
(Li et al., 1995), anti-HIV (Selvam et al., 2001), COX-2
inhibitors (Dannhardt et al., 2002), selective 5-HT receptor
Results and discussion
Chemistry
We have synthesized amides of pyridoquinolone 3a–l, 4a–l,
5a–l, 6a–l, 7a–l, and 8a–l from substituted aniline, substi-
tuted phenyl thioureas, and 4-amino-N-(substitutedphe-
nyl)benzenesulfonamide as illustrated in Scheme 1: their
structures were confirmed by elemental analysis, IR, and 1H
NMR spectral data. IR absorption bands in cm-1 were ob-
severed at 3412 (NH), 3360 (OH), 2942, 2865 (CH), 1739
([C=O of quinolone), 1640 (amide-I), 1535 (amide-II),
1305 (C–N), 1250 (amide-III), 810 (C–Cl), 1325, 1180
(S=O, sym, asym), and 1160 ([C=S), 1075 (S–N); some
additional peaks appeared due to substitution in aromatic
ring at 1512, 1352 (N=O sym, asym), 1265, 1046 (C–O–C),
and 2236 ([C:N). In 1H NMR spectra, the following
common signals appeared at dH (ppm) values: a singlet
N. B. Patel (&) Á S. D. Patel Á H. I. Chauhan
Department of Chemistry, Veer Narmad South Gujarat
University, Surat, Gujarat 395 007, India
e-mail: drnavin@satyam.net.in
123

Med Chem Res (2011) 20:1054–1067
1055
X
N
X
N
R
N
O
H2N
O
N
HO (CH2)2
COOH
NH
Pyridine 0-5 °C
Stirring, 4-5 hr
1a, 1b
HO (CH2)2
R
O
SOCl2
3a-l, 4a-l
80 oC
Refluxed
R
X
X
SO2NH
H2N
N
N
O
O
Pyridine 0-5 °C
Stirring, 4-5 hr
O
N
N
HO (CH2)2
HO (CH2)2
COCl
NH
R
2a, 2b
NHSO2
5a-l, 6a-l
X
N
S
R
N
H2N
C
NH
O
Pyridine 0-5 °C
Stirring, 4-5 hr
NH
S
HO (CH2)2
C
O
NH
R
7a-l, 8a-l
,
1b
,
,
,
1a
,
X = OH for
4a-l
6a-l
,
8a-l
2a
2b
X = Cl for
5a-l
7a-l
3a-l
,
,
R =
a
-H
-H
-H
-H
b
3-Cl
3-Cl
3-Cl
3-Cl
c
d
e
f
g
h
i
j
K
l
3
4
5
6
7
4-Cl
4-Cl
4-Cl
4-Cl
2-OCH3 4-OCH3 2-NO2
2-OCH3 4-OCH3 2-NO2
2-OCH3 4-OCH3 3-NO2
2-OCH3 4-OCH3 3-NO2
3-NO2
3-NO2
4-NO2
4-NO2
3-NO2
4-NO2
4-NO2
2-CH3
2-CH3
4-NO2
2-CH3
2-CH3
3-CH3
3-CH3
2-CH3
3-CH3 4-CH3
3-CH3 4-CH3
4-CH3 2,5-di-CH3
4-CH3 2,5-di-CH3
3-CH3 4-CH3
2,5-di-CH3
2,5-di-CH3
2-CN, 4-NO2
2-CN, 4-NO2
3-Cl
3-OH 4-OH 2-OCH3 4-OCH3 2-NO2
-H
-H
8
3-OH 4-OH 2-OCH3 4-OCH3 2-NO2
3-NO2
4-NO2
2-CH3
3-CH3 4-CH3
3-Cl
Scheme 1 Synthetic route of compounds 3a–l, 4a–l, 5a–l, 6a–l, 7a–l, 8a–l
signal at d 7.80, and 8.50 corresponding to H-2 and H-5 of
quinolone ring, respectively; a multiplet at d 3.20 corre-
sponding to[N–(CH2)2–O; a singlet at d 4.25 corresponding
to CH2OH; a multiplet at d 8.75–9.50 corresponding to
pyrido ring; a singlet at d 5.40 corresponding to Ar–OH; a
singlet at d 10.10 corresponding to[CO.NH; and a singlet
single at d 10.20 and 10.28 corresponding to –SONH2 and
[CS.NH, respectively, Due to the substitution on aromatic
ring, a singlet appeared at d 6.56 and 3.85 corresponding to
Ar–OH and Ar–OCH3, repectively. Substituted phenyl thio-
urea derivatives (Venkatesh and Pandeya, 2009; Bhusari
et al., 2008) and substituted 4-amino-N-(substitutedphe-
nyl)benzenesulfonamide (Hirpara et al., 2004) have been
synthesized as per the previously reported methods (Table 1).
123

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Med Chem Res (2011) 20:1054–1067
Table 1 Antibacterial and antifungal activity of synthesized compounds
Zone of inhibition in mm at 100 lg/ml
Compd.
Gram negative
Gram positive
Fugal species
E. coli
P. aeruginosa
S. aureus
B. subtilis
C. albicans
Z.I
A.I
Z.I
A.I
Z.I.
A.I.
Z.I.
A.I.
Z.I.
A.I.
3a
3b
3c
3d
3e
3f
12
07
06
08
00
11
09
09
07
10
04
10
08
04
10
06
11
09
08
06
09
00
10
09
06
10
08
05
09
07
11
09
00
05
10
08
09
09
04
00
08
08
12
00
10
0.8
09
07
06
08
06
11
09
10
04
10
05
08
08
04
08
00
10
09
10
06
10
06
09
08
07
10
00
05
10
05
09
09
04
07
10
08
10
08
04
06
08
07
10
04
11
0.52
0.41
0.35
0.47
0.35
0.64
0.52
0.58
0.23
0.58
0.29
0.47
0.47
0.23
0.47
–
12
08
05
09
06
08
09
10
00
10
05
08
07
00
12
06
10
10
07
08
06
05
09
08
08
11
06
06
09
06
09
09
00
05
10
08
09
08
00
06
10
08
10
04
11
0.7
11
09
07
10
06
10
06
06
05
09
07
09
06
06
10
08
12
11
08
07
06
06
08
09
10
09
07
06
10
08
10
10
06
06
09
09
08
09
06
08
11
08
11
06
12
0.68
0.6
05
03
02
03
02
04
03
04
00
04
00
00
01
00
05
01
05
04
02
00
00
01
03
02
02
04
01
02
03
02
03
03
00
01
04
02
03
03
00
01
04
02
04
00
05
0.55
0.33
0.22
0.33
0.22
0.44
0.33
0.44
–
0.46
0.4
0.47
0.29
0.52
0.66
0.47
0.52
0.66
–
0.43
0.62
0.35
0.62
0.35
0.35
0.31
0.6
0.53
–
0.73
0.6
3g
3h
3i
0.6
0.46
0.66
0.26
0.66
0.53
0.26
0.66
0.4
3j
0.66
0.29
0.47
0.41
–
0.44
–
3k
3l
0.43
0.6
–
4a
4b
4c
4d
4e
4f
0.35
0.35
0.62
0.5
0.11
–
0.7
0.55
0.11
0.55
0.44
0.22
–
0.66
0.58
0.58
0.41
0.47
0.66
0.29
0.52
0.47
0.47
0.64
0.66
0.66
0.52
0.66
0.52
0.52
–
0.73
0.6
0.58
0.52
0.58
0.35
0.58
0.35
0.52
0.47
0.41
0.58
–
0.75
0.68
0.5
4g
4h
4i
0.53
0.4
0.43
0.35
0.35
0.5
0.6
–
4j
–
0.11
0.33
0.22
0.22
0.44
0.11
0.22
0.33
0.22
0.33
0.33
–
4k
4l
0.66
0.6
0.6
5a
5b
5c
5d
5e
5f
0.4
0.62
0.6
0.66
0.53
0.33
0.6
0.43
0.35
0.62
0.5
0.29
0.58
0.29
0.52
0.52
0.23
0.41
0.58
0.47
0.58
0.47
0.23
0.35
0.47
0.41
0.58
0.23
0.64
0.46
0.73
0.6
5g
5h
5i
0.62
0.62
0.35
0.35
0.6
–
5j
0.33
0.66
0.53
0.6
0.29
0.58
0.47
0.52
0.47
–
0.11
0.44
0.22
0.33
0.33
–
5k
5l
0.6
6a
6b
6c
6d
6e
6f
0.5
0.6
0.6
0.26
–
0.35
0.5
0.66
0.58
0.47
0.58
0.26
0.64
0.11
0.44
0.22
0.44
–
0.53
0.53
0.8
0.68
0.5
6g
6h
6i
0.68
0.35
0.75
–
0.66
0.55
123

Med Chem Res (2011) 20:1054–1067
1057
Table 1 continued
Zone of inhibition in mm at 100 lg/ml
Compd.
Gram negative
Gram positive
Fugal species
C. albicans
Z.I. A.I.
E. coli
P. aeruginosa
S. aureus
B. subtilis
Z.I
A.I
Z.I
A.I
Z.I.
A.I.
Z.I.
A.I.
6j
05
10
06
10
08
12
05
08
10
00
10
00
11
06
09
11
09
06
00
08
05
09
12
06
09
06
10
15
0.33
0.66
0.4
00
11
08
09
06
11
03
06
08
08
09
04
10
00
09
10
07
06
04
08
04
10
10
00
09
04
09
17
–
05
11
08
09
08
12
00
08
12
08
11
06
10
06
08
11
08
06
04
08
00
07
10
05
09
00
09
17
0.29
0.64
0.47
0.52
0.47
0.7
06
09
06
11
09
11
06
09
09
06
12
08
09
06
10
15
10
07
00
06
05
07
09
07
08
06
10
16
0.35
0.6
00
04
02
03
02
05
00
02
04
01
05
02
04
00
03
04
03
00
00
02
01
00
04
00
03
01
03
–
6k
0.64
0.47
0.52
0.35
0.64
0.17
0.35
0.47
0.47
0.52
0.23
0.58
–
0.44
0.22
0.33
0.22
0.55
–
6l
0.35
0.68
0.6
7a
0.66
0.53
0.80
0.33
0.53
0.66
–
7b
7c
0.68
0.35
0.6
7d
–
7e
0.47
0.7
0.22
0.44
0.11
0.55
0.22
0.44
–
7f
0.6
7g
0.47
0.64
0.35
0.75
0.5
7h
0.66
–
7i
7j
0.73
0.4
0.58
0.66
0.47
0.64
0.47
0.66
0.26
0.47
–
0.6
7k
0.35
0.62
0.93
0.66
0.43
–
7l
0.6
0.52
0.58
0.41
0.35
0.23
0.47
0.23
0.58
0.58
–
0.33
0.44
0.33
–
8a
0.73
0.6
8b
8c
0.4
8d
–
–
8e
0.53
0.33
0.6
0.35
0.31
0.43
0.6
0.22
0.11
–
8f
8g
0.41
0.58
0.29
0.52
–
8h
0.8
0.44
–
8i
0.4
0.43
0.5
8j
0.6
0.52
0.23
0.52
1
0.33
0.11
0.33
8k
0.4
0.35
0.62
1
8l
0.66
1
0.52
1
Ciprofloxacin
Amphoterian-B
9
1
Z.I Zone of inhibition in mm, A.I. Activity index
A.I. = Zone of inhibition of compounds/Zone of inhibition of standard drug
Antimicrobial activity
demostrated good activity against E. coli; whereas amides
3a, 3f, 4e, sulfonamides 5g, 6g and thioureido amides 7c,
7j, 8a, 8h demostrated strong activity against E. coli.
Amides 3a, 3f, 3g, 3h, 3j, 4e, 4g, 4i, 4f, 4k, sulfona-
mides 5b, 5e, 5g, 5h, 5k, 6a, 6g, 6i, 6k, and thioureido
amides 7c, 7j, 7l, 8a, 8g, 8h, 8j, 8l demostrated good
activity against P. aeruginosa. Amides 3a, 3d, 3e, 3g–j,
4c–f, 4i, 4k, sulfonamides 5b–h, 5k, 6a, 6d, 6e, 6g, 6i, 6k
and thioureido amides 7a, 7c, 7f, 7h, 7j, 7k, 8a, 8c, 8h, 8j,
8l showed good activity against S. aureus.
Antibacterial and antifungal activity of all the synthesized
compounds have been screened against five different
strains, e.g., two Gram-positive S. aureus, B. subtilis, two
Gram-negative E. coli, P. aeruginosa bacteria and fungi C.
albicans by cup–plate method (Collee et al., 1996) at
100 lg/mL concentration, compared with standard drug
ciprofloxacin and amphotericin-B.
Amides 3d, 3g, 3h, 3j, 3l, 4a, 4f, 4c, 4g, 4i, 4k, 4l,
sulfonamides 5b, 5c, 5e, 5k, 5l, 6a, 6b, 6e, 6f, 6k, and
thioureido amides 7a, 7b, 7e, 7f, 7h, 7l, 8b, 8e, 8g, 8j, 8l;
Amides 3a, 3b, 3d, 3f, 3j, 3l, 4c, 4d, 4f, 4g, 4k, 4l,
sulfonamides 5a, 5b, 5e–h, 5l, 6a, 6b, 6e, 6f, 6g, 6k, and
123

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Med Chem Res (2011) 20:1054–1067
thioureido amides 7a–c, 7e, 7f, 7j, 7l, 8b, 8h, 8j, 8l dem-
ostrated good activity against B. substilis; whereas amide
4e, sulfonamides 6i, and thioureido amides 7h, 8a demo-
strated srong activity against B. substilis.
malonate and cyclized in diethyl ether; further condensation
with chloroethanol gave ester, which finally hydrolyzed to
title compounds (Lee et al., 1992). 1H NMR (DMSO-d6): d
3.61 (m, 4H, [N(CH2)2O), 4.25 (s, 1H, CH2OH), 8.50
(s, H-2, quinolone), 7.80 (s, H-5, quinolone), 5.65 (s, 1H,
Ar–OH), 8.75–9.40 (m, 3H, pyrido), and 13.00 (s, 1H,
COOH).
Amides 3a, 4c, 4e; sulfonamide 6i, and thioureido
amides 7c, 7h, showed good activity against C. albicans.
Conclusion
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl chloride (2a)
The structure–activity relationship study demonstrated that
electron withdrawing as well as eletrodonating groups at
phenyl ring were active; whereas chloro and hydroxyl
groups at C–6 possition showed similar activity. Variations
in antimicrobial activities of amides were observed.
Activities of amides in increasing order:
The mixture of 6-chloro-1-(2-hydroxyethyl)-4-oxo-1,
4-dihydro-[1,7]phenanthroline-3-carboxylic acid (1a)
(0.01 mol) and thionyl chloride (0.01 mol) was refluxed
using chloroform as a solvent in water bath at 80°C for
5–6 h in anhydrous condition with the help of calcium
chloride guard tube, until the HCl gas evolution ceased, and
then solvent was removed by distillation. The solid material
of the title compound was obtained and used in next step.
Thioureido amides \ Sulfonamides \ Amide
Activities against bacteria in increasing order:
P. aeruginosa \ S. aureus \ B. substilis \ E. coli
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl chloride (2b)
Experimental
The mixture of 6-hydroxy-1-(2-hydroxyethyl)-4-oxo-1,
4-dihydro-[1,7]phenanthroline-3-carboxylic acid (1b)
(0.01 mol) and thionyl chloride (0.01 mol) was refluxed
using chloroform as a solvent in water bath at 80°C for
5–6 h in anhydrous condition with the help of calcium
chloride guard tube, until the HCl gas evolution ceased, and
then solvent was removed by distillation. The solid material
of the title compound was obtained and used in next step.
General
Melting points (m.p.) were determined in open capillaries
and left uncorrected. The IR spectra were recorded on
1
Shimadzu FTIR spectrophotometer, using KBr pallets. H
NMR spectra were recorded in (DMSO-d6) using Bruker
DRX-300 spectrometer at 300 MHz; the chemical shifts are
reported in part per million (d ppm) using tetramethylsilane
(TMS) as an internal standard. Elemental analysis (C, H,
and N) of compounds was performed on Carlo Erba 1108.
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(substitutedphenyl)amide (3a–l)
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
Substituted aniline (0.005 mol) was dissolved in dry pyri-
dine and added dropwise in solution of carbonyl chloride
(2a) (0.005 mol) in pyridine within 1.5 h with constant
stirring at 0–5°C and refluxed for 8 h; then, material was
poured into acidic crushed ice, and the solid mass was
filtered and washed thoroughly with NaHCO3 solution for
neutralization. The purity of the compounds was monitored
by TLC on silica gel glass plate using benzene:ethylacetate
(1:1) as mobile phase.
[1,7]phenanthroline-3-carboxylicacid (1a)
The parent molecule was prepared from 5-amino-8-chloro
quinoline on reaction with diethyl ethoxymethelene mal-
onate and cyclized in diethyl ether; further condensation
with chloroethanol gave ester, which finally hydrolyzed to
1
title compounds (Lee et al., 1992). H NMR (DMSO-d6):
d 3.61 (m, 4H, [N(CH2)2O), 4.25 (s, 1H, CH2OH), 8.50
(s, H-2, quinolone), 7.80 (s, H-5, quinolone), 8.75–9.40
(m, 3H, pyrido), and 13.00 (s, 1H, COOH).
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid phenylamide (3a)
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
Yield = 62%, m.p. 256–258°C. IR (KBr) cm-1: 3412
(NH); 3360 (OH); 2942, 2865 (CH); 1739 ([C=O of
quinolone); 1640 (amide-I); 1535 (amide-II); 1305 (C–N);
[1,7]phenanthroline-3-carboxylicacid (1b)
The parent molecule was prepared from 5-amino-8-hydroxy
quinoline on reaction with diethyl ethoxymethelene
1
1250 (amide-III); and 810 (C–Cl). H NMR (DMSO-d6):
123

Med Chem Res (2011) 20:1054–1067
1059
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(3-nitrophenyl)amide (3g)
d 3.25 (m, 4H, [N(CH2)2O); 4.45 (s, 1H, CH2OH); 8.71
(s, H-2, quinolone); 8.88 (s, H-5, quinolone); 8.94–9.55
(m, 3H, pyrido); 10.10 (s, 1H, CO.NH); and 7.28–7.92
(m, 5H, Ar–H). Anal. Calcd. for C21H16O3N3Cl: C, 64.11; H,
4.10; and N, 10.69. Found: C, 64.12; H, 4.12; and N, 10.65.
Yield = 66%, m.p. 277–279°C. IR (KBr) cm-1: 3433
(NH); 3355 (OH); 2937, 2865 (CH); 1745 ([C=O of
quinolone); 1645 (amide-I); 1525 (amide-II); 1510, 1330
(N=O sym, asym); 1320 (C–N); 1235 (amide-III); and 792
(C–Cl). 1H NMR (DMSO-d6): d 3.28 (m, 4H, [N
(CH2)2O); 4.25 (s, 1H, CH2OH); 8.61 (s, H-2, quinolone);
8.87 (s, H-5, quinolone); 8.81–9.65 (m, 3H, pyrido); 10.21
(s, 1H, CO.NH); and 7.18–7.65 (m, 4H, Ar–H). Anal.
Calcd. for C21H15O5N4Cl: C, 57.52; H, 3.45; and N, 12.79.
Found: C, 57.51; H, 3.42; and N, 12.77.
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(3-chlorophenyl)amide (3b)
Yield = 53%, m.p. 278–280°C.
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(4-chlorophenyl)amide (3c)
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(4-nitrophenyl)amide (3h)
Yield = 65%. m.p. 247–249°C. IR (KBr) cm-1: 3425
(NH); 3365 (OH); 2937; 2864 (CH); 1745 ([C=O of
quinolone); 1645 (amide-I); 1525 (amide-II); 1315 (C–N);
1254 (amide-III); and 786 (C–Cl). 1H NMR (DMSO-d6): d
3.20 (m, 4H, [N(CH2)2O); 4.35 (s, 1H, CH2OH); 8.70
(s, H-2, quinolone); 8.84 (s, H-5, quinolone); 8.95–9.55 (m,
3H, pyrido); 10.15 (s, 1H, CO.NH); and 7.20–7.95 (m, 4H,
Ar–H). Anal. Calcd. for C21H15O3N3Cl2: C, 59.01; H, 3.54;
and N, 9.84. Found: C, 59.05; H, 3.56; and N, 9.82.
Yield = 62%, m.p. 250–252°C.
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(2-methylphenyl)amide (3i)
Yield = 53%, m.p. 247–249°C. IR (KBr) cm-1: 3435
(NH); 3358 (OH); 2925, 2861 (CH); 1745 ([C=O of
quinolone); 1645 (amide-I); 1525 (amide-II); 1308 (C–N);
1232 (amide-III); and 798 (C–Cl). 1H NMR (DMSO-d6): d
3.27 (m, 4H, [N(CH2)2O); 4.25 (s, 1H, CH2OH); 8.61
(s, H-2, quinolone); 8.79 (s, H-5, quinolone); 8.85–9.61 (m,
3H, pyrido); 10.14 (s, 1H, CO.NH); 7.22–7.80 (m, 4H,
Ar–H); and 2.22 (s, 3H, Ar–CH3). Anal. Calcd. for
C22H18O3N3Cl: C, 64.85; H, 4.46; and N, 10.32. Found: C,
64.81; H, 4.42; and N, 10.37.
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(2-methoxyphenyl)amide (3d)
Yield = 67%, m.p. 255–257°C.
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(4-methoxyphenyl)amide (3e)
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(3-methylphenyl)amide (3j)
Yield = 62%, m.p. 271–272°C. IR (KBr) cm-1: 3427
(NH); 3360 (OH); 2935, 2861 (CH); 1752 ([C=O of
quinolone); 1652 (amide-I); 1535 (amide-II); 1312 (C–N);
1245 (amide-III); 1235, 1040 (C–O–C); and 786 (C–Cl).
1H NMR (DMSO-d6): d 3.21 (m, 4H, [N(CH2)2O); 4.27
(s, 1H, CH2OH); 8.65 (s, H-2, quinolone); 8.88 (s, H-5,
quinolone); 8.97–9.61 (m, 3H, pyrido); 10.25 (s, 1H,
CONH); 7.21–7.79 (m, 4H, Ar–H); and 3.85 (s, 3H,
Ar–OCH3). Anal. Calcd. for C22H18O4N3Cl: C, 62.40; H,
4.29; and N, 9.93. Found: C, 62.38; H, 4.27; and N, 9.90.
Yield = 58%, m.p. 268–270°C.
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(4-methylphenyl)amide (3k)
Yield = 64%, m.p. 241–243°C. IR (KBr) cm-1: 3425
(NH); 3345 (OH); 2935, 2865 (CH); 1752 ([C=O of
quinolone); 1648 (amide-I); 1521 (amide-II); 1315 (C–N);
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(2-nitrophenyl)amide (3f)
1
1237 (amide-III); and 788 (C–Cl). H NMR (DMSO-d6):
d 3.29 (m, 4H, [N(CH2)2O); 4.21 (s, 1H, CH2OH); 8.56
(s, H-2, quinolone); 8.85 (s, H-5, quinolone); 8.90–9.62
(m, 3H, pyrido); 10.15 (s, 1H, CO.NH); 7.21–7.82 (m, 4H,
Yield = 55%, m.p. 260–262°C.
123

1060
Med Chem Res (2011) 20:1054–1067
Ar–H); 2.25 (s, 3H, Ar–CH3). Anal. Calcd. for C22H18
O3N3Cl: C, 64.85; H, 4.46; and N, 10.32. Found: C, 64.82;
H, 4.41; and N, 10.35.
(m, 3H, pyrido); 10.15 (s, 1H, CO.NH); 5.62 (s, 1H,
Ar–OH); and 6.85–7.45 (m, 4H, Ar–H). Anal. Calcd. for
C21H16O4N3Cl: C, 61.60; H, 3.94; and N, 10.27. Found: C,
61.62; H, 3.92; and N, 10.22.
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(2,5-dimethylphenyl)amide (3l)
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(2-methoxyphenyl)amide (4d)
Yield = 60%, m.p. 265–267°C.
Yield = 62%, m.p. 261–263°C.
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(substitutedphenyl)amide (4a–l)
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(4-methoxyphenyl)amide (4e)
Substituted aniline (0.005 mol) was dissolved in dry pyri-
dine and added dropwise in solution of carbonyl chloride
(2b) (0.005 mol) in pyridine within 1.5 h with constant
stirring at 0–5°C and refluxed for 8 h, then refluxed
material was poured into acidic crushed ice, the solid mass
was filtered and washed thoroughly with NaHCO3 solution
for neutralization. The purity of the compounds was
monitored by TLC on silica gel glass plate using ben-
zene:ethylacetate (1:1) as mobile phase.
Yield = 65%, m.p. 258–260°C. IR (KBr) cm-1: 3422
(NH); 3339 (OH); 2961, 2852 (CH); 1752 ([C=O of
quinolone); 1664 (amide-I); 1561 (amide-II); 1310 (C–N);
1245 (amide-III) 1225, and 1038 (C–O–C). 1H NMR
(DMSO-d6): d 3.68 (m, 4H, [N(CH2)2O); 4.37 (s, 1H,
CH2OH); 8.68 (s, H-2, quinolone); 8.25 (s, H-5, quino-
lone); 9.15–9.65 (m, 3H, pyrido); 10.15 (s, 1H, CO.NH);
5.61 (s, 1H, Ar–OH); 6.85-7.45 (m, 4H, Ar–H); and 3.95
(s, 3H, Ar–OCH3). Anal. Calcd. for C22H19O5N3: C, 65.16;
H, 4.73; and N,10.37. Found: C, 65.15; H, 4.51; and N, 10.35.
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid phenylamide (4a)
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(2-nitrophenyl)amide (4f)
Yield = 58%, m.p. 244–246°C. IR (KBr) cm-1: 3425
(NH); 3345 (OH); 2965, 2854 (CH); 1749 ([C=O of
quinolone); 1668 (amide-I); 1565 (amide-II); 1315 (C–N);
and 1258 (amide-III). 1H NMR (DMSO-d6): d 3.60 (m, 4H,
[N(CH2)2O); 4.35 (s, 1H, CH2OH); 8.70 (s, H-2, quino-
lone); 8.15 (s, H-5, quinolone); 9.10–9.60 (m, 3H, pyrido);
10.10 (s, 1H, CO.NH); 5.65 (s, 1H, Ar–OH); and 6.95–7.40
(m, 5H, Ar–H). Anal. Calcd. for C21H17O4N3: C, 67.18; H,
4.57; and N, 11.20. Found: C, 67.15; H, 4.55; and N, 11.18.
Yield = 60%, m.p. 266–267°C.
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(3-nitrophenyl)amide (4g)
Yield = 66%, m.p. 235–237°C. IR (KBr) cm-1: 3428
(NH); 3325 (OH); 2965, 2858 (CH); 1745 ([C=O of
quinolone); 1662 (amide-I); 1565 (amide-II); 1512, 1339
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(3-chlorophenyl)amide (4b)
1
(N=O sym, asym); 1307 (C–N); and 1252 (amide-III). H
NMR (DMSO-d6): d 3.65 (m, 4H, [N(CH2)2O); 4.32 (s,
1H, CH2OH); 8.71 (s, H-2, quinolone); 8.15 (s, H-5,
quinolone); 9.10–9.62 (m, 3H, pyrido); 10.12 (s, 1H,
CO.NH); 5.62 (s, 1H, Ar–OH); and 6.79–7.35 (m, 4H,
Ar–H). Anal. Calcd. for C21H16O6N4: C, 59.98; H, 3.84;
and N, 13.33. Found: C, 59.95; H, 3.82; and N, 13.31.
Yield = 64%, m.p. 265–267°C.
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(4-chlorophenyl)amide (4c)
Yield = 62%, m.p. 261–263°C. IR (KBr) cm-1: 3421
(NH); 3335 (OH); 2961, 2851 (CH); 1751 ([C=O of
quinolone); 1665 (amide-I); 1569 (amide-II); 1312 (C–N);
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(4-nitrophenyl)amide (4h)
1
1252 (amide-III); and 788 (C–Cl). H NMR (DMSO-d6):
d 3.61 (m, 4H, [N(CH2)2O); 4.25 (s, 1H, CH2OH); 8.65
(s, H-2, quinolone); 8.10 (s, H-5, quinolone); 9.12–9.65
Yield = 64%, m.p. 255–258°C.
123

Med Chem Res (2011) 20:1054–1067
1061
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(2-methylphenyl)amide (4i)
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
[4-(3-chlorophenylsulfamoyl)phenyl]amide (5b)
Yield = 55%, m.p. 247–249°C. IR (KBr) cm-1: 3435
(NH); 3320 (OH); 2955, 2854 (CH); 1751 ([C=O of
quinolone); 1665 (amide-I); 1561 (amide-II); 1310 (C–N);
and 1245 (amide-III). 1H NMR (DMSO-d6): d 3.67 (m, 4H,
[N(CH2)2O); 4.21 (s, 1H, CH2OH); 8.65 (s, H-2, quino-
lone); 8.05 (s, H-5, quinolone); 9.12–9.55 (m, 3H, pyrido);
10.18 (s, 1H, CO.NH); 5.65 (s, 1H, Ar–OH); 6.71–7.25
(m, 4H, Ar–H); and 2.14 (s, 3H, Ar–CH3). Anal. Calcd. for
C22H19O4N3: C, 67.84; H, 4.92; and N, 10.80. Found: C,
67.82; H, 4.91; and N, 10.78.
Yield = 60%, m.p. 239–240°C. IR (KBr) cm-1: 3425
(NH); 3365 (OH); 2945, 2850 (CH); 1742 ([C=O of
quinolone); 1680 (amide-I); 1565 (amide-II); 1325, 1180
(S=O, sym, asym); 1310 (C–N); 1255 (amide-III); 1075
1
(S–N); and 798 (C–Cl). H NMR (DMSO-d6): d 3.58 (m,
4H, [N(CH2)2O); 4.44 (s, 1H, CH2OH); 8.68 (s, H-2,
quinolone); 7.95 (s, H-5, quinolone); 8.98–9.75 (m, 3H,
pyrido); 10.10 (s, 1H, CO.NH); 10.32 (s, 1H, SO2NH); and
7.15–7.70 (m, 4H, Ar–H). Anal. Calcd. for C27H20
O5N4SCl2: C, 55.67; H, 3.46; and N, 9.62. Found: C, 55.62;
H, 3.42; and N, 9.60.
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylic acid
(3-methylphenyl)amide (4j)
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
[4-(4-chlorophenylsulfamoyl)phenyl]amide (5c)
Yield = 67%, m.p. 270–271°C.
Yield = 56%, m.p. 260–262°C.
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(4-methylphenyl)amide (4k)
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid [4-(2-
methoxyphenylsulfamoyl)phenyl]amide (5d)
Yield = 62%, m.p. 261–263°C.
Yield = 64%, m.p. 257–259°C. IR (KBr) cm-1: 3431
(NH); 3361 (OH); 2937, 2848 (CH); 1748 ([C=O of
quinolone); 1665 (amide-I); 1557 (amide-II); 1325, 1180
(S=O, sym, asym); 1310 (C–N); 1255 (amide-III); 1212,
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
(2,5-dimethylphenyl)amide (4l)
1
1035 (C–O–C); 1075 (S–N); and 798 (C–Cl). H NMR
(DMSO-d6): d 3.62(m, 4H, [N(CH2)2O); 4.47 (s, 1H,
CH2OH); 8.61 (s, H-2, quinolone); 7.90 (s, H-5, quino-
lone); 8.91–9.72 (m, 3H, pyrido); 10.15 (s, 1H, CO.NH);
9.95 (s, 1H, SO2NH); 7.01–7.65 (m, 4H, Ar–H); and 3.82
(s, 3H, Ar–OCH3). Anal. Calcd. for C28H23O6N4SCl: C,
58.12; H, 4.01; and N, 9.69. Found: C, 58.10; H, 4.06; and
N, 9.64.
Yield = 57%, m.p. 255–257°C.
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid [4-
(phenylsulfamoyl)phenyl]amide (5a–l)
4-Amino-N-(substitutedphenyl)benzenesulfonamides (0.005
mol) was dissolved in dry pyridine and added dropwise in
solution of carbonyl chloride 2a (0.005 mol) in pyridine
within 1.5 h with constant stirring at 0–5°C and refluxed for
8 h, thenrefluxedmaterialwaspouredintoacidiccrushedice,
the solid mass was filtered and washed thoroughly with
NaHCO3 solution for neutralization. The purity of the com-
pounds was monitored by TLC on silica gel glass plate using
benzene:ethylacetate (1:1) as mobile phase.
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid [4-(4-
methoxyphenylsulfamoyl)phenyl]amide (5e)
Yield = 52%, m.p. 274–276°C.
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
[4-(3-nitrophenylsulfamoyl)phenyl]amide (5f)
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
[4-(phenylsulfamoyl)phenyl]amide (5a)
Yield = 55%, m.p. 247–249°C. IR (KBr) cm-1: 3426
(NH); 3358 (OH); 2928, 2835 (CH); 1751 ([C=O of
quinolone); 1671 (amide-I); 1562 (amide-II); 1528, 1332
(N=O sym, asym); 1335, 1182 (S=O, sym, asym); 1315
Yield = 66%, m.p. 241–243°C.
123

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Med Chem Res (2011) 20:1054–1067
1
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid [4-(2,5-di-
methyphenylsulfamoyl)phenyl]amide (5k)
(C–N); 1265 (amide-III); and 1065 (S–N); 795 (C–Cl). H
NMR (DMSO-d6): d 3.62 (m, 4H, [N(CH2)2O); 4.47 (s,
1H, CH2OH); 8.61 (s, H-2, quinolone); 7.90 (s, H-5,
quinolone); 8.91–9.72 (m, 3H, pyrido); 10.15 (s, 1H,
CO.NH); 9.95 (s, 1H, SO2NH); and 7.01–7.65 (m, 4H,
Ar–H). Anal. Calcd. for C27H20O7N5SCl: C, 54.63; H,
3.40; and N, 11.81. Found: C, 54.60; H, 3.38; and N, 11.78.
Yield = 60%, m.p. 258–260°C.
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid [4-(2-cyno-4-
nitrophenylsulfamoyl)phenyl]amide (5l)
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
[4-(4-nitrophenylsulfamoyl)phenyl]amide (5g)
Yield = 64%, m.p. 233–235°C. IR (KBr) cm-1: 3428
(NH); 3335 (OH); 2925, 2818 (CH); 2236 ([C:N); 1755
([C=O of quinolone); 1665 (amide-I); 1565 (amide-II);
1528, 1332 (N=O sym, asym); 1325, 1174 (S=O, sym,
asym); 1304 (C–N); 1260 (amide-III); 1062 (S–N); and
795 (C–Cl). 1H NMR (DMSO-d6): d 3.67 (m, 4H,
[N(CH2)2O); 4.42 (s, 1H, CH2OH); 8.65 (s, H-2, quino-
lone); 7.88 (s, H-5, quinolone); 8.81–9.65 (m, 3H, pyrido);
10.15 (s, 1H, CO.NH); 9.95 (s, 1H, SO2NH); and 7.19–7.65
(m, 3H, Ar–H). Anal. Calcd. for C27H20O7N5SCl: C, 59.78;
H, 4.12; and N, 9.96. Found: C, 59.74; H, 4.09; and N,
9.92.
Yield = 61%, m.p. 259–261°C.
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
[4-(2-methyphenylsulfamoyl)phenyl]amide (5h)
Yield = 63%, m.p. 236–237°C. IR (KBr) cm-1: 3420
(NH); 3345 (OH); 2932, 2821 (CH); 1741 ([C=O of
quinolone); 1665 (amide-I); 1565 (amide-II); 1325, 1179
(S=O, sym, asym); 1310 (C–N); 1262 (amide-III); 1062
(S–N); and 805 (C–Cl). 1H NMR (DMSO-d6): d 3.62
(m, 4H, [N(CH2)2O); 4.47 (s, 1H, CH2OH); 8.69 (s, H-2,
quinolone); 7.91 (s, H-5, quinolone); 8.85–9.68 (m, 3H,
pyrido); 10.10 (s, 1H, CO.NH); 9.91 (s, 1H, SO2NH);
7.15–7.70 (m, 4H, Ar–H); and 2.10 (s, 3H, Ar–CH3). Anal.
Calcd. for C27H20O7N5SCl: C, 59.78; H, 4.12; and N, 9.96.
Found: C, 59.75; H, 4.10; and N, 9.95.
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
[4-(substitutedphenylsulfamoyl)phenyl]amide (6a–l)
4-Amino-N-(substitutedphenyl)benzenesulfonamides (0.005
mol) was dissolved in dry pyridine and added dropwise in
solution of carbonyl chloride 2b (0.005 mol) in pyridine
within 1.5 h with constant stirring at 0–5°C and refluxed
for 8 h, Then, refluxed material was poured into acidic
crushed ice, and the solid mass was filtered and washed
thoroughly with NaHCO3 solution for neutralization. The
purity of the compounds was monitored by TLC on silica
gel glass plate using benzene:ethylacetate (1:1) as mobile
phase.
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
[4-(3-methyphenylsulfamoyl)phenyl]amide (5i)
Yield = 59%, m.p. 231–233°C.
6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
[4-(4-methyphenylsulfamoyl)phenyl]amide (5j)
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid
[4-(phenylsulfamoyl)phenyl]amide (6a)
Yield = 67%, m.p. 255–257°C. IR (KBr) cm-1: 3425
(NH); 3341 (OH); 2935, 2825 (CH); 1745 ([C=O of
quinolone); 1670 (amide-I); 1562 (amide-II); 1321, 1175
(S=O, sym, asym); 1315 (C–N); 1265 (amide-III); 1058
Yield = 62%, m.p. 235–237°C.
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid [4-(3-
chlorophenylsulfamoyl)phenyl]amide (6b)
1
(S–N); and 795 (C–Cl). H NMR (DMSO-d6): d 3.67 (m,
4H, [N(CH2)2O); 4.42 (s, 1H, CH2OH); 8.65 (s, H-2,
quinolone); 7.88 (s, H-5, quinolone); 8.81–9.65 (m, 3H,
pyrido); 10.15 (s, 1H, CO.NH); 9.95 (s, 1H, SO2NH);
7.19–7.65 (m, 4H, Ar–H); and 2.10 (s, 3H, Ar–CH3). Anal.
Calcd. for C27H20O7N5SCl: C, 59.78; H, 4.12; and N, 9.96.
Found: C, 59.74; H, 4.09; and N, 9.92.
Yield = 65%, m.p. 271–273°C. IR (KBr) cm-1: 3432
(NH); 3395 (OH); 2945, 2858 (CH); 1746 ([C=O of
quinolone); 1668 (amide-I); 1528 (amide-II); 1352, 1165
(S=O, sym, asym); 1314 (C–N); 1265 (amide-III); 1075
(S–N); and 795 (C–Cl). 1H NMR (DMSO-d6): d 3.67
123

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1063
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid [4-(4-
nitrophenylsulfamoyl)phenyl]amide (6g)
(m, 4H, [N(CH2)2O); 4.42 (s, 1H, CH2OH); 8.65 (s, H-2,
quinolone); 7.88 (s, H-5, quinolone); 8.81–9.65 (m, 3H,
pyrido); 10.15 (s, 1H, CO.NH); 9.95 (s, 1H, SO2NH); 5.60
(s, 1H, Ar–OH); 7.19-7.65 (m, 4H, Ar–H). Anal. Calcd. for
C27H21O6N4SCl: C, 57.44; H, 3.75; and N, 9.93. Found: C,
57.42; H, 3.72; and N, 9.90.
Yield = 63%, m.p. 255–257°C.
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid [4-(2-
methylphenylsulfamoyl)phenyl]amide (6h)
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid [4-(4-
chlorophenylsulfamoyl)phenyl]amide (6c)
Yield = 60%, m.p. 275–277°C. IR (KBr) cm-1: 3438
(NH); 3375 (OH); 2939, 2852 (CH); 1752 ([C=O of
quinolone); 1665 (amide-I); 1538 (amide-II); 1338, 1165
(S=O, sym, asym); 1305 (C–N); 1261 (amide-III); and
1060 (S–N). 1H NMR (DMSO-d6): d 3.66 (m, 4H,
[N(CH2)2O); 4.45 (s, 1H, CH2OH); 8.60 (s, H-2, quino-
lone); 7.89 (s, H-5, quinolone); 8.74–9.69 (m, 3H, pyrido);
10.10 (s, 1H, CO.NH); 9.95 (s, 1H, SO2NH); 5.62 (s, 1H,
Ar–OH); 7.05–7.41 (m, 4H, Ar–H); and 2.21 (s, 3H, Ar-
CH3). Anal. Calcd. for C28H24O6N4S: C, 61.75; H, 4.45;
and N,10.29. Found: C, 61.72; H, 4.42; and N,10.27.
Yield = 54%, m.p. 258–260°C.
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid [4-(2-
methoxyphenylsulfamoyl)phenyl]amide (6d)
Yield = 66%, m.p. 245–248°C. IR (KBr) cm-1: 3435
(NH); 3385 (OH); 2942, 2848 (CH); 1755 ([C=O of
quinolone); 1674 (amide-I); 1532 (amide-II); 1345, 1166
(S=O, sym, asym); 1320 (C–N); 1261 (amide-III); 1269,
1
1040 (C–O–C); and 1065 (S–N). H NMR (DMSO-d6): d
3.61 (m, 4H, [N(CH2)2O); 4.47 (s, 1H, CH2OH); 8.69
(s, H-2, quinolone); 7.85 (s, H-5, quinolone); 8.79–9.62
(m, 3H, pyrido); 10.25 (s, 1H, CO.NH); 10.12 (s, 1H,
SO2NH); 5.64 (s, 1H, Ar–OH); 7.20–7.52 (m, 4H, Ar–H);
and 3.78 (s, 3H, Ar–OCH3). Anal. Calcd. for C28H24
O7N4S: C, 59.99; H, 4.32; and N,10.00. Found: C, 59.96;
H, 4.30; and N,10.02.
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid [4-(3-
methylphenylsulfamoyl)phenyl]amide (6i)
Yield = 58%, m.p. 240–241°C.
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid [4-(4-
methylphenylsulfamoyl)phenyl]amide (6j)
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid [4-(4-
methoxyphenylsulfamoyl)phenyl]amide (6e)
Yield = 62%, m.p. 264-266°C. IR (KBr) cm-1: 3435
(NH); 3371 (OH); 2935, 2845 (CH); 1745 ([C=O of
quinolone); 1668 (amide-I); 1535 (amide-II); 1340, 1168
(S=O, sym, asym); 1315 (C–N); 1265 (amide-III); and
1065 (S–N). 1H NMR (DMSO-d6): d d 3.60 (m, 4H,
[N(CH2)2O); 4.48 (s, 1H, CH2OH); 8.62 (s, H-2, quino-
lone); 7.88 (s, H-5, quinolone); 8.65–9.65 (m, 3H, pyr-
ido); 10.15 (s, 1H, CO.NH); 9.98 (s, 1H, SO2NH); 5.68
(s, 1H, Ar–OH); 7.15–7.48 (m, 4H, Ar–H); and 2.15
(s, 3H, Ar-CH3). Anal. Calcd. for C28H24O6N4S: C,
61.75; H, 4.45; and N,10.29. Found: C, 61.70; H, 4.44;
and N,10.31.
Yield = 59%, m.p. 275–277°C.
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid [4-(3-
nitrophenylsulfamoyl)phenyl]amide (6f)
Yield = 67%, m.p. 263–265°C. IR (KBr) cm-1: 3441
(NH); 3387 (OH); 2937, 2845 (CH); 1749 ([C=O of
quinolone); 1672 (amide-I); 1535 (amide-II); 1525, 1325
(N=O sym, asym); 1335, 1162 (S=O, sym, asym); 1315
(C–N); 1265 (amide-III); and 1065 (S–N). 1H NMR
(DMSO-d6): d 3.65 (m, 4H, [N(CH2)2O); 4.48 (s, 1H,
CH2OH); 8.65 (s, H-2, quinolone); 7.84 (s, H-5, quinolone);
8.75–9.61 (m, 3H, pyrido); 10.15 (s, 1H, CO.NH); 10.15 (s,
1H, SO2NH); 5.65 (s, 1H, Ar–OH); and 7.15–7.45 (m, 4H,
Ar–H). Anal. Calcd. for C27H21O8N5S: C, 56.34; H, 3.68;
and N,12.17. Found: C, 56.32; H, 3.65; and N,12.15.
6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid [4-(2,5-di-
methylphenylsulfamoyl)phenyl]amide (6k)
Yield = 67%, m.p. 277–279°C.
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6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carboxylicacid [4-(2-cyno-4-
nitrophenylsulfamoyl)phenyl]amide (6l)
1-[6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-(4-
hydroxyphenyl)thiourea (7c)
Yield = 65%, m.p. 280–282°C. IR (KBr) cm-1: 3428
(NH); 3365 (OH); 2925, 2832 (CH); 2236 ([C:N); 1751
([C=O of quinolone); 1665 (amide-I); 1532 (amide-II);
1528, 1332 (N=O sym, asym); 1345, 1160 (S=O, sym,
asym); 1325 (C–N); 1262 (amide-III); and 1056 (S–N). 1H
NMR (DMSO-d6): d 3.68 (m, 4H, [N(CH2)2O); 4.47
(s, 1H, CH2OH); 8.65 (s, H-2, quinolone); 7.85 (s, H-5,
quinolone); 8.62–9.62 (m, 3H, pyrido); 10.10 (s, 1H,
CO.NH); 9.95 (s, 1H, SO2NH); 5.69 (s, 1H, Ar–OH); and
7.10-7.52 (m, 3H, Ar–H). Anal. Calcd. for C28H20O8N4S:
C, 58.73; H, 3.52; and N,9.79. Found: C, 58.70; H, 3.50;
and N,9.76.
Yield = 60%, m.p. 275–276°C. IR (KBr) cm-1: 3445
(NH); 3315 (OH); 2945, 2865 (CH); 1741 ([C=O of
quinolone); 1645 (amide-I); 1540 (amide-II); 1305 (C–N);
1258 (amide-III); 1165 ([C=S); and 766 (C–Cl). 1H NMR
(DMSO-d6): d 3.45 (m, 4H, [N(CH2)2O); 4.25 (s, 1H,
CH2OH); 8.85 (s, H-2, quinolone); 8.24 (s, H-5, quino-
lone); 8.85–9.35 (m, 3H, pyrido); 10.10 (s, 1H, CO.NH);
10.35 (s, 1H, CS.NH); 7.25–7.85 (m, 4H, Ar–H); and 5.65
(s, 1H, Ar–OH). Anal. Calcd. for C22H17O4N4SCl: C,
56.40; H, 3.66; and N,11.97. Found: C, 56.37; H, 3.64; and
N,11.95.
1-[6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-(2-
methoxyphenyl)thiourea (7d)
1-[6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-
(substitutedphenyl)thiourea (7a–l)
Yield = 57%, m.p. 277–279°C.
Substitutedphenyl thioureas (0.005 mol) was dissolved in
dry pyridine and added dropwise in solution of carbonyl
chloride 2a (0.005 mol) in pyridine within 1.5 h with
constant stirring at 0–5°C and refluxed for 8 h, Then,
refluxed material was suspended into acidic crushed ice,
and the solid mass was filtered and washed thoroughly
with NaHCO3 solution for neutralization. The purity of
the compounds were monitored by TLC on silica gel
glass plate using benzene:ethylacetate (1:1) as mobile
phase.
1-[6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-(4-
methoxyphenyl)thiourea (7e)
Yield = 60%, m.p. 255–256°C. IR (KBr) cm-1: 3452
(NH); 3325 (OH); 2935, 2860 (CH); 1748 ([C=O of
quinolone); 1656 (amide-I); 1535 (amide-II); 1315 (C–N);
1269, 1040 (C–O–C); 1255 (amide-III); 1160 ([C=S); and
769 (C–Cl). 1H NMR (DMSO-d6): d 3.52 (m, 4H,
[N(CH2)2O); 4.30 (s, 1H, CH2OH); 8.78 (s, H-2, quino-
lone); 8.30 (s, H-5, quinolone); 8.75–9.25 (m, 3H, pyrido);
10.05 (s, 1H, CO.NH); 10.15 (s, 1H, CS.NH); 7.26–7.75
(m, 4H, Ar–H); and 3.85 (s, 3H, Ar–OCH3). Anal. Calcd.
for C23H19O4N4SCl: C, 57.25; H, 3.62; and N,11.93.
Found: C, 57.25; H, 3.64; and N,11.95.
1-[6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-phenylthiourea (7a)
Yield = 55%, m.p. 257–258°C. IR (KBr) cm-1: 3434
(NH); 3322 (OH); 2950, 2860 (CH); 1735 ([C=O of
quinolone); 1650 (amide-I); 1540 (amide-II); 1300 (C–N);
1256 (amide-III); 1190 ([C=S); and 766 (C–Cl). 1H NMR
(DMSO-d6): d 3.31 (m, 4H, [N(CH2)2O); 4.35 (s, 1H,
CH2OH); 8.70 (s, H-2, quinolone); 8.14 (s, H-5, quino-
lone); 8.88–9.45 (m, 3H, pyrido); 10.05 (s, 1H, CO.NH);
10.25 (s, 1H, CS.NH); and 7.30–7.92 (m, 5H, Ar–H). Anal.
Calcd. for C22H17O3N4SCl: C, 58.40; H, 3.79; and N,12.39.
Found: C, 58.38; H, 3.76; and N,12.36.
1-[6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-(2-
nitrophenyl)thiourea (7f)
Yield = 67%, m.p. 284–286°C.
1-[6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-(3-
nitrophenyl)thiourea (7g)
1-[6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-(3-
hydroxyphenyl)thiourea (7b)
Yield = 56%, m.p. 261–263°C. IR (KBr) cm-1: 3456
(NH); 3330 (OH); 2925, 2865 (CH); 1755 ([C=O of
quinolone); 1665 (amide-I); 1520 (amide-II); 1528, 1332
Yield = 65%, m.p. 244–246°C.
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Med Chem Res (2011) 20:1054–1067
1065
1-[6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-
(3-chlorophenyl)thiourea (7l)
(N=O); 1325 (C–N); 1245 (amide-III); 1165 ([C=S); and
777 (C–Cl). 1H NMR (DMSO-d6): d 3.51 (m, 4H,
[N(CH2)2O); 4.41 (s, 1H, CH2OH); 8.80 (s, H-2, quino-
lone); 8.25 (s, H-5, quinolone); 8.68–9.20 (m, 3H, pyrido);
10.00 (s, 1H, CO.NH); 10.22 (s, 1H, CS.NH); and
7.24–7.71 (m, 4H, Ar–H). Anal. Calcd. for C22H16O5N5
SCl: C, 53.11; H, 3.24; and N,14.09. Found: C, 53.09; H,
3.24; and N,14.07.
Yield = 60%, m.p. 251–253°C. IR (KBr) cm-1: 3435
(NH); 3325 (OH); 2945, 2845 (CH); 1745 ([C=O of
quinolone); 1665 (amide-I); 1562 (amide-II); 1312 (C–N);
1245 (amide-III); 1160 ([C=S); and 764 (C–Cl). 1H NMR
(DMSO-d6): d 3.35 (m, 4H, [N(CH2)2O); 4.37 (s, 1H,
CH2OH); 8.75 (s, H-2, quinolone); 8.10 (s, H-5, quino-
lone); 8.90–9.52 (m, 3H, pyrido); 9.90 (s, 1H, CO.NH);
10.22 (s, 1H, CS.NH); and 7.18–7.95 (m, 4H, Ar–H). Anal.
Calcd. for C22H18O4N4S: C, 60.81; H, 4.18; and N,12.90.
Found: C, 60.78; H, 4.15; and N,12.85.
1-[6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-
(4-nitrophenyl)thiourea (7h)
Yield = 61%, m.p. 249–251°C. IR (KBr) cm-1: 3445
(NH); 3325 (OH); 2920, 2862 (CH); 1748 ([C=O of
quinolone); 1662 (amide-I); 1528 (amide-II); 1535, 1340
(N=O); 1320 (C–N); 1235 (amide-III); 1160 ([C=S); and
772 (C–Cl). 1H NMR (DMSO-d6): d 3.55 (m, 4H,
[N(CH2)2O); 4.47 (s, 1H, CH2OH); 8.75 (s, H-2, quino-
lone); 8.15 (s, H-5, quinolone); 8.65–9.15 (m, 3H, pyrido);
10.05 (s, 1H, CO.NH); 10.28 (s, 1H, CS.NH); and
7.14–7.65 (m, 4H, Ar–H). Anal. Calcd. for C23H19O3N4
SCl: C, 59.22; H, 4.11; and N,12.02. Found: C, 59.20; H,
4.09; and N,12.04.
1-[6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-
(substitutedhydroxyphenyl)thiourea (8a–l)
Substitutedphenyl thioureas (0.005 mol) was dissolved in
dry pyridine and added dropwise the solution of carbonyl
chloride 2b (0.005 mol) in pyridine within 1.5 h with
constant stirring at 0–5°C and refluxed for 8 h; then,
refluxed material was poured into acidic crushed ice; and
the solid mass was filtered and was washed thoroughly with
NaHCO3 solution for neutralization. The purity of the
compounds was monitored by TLC on silica gel glass plate
using benzene:ethylacetate (1:1) as mobile phase.
1-[6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-
(2-methylphenyl)thiourea (7i)
1-[6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-phenylthiourea (8a)
Yield = 67%, m.p. 243–244°C.
1-[6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-(3-
methylphenyl)thiourea (7j)
Yield = 66%, m.p. 246–247°C.
1-[6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-
(3-hydroxyphenyl)thiourea (8b)
Yield = 62%, m.p. 241–243°C.
1-[6-Chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-(4-
methylphenyl)thiourea (7k)
Yield = 62%, m.p. 281–283°C.
1-[6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-
(4-hydroxyphenyl)thiourea (8c)
Yield = 63%, m.p. 263–265°C. IR (KBr) cm-1: 3452
(NH); 3330 (OH); 2922, 2865 (CH); 1752 ([C=O of
quinolone); 1665 (amide-I); 1522 (amide-II); 1325 (C–N);
1231 (amide-III); 1165 ([C=S); and 762 (C–Cl). 1H NMR
(DMSO-d6): d 3.57 (m, 4H, [N(CH2)2O); 4.51 (s, 1H,
CH2OH); 8.65 (s, H-2, quinolone); 8.20 (s, H-5, quino-
lone); 8.62–9.20 (m, 3H, pyrido); 10.12 (s, 1H, CO.NH);
10.22 (s, 1H, CS.NH); 7.25–7.74 (m, 4H, Ar–H); and 2.22
(s, 1H, Ar–CH3). Anal. Calcd. for C23H19O3N4SCl: C,
59.22; H, 4.11; and N,12.02. Found: C, 59.24; H, 4.13; and
N,12.00.
Yield = 56%, m.p. 246–248°C. IR (KBr) cm-1: 3425
(NH); 3315 (OH); 2952, 2838 (CH); 1745 ([C=O of
quinolone); 1662 (amide-I); 1562 (amide-II); 1315 (C–N);
1248 (amide-III); and 1165 ([C=S). 1H NMR (DMSO-d6):
d 3.42 (m, 4H, [N(CH2)2O); 4.35 (s, 1H, CH2OH); 8.74
(s, H-2, quinolone); 8.15 (s, H-5, quinolone); 8.88–9.45
(m, 3H, pyrido); 9.95 (s, 1H, CO.NH); 10.15 (s, 1H,
CS.NH); 7.18–7.95 (m, 4H, Ar–H); and 5.40, 6.20 (s, 1H,
123

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Med Chem Res (2011) 20:1054–1067
Ar–OH). Anal. Calcd. for C22H18O5N4S: C, 58.65; H, 4.03;
and N,12.44. Found: C, 58.62; H, 4.01; and N,12.42.
quinolone); 1665 (amide-I); 1562 (amide-II); 1321 (C–N);
1352 (N=O sym, asym); 1252 (amide-III); and 1168
([C=S). 1H NMR (DMSO-d6): d 3.52 (m, 4H, [N
(CH2)2O); 4.40 (s, 1H, CH2OH); 8.85 (s, H-2, quinolone);
8.14 (s, H-5, quinolone); 8.01–9.15 (m, 3H, pyrido); 9.85
(s, 1H, CO.NH); 10.25 (s, 1H, CS.NH); and 7.15–7.85
(m, 4H, Ar–H). Anal. Calcd.for C23H20O4N4S:C, 61.59;
H,4.50; and N,12.50. Found: C,61.55; H,4.48; and N, 12.47.
1-[6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-
(2-methoxyphenyl)thiourea (8d)
Yield = 56%, m.p. 241–243°C.
1-[6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-
(4-methoxyphenyl)thiourea (8e)
1-[6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-(2-
methylphenyl)thiourea (8i)
Yield = 60%, m.p. 233–235°C. IR (KBr) cm-1: 3445
(NH); 3324 (OH); 2945, 2825 (CH); 1748 ([C=O of
quinolone); 1665 (amide-I); 1565 (amide-II); 1323 (C–N);
1252 (amide-III); 1235, 1020 (C–O–C); and 1161 ([C=S).
1H NMR (DMSO-d6): d 3.44 (m, 4H, [N(CH2)2O); 4.45
(s, 1H, CH2OH); 8.78 (s, H-2, quinolone); 8.05 (s, H-5,
quinolone); 8.08–9.35 (m, 3H, pyrido); 9.98 (s, 1H,
CO.NH); 10.18 (s, 1H, CS.NH); 7.28–7.85 (m, 4H, Ar–H);
and 3.85 (s, 1H, Ar–OCH3). Anal. Calcd. for C23H20O5
N4S: C, 59.47; H, 4.34; and N,12.07. Found: C, 59.45; H,
4.24; and N,12.05.
Yield = 60%, m.p. 235–237°C.
1-[6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-(3-
methylphenyl)thiourea (8j)
Yield = 52%, m.p. 237–239°C.
1-[6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-
(4-methylphenyl)thiourea (8k)
1-[6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-(2-
nitrophenyl)thiourea (8f)
Yield = 60%, m.p. 251–253°C. IR (KBr) cm-1: 3452
(NH); 3315 (OH); 2945, 2810 (CH); 1742 ([C=O of
quinolone); 1675 (amide-I); 1565 (amide-II); 1328 (C–N);
1245 (amide-III); and 1160 ([C=S). 1H NMR (DMSO-d6):
d 3.47 (m, 4H, [N(CH2)2O); 4.35 (s, 1H, CH2OH); 8.75
(s, H-2, quinolone); 8.18 (s, H-5, quinolone); 8.05–9.25
(m, 3H, pyrido); 9.88 (s, 1H, CO.NH); 10.28 (s, 1H,
CS.NH); 7.05–7.78 (m, 4H, Ar–H); and 2.44 (s, 3H, Ar–
CH3). Anal. Calcd. for C23H20O4N4S: C, 61.59; H, 4.50;
and N,12.50. Found: C, 61.54; H, 4.47; and N,12.46.
Yield = 63%, m.p. 253–254°C.
1-[6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-
(3-nitrophenyl)thiourea (8g)
Yield = 56%, m.p. 244–246°C. IR (KBr) cm-1: 3450
(NH); 3314 (OH); 2948, 2828 (CH); 1748 ([C=O of
quinolone); 1675 (amide-I); 1564 (amide-II); 1315 (C–N);
1248 (amide-III); 1512, 1352 (N=O sym, asym); and
1168 ([C=S). 1H NMR (DMSO-d6): d 3.48 (m, 4H,
[N(CH2)2O); 4.42 (s, 1H, CH2OH); 8.88 (s, H-2, quino-
lone); 8.11 (s, H-5, quinolone); 8.15–9.25 (m, 3H, pyrido);
9.92 (s, 1H, CO.NH); 10.15 (s, 1H, CS.NH); and 7.25–7.75
(m, 4H, Ar–H). Anal. Calcd. for C23H20O5N4S: C, 55.10;
H, 3.58; and N,14.61. Found: C, 55.05; H, 3.45; and
N,14.59.
1-[6-Hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-
[1,7]phenanthroline-3-carbonyl]-3-
(3-chlorophenyl)thiourea (8l)
Yield = 51%, m.p. 246–248°C.
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