Synthesis and study of 1-ethyl-3-carbohydrazide and 3-[1-oxo-2-hydrazino-3- {p-toluenesulfon}]quinolone derivatives against bacterial infections

Article abstract of DOI:10.1016/j.ejmech.2013.06.056

We have synthesized newer series of quinolone derivatives substituted with hydrazine group (6a-e) and sulfonamide group (7a-e). These compounds were screened for antibacterial activity. All these compounds were fully characterized by spectroscopic means and elemental analysis. From minimum inhibitory concentration (MIC) data, it has been observed that all the synthesized compounds exhibited good antibacterial activity in vitro.

Full text of DOI:10.1016/j.ejmech.2013.06.056

European Journal of Medicinal Chemistry 67 (2013) 464e468
Contents lists available at SciVerse ScienceDirect
European Journal of Medicinal Chemistry
journal homepage: http://www.elsevier.com/locate/ejmech
Short communication
Synthesis and study of 1-ethyl-3-carbohydrazide and 3-[1-oxo-2-
hydrazino-3-{p-toluenesulfon}]quinolone derivatives against
bacterial infections
*
Nivedita Srivastava , Anil Kumar
Department of Applied Chemistry, Faculty of Engineering and Technology, M.J.P. Rohilkhand University, Bareilly 243006, U.P., India
a r t i c l e i n f o
a b s t r a c t
Article history:
We have synthesized newer series of quinolone derivatives substituted with hydrazine group (6aee) and
sulfonamide group (7aee). These compounds were screened for antibacterial activity. All these com-
pounds were fully characterized by spectroscopic means and elemental analysis. From minimum
inhibitory concentration (MIC) data, it has been observed that all the synthesized compounds exhibited
good antibacterial activity in vitro.
Received 21 March 2013
Received in revised form
20 June 2013
Accepted 24 June 2013
Available online 9 July 2013
Ó 2013 Elsevier Masson SAS. All rights reserved.
Keywords:
Quinolone
Fluoroquinolone
Hydrazine
Sulfonamide
Antibacterial
Broad spectrum
1. Introduction
inhibit or control the urinary tract infection. Quinolones [9] are
chemotherapeutic gyrase or topoisomerases-II inhibitors, eradi-
Urinary tract infection is most common disease in human body.
More than 150 millions cases are reported per year worldwide [1].
UTI infection is bacterial infection which affects urinary tract path
of the body. If it is not treated in time, bacteria travel to the urethra
and multiply, causing kidney infection [2]. Urinary tract infection is
more common in ladies as the urethra part of female is shorter than
male [3]. UTI is a pathogenic infection and is becoming resistant to
all available antibiotics.
The most responsible bacterium for UTI is gram negative bac-
teria, which belongs to the family Enterobacteriaceae. Gram nega-
tive members of this family are Escherichia coli, Salmonella typhi,
Pseudomonas aeruginosa. Gram positive bacteria viz Staphylococcus
sp. is also responsible for UTI [4,5]. Quinolone is group of synthetic
compounds with potent antimicrobial activity and is used orally
and parentally in wide variety of infectious disease [6e8].
Our aim is to synthesize newer compounds which may prove to
be more potent towards these pathogenic infections and thus
cating bacteria by interfering with DNA replication. Sulfonamides
[10] are also used as antibacterial agents. They inhibit cell meta-
bolism of bacteria as it mimics p-amino benzoic acid (PABA), one of
the normal constitutes of folic acid. The enzyme accepts sulfon-
amide into its active site as the structure of sulfonamide is similar to
PABA. Once it is bound, the sulfonamide prevents PABA from
binding.
In our study we have synthesized quinolone compounds,
substituted with hydrazine group and-1-oxo-2-hydrazino-3-(p-
toluenesulfon) group at 3 position and want to see the results of
these molecules as antibacterial. The combination therapy of sul-
fonamide and quinolone (7aee) is new approach for the treatment
of bacterial infections.
2. Results & discussion
2.1. Chemistry
We have already prepared the des-ethyl quinolone derivatives,
substituted with carbohydrazide and sulfonyl groups at C-3, but
these compounds did not give satisfactory results [11]. Therefore we
have synthesized the quinolones (6aee) and (7aee) with N-1-ethyl
* Corresponding author. Tel.: þ91 9415157863.
E-mail addresses: drnimjpru@rediffmail.com, niveditacdri2000@yahoo.com
(N. Srivastava).
0223-5234/$ e see front matter Ó 2013 Elsevier Masson SAS. All rights reserved.
http://dx.doi.org/10.1016/j.ejmech.2013.06.056

N. Srivastava, A. Kumar / European Journal of Medicinal Chemistry 67 (2013) 464e468
465
substitution. This is the first report in which better results are ob-
tained (Table 1) by the incorporation of sulfonamide moiety at 3-
position of quinolone compounds.
ciprofloxacin are 2 times more potent to the synthesized compound
6b & 7a, while the compound 6c have only 1/4 activity of cipro-
floxacin and norfloxacin against E. coli (Table 1).
Firstly substituted aniline 1 was condensed with diethyl ethoxy
methylene malonate 2 to give ethyl anilinomethylenemalonate 3
derivatives as reported by Claisen [12]. Each substituted ethyl anili-
nomethylenemalonate 3 was refluxed with diphenyl ether to give
corresponding 1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl
ester 4 derivatives [13,14], which on refluxing with ethyl iodide and
potassium carbonate for 10 h in the presence of DMF as solvent
afforded substituted 1-ethyl-1,4-dihydro-4-oxoquinoline-3-carboxy
lic acid ethyl ester 5 derivatives. Each 5 derivative on refluxing with
hydrazine monohydrate in absolute ethanol afforded 1-ethyl-4-oxo-
1,4-dihydroquinoline-3-carbohydrazide derivatives 6 respectively.
Each carbohydrazide derivative 6 on treatment with p-toluene-
sulfonyl chloride in the presence of pyridine as base using dichloro-
methane and ethyl acetate as solvent, gave the corresponding
substituted-1-ethyl-4-oxo-1,4-dihydro-3-[1-oxo-2-hydrazino-3-{p-
toluenesulfon}]quinoline derivatives 7 (Scheme 1) respectively. All
the compounds were purified by crystallization. Spectral (IR,1H NMR,
13C NMR and EI-MS) data and elemental analysis reported in exper-
imental section of this paper is in agreement with structures assigned
to them.
All the synthesized compounds 6aee & 7aec, e are equipotent as
the standard ciprofloxacin against S. typhi. The activity of compound
7d is 1/2, when compared with standard ciprofloxacin against
S. typhi. Except 7d, all the compound 6aee & 7aee are 4 times more
potent to the standard norfloxacin. Compound 7d is also 2 times
more potent to the norfloxacin against S. typhi (Table 1).
3. Conclusion
We reported the preparation of (6aee) by the incorporation of
hydrazine moiety at 3-position of quinolone (5aee). This hydrazine
substituted quinolone derivatives (6aee) was further treated with
p-toluenesulfonyl chloride to give sulfonamide substituted quino-
lone derivatives (7aee). It is observed that both series of synthe-
sized compounds (6aee) and (7aee) show good antibacterial
activity against some pathogens. The biological activity of quino-
lones having N-1 ethyl show better result in comparison to N-1-
des-ethyl quinolone derivatives [11]. Incorporation of sulfon-
amide as well as hydrazine moiety at 3-position of N-1-ethyl
quinolones show good antibacterial results. Results are awaited to
see the effect of piperazine and other bases, at C-7 position, in our
series of compounds.
2.2. Biological results
4. Experimental protocols
All synthesized compounds 6aee having hydrazine and 7aee
having sulfonamide moieties at C-3 position were subjected for the
antibacterial activity in vitro. These compounds were evaluated
against gram negative namely E. coli (ETEC), S. typhi and P. aerugi-
nosa and gram positive Staphylococcus aureus strains by using disc
diffusion technique. All the results reported here in the form of
minimum inhibitory concentrations (MICs) and compared with
standard reference marketed drug norfloxacin & ciprofloxacin
(Table 1). Minimum inhibitory concentration (MIC) reveals that all
these synthesize compounds are good or equivalent as the refer-
ence marketed drug norfloxacin and ciprofloxacin.
Minimum inhibitory concentration (MIC) reveals that the all the
synthesized compounds 6aee & 7aee are potent as standard
reference drug norfloxacin and ciprofloxacin against pathogen P.
aeruginosa and S. aureus (Table 1).
The compounds 6a, 6d, 6e & 7bee have equivalent minimum
inhibitory concentration as the reference drug norfloxacin and
ciprofloxacin against E. coli. The reference norfloxacin and
4.1. General
Spectral data were recorded as follows: IR Spectra was run on a
PerkineElmer and Shimadzu 8201 PC, FT Infrared spectropho-
tometer (nmax in cmꢀ1). Mass spectra were recorded on Jeol SX-102
(FAB). 1H NMR (400 MHz) and 13C NMR (75 MHz) spectra have been
recorded on Bruker Avance 400. Melting points were determined in
open capillary method and were uncorrected. All reagents used
were of commercial grade and were used as received without
further purification unless otherwise specified. Dry DMF and
anhydrous potassium carbonate were used wherever required.
Reagent grade solvents were used in all other cases unless other-
wise specified. Organic solutions were dried over anhydrous
Na2SO4 and concentrated with a Buchi rotary evaporator at low
pressure. Yield of purified products was not optimized.
4.2. General procedure for the preparation of (6) and (7)
4.2.1. Substituted-1-ethyl-1,4-dihydro-4-oxoquinoline-3-carbo
hydrazide derivatives (6aee)
Table 1
Biological screening data of compounds (6aee) and (7aee).
In 100 mL round bottomed flask, each substituted-1-ethyl-1,4-
dihydro-4-oxoquinoline-3-carboxylic acid ethyl ester (5aee) (0.01
mol) was refluxed with hydrazine monohydrate (0.01 mol) in ab-
solute ethanol (9 mL) for 10 h to give corresponding substituted-1-
ethyl-4-oxo-1,4-dihydroquinoline-3-carbohydrazide (6aee). The
excess solvent was evaporated off and the resulting mixture was
poured into crushed ice. The solid separated was filtered on sin-
tered funnel, washed with water and dried. The crude solid was
purified by recrystallization twice from ethanol to give (6aee) as
white solid. Purity of the compound was checked on silica gel TLC
plates. TLC was run in chloroformemethanol (9:1) as eluent.
Comp no.
Minimum inhibitory concentrations (MICs)
Gram-negative
m
g/mL
Gram-positive
P. aeruginosa
E. coli (ETEC)
S. typhi
S. aureus
6a
6b
6c
6d
6e
7a
7b
7c
7d
7e
Nor
Cip
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.125
0.25
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.125
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.125
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.0625
0.25
0.0625
4.2.2. Substituted-1-ethyl-4-oxo-1,4-dihydro-3-[1-oxo-2-hydrazino-
3-{p-toluenesulfon}]quinoline derivatives (7aee)
In 100 mL round bottomed flask, each substituted-1-ethyl-1,4-
dihydro-4-oxoquinoline-3-carbohydrazide derivatives (6aee)(0.005
mol) was mixed with pyridine (0.01 mol), dichloromethane (6 mL)
P. aeruginosa
¼
Pseudomonas aeruginosa, E. coli
¼
Escherichia coli,
S. typhi ¼ Salmonella typhi, S. aureus ¼ Staphylococcus aureus, Nor. ¼ Norfloxacin,
Cip. ¼ Ciprofloxacin.

466
N. Srivastava, A. Kumar / European Journal of Medicinal Chemistry 67 (2013) 464e468
COOEt
COOEt
R6
R7
COOEt
125-1300C, 2 h
-EtOH
R6
R7
EtO
+
NH2
COOEt
N
H
2
1a-e
3a-e
O
O
COOEt
R6
COOEt
R6
R7
C2H5I, K2CO3
Diphenyl ether,
refluxed
DMF, 800C, 10h.
R7
N
H
N
4a-e
C2H5
O
N
O
O
CONHNH 2
R6
(i), Ethanol
NH
R6
(ii),Pyridine/CH2Cl2,
NH
SO2
reflux
R7
CH3COOEt,4h
R7
N
C2H5
6a-e
C2H5
7a-e
CH3
(ii) p-toluenesulfonyl chloride
(i) NH2-NH2.H2O
R6
H
R7
H
a
F
Cl
H
F
H
b
c
H
Cl
Cl
d
e
Scheme 1. Synthesis of carbohydrazide (6aee) and sulfonamide (7aee) derivatives.
and ethyl acetate (6 mL). The reaction mixture was placed in ice bath
and the p-toluenesulfonyl chloride (0.005 mol) was added into the
reaction mixture in two portions and stirred for 4 h under ice con-
dition. The reaction mixture was allowed to stand in ice for 30 min.
The reaction mixture was filtered on sintered funnel. Crude solid was
washed with water and dried. The solid compound (7aee) was
recrystallized (twice) with dichloromethane. Purity of the compound
was checked on silica gel TLC plates. TLC was run in chloroforme
methanol (9.5:0.5) as eluent.
4H, ArH), 4.43e4.26 (m, 4H, eCH2CH3, eNH2), 1.48 (t, 3H, e
CH2CH3); 13C NMR (75 MHz, CDCl3-d)
(ppm): 174.60, 164.05,
143.59, 139.10, 135.41, 129.71, 128.10, 126.79, 126.01, 110.21, 48.03,
14.39; MS m/z: 231 (Mþ), Anal. Calcd for C12H13N3O2: C, 62.33; H,
5.62; N, 18.18. Found: C, 62.26; H, 5.57; N, 18.05.
d
5.2. Ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carbohydrazide
(6b)
Solvent of crystallization ethanol. Yield 81.43%. Mp 205 ꢁC. IR
(KBr) nmax: 3645e3018 (br), 1656 (s, >CO hydrazide Str.) 1604 (s,
>CO), 1492 (w), 1216 (s), 762 (s) cmꢀ1. 1H NMR (400 MHz; CDCl3-d)
5. Spectral data
5.1. Ethyl-1,4-dihydro-4-oxoquinoline-3-carbohydrazide (6a)
d
(ppm): 10.76 (s, 1H, eCONHe), 8.75 (s, 1H, H-2), 8.16e7.45 (m, 3H,
ArH), 4.35 (q, 2H, eCH2CH3), 4.19 (s, 2H, eNH2), 1.57 (t, 3H, e
CH2CH3); 13C NMR (100 MHz, CDCl3-d)
(ppm): 175.07, 165.30,
Solvent of crystallization ethanol. Yield 86.35%. Mp >300 ꢁC. IR
(KBr) nmax: 3651e3021 (br), 1654 (s, >CO hydrazide), 1615 (s, >CO
ketone),1494 (w), 1218 (s), 764 (s) cmꢀ1. 1H NMR (400 MHz; DMSO-
d
146.62, 135.15, 129.73, 129.66, 121.54, 121.29, 118.01, 110.61, 49.33,
14.54; MS m/z: 250 (Mþ), Anal. Calcd for C12H12FN3O2: C, 57.60; H,
4.80; N, 16.80. Found: C, 57.12; H, 4.44; N, 16.69.
d6) d (ppm): 10.92 (s, 1H, eCONHe), 8.87 (s, 1H, H-2), 8.47e7.40 (m,

N. Srivastava, A. Kumar / European Journal of Medicinal Chemistry 67 (2013) 464e468
467
5.3. 6-Chloro-1-ethyl-1,4-dihydro-4-oxoquinoline-3-carbohydrazide
(6c)
175.29, 165.79, 148.08, 143.92, 136.29, 132.79, 130.02, 129.01, 127.99,
126.80, 125.02, 121.02, 119.90, 110.59, 49.33, 21.20, 14.54; MS m/z:
404 (Mþ), Anal. Calcd for C19H19FN3O4S: C, 56.43; H, 4.70; N, 10.39.
Found: C, 56.40; H, 4.68; N, 10.34.
Solvent of crystallization ethanol. Yield 79.10%. Mp 238 ꢁC. IR
(KBr) nmax: 3603e3008 (br), 1655 (s, >CO hydrazide Str.) 1607 (s,
>CO), 1483 (w), 1216 (s), 764 (s) cmꢀ1. 1H NMR (400 MHz; CDCl3-d)
5.8. 6-Chloro-1-ethyl-4-oxo-1,4-dihydro-3-[1-oxo-2-hydrazino-3-
{p-toluenesulfon}]quinoline (7c)
d
(ppm): 10.75 (s, 1H, eCONHe), 8.76 (s,1H, H-2), 8.50e7.49 (m, 3H,
ArH), 4.35 (q, 2H, eCH2CH3), 4.20 (s, 2H, eNH2), 1.60 (t, 3H, e
CH2CH3); 13C NMR (75 MHz, CDCl3-d)
(ppm): 174.89, 165.21,
d
Solvent of crystallization dichloromethane. Yield 81.57%. Mp
232 ꢁC. IR (KBr) nmax: 3457e3020 (br), 1689 (s, >CO hydrazide),
1603 (s, >CO), 1479 (s), 1336 (s, eSO2e asym. str.), 1216 (s), 1151 (s,
146.92, 137.14, 133.19, 131.51, 129.11, 127.10, 117.38, 111.55, 49.25,
14.55; MS m/z: 266 (Mþ), Anal. Calcd for C12H12ClN3O2: C, 54.13; H,
4.51; N, 15.78. Found: C, 54.11; H, 4.49; N, 15.63.
eSO2e sym. str.), 758 (s) cmꢀ1 1H NMR (400 MHz; DMSO-d6)
.
d
(ppm): 11.24 (s, 1H, eCONHe), 9.98 (s, 1H, eNHSO2e), 8.79 (s, 1H,
5.4. 7-Chloro-1-ethyl-1,4-dihydro-4-oxoquinoline-3-carbohydrazide
(6d)
H-2), 8.21 (d, 1H, H-5), 7.94 (d, 1H, H-7), 7.89 (d, 1H, H-8), 7.71 (dd,
2H, ArH), 7.38 (dd, 2H, ArH), 4.47 (q, 2H, eCH2CH3), 2.38 (s, 3H, e
CH3), 1.34 (t, 3H, eCH2CH3); 13C NMR (75 MHz, DMSO-d6)
d (ppm):
Solvent of crystallization ethanol. Yield 77.37%. Mp 226 ꢁC. IR
173.89, 163.20, 148.47, 143.49, 137.31, 135.73, 133.18, 130.26, 129.55,
128.14, 127.49, 125.19, 120.08, 109.97, 48.63, 21.04, 14.42; MS m/z:
420 (Mþ), Anal. Calcd for C19H19ClN3O4S: C, 54.28; H, 4.52; N, 10.00.
Found: C, 54.24; H, 4.49; N, 9.94.
(KBr) nmax: 3578e3014 (br), 1657 (s, >CO hydrazide), 1597 (s, >CO),
1465 (w), 1217 (s), 762 (s) cmꢀ1 1H NMR (400 MHz; DMSO-d6)
.
d
(ppm): 10.73 (s, 1H, eCONHe), 8.81 (s,1H, H-2), 8.42e7.43 (m, 3H,
ArH), 4.44e4.37 (m, 4H, eCH2CH3, eNH2), 1.54 (t, 3H, eCH2CH3);
13C NMR (100 MHz, CDCl3-d)
(ppm): 175.33, 165.14, 147.18, 139.51,
d
5.9. 7-Chloro-1-ethyl-4-oxo-1,4-dihydro-3-[1-oxo-2-hydrazino-3-
{p-toluenesulfon}]quinoline (7d)
139.42, 129.23, 126.30, 125.68, 115.53, 111.69, 49.10, 14.45; MS m/z:
266 (Mþ), Anal. Calcd for C12H12ClN3O2: C, 54.13; H, 4.51; N, 15.78.
Found: C, 54.02; H, 4.48; N, 15.62.
Solvent of crystallization dichloromethane. Yield 79.89%. Mp
227 ꢁC. IR (KBr) nmax: 3408e3014 (br), 1666 (s, >CO hydrazide),
1599 (s, >CO), 1469 (w), 1336 (s, eSO2e asym. str.), 1216 (s), 1149 (s,
5.5. 7-Chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-car
bohydrazide (6e)
eSO2e sym. str.), 762 (s) cmꢀ1 1H NMR (400 MHz; DMSO-d6)
.
d
(ppm): 11.30 (s, 1H, eCONHe), 9.62 (s, 1H, eNHSO2e), 8.62 (s, 1H,
Solvent of crystallization ethanol. Yield 81.49%. Mp 263 ꢁC. IR
(KBr) nmax: 3651e3016 (br), 1640 (s, >CO hydrazide), 1616 (s,
>CO), 1498 (w), 1217 (s), 769 (s) cmꢀ1. 1H NMR (400 MHz, DMSO-
H-2), 8.29 (d, 1H, H-5), 7.87 (d, 1H, H-8), 7.81 (dd, 2H, ArH), 7.41 (d,
1H, H-6), 7.22 (dd, 2H, ArH), 4.32 (q, 2H, eCH2CH3), 2.35 (s, 3H, e
CH3), 1.41 (t, 3H, eCH2CH3); 13C NMR (75 MHz, DMSO-d6)
d (ppm):
d6)
H-5), 8.19 (d, 1H, H-8), 4.80e4.76 (m, 4H, eCH2CH3, eNH2), 1.91
(t, 3H, eCH2CH3); 13C NMR (75 MHz, CDCl3-d)
(ppm): 175.39,
d (ppm): 11.04 (s, 1H, eCONHe), 9.17 (s, 1H, H-2), 8.57 (d, 1H,
174.49, 163.20, 148.82, 143.47, 139.49, 138.46, 135.74, 129.53, 128.46,
127.49, 125.72, 125.62, 117.06, 110.17, 48.45, 21.03, 14.41; MS m/z:
420 (Mþ), Anal. Calcd for C19H19ClN3O4S: C, 54.28; H, 4.52; N, 10.00.
Found: C, 54.22; H, 4.48; N, 9.98.
d
165.02, 155.78, 147.09, 135.98, 128.22, 126.10, 118.16, 114.01,
113.71, 49.44, 14.52; MS m/z: 284 (Mþ), Anal. Calcd for
C
12H11ClFN3O2: C, 50.70; H, 3.87; N, 14.78. Found: C, 50.11; H,
5.10. 7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-3-[1-oxo-2-
hydrazino-3-{p-toluenesulfon}]quinoline (7e)
3.78; N, 14.68.
5.6. 1-Ethyl-4-oxo-1,4-dihydro-3-[1-oxo-2-hydrazino-3-{p-toluene
sulfon}]quinoline (7a)
Solvent of crystallization dichloromethane. Yield 82.32%. Mp
212 ꢁC. IR (KBr) nmax: 3459e3022 (br), 1670 (s, >CO hydrazide),
1605 (s, >CO), 1482 (s), 1336 (s, eSO2e asym. str.), 1217 (s), 1142 (s,
Solvent of crystallization dichloromethane. Yield 88.74%. Mp
228 ꢁC. IR (KBr) nmax: 3475.6e2948 (br), 1647 (s, >CO hydrazide),
1603 (s, >CO), 1479 (w), 1327 (s, eSO2e asym. str.), 1216 (s), 1150 (s,
eSO2e sym. str.), 763 (s) cmꢀ1 1H NMR (400 MHz; DMSO-d6)
.
d
(ppm): 10.11 (s, 1H, eCONHe), 8.95 (s, 1H, eNHSO2e), 7.70 (s, 1H,
eSO2e sym. str.), 763 (s) cmꢀ1 1H NMR (400 MHz; DMSO-d6)
.
H-2), 7.19 (d, 1H, H-5), 7.03 (d, 1H, H-8), 6.63 (dd, 2H, ArH), 6.29 (dd,
2H, ArH), 3.39 (q, 2H, eCH2CH3), 2.38 (s, 3H, eCH3), 1.25 (t, 3H, e
d
(ppm): 11.40 (s, 1H, eCONHe), 9.92 (s, 1H, eNHSO2e), 8.82 (s, 1H,
H-2), 8.32e7.37 (m, 8H, ArH), 4.47 (q, 2H, eCH2CH3), 2.38 (s, 3H, e
CH3), 1.35 (t, 3H, eCH2CH3); 13C NMR (75 MHz, DMSO-d6)
(ppm):
CH2CH3); 13C NMR (75 MHz, DMSO-d6)
d (ppm): 173.75, 163.08,
156.16, 152.88, 148.72, 143.50, 135.72, 129.55, 127.49, 126.50, 126.24,
120.39, 112.21, 109.62, 48.81, 21.04, 14.50; MS m/z: 438 (Mþ), Anal.
Calcd for C19H18FClN3O4S: C, 52.05; H, 4.11; N, 9.58. Found: C, 51.98;
H, 4.08; N, 9.48.
d
175.04, 163.53, 148.13, 143.44, 138.55, 135.79, 133.34, 129.53, 127.49,
126.94, 126.37, 125.36, 117.46, 109.54, 48.37, 21.04, 14.46; MS m/z:
386 (Mþ), Anal. Calcd for C19H20N3O4S: C, 59.06; H, 5.18; N, 10.88.
Found: C, 58.98; H, 5.15; N, 10.72.
Acknowledgements
5.7. 1-Ethyl-6-fluoro-4-oxo-1,4-dihydro-3-[1-oxo-2-hydrazino-3-
{p-toluenesulfon}]quinoline (7b)
This work was financially supported by the University Grant
Commission (UGC), grant no 31-128/2005 SR. We gratefully
acknowledge the UGC, New Delhi for financial support and So-
phisticated Analytical Instrument Facility (SAIF), Central Drug
Research Institute, Lucknow-226001 (India) for providing spectral
data on payment basis. We are also thankful to BioGenics, Research
and Training Centre in Biotechnology, Hubli-580031, Karnataka for
providing antibacterial assays to generate MIC data on payment
basis.
Solvent of crystallization dichloromethane. Yield 83.43%. Mp
238 ꢁC. IR (KBr) nmax: 3475e3021 (br), 1665 (s, >CO hydrazide),
1610 (s, >CO), 1488 (w), 1343 (s, eSO2e asym. str.), 1216 (s), 1147 (s,
eSO2e sym. str.), 761 (s) cmꢀ1 1H NMR (400 MHz, DMSO-d6)
.
d
(ppm): 11.30 (s,1H, eCONHe),10.01 (s,1H, eNHSO2e), 8.78 (s,1H,
H-2), 8.03e7.77 (m, 7H, ArH), 4.49 (q, 2H, eCH2CH3), 2.38 (s, 3H, e
CH3), 1.35 (t, 3H, eCH2CH3); 13C NMR (75 MHz, DMSO-d6)
(ppm):
d

468
N. Srivastava, A. Kumar / European Journal of Medicinal Chemistry 67 (2013) 464e468
[9] (a) T. Plech, M. Wujec, U. Kosikowska, A. Malm, B. Rajtar, M.P. Dacewicz, Eur. J.
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