An efficient synthesis of dihydro selenolo (2,3-b)quinoline-2-carboxylic ethyl esters and 2-selenoxo-1, 2-dihydro-3-carbethoxy ethyl quinolines - their anti-bacterial studies

Article abstract of DOI:10.1080/10426500490485101

The compounds dihydro selenolo(2,3-b)quinoline-2-carboxylic ethyl esters and 2-selenoxo-1, 2-dihydro-3-carbethoxy ethyl quinolines were synthesized in varying yields upon reacting 3-(2-chloro-3-quinolyl)-acrylic methyl esters with the nucleophilic reagent sodium hydrogen selenide in ethanol medium under nitrogen atmosphere.

Full text of DOI:10.1080/10426500490485101

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Phosphorus, Sulfur, and Silicon
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AN EFFICIENT SYNTHESIS
OF DIHYDRO SELENOLO
(2,3-b)QUINOLINE-2-
CARBOXYLIC ETHYL ESTERS
AND 2-SELENOXO-1, 2-
DIHYDRO-3-CARBETHOXY
ETHYL QUINOLINES—THEIR
ANTI-BACTERIAL STUDIES
V. Nithyadevi a , P. Selvi a & S. P. Rajendran a
a Department of Chemistry, Bharathiar University ,
Coimbatore, TamilNadu, India
Published online: 16 Aug 2010.
To cite this article: V. Nithyadevi , P. Selvi & S. P. Rajendran (2004) AN EFFICIENT
SYNTHESIS OF DIHYDRO SELENOLO (2,3-b)QUINOLINE-2-CARBOXYLIC ETHYL ESTERS
AND 2-SELENOXO-1, 2-DIHYDRO-3-CARBETHOXY ETHYL QUINOLINES—THEIR ANTI-
BACTERIAL STUDIES, Phosphorus, Sulfur, and Silicon and the Related Elements,
179:11, 2355-2364, DOI: 10.1080/10426500490485101
To link to this article: http://dx.doi.org/10.1080/10426500490485101
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Phosphorus, Sulfur, and Silicon, 179:2355–2364, 2004
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ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500490485101
AN EFFICIENT SYNTHESIS OF DIHYDRO
SELENOLO (2,3-b)QUINOLINE-2-CARBOXYLIC
ETHYL ESTERS AND 2-SELENOXO-1,
2-DIHYDRO-3-CARBETHOXY ETHYL
QUINOLINES—THEIR ANTI-BACTERIAL STUDIES
V. Nithyadevi, P. Selvi, and S. P. Rajendran
Department of Chemistry, Bharathiar University, Coimbatore,
TamilNadu, India
(Received March 16, 2004; accepted April 28, 2004)
The compounds dihydro selenolo(2,3-b)quinoline-2-carboxylic ethyl es-
ters and 2-selenoxo-1, 2-dihydro-3-carbethoxy ethyl quinolines were
synthesized in varying yields upon reacting 3-(2-chloro-3-quinolyl)-
acrylic methyl esters with the nucleophilic reagent sodium hydrogen
selenide in ethanol medium under nitrogen atmosphere.
Keywords: Condensation; cyclization using NaHSe in absolute ethanol;
dehydroxychlorination; esterification; hydrolysis; Vilsmeier-Haack
Reaction
INTRODUCTION
Organoselenium compounds have been extensively investigated due to
their close association with various types of activities such as antifun-
gal and antibacterial activities,1–3 cardiovascular and antihistaminic
actions,4 antiadrenalin, antiradiation,5 antileukemic activity,6 antitu-
mour activity,7 analgesic, antirhuematic and antipyretic activities,8
parathyroid scanning for the deduction of lymphomas,9etc.
Selenium also exhibits protective effects,10 transcriptional activi-
ties,11 cell cycle control,12 growth influence,13 preterm delivery,13 pre-
vention of endemic arsenism,14 etc.
We wish to thank Bharathiar University for the award of URF to one of us (V. N).
We also thank the services rendered by the Dept of Chemistry Bharathiar University at
Coimbatore, IICT at Hyderabad and Sophisticated Instumentation facility at IISc Ban-
galore for recording elemental analysis, Proton NMR, IR and Mass spectra. We greatly
acknowledge Dr. P. Lakshmanaperumalsamy and Mr. Subashkumar-Division of micro-
biology, Dept of Environmental Sciences, Bharathiar University, Coimbatore, for the mi-
crobial studies rendered by them.
Address correspondence to S. P. Rajendran, Department of Chemistry, Bharathiar
University, Coimbatore 641046, Tamil Nadu, India. E-mail: rajendransp@yahoo.com
2355

2356
V. Nithyadevi et al.
Even though there are many inorganic selenium reagents and
organoselenium reagents, the role of NaHSe is excellent when it is
used for the introduction of selenium into organic molecules. The
ethanolic solution of sodium hydrogen selenide. The reducing agent
is advantageous in that it provides a superior solvent for nucleophilic
displacement reactions in water-insoluble or hydrolysis-sensitive or-
ganic compounds. Early workers from our laboratory have synthe-
sised selenolo(2,3-b)quinolines15–17using 2-quinolone-3-ethanols and 2-
chloro-3-vinyl quinolines as the starting compounds. In view of their
expected activities, we pursued our investigation on selenium heterocy-
cles, and we report herein a convenient synthesis of dihydroselenolo(2,3-
b)quinoline-2-carboxylic ethyl esters and 2-selenoxo-1, 2-dihydro-3-
carbethoxy ethyl quinolines from 3-(2-chloro-3-quinolyl)acrylic esters18
(5) (Scheme 1).
EXPERIMENTAL
Melting points were determined using Raaga melting point apparatus
and were uncorrected. The IR spectra were recorded on FTIR 8201(PC)S
spectrometer as KBr pellets, and the absorption frequencies are ex-
pressed in reciprocal centimeters (cm−1). Proton NMR spectra were
recorded on a Gemini-200 MHz or on a Varian AMX 400 spectrom-
eter in CDCl3. The chemical shifts were expressed in δ (ppm) down-
field from tetramethylsilane (TMS) as an internal standard. Elemen-
tal analysis was performed by Elementar Analyser Vario EL III, and
the values are within the permissible limits ( 0.5). The mass spectra
were recorded by EIMS technique on an Autospec mass spectrome-
ter. The crude products were checked by thin layer chromatography
(TLC) and purified by column chromatography using silica gel (60–
120 mesh).
In our present work selenium heterocycles were synthesized from the
potential precursor 2-chloro-3-formyl quinolines, which were prepared
by following O. Meth-cohn procedure.19 2-chloro-3-formyl quinolines (1)
were converted to the oxo compounds (2) by refluxing with 4MHCl.
These were then condensed with malonic acid under the conditions of
Knoevenagel reaction to furnish 3-(2-oxo-1,2-dihydro-3-quinolyl)acrylic
acids20 (3).
Esterification of (3) in absolute methanol and concentrated sul-
phuric acid at reflux temperature for 5–6 h furnished 3-(2-oxo-3-
quinolyl)acrylic methyl ester18 (4) (Scheme 1). Upon dehydroxychlo-
rination with freshly distilled phosphorus oxychloride, the compound
(4) resulted in 3-(2-chloro-3-quinolyl)acrylic methyl ester (5).

Selenolo and Selenoxo Quinolines
2357
SCHEME 1
Preparation of dihydroselenolo(2,3-b)-quinoline-2-
carboxylic ethyl esters and 2-selenoxo-1,2-dihydro-3-
carbethoxy ethyl quinolines (6) and (7)
To a freshly prepared solution of sodium hydrogen selenide21 under ni-
trogen atmosphere (selenium powder 1.12 g, 0.01417 mole and sodium

2358
V. Nithyadevi et al.
borohydride 0.0134 mole, 0.505 g) in ethanol, chloro ester (5) (1 g,
0.00808 mole) was added and heated under reflux temperature for 5–
6 h on a steam bath. Thereafter, the solution was evaporated and the
residue was dissolved in chloroform followed by washing with water.
The organic extract was dried and evaporated. Thin layer chromatog-
raphy (TLC) analysis of the residue showed three spots. Column chro-
matography was used to purify the crude product. The isolated products
were recrystallized from petroleum ether. The first product was left as
an unidentified one, since it was a pasty mass.
The second and third products were identified as dihydrosele-
nolo(2,3-b)quinoline-2-caboxylic ethyl esters (6) and 2-selenoxo-1,2-
dihydro-3-carbethoxy ethyl quinolines (7), respectively.
Antibacterial activity of dihydroselenolo(2, 3-b)quinoline-2-
carboxylic ethyl ester (6a), 8-methyl-dihydroselenolo(2,3-b)quinoline-2-
carboxylic ethyl ester (6c), 6-methoxy dihydroselenolo(2,3-b)quinoline-
2-carboxylic ethyl ester (6d), and 8-methyl-2-selenoxo-1,2-dihydro-3-
carbethoxy ethyl quinoline (7c) were screened for the in vitro growth
inhibitory activity against the pathogens Escherichia coli, Salmonella
typhi, Staphylococcus aureus, and Pseudomonas flourosence.
Methodology for Antibacterial Studies
Antibacterial activity of the synthesized compounds were determined
by Disc diffusion technique.22 The bacterial inoculum 105 of cells were
enriched in to 5 ml of the nutrient broth (NaCl-5.0 g, Peptone-5 g, beef
extract-3 g, yeast extract-3 g in 1000 ml of distilled water, pH = 7.3
0.2). Enriched bacterial cells were swabbed onto Muller Hinton Agar
medium (Himedia India). The test compounds were dissolved in CHCl3
to a final concentration of 2, 1, and 0.5% and soaked in filter paper discs
(5 mm diameters and 1 mm thickness). These discs were placed on the
seeded plates and incubated at 37◦C for 24 h. The zones of inhibition
around the discs were measured after 24 h. Norfloxacin(Nx) (10 mcg)
and Amoxycillin(Ac) (30 mcg) were used as the standard to compare the
antibacterial activity of the compounds.
Physical and Spectroscopic Data of 6 and 7
Dihydroselenolo(2,3-b)-Quinoline-2-carboxylic
Ethyl Ester (6a)
Colorless crystals, yield, 20%, m.p. 99–100◦C. Calc.: C, 54.91; H,
4.27; N, 4.57. Found: C, 55.03: H, 4.30: N, 4.59. IR(KBr, cm−1): 1722
1
( C O of ester), 1172 ( C O of ester). H NMR(CDCl3)δppm: 1.34 (t,
J = 7.2 Hz, CH3 of ester), 4.25 (q, J = 7.2 Hz, CH2 of ester), 3.61–

Selenolo and Selenoxo Quinolines
2359
3.65 (m, CH2 CH ), 7.24–7.92 (m, 5H, C4, C5, C6, C7, C8-H), M F:
C14H13O2NSe, Mass (m/z)M+, 306.
7-Methyl-dihydroselenolo(2,3-b)quinoline-2-carboxylic
Ethyl Ester (6b)
Colorless crystals, yield, 21%, m.p. 152–153◦C. Calc.: C, 56.25; H,
4.72; N, 4.37. Found:, C, 56.20: H, 4.62; N, 4.35. IR(KBr, cm−1): 1711
1
(C O of ester), 1252 ( C O of ester). H NMR(CDCl3)δppm: 1.44 (t,
J = 7.2 Hz, CH3 of ester), 4.45 (q, J = 7.2 Hz, CH2 of ester), 2.62 (s,
3H, CH3), 3.68–3.73 (m, CH2 CH ), 8.26 (s, 1H, C8-H), 7.86 (d,
J = 9.4 Hz, C5-H), 7.43 (d, J = 8.2 Hz, C6-H), 8.58 (s, C4-H). M.F:
C15H15O2NSe. Mass (m/z)M+, 320.
8-Methyl-dihydroselenolo(2,3-b)quinoline-2-carboxylic
Ethyl Ester (6c)
Colorless crystals, yield, 22%, m.p. 94–95◦C. Calc.: C, 56.25; H, 4.72;
N, 4.37. Found: C, 56.20; H, 4.52; N, 4.35. IR(KBr, cm−1); 1721 ( C O of
ester), 1206 (C O of ester). H1 NMR(CDCl3)δppm: 1.25 (t, J = 4.4 Hz,
CH3 of ester), 4.20 (q, J = 7.6 Hz, CH2 of ester), 2.71 (s, 3H, CH3),
3.63–3.67 (m, CH2 CH ), 7.75 (s, 1H, C4-H), 7.52 (d, J = 7.6 Hz,
C5-H), 7.44 (d, J = 6.6 Hz, C7-H), 7.34 (t, J = 7.8 Hz, C6-H), M.F:
C15H15O2NSe, Mass(m/z) M+: 320.
6-Methoxy Dihydroselenolo(2,3-b)quinoline-2-carboxylic
Ethyl Ester (6d)
Colorless crystals, yield, 19%, m.p. 110–111◦C. Calc.: C, 53.58; H,
4.49; N, 4.16. Found: C, 53.40; H, 4.42; N, 4.10. IR(KBr, cm−1): 1700
( C O of ester), 1170 ( C O of ester), H1NMR(CDCl3)δppm: 1.43 (t,
J = 7.2 Hz, CH3 of ester), 4.42 (q, J = 7.2 Hz, CH2 of ester), 3.96
(s, 3H, OCH3), 3.81–3.86 (m, CH2 CH ), 8.51 (s, 1H, C4-H), 8.25 (s,
1H, C5-H), 7.46 (d, J = 9.4 Hz, C8-H), 8.02 (d, 1H, J = 9.4 Hz, C7-H),
M. F: C15H15O3NSe, Mass(m/z)M+, 336.
8-Methoxy-dihydroselenolo(2,3-b)quinoline-2-carboxylic
Ethyl Ester (6e)
Colorless crystals, yield, 17%, m.p. 59–60◦C. Calc.: C, 53.58; H, 4.49;
N, 4.16. Found: C, 53.50; H, 4.48; N, 4.16. IR(KBr, cm−1): 1730 ( C O of
ester), 1175 ( C O of ester), H1NMR(CDCl3)δppm: 1.46 (t, J = 7.2 Hz,
CH3 of ester), 4.44 (q, J = 7.2 Hz,CH2 of ester), 3.98 (s, 3H, OCH3),
3.89–3.95 (m, CH2 CH ), 8.51 (s, 1H, C4-H), 7.32–8.07 (m, 3H, C5,
C6, C7-H), M. F: C15H15O3NSe, Mass(m/z)M+, 336.

2360
V. Nithyadevi et al.
Dihydroselenolo(2,3-b)benzo(h)quinoline-2-carboxylic
Ethyl Ester (6f)
Colorless crystals, yield, 17%, m.p. 195–196◦C. Calc.: C, 60.68; H,
4.24; N, 3.93; Found: C, 60.65; H, 4.20; N, 3.90. IR(KBr, cm−1): 1720
(C O of ester), 1172 ( C O of ester). H1NMR(CDCl3)δppm: 1.46 (t,
J = 7.2 Hz, CH3 of ester), 4.44 (q, J = 7.2 Hz, CH2 of ester), 3.92–3.97
(m, CH2 CH ), 7.45–9.43 (m, 7H, C4, C5, C6, C7, C8, C9, C10-H), M.
F: C18H15O2NSe, Mass(m/z)M+, 356.
6, 8-Methyl-dihydroselenolo(2,3-b)quinoline-2-carboxylic
Ethyl Ester (6g)
Colorless crystals,yield, 23%, m.p. 85–86◦C. Calc.: C, 57.49; H, 5.13;
N, 4.19. Found: C, 57.49; H, 5.12; N, 4.16. IR(KBr, cm−1): 1725 (C O of
ester), 1180 (C O of ester), H1NMR(CDCl3)δppm: 1.42 (t, J = 7.2 Hz,
CH3 of ester), 4.34 (q, J = 7.2 Hz, CH2 of ester), 2.41, 2.53 (seach
,
3H, CH3), 3.79–3.85 (m, CH2 CH ) 8.11 (s, 1H, C4-H), 7.52 (s, 1H,
C7-H), M. F: C16H17O2NSe, Mass(m/z)M+, 334
2-Selenoxo-1,2-dihydro-3-carbethoxy Ethyl Quinoline (7a)
Colorless crystals, yield, 65%, m.p. 135–136◦C. Calc.: C, 54.55; H,
4.90; N, 4.54. Found: C, 54.50; H, 4.89; N, 4.50. IR(KBr, cm−1): 1732(C O
of ester), 3414 ( NH), 1259 (C Se), H1NMR(CDCl3) δ ppm: 1.23 (t,
J = 6.2 Hz, CH3 of ester), 4.13 (q, J = 7.4 Hz, OCH2 of ester), 2.78 (t,
J = 7.2 Hz, CH2 CH2 COO−), 3.01 (t, J = 7.2 Hz, CH2 CH2 COO−),
7.69 (s, 1H, C4 H), 7.23–7.54 (m, 4H, C5, C6, C7, C8-H), M. F:
C14H15O2NSe, Mass(m/z)M+, 308.
7-Methyl- 2-selenoxo-1,2-dihydro-3-carbethoxy Ethyl
Quinoline (7b)
Colorless crystals, yield, 55%, m.p. 101–102◦C. Calc.: C, 55.90; H,
5.32; N, 4.35. Found: C, 55.89; H, 5.32; N, 4.30. IR(KBr, cm−1): 1732
(C O of ester), 3443 (NH), 1230 (C Se), H1 NMR(CDCl3) δppm: 1.21
(t, J = 7.2 Hz, CH3 of ester), 4.11 (q, J = 7.4 Hz, OCH2 of ester),
2.56 (s, 3H, CH3), 2.73 (t, J = 8.4 Hz, CH2 CH2 COO−), 3.03 (t,
J = 7.2 Hz, CH2 CH2 COO−), 7.81 (s, 1H, C4-H), 7.72 (s, C8-H), 7.61
(d, J = 8.2 Hz, C5-H), 7.29 (d, J = 7.4 Hz, C6-H), M. F: C15H17O2NSe,
Mass(m/z)M+, 322.
8-Methyl-2-selenoxo-1,2-dihydro-3-carbethoxy Ethyl
Quinoline (7c)
Colorless crystals, yield, 55%, m.p. 140–142◦C. Calc.: C, 55.90; H,
5.32; N, 4.35, Found: C, 55.89; H, 5.32; N, 4.30. IR(KBr, cm−1): 1722
( C O of ester), 3417 ( NH), 1252 (C Se), H1 NMR(CDCl3) δppm:

Selenolo and Selenoxo Quinolines
2361
1.26 (t, J = 7.8 Hz, CH3 of ester), 4.17 (q, J = 7.8 Hz, OCH2 of es-
ter), 2.51 (s, 3H, CH3), 2.89 (t, J = 7.8 Hz, CH2 CH2 COO−), 3.34
(t, J = 6.6 Hz, CH2 CH2 COO−), 7.76 (s,1H, C4 H), 7.24–7.54 (m,3H,
C5,C6,C7 H), M. F: C15H17O2NSe, Mass (m/z) M+, 322.
6-Methoxy-2-selenoxo-1,2-dihydro-3-carbethoxy Ethyl
Quinoline (7d)
Colorless crystals, yield, 57%, m.p. 146–148◦C. Calc.: C, 53.26; H,
5.07; N, 4.14. Found: C, 53.20; H, 5.00; N, 4.10. IR(KBr, cm−1): 1707
( C O of ester), 3416( NH), 1228 (C Se), H1 NMR(CDCl3) δppm: 1.21
(t, J = 7.2 Hz, CH3 of ester), 4.11 (q, J = 7.4 Hz, OCH2 of ester),
3.91 (s, 3H, CH3), 2.72 (t, J = 7.2 Hz, CH2 CH2 COO−), 3.02 (t, J =
7.2 Hz, CH2 CH2 COO−), 7.01–7.95 (m, 4H, C4, C5, C6, C7-H), M. F:
C15H17O3NSe, Mass(m/z)M+, 338.
8-Methoxy-2-selenoxo-1,2-dihydro-3-carbethoxy
Ethyl Quinoline (7e)
Colorless crystals, yield, 50%, m.p. 105–107◦C. Calc.: C, 53.26; H,
5.07; N, 4.14. Found: C, 53.20; H, 5.00; N, 4.10. IR(KBr, cm−1): 1730
(C O of ester), 3415 ( NH), 1292 (C Se), H1NMR(CDCl3) δppm: 1.23
(t, J = 7.2 Hz, CH3 of ester), 4.17 (q, J = 7.8 Hz, OCH2 of ester), 4.05
(s, 3H, OCH3), 2.77 (t, J = 8.2 Hz, CH2 CH2 COO−), 3.11(t, J = 7.4
Hz, CH2 CH2 COO−), 7.71 (s, 1H, C4-H), 6.98–7.35 (m, 3H, C5, C6,
C7-H), M. F: C15H17O3NSe, Mass(m/z)M+: 338.
2-Selenoxo-1,2-dihydro-3-carbethoxy
Ethyl-benzo(h)quinoline (7f)
Colorless crystals, yield, 60%, m.p. 235–236◦C. Calc.: C, 60.34; H,
4.78; N, 3.90. Found: C, 60.30; H, 4.78; N, 3.89. IR(KBr, cm−1): 1730
(C O of ester), 3410 ( NH), 1230 (C Se), H1NMR(CDCl3) δppm: 1.36
(t, J = 7.8 Hz, CH3 of ester), 4.23 (q, J = 7.8 Hz, OCH2 of es-
ter), 2.92 (t, J = 7.8 Hz, CH2 CH2 COO−), 3.44 (t, J = 6.6 Hz,
CH2 CH2 COO−), 7.45–9.13(m, 7H, C4, C5, C6, C7, C8, C9, C10-H),
M. F: C18H17O2NSe, Mass(m/z)M+, 358.
6, 8-Dimethyl-2-selenoxo-1, 2-dihydro-3-carbethoxy
Ethyl Quinoline (7g)
Colorless crystals, yield, 60%, m.p. 245–246◦C. Calc.: C, 57.14; H,
5.69; N, 4.17. Found: C, 57.11; H, 5.67; N, 4.16. IR(KBr, cm−1): 1735
(C O of ester), 3420 ( NH), 1245 (C Se), H1 NMR(CDCl3) δppm: 1.16
(t, J = 7.6 Hz, CH3 of ester), 4.05 (q, J = 7.6 Hz, OCH2 of ester),
2.35, 2.41 (seach, 3H, CH3), 2.89 (t, J = 7.6 Hz, CH2 CH2 COO−),
3.34 (t, J = 6.4 Hz, CH2 CH2 COO−), 7.86 (s, 1H, C4-H), 8.01

2362
V. Nithyadevi et al.
FIGURE 1
(s, 1H, C7-H), 8.17 (s, 1H, C5-H). M. F: C16H19O2NSe, Mass(m/z)M+,
336.
RESULTS AND DISCUSSION
Raja and Shanmugam23 synthesized the novel diselenolo(3,4-
b)quinolines by reacting the vinyl quinolines with NaHSe prepared
in situ. The present work was started by reacting 8-methyl-3-(2-chloro-
3-quinolyl)acrylic methyl ester (5c) with NaHSe. The products obtained
were not the expected methyl esters, but the unexpected ethyl esters
which was an interesting observation. The conversion from (5c) to (6c)
was found to be due to reduction, cyclisation and transesterification
in the presence of excess ethanol and the eliminated acid within the
reaction medium (Figure 1).
The conversion from (5c) to (7c) (Figure 2) was found to be due to
reduction and transesterification in the presence of excess ethanol and
the eliminated acid within the reaction medium The above reaction
sequence was further extended to synthesize other derivatives 6a, 6b,
6d, 6e, 6f, 6g, 7a, 7b, 7d, 7e, 7f, and 7g, respectively.
FIGURE 2

Selenolo and Selenoxo Quinolines
TABLE I Antibacterial Activity
2363
Diameter of inhibition zone in mm
Staphylococcus
Pseudomonas
flourosence
Escherichia coli Salmonella typhi
aureus
Compound 2% 1% 0.5% 2% 1% 0.5% 2% 1% 0.5% 2% 1% 0.5%
6a
6c
6d
7c
10
13
14
—
16
11
12
—
11
11
10
—
—
11
15
—
14
10
11
—
10
—
10
—
9
14
10
11
—
10
—
—
—
14
—
14
—
10
—
14
—
—
—
12
—
11
14
—
Dihydroselenolo(2,3-b)-quinoline-2-carboxylic ethyl ester (6a)
showed intermediate activity against the test organism Escherichia coli
at 1% CHCl3. 8-methyl-dihydroselenolo (2,3-b) quinoline-2-carboxylic
ethyl ester (6c) and 8-methyl-2-selenoxo-1,2-dihydro-3-carbethoxy
ethyl quinoline (7c) were resistant to all the pathogenic bacteria. 6-
methoxy dihydroselenolo (2,3-b)quinoline-2-carboxylic ethyl ester (6d)
showed intermediate activity against the test organism Salmonella
typhi at 2% CHCl3 (Table I).
The overall results showed that the derivatives did not reach the
effectiveness of the conventional bactericides Norfloxacin and Amoxy-
cillin.
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