Preparation and Antibacterial Activity of Some New 4-(2-Heterylidenehydrazinyl)-7-chloroquinoline Derivatives

Article abstract of DOI:10.1155/2018/4301847

N-(4-Substituted phenyl)acetamides, which were prepared from acetic anhydride and p-substituted anilines, were utilized as precursors for reactions to Vilsmeier-Haack reagent to form 6-substituted-2-chloroquinoline-3-carbaldehydes 3a-c. Meanwhile, a similar reagent was applied to 1-[1-(4-substituted phenyl)ethylidene]-2-phenylhydrazines as substrates, which were synthesized from phenylhydrazine hydrochloride and p-substituted acetophenones, and 1,3-diarylpyrazole-4-carbaldehydes 3d-f were observed as a result. Reactions between the aldehydes 3a-f and 7-chloro-4-hydrazinylquinoline 2, obtained from reaction of 4,7-dichloroquinoline 1 and hydrazine hydrate, formed six new hydrazone compounds, namely, 4-{2-[(6-substituted-2-chloroquinolin-3-yl)methylidene]hydrazinyl}-7-chloroquinolines 4a-c and 4-(2-{[3-(4-substituted phenyl)-1-phenyl-1H-pyrazol-4-yl]methylene}hydrazinyl)-7-chloroquinolines 4d-f. The chemical structures of all synthesized compounds were elucidated by the analysis of IR, ¹H, ¹³C-NMR, and HRMS spectral data. Additionally, all of the synthesized hydrazones were evaluated in terms of cytotoxic activity against four strains of bacteria and four strains of fungus at several concentrations of substrates. As a result, three of them, 4a-c, possess the good ability as growth inhibitor of Bacillus subtilis and Aspergillus Niger at the concentration of 25 μg/mL and 50 μg/mL, respectively, while compound 4e only shows a cytotoxic activity against Aspergillus Niger at the concentration of 25 μg/mL.

Full text of DOI:10.1155/2018/4301847

Hindawi
Journal of Chemistry
Volume 2018, Article ID 4301847, 7 pages
https://doi.org/10.1155/2018/4301847
Research Article
Preparation and Antibacterial Activity of Some New
4-(2-Heterylidenehydrazinyl)-7-chloroquinoline Derivatives
1
Trong Duc Le ,1 Ngoc Nam Pham ,2 and Tien Cong Nguyen
1Department of Chemistry, Ho Chi Minh City University of Education, Ho Chi Minh City 700000, Vietnam
2Department of Organic Chemistry, Ho Chi Minh City University of Science, Vietnam National University,
Ho Chi Minh City 700000, Vietnam
Correspondence should be addressed to Tien Cong Nguyen; congnt@hcmup.edu.vn
Received 8 August 2017; Revised 30 October 2017; Accepted 7 November 2017; Published 15 January 2018
Academic Editor: Gabriel Navarrete-Vazquez
Copyright © 2018 Trong Duc Le et al. Tis is an open access article distributed under the Creative Commons Attribution License,
which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
N-(4-Substituted phenyl)acetamides, which were prepared from acetic anhydride and p-substituted anilines, were utilized as
precursors for reactions to Vilsmeier-Haack reagent to form 6-substituted-2-chloroquinoline-3-carbaldehydes 3a–c. Meanwhile,
a similar reagent was applied to 1-[1-(4-substituted phenyl)ethylidene]-2-phenylhydrazines as substrates, which were synthesized
from phenylhydrazine hydrochloride and p-substituted acetophenones, and 1,3-diarylpyrazole-4-carbaldehydes 3d–f were
observed as a result. Reactions between the aldehydes 3a–f and 7-chloro-4-hydrazinylquinoline 2, obtained from reaction
of 4,7-dichloroquinoline 1 and hydrazine hydrate, formed six new hydrazone compounds, namely, 4-{2-[(6-substituted-2-
chloroquinolin-3-yl)methylidene]hydrazinyl}-7-chloroquinolines 4a–c and 4-(2-{[3-(4-substituted phenyl)-1-phenyl-1H-pyrazol-
4-yl]methylene}hydrazinyl)-7-chloroquinolines 4d–f. Te chemical structures of all synthesized compounds were elucidated by the
analysis of IR, 1H, 13C-NMR, and HRMS spectral data. Additionally, all of the synthesized hydrazones were evaluated in terms of
cytotoxic activity against four strains of bacteria and four strains of fungus at several concentrations of substrates. As a result, three
of them, 4a–c, possess the good ability as growth inhibitor of Bacillus subtilis and Aspergillus niger at the concentration of 25 ꢀg/mL
and 50 ꢀg/mL, respectively, while compound 4e only shows a cytotoxic activity against Aspergillus niger at the concentration of
25 ꢀg/mL.
1. Introduction
2-chloroquinoline-3-carbaldehyde possessed a moderate to
good antibacterial activity against both Gram-positive and
Gram-negative bacteria [12].
Quinoline derivatives, which widely occur in nature, espe-
cially alkaloids, have become an important skeleton in
synthetic chemistry due to their variety of applications
in medicinal, bioorganic, and industrial chemistry. Some
hydrazone derivatives possessing a quinoline moiety have
been well known as having a broad spectrum of biological
activities such as antibacterial [1], anticancer [2], antitubercu-
lar [3–5], antifungal [6], anti-infammatory [7], antimalarial
[8], and antimicrobial [9, 10]. According to Ferreira et al.
[11], hydrazone derivatives, which were prepared from the
reaction of 7-chloro-4-hydrazinylquinoline and heteroaro-
matic aldehydes, showed a good antimycobacterial activity
in comparison with some drugs such as ethambutol and
rifampicin. Additionally, some hydrazones being born from
Besides, pyrazole derivatives have been of great interest
in medicinal chemistry for their role as potent antiparasitic
[13], antimicrobial [14], and antitumor agents [15]. (4-
Chlorophenyl)-[1-(4-nitrophenyl)-3-phenylpyrazol-4-yl-
methylene]amine [13] compound possesses a good activity
against L. infantum with IC50 of 12.4 ꢀM while 5-(3-isobutyl-
1-phenyl-1H-pyrazol-4-yl)-2-substituted-1,3,4-oxadiazoles
[15] have an anticancer activity against breast and liver cell
line with IC50 of around 2–7 ꢀM and 4–13 ꢀM, respectively.
In this article, 7-chloro-4-hydrazinylquinoline 2 was
prepared from the reaction of 4,7-dichloroquinoline 1
and hydrazine hydrate and then was utilized as the key
intermediate material for the synthesis of some new

2
Journal of Chemistry
hydrazones containing 2-chloroquinoline or pyrazole
and was kept overnight to separate the solid. Te yellow
moiety. Te new synthesized hydrazones including 4-{2-[(6-
precipitates were fltered and recrystallized from ethanol to
give compound 2. Yield: 80%; mp. 224-225∘C (literature [1]:
223–225∘C). IR (], cm−1): 3255, 3258 (–NH– and –NH ), 3055
substituted-2-chloroquinolin-3-yl)methylidene]hydrazinyl}-
7-chloroquinoline 4a–c and 4-(2-{[3-(4-substituted phenyl)-
1-phenyl-1H-pyrazol-4-yl]methylene}hydrazinyl)-7-chloro-
quinoline 4d–f were evaluated for antimicrobial activities
against eight kinds of microorganisms. Te chemical
structure of the hydrazones was elucidated by IR, NMR, and
HRMS spectral analysis and their biological activities were
reported for the frst time.
2
1
(Csp2-H), 2931 (Csp3-H), 1600 (C=C) and 1566 (C=N); H-
NMR (500 MHz, DMSO−d ) ꢁ (ppm), J (Hz): 8.60 (1H, br,
6
>NH), 8.39 (1H, br, Ar-H), 8.16 (1H, d, J = 9.0, Ar-H), 7.76 (1H,
s, Ar-H), 7.39 (1H, dd, ꢂ1 = 9.0, ꢂ2 = 2.0, Ar-H), 6.87 (1H, br, Ar-
H) and 4.45 (2H, br, –NH ); 13C-NMR (125 MHz, DMSO–d6)
2
ꢁ (ppm): 152.8, 151.8, 148.8, 133.2, 127.4, 123.8, 115.9 and 98.8
(S1–S3 from Supplementary materials).
2. Materials and Methods
Preparation of 4-(2-Heterylidenehydrazinyl)-7-chloroquino-
line Compounds 4a–f . Appropriate 2-chloroquinoline-3-
carbaldehyde derivatives 3a–c or 1,3-diphenylpyrazole-4-
carbaldehyde derivatives 3d–f (1 mmol) were dissolved in
absolute ethanol (10 mL) with a few drops of glacial acetic
acid. Tis mixture was stirred for 10 minutes and then
compound 2 (0.19 g, 1 mmol) was added in. Te reaction
mixture was refuxed for 3 hours. At the completion of
reaction, the mixture was cooled to room temperature to
separate the solid, which was fltered and recrystallized from
suitable solvent to give products 4a–f, respectively.
All chemicals were purchased from Merck or Aldrich and
solvents were commercial and were used without any further
purifcation.
Melting points were determined with a Gallenkamp dig-
ital Melting-point apparatus 5A-6797 and were uncorrected.
Te IR absorption spectra were scanned on Shimadzu
FTIR 8400S spectrum using potassium bromide (KBr) pel-
lets.
1
All the H, 13C-NMR, HSQC, and HMBC spectra were
recorded on a Bruker Advance 500 MHz model spectrometer
using DMSO-d6 as solvents and internal standard. Te spin-
spin coupling constants (J) are given in Hz. Peak multiplicity
is reported as s (singlet), d (doublet), dd (double-doublet), t
(triplet), q (quartet), m (multiplet), and br (broad).
Mass spectrometric data were recorded on a micrOTOF-
QII Bruker.
All the synthesized hydrazones were evaluated to in
terms of antimicrobial activities against microorganism. Te
method for these experiences was based on the literature
[18, 19].
3. Result and Discussion
Tin-layer chromatography (TLC) was performed on
silica-gel sheets (silica gel 60 F254, Merck) and visualized in
ultraviolet light (254 nm).
Te synthesis of the hydrazones containing quinoline
heterocycles was performed following the steps shown in
Scheme 1.
7-Chlorohydrazinylquinoline 2 was prepared from the reac-
tion of 4,7-dichloroquinoline 1 and hydrazine hydrate. Its 1H-
NMR spectrum (S2 from Supplementary materials) showed
two broad singlet signals of hydrazine group (–NHNH ) at
2
ꢁ 8.6 and 4.5. Additionally, there were a doublet signal at ꢁ
H
8.16 with spin-spin coupling of 9.0 Hz attributed to H5 anHd
2-Chloroquinoline-3-carbaldehydes 3a–c were prepared
according to the literature [16]. p-Substituted aniline was
added to the solution of acetic anhydride in acetic acid, fol-
lowing by being refuxed in 2 hours. Consequently, cooling to
room temperature and pouring into ice water were performed
to collect N-(4-substituted phenyl)acetamide derivatives,
which then reacted to the mixture of dimethylformamide and
phosphoryl chloride (Vilsmeier-Haack reagent) to form 2-
chloroquinoline-3-carbaldehyde derivatives 3a–c.
1,3-Diarylpyrazole-4-carbaldehydes 3d–f were prepared
according to the literature [17]. Phenylhydrazine hydrochlo-
ride was slowly added to the mixture of 4ꢀ-substituted
acetophenones and acetic acid in ethanol. Te reaction
mixture was stirred and then was poured into water to sep-
arate the product 1-(1-phenylethylidene)-2-phenylhydrazine,
which was treated with Vilsmeier-Haack reagent at 80–90∘C
in 15 hours to form 1,3-diphenylpyrazole-4-carbaldehyde
derivatives 3d–f.
a double-doublet signal at 7.39 attributed to H6. Meanwhile,
H8 gave a singlet signal at ꢁ 7. 76. Two signals app earing at
H
ꢁ 8.39 and 6.87 were attributed to H2 and H3, respectively.
H
Teoretically, H2 and H3 usually appear as doublet signals
due to having spin-spin coupling together. However, in our
case, the ring system may lead to them becoming hydroxylic
protons, and, so, the broad signals were obtained.
Compound 2 was utilized as a precursor for preparation
of six new hydrazones according to Scheme 1. Te
reaction of 4,7-dichloroquinoline
1
with hydrazine
hydrate formed 7-chlorohydrazinylquinoline 2, which was
treated by 2-chloroquinoline-3-carbaldehyde derivatives
3a–c to form 4-{2-[(6-substituted-2-chloroquinolin-3-
yl)methylidene]hydrazinyl}-7-chloroquinoline compounds
4a–c. Meanwhile, 4-(2-{[3-(4-substituted phenyl)-1-phenyl-
1H-pyrazol-4-yl]methylene}hydrazinyl)-7-chloroquinoline
compounds 4d–f were produced by the reaction of
compound
2
and 1,3-diphenylpyrazole-4-carbaldehyde
Preparation of 7-Chloro-4-hydrazinylquinoline 2. 4,7-Dichlo-
roquinoline (10 g, 5 mmol) was dissolved in ethanol (20 mL)
in which hydrazine hydrate (35 mL, 50 mmol) was slowly
dropped. Te reaction mixture was refuxed for 2 hours.
Consequently, this mixture was cooled to room temperature
derivatives 3d–f.
Te reaction of 2 and some heteroaromatic 3a–f occurred
easily and may be observed clearly by both changing color
of reaction solution and the appearance of precipitates in the
progress of reaction.

Journal of Chemistry
3
Cl
N
NH2
N
Cl
N
Cl
HN
N
X
HN
N
X
OHC
N2H4·H2O (80%), ethanol
(3a–c)
reflux 2 h
reflux 3 h
N
Cl
Cl
Cl
(2)
(4a–c)
(1)
Y
N
reflux 3 h
N
OHC
(3d–f)
X = H (a), CH3 (b), OC2H5 (c)
Y = H (d), Cl (e), NO2 (f)
Y
N
N
N
HN
N
(4d–f)
Cl
Scheme 1: Pathway for preparation of 4-(2-heterylidenehydrazinyl)-7-chloroquinoline derivatives.
Table 1: Te physical properties and IR spectral data of the 4a–f compounds.
] (cm−1
)
Solvent
Mp.
(∘C)
Yield
(%)
Comp.
Structure
X or Y
H
C=C
C=N
1615
1566
1615
1566
1620
1582
1651
1582
1613
1575
1620
1555
recrystallized
C–H
3055
NH
3179
3179
3232
3256
3241
3215
Cl
N
4a
4b
4c
4d
4e
4f
DMF : H O
236
239
239
236
233
236
83
83
81
2
N
X
2895
3055
2978
3040
HN
CH
DMF : H O
3
2
OEt
H
EtOH
Cl
N
Y
Dioxane : H O
84
85
83
3063
3063
3060
2
N
N
N
Cl
DMF : H O
2
HN
NO
Ac : H O
Cl
2
2
N
More information can be found in Supplementary Materials.
In IR spectra, the specifc vibration of amino group
Both the 1H-NMR (500 MHz, DMSO-d6) and 13C-NMR
(125 MHz, DMSO-d6) spectra of these compounds showed
all of the signals matching with the expected structures. Te
1H-NMR spectra of each of the compounds 4a–f showed
(–NH , double peak) at 3255–3258 cm−1 disappeared while
2
the sharpness peak of N–H bonds still appeared around
3200 cm−1; the stretching bands of the C=N bonds were
recognized at 1555–1582 cm−1. Tese data are similar to those
of the 7-chloro-4-quinolinylhydrazone compounds described
in literature [3].
the singlet signals at ꢁ 8.51–8.83 and 11.11–11.70, which were
H
attributed to –CH=N– (H13) and –NH– (H11), respectively.
Furthermore, each of the 13C spectra presented a signal
around 136−139 ppm, which made cross peak with the signal
of H13 in the HSQC spectra and so it was attributed to
−CH=N− (C13). Besides, singlet signal of the methyl group
in molecule of 4b appeared at 2.54 ppm; the signals of the
ethyl group in 4c were assigned as quartet at 4.21 ppm (2H, J
= 7.0 Hz) and triplet at 1.44 ppm (3H, J = 7.0 Hz). Te singlet at
Te physical properties and IR spectral data of the 4a–f
compounds were presented in Table 1.
Te structures of the hydrazones were further confrmed
by the HRMS data. Molecular ion peaks in the mass spectra
of the products were in conformity with desired molecular
formulas of them (see Tables 2 and 3).

4
Journal of Chemistry

Journal of Chemistry
5

6
Journal of Chemistry
Table 4: Antimicrobial activity of hydrazones 4a–f.
Minimum inhibitory concentration (MIC: ꢀg/mL)
Samp.
Bacterial strains
Fungal strains
FO
EC
PA
BS
25
25
25
SA
AN
50
50
50
SC
CA
4a
4b
4c
4d
4e
4f
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
(−)
25
(−)
(−)
(−)
(−) means negative; EC, PA, BS, and SA stand for Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, and Staphylococcus aureus; AN, FO, SC, and CA
stand for Aspergillus niger, Fusarium oxysporum, Saccharomyces cerevisiae, and Candida albicans.
ꢁ 9.01–9.15 in the 1H-NMR spectra of compounds 4a–c was
4. Conclusion
H
assigned to proton in the 23th position (H23) while the singlet
1
By a simple and convenient method, 7-chloro-4-hydrazi-
nylquinoline 2 and six aldehydes including 2-chloro-
6-substituted quinoline-3-carbaldehydes 3a–c and 1,3-
diarylpyrazole-4-carbaldehydes 3d–f were prepared. Te
reaction of hydrazine 2 with the heteroaromatic aldehydes
3a–f formed six new 4-(2-heterylidenehydrazinyl)-7-
chloroquinoline compounds 4a–f. Teir chemical structures
were elucidated by the analysis of IR, NMR, and HRMS
spectral data. It was found that the confguration of
hydrazones was E except (Z)-4-{2-[(1,3-diphenyl-1-phenyl-
1H-pyrazol-4-yl)methylene]hydrazinyl}-7-chloroquinoline
compound 4d. All of them were tested for the antimicrobial
activities against eight kinds of bacteria and fungus.
Te results showed that the hydrazones containing 2-
chloroquinoline moiety 4a–c possess good activities in
growth inhibition of Bacillus subtilis and Aspergillus niger
at the concentration of 25 and 50 ꢀg/mL, respectively.
In general, the hydrazones containing 1,3-diarylpyrazole
moieties 4d–f had been inactive but compound 4f exhibited
high biological activity against Aspergillus niger at the
concentration of 25 ꢀg/mL.
at ꢁ 9.11–9.17 in the H-NMR spectra of compounds 4d–f
wasHassigned to proton of the pyrazole ring (H15). A complete
assignment of H and 13C NMR spectra of the hydrazones
1
was based on analysis of NMR and 2D spectra (the HMBC
correlations of 4b and 4e compounds were shown in the
structures at Tables 2 and 3) and is presented in Tables 2 and
3.
Te confguration of –CH=N– bonds of hydrazone com-
pounds was identifed by their NOESY spectral analysis.
Te supposal confguration of compound 4d was Z due to
the correlation between H2 and H22/28, which was shown
in its NOESY spectrum. Meanwhile, the NOESY spectrum
of compound 4e presented a cross peak of correlation of
H13 and H8, which confrmed the E confguration of this
compound. Tere was a remark that the carbon signal of
–CH=N– group in Z confguration appears at the higher
magnetic feld than in E confguration [20]. In our case,
the same observation was collected with the carbon signal
of –CH=N– group of compound 4d appearing at ꢁ 136.4
C
whereas the others were collected at ꢁ 139.0. Furthermore,
C
the 13C-NMR spectrum of compound 4f showed the signal of
–CH=N– group at ꢁ 138.9, and, thus, its confguration was
supposed to be E. TCese data were presented in Table 3.
All synthesized compounds were tested for antibacterial
and antifungal activities. Four kinds of bacteria including
Escherichia coli (ATCC 25922), Pseudomonas aeruginosa
(ATCC 25923), Bacillus subtilis (ATCC 11774), and Staphy-
lococcus aureus (ATCC 11632) and four fungus involving
Aspergillus niger (439), Fusarium oxysporum (M42), Candida
albicans (ATCC 7754), and Saccharomyces cerevisiae (SH
20) were utilized for these experiments. Te results were
presented in Table 4.
Conflicts of Interest
Te authors declare that there are no conficts of interest
regarding the publication of this paper.
Supplementary Materials
Supplementary data associated with this article can be found
in the attached fle. Tese data include NMR (1H, 13C,
HSQC, HMBC, and NOESY), IR, and HRMS spectra of
the synthesized compounds (2, 3a–f, 4a–f): IR spectrum of
As the data has shown, the series of 7-chloro-4-[2-
1
(2-chloroquinolin-3-yl-methylene)hydrazinyl]quinoline
compound (2); H NMR spectrum of compound (2); 13C
1
compounds 4a–c possess antibacterial and antifungal
activities against Bacillus subtilis at the concentration of
25 ꢀg/mL and Aspergillus niger at the concentration of
NMR spectrum of compound (2); H NMR spectrum of
compound (3a); 1H NMR spectrum of compound (3b);
1H NMR spectrum of compound (3c); H NMR spectrum
1
1
50 ꢀg/mL, respectively.
of compound (3d); H NMR spectrum of compound (3e);
Meanwhile, in the other series, there was only 7-chloro-
1H NMR spectrum of compound (3f); IR spectrum of
4-(2-((3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)methyl-
compound (4a); 1H NMR spectrum of compound (4a);
ene)hydrazinyl)quinoline 4f showing the antifungal activity
against Aspergillus niger at the concentration of 25 ꢀg/mL.
13C NMR spectrum of compound (4a); HRMS spectrum
of compound (4a); IR spectrum of compound (4b); 1H

Journal of Chemistry
7
NMR spectrum of compound (4b); 13C NMR spectrum of
compound (4b); HSQC spectrum of compound (4b); HMBC
spectrum of compound (4b); NOESY spectrum of compound
(4b); HRMS spectrum of compound (4b); IR spectrum of
compound (4c); 1H NMR spectrum of compound (4c);
13C NMR spectrum of compound (4c); HRMS spectrum of
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1
compound (4c); IR spectrum of compound (4d); H NMR
spectrum of compound (4d); 13C NMR spectrum of com-
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