Synthesis, characterization and antimicrobial evaluation of novel (E)-N′-(4-(1-((3,4-dimethoxypyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)benzylidene)benzohydrazide derivatives

Article abstract of DOI:10.13005/ojc/320445

The synthesis of novel 1,2,3-triazole-hydrazone derivatives embedded with 3,4-dimethoxy pyridine ring nucleus is described. These derivatives were prepared utilizing, 2-(chloromethyl)-3,4-dimethoxypyridine 1, 4-ethynylbenzaldehye 5 and various benzohydrazides7a-7j. The structures of the newly synthesized 1,2,3-triazole-hydrazones 8a-j was established on the basis of the spectroscopic techniques like ¹H NMR, mass and IR data. They were evaluated against a panel of bacterial and fungal pathogens such as Staphylococcus. pyogens, Staphylococcus. Aureus (Gram positive bacteria), Escherichia.coli, Pseudomonas. aeruginosa (Gram negative bacteria) and Aspergillus niger and Candida albicans (Fungal stains). Compounds 8b, 8c, 8d, 8e and 8f with R = 4-OH, 4-OMe, 4-SO₂Me, 3,45,-OMe and 3-NO₂ respectively showed moderate antibacterial activity while compounds 8b, 8d, 8i and 8j with R = 4-OH, 4-SO₂Me, 3,5-dichloro and 2,5-difluoro substitution exhibited very good fungal activity.

Full text of DOI:10.13005/ojc/320445

ISSN: 0970-020 X
CODEN: OJCHEG
2016, Vol. 32, No. (4):
Pg. 2155-2161
ORIENTAL JOURNAL OF CHEMISTRY
An International Open Free Access, Peer Reviewed Research Journal
www.orientjchem.org
Synthesis, Characterization and Antimicrobial Evaluation
of Novel (E)-N’-(4-(1-((3,4-dimethoxypyridin-2-yl)methyl)-1H-
1,2,3-triazol-4-yl)benzylidene)benzohydrazide Derivatives
SWAMY SAIDUGARI1,2*,LAKSHMANA RAO VADALI1, K VIDYA2 and B RAM3
1Mylan Laboratories Limited, Bollaram, Jinnaram (Mandal),
Medak (Dist), Hyderabad, Telangana State, India.
2JNTU-H College of Engineering, Nachupally (Kondagattu),
Kodimyalmandal, Jagityal, Karimnagar -505 501, Telengana State, India.
3Green Evolution Laboratories, Wangapally Village, Telangana State, 500085, India.
*Corresponding author E-mail:swamysaidugari2015@gmail.com
http://dx.doi.org/10.13005/ojc/320445
(Received: May 30, 2016; Accepted: August 02, 2016)
ABSTRACT
The synthesis of novel 1,2,3-triazole-hydrazone derivatives embedded with 3,4-dimethoxy
pyridine ring nucleus is described. These derivatives were prepared utilizing, 2-(chloromethyl)-3,4-
dimethoxypyridine 1, 4-ethynylbenzaldehye 5 and various benzohydrazides7a-7j.The structures of the
newly synthesized 1,2,3-triazole-hydrazones 8a-j was established on the basis of the spectroscopic
techniques like 1H NMR, mass and IR data. They were evaluated against a panel of bacterial and
fungal pathogens such as Staphylococcus.pyogens, Staphylococcus.Aureus (Gram positive bacteria),
Escherichia.coli, Pseudomonas. aeruginosa (Gram negative bacteria) and Aspergillus niger and
Candida albicans (Fungal stains).Compounds 8b, 8c, 8d, 8e and 8f with R = 4-OH, 4-OMe, 4-SO2Me,
3,45,-OMe and 3-NO2 respectively showed moderate antibacterial activity while compounds 8b, 8d,
8i and 8j with R = 4-OH, 4-SO2Me, 3,5-dichloro and 2,5-difluoro substitution exhibited very good
fungal activity.
Keywords: 1,2,3-triazole, Hydrazone, 4-ethynylbenzaldehyde, Synthesis, Antifungal activity.
INTRODUCTION
because they are more expected to be water soluble
than normal aromatic compounds, and are stable in
biological systems1.These triazole products readily
connect with biological targets, through hydrogen
bonding and dipole interactions2. Some of the
pharmaceutically prominent triazole antifungal drugs
are fluconazole3, isavuconazole4, itraconazole5,
The growth of 1,2,3-triazoles for drug
discovery and industrial use has been shown to be
very resourceful.The interest in the 1,2,3-triazole is
due to it being non-toxic, benign and stable.Triazoles
are predominantly attractive for medicinal use

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voriconazole6, pramiconazole7, and posaconazole8. acetylene in presence of Pd(PPh3)2Cl2 , CuI , Et3N
Also, the examples of triazole crop protection in THF gave the corresponding trimethylatedsillyl
fungicides includesepoxiconazole9, triadimenol10, derivative4. De-protection of the trimethylsillyl group
propiconazole11, metconazole12, cyproconazole13, in presence of K2CO3 in methanol resulted in the
tebuconazole14, flusilazole15 and paclobutrazol16. desired benzaldehyde5.
Derivatives of 1,2,3-triazole have been found to have
anti-HIV17, anti-allergenic 18, cytostatic19, virostatic20,
The structures of the synthesized
anti-inflammatory21 activities, furthermore, these compounds were confirmed by 1H NMR, Mass and
triazoles are also being studied for the treatment of IR data. As a representative example, the 1H NMR
obesity22 and anti-oxidant activity23.
spectra of (E)-N’-(4-(1-((3,4-dimethoxypyridin-2-
yl)methyl)-1H-1,2,3-triazol-4-yl)benzylidene)-4-
Hydrazone derivatives of heteroaromatic methoxybenzohydrazide is as follows, the protons
compounds have also been reported to possess resonating at 11.78 ppm and 8.48 ppm as broad
anti-inflammatory24,25, anticancer26, antitumor27, singlet corresponds to the characteristic –CONH
antibacterial or plant-growth activity28, 29
.
and –CH=N- respectively, while the protons
resonating at 8.72 ppm (pyridine ring proton) and
The frequency of bacterial and fungal 7.23 ppm (overlap of triazole and pyridine ring proton
infections is an important contemporary problem signal), is assigned to triazole ring and pyridine
due to the emerging new infectious diseases ring protons. The multiplet at 7.94-7.91 ppm (four
and increasing multi-drug resistance of microbial proton integration), a broad singlet at 7.81 ppm (two
pathogens30. The widespread use of antibiotics has proton integration) and a doublet at 7.07 ppm (two
contributed to the growing infection rate since fungal proton integration is assigned to the protons of the
infections occur after antibiotic therapy, which has the 4-methoxy phenyl ring and the phenyl ring flanked
effect of killing the beneficial bacteria that normally to triazole ring.The aliphatic protons are observed in
suppress fungi. The development of new effective the expected region.The mass and IR spectral data
antifungal and antibacterial agents is strongly needed. of the hydrazone compounds are in agreement with
Herein, we report the synthesis and antimicrobial the desired structures.
evaluation of new 1,2,3 triazole derivatives linked with
pyridine and hydrazone fragments.The structures of Antibacterial and antifungal activity
the synthesized compounds were determined by 1H
NMR, mass and IR spectroscopy.
The screening results of (E)-N’-(4-(1-((3,4-
dimethoxypyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)
benzylidene)benzohydrazide derivatives 8a-j are
tabulated in table 1. From table-1 it is observed that
hydrazone derivatives 8b, 8c, 8d, 8e and 8f with
R = 4-OH, 4-OMe, 4-SO2Me, 3,4,5,-OMe and 3-NO2
RESULTS AND DISCUSSION
Chemistry
The synthesis of new (E)-N’-(4-(1-((3,4- respectively showed moderate antibacterial activity
dimethoxypyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl) while the hydrazone derivatives 8a, 8i and 8j with
benzylidene)benzohydrazide derivatives is illustrated R = H, 3,5-dichloro and 2,5-difluoro showed weak
in Scheme-1. The reaction of 2-(chloromethyl)-3,4- antibacterial against both Gram positive and Gram
dimethoxypyridine1 with sodium azide in DMF at negative bacteria with reference to ciprofloxacin as
90°C afforded azide derivative 2.Copper(I)-catalyzed, the standard drug.
Huisgen [3+2] cycloaddition reaction31-32 of azide2
with 4-ethynylbenzaldehyde5 in acetonitrile at reflux
In case of fungal screening evaluation,
produced 4-(1-((3,4-dimethoxypyridin-2-yl)methyl)- hydrazone derivatives 8b, 8d, 8i and 8j with R = 4-OH,
1H-1,2,3-triazol-4-yl)benzaldehyde6 in 95% yield. 4-SO2Me, 3,5-dichloro and 2,5-difluoro substitution
Condensation of aldehyde6 with benzohydrazides exhibited very good fungal activity and the remaining
7a-7j in ethanol resulted in the formation of hydrazone derivatives in the series showed moderate
hydrazonederivatives 8a – j in quantitative yields. antifungal activity against the tested fungal strains
The synthesis 4-ethynylbenzaldehyde5 is achieved as with reference to Greseofluvin as the standard
follows, reaction of 4-iodobenzaldehyde3 with TMS- drug.

SAIDUGARI et al., Orient. J. Chem., Vol. 32(4), 2155-2161 (2016)
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EXPERIMENTAL
2-(azidomethyl)-3,4-dimethoxypyridine 2
Sodium azide (0.365 g, 5.60 mmol) was
added to a solution of compound 1(1g, 5.33 mmol)
in DMF (5 mL) at room temperature. The reaction
mixture was heated to 100°C for 1h.After completion
of the reaction (by T.L.C), the reaction contents
were cooled to room temperature and diluted with
ethylacetate (15 mL) and water (5 mL).The organic
layer was separated and washed with brine solution
(2 X 5 mL), separated, dried over anhydrous sodium
sulphate, filtered and concentrated under reduced
pressure to obtain the crude compound 2.The crude
compound was utilized in the next step without
further purification.
The solvents were purified according to
standard procedures prior to use, and all commercial
chemicals were used as received. For thin-layer
chromatography (TLC) analysis, Merck pre-coated
plates (silica gel 60 F254) were used and spots were
visualized with UV light.Merck silica gel 60 (230-400
mesh) was used for flash column chromatography
and the eluting solvents are indicated in the
procedures. Melting point (m.p.) determinations
were performed by using Mel-temp apparatus and
are uncorrected. 1H NMR spectra were recorded in
Varian MR-400 MHz instrument. Chemical shifts
are reported in d ppm (parts per million) downfield
from tetramethylsilane (TMS) with reference to
internal standard and the signals were reported as s
(singlet), d (doublet), dd (doblet of doblet), t (triplet),
q (quartet), m (multiplet) and coupling constants are
in Hz. The mass spectra were recorded on Agilent
ion trap MS. Infrared (IR) spectra were recorded on
a Perkin Elmer FT-IR spectrometer.
4-(2-(trimethylsilyl)ethynyl)benzaldehyde 4
To a solution of 4-iodobenzaldehyde 3
(1g, 4.30 mmol) in tetrahydrofuran (12 mL), in a
seal tube, were added sequentially, copper(I) iodide
(0.14 mmol), triphenylphosphine (0.39 mmol),
bis(triphenylphosphine)palladium(II) dichloride
(0.14 mmol) and trimethylsilylacetylene (0.59 mL,
4.14 mmol) under argon atmosphere. After string
O
N
O
O
O
O
b
a
O
N
+
N
N
CHO
Cl
N3
N
N
CHO
1
2
6
5
R
O
c
CHO
CHO
CHO
NH
H2N
7a-7j
O
e
d
O
N
O
N
N
N
I
NH
N
R
TMS
8a - 8j
3
4
5
8a. R = H
8b. R = 4-OH
8c. R = 4-OMe
8f. R = 3-NO2
8g. R = 4-Br
8h. R = 4-Cl
8d. R = 4-SO2Me
8e. R = 3,4,5-OMe
8i. R = 3,5-dichloro
8j. R = 2,5-difluoro
Reaction conditions:a) NaN3, DMF, 90°C; b) CuI, acetonitrile, reflux, 1h; c) Benzohydrazides7a-j, ethanol, reflux, 1 h;
d) Bis(triphenylphosphine)palladium(II) dichloride, Trimethylacetylene, CuI, Triphenylphosphine, Triethylamine, THF,
65°C, 2 h; e) potassium carbonate, Methanol, room temperature, 1 h;
Scheme 1: Synthesis of Novel 1,2,3-triazole-carbohydrazide derivatives

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for 15 min, triethylamine (12.9 mmol) was added 4-(1-((3,4-dimethoxypyridin-2-yl)methyl)-1H-1,2,3-
and the resultant mixture was heated at 65ÚC for triazol-4-yl)benzaldehyde 6
30 min.The reaction contents were diluted with ethyl
4-ethynylbenzaldehyde 5 (1g, 7.68 mol)
acetate (15 mL), washed with water (2 X 15 mL), was added to a solution of compound 3 (0.67g,
washed with brine solution (10 mL).The organic layer 5.15 mmol) in acetonitrile (10 mL) followed by the
was separated and dried over Na2SO4. The solvent addition of CuI(10 mol %). The reaction mixture
was evaporated under reduced pressure to obtain was heated to reflux for 1h. After completion of the
compound 4 as a viscous pale yellow oily liquid.The reaction (monitored by T.L.C), the reaction mixture
crude compound was utilized in the next step without was diluted with ethylacetate (20 mL) and water
further purification.
(20 mL). The organic layer was washed with briene
solution, separated and dried over Na2SO4, filtered
and concentrated under reduced pressure to obtain
4-ethynylbenzaldehyde 5
A mixture of 4-((trimethylsilyl)ethynyl) 6.Yellow solid;Yield:90%;M.p.:131–132°C;IR (KBr):
benzaldehyde 4 (1g, 4.94 mmol) and potassium Umax 3351, 3130, 3100, 3047, 3017, 2986, 2945,
carbonate (1g, 7.41 mmol) were stirred in methanol 2841, 2722, 2604, 1696, 1608, 1589, 1494, 1452,
(25 mL) at room temperature for 1 hour.The reaction 1429, 1400, 1349, 1304, 1270, 1232, 1210, 1171,
mixture was diluted with ethylacetate (20 mL) and 1144, 1103, 1069, 1046, 996, 971, 947, 907, 832,
washed with water (2 x 20 mL) followed by brine 755, 728, 688, 657, 626, 553, 515, 486, 463 cm-1; 1H
solution.The organic solvent was concentrated under NMR (400 MHz, DMSO-d6): d 10.0 (s, 1H), 8.78 (brs,
reduced pressure to obtain compound 5. Yellow 1H), 8.18 (brs, 1H), 8.10 (d, J = 7.8 Hz, 2H), 7.94 (d,
solid; Yield: 0.29 g (90%); M.p.: 84-86°C;IR (KBr): J = 7.8 Hz, 2H), 7.10 (brs, 1H), 5.78 (s, 2H), 3.96 (s,
Umax 3454, 329, 3220, 2836, 2784, 2739, 2098, 1930, 3H), 3.78 (s, 3H); ESI- MS: m/z, 324.9(M+1).
1699, 1686, 1601, 1560, 1408, 1386, 1364, 1303,
1286, 1206, 1163, 1102, 1012, 975, 954, 924, 844, Experimental procedure for synthesis of
829, 739, 679, 581, 530, 508 cm-1;1H NMR (400 MHz, benzohydrazides7a-j [34-35]
CDCl3): d 3.30 (1 H, s), 7.66 (d, J = 8.20 Hz, 2H),
7.86 (d, J = 8.20 Hz, 2H), 10.02 (s, 1H).
Benzoic acids a-j (8.12 mmol) was dissolved
in ethanol (15 mL) and added catalytic qty of conc.
H2SO4 and heated to reflux for 10 h. Ethanol was
Table 1: Results of Antibacterial and Antifungal activity of Compounds 8a-j
Compound no.
Gramnegative bacteria
Gram positive bacteria
S.aureus
Fungi
C. albicans
E. coli
P.aeruginosa S.pyogens
A. niger
Zone of inhibition expressed in mm
8a
8b
8c
8d
8e
8f
8g
8h
12
17
16
20
20
19
-
11
18
17
21
22
20
-
9
14
12
18
17
18
-
-
9
12
22
24
10
16
14
19
17
18
-
20
26
22
25
19
20
21
19
26
25
18
22
17
20
16
18
19
17
22
23
-
-
-
8i
8j
12
11
28
11
13
27
28
10
11
22
Ciprofloxacin
Greseofluvin
Standard drug concentration: 250µg/mL; “—_ No activity

SAIDUGARI et al., Orient. J. Chem., Vol. 32(4), 2155-2161 (2016)
2159
evaporated and the obtained residue was diluted
with ethylacetate (25 mL). The organic layer was
washed with aqueous saturated NaHCO3 (3 X 15
mL) followed by water (2 X 15 mL) and brine solution
(20 mL).The organic layer was separated, dried over
sodium sulphate, filtered and evaporated to obtain
respective ethyl benzoates.
2H), 7.96-7.80 (m, 5H), 7.15 (brs, 1H), 6.86 (d, J =
10.6 Hz, 2H), 5.72 (s, 2H), 3.90 (s, 3H), 3.80 (s, 3H);
ESI- MS: m/z, 459.0 (M+1).
(E)-N’-(4-(1-((3,4-dimethoxypyridin-2-yl)
methyl)-1H-1,2,3-triazol-4-yl)benzylidene)-4-
methoxybenzohydrazide 8c
Off white solid;Yield:84%;M.p.:96–97°C;IR
To the above prepared respective ethyl
benzoates (6.65 mmol) in ethanol was added
hydrazine-hydrate (40.0 mmol) and refluxed for 8 h.
Ethanol was evaporated from the reaction mixture
and the precipitated solids were slurred with pet-
ether (5 times) and filtered at the pump and dried to
obtain benzohydrazides7a-7j.
(KBr): Umax 3570, 3527, 3453, 3409, 3366, 3288,
3158, 3093, 2939, 2836, 1647, 1603, 1539, 1498,
1456, 1426, 1355, 1302, 1256, 1179, 1143, 1109,
1068, 1025, 988, 915, 837, 760, 725, 689, 614, 567,
537, 509, 455 cm-1; 1H NMR (400 MHz, DMSO-d6):
d 11.78 (brs, 1H, -CONH), 8.72 (brs,1H), 8.48 (brs,
1H, -CH=N-), 8.13 (brs, 1H), 7.94-7.91 (m, 4H), 7.81
(brs, 2H), 7.23 (brs, 1H, triazole), 7.07 (d, J = 10.4
Hz, 2H, ), 5.72 (brs, 2H), 3.91 (s, 3H), 3.84 (s, 3H),
3.81 (s, 3H); ESI- MS: m/z, 443.0(M+1).
General procedure for the synthesis of hydrazone
derivatives 8a-8j
To a solution of compound 6 (100 mg,
0.308 mmol) in ethanol was added corresponding
benzohydrazides 7a-7j (0.308 mmol) and heated to
reflux for 30 min.The precipitated solids were filtered
at the pump and dried to afford hydrazone derivatives
8a-8j in quantitative yields.
(E)-N’-(4-(1-((3,4-dimethoxypyridin-2-yl)
methyl)-1H-1,2,3-triazol-4-yl)benzylidene)-4-
(methylsulfonyl)benzohydrazide 8d
Yellow solid;Yield: 82%; M.p.: 134–135°C;
IR (KBr): Umax 3570, 3527, 3453, 3409, 3366, 3288,
3158, 3093, 2939, 2836, 1647, 1603, 1539, 1498,
1456, 1426, 1355, 1302, 1256, 1179, 1143, 1109,
1068, 1025, 988, 915, 837, 760, 725, 689, 614, 567,
(E)-N’-(4-(1-((3,4-dimethoxypyridin-2-yl)
methyl)-1H-1,2,3-triazol-4-yl)benzylidene)
benzohydrazide 8a
1
537, 509, 455 cm-1; H NMR (400 MHz, DMSO-
Pale yellow solid; Yield: 90%; M.p.: 101–
d6): d 12.11 (brs, 1H), 8.67 (brs,1H), 8.48 (s, 1H),
8.17-8.02 (m, 5H), 7.97 (d, J = 10.8 Hz, 2H), 7.89
(d, J = 10.8 Hz, 2H), 7.15 (brs, 1H), 5.72 (brs, 2H),
3.90 (s, 3H), 3.80 (s, 3H), 3.30 (s, 3H); ESI- MS:
m/z, 521.0 (M+1).
102°C;IR (KBr):Umax 3425, 3260, 3138, 3057, 3023,
2974, 2944, 2842, 1655, 1584, 1538, 1489, 1456,
1426, 1358, 1299, 1278, 1228, 1177, 1139, 1101,
1066, 997, 972, 947, 914, 821, 804, 762, 718, 626,
534, 493 cm-1;1H NMR (400 MHz, DMSO-d6): d 11.89
(brs, 1H), 8.66 (s, 1H), 8.44 (s, 1H), 8.13 (brs, 1H),
7.99-7.92 (m, 4H), 7.80 (d, J = 10.8 Hz, 2H), 7.63-
7.52 (m, 3H), 7.16 (brs, 1H), 5.72 (brs, 2H), 3.91 (s,
3H), 3.81 (s, 3H); ESI -MS: m/z, 443.0 (M+1).
(E)-N’-(4-(1-((3,4-dimethoxypyridin-2-yl)
methyl)-1H-1,2,3-triazol-4-yl)benzylidene)-3,4,5-
trimethoxybenzohydrazide 8e
Pale yellow solid; Yield: 84%; M.p.: 89–
90°C;1H NMR (400 MHz, DMSO-d6): d 11.74 (brs,
1H), 8.65 (s,1H), 8.48 (s, 1H), 7.96 (d, J = 10.8 Hz,
2H), 7.80 (d, J = 10.8 Hz, 2H), 7.24 (s, 2H), 5.72 (brs,
2H), 3.90 (s, 3H), 3.89 (s, 3H); ESI MS: m/z, 533.0
(M+1).
(E)-N’-(4-(1-((3,4-dimethoxypyridin-2-yl)
methyl)-1H-1,2,3-triazol-4-yl)benzylidene)-4-
hydroxybenzohydrazide 8b
Pale yellow solid; Yield: 88%; M.p.: 128–
129°C;IR (KBr):Umax 3270, 3147, 3020, 2944, 2837,
2792, 2672, 2601, 1907, 1645, 1607, 1588, 1542,
1508, 1492, 1450, 1358, 1301, 1281, 1237, 1173,
1143, 1105, 1072, 995, 972, 951, 912, 838, 809,
761, 721, 685, 622, 598, 507 cm-1;1H NMR (400
MHz, DMSO-d6): d 11.68 (brs, 1H), 10.13 (brs, 1H),
8.66 (brs, 1H), 8.44 (brs, 1H), 8.10 (d, J = 9.6 Hz,
(E)-N’-(4-(1-((3,4-dimethoxypyridin-2-yl)
methyl)-1H-1,2,3-triazol-4-yl)benzylidene)-3-
nitrobenzohydrazide 8f
Yellow solid; Yield: 92%; M.p.: 84–85°C;
1H NMR (400 MHz, DMSO-d6): d 11.20 (brs, 1H),
10.16 (brs, 1H), 8.77 (brs,1H), 8.60 (brs, 1H), 8.44

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(d, J = 9.8 Hz, 2H), 8.26 (d, J = 9.6 Hz, 2H), 7.70-
Pale yellow solid; Yield: 88%; M.p.: 140–
7.62 (m, 3H), 5.72 (brs, 2H), 3.90 (s, 3H), 3.80 (s, 141°C;IR (KBr): Umax 3446, 3307, 3131, 3071, 3019,
3H); ESI -MS: m/z, 488.0 (M+1).
2974, 2943, 2839, 2598, 1663, 1606, 1585, 1546,
1490, 1453, 1424, 1359, 1301, 1274, 1229, 1180,
(E)-N’-(4-(1-((3,4-dimethoxypyridin-2-yl) 1128, 1073, 996, 971, 949, 906, 883, 822, 779, 751,
methyl)-1H-1,2,3-triazol-4-yl)benzylidene)-4- 727, 690, 669, 620, 579, 538, 498 cm-1; 1H NMR (400
bromobenzohydrazide 8g
MHz, DMSO-d6): d 12.11 (* 11.96, s, 1H), 8.66 (* 8.58,
Yellow solid;Yield:83%;M.p.:129–130°C;IR s,1H), 8.32 (* 8.09, s, 1H), 8.20 (brs, 1H), 7.97 (d, J =
(KBr): Umax 3460, 3228, 3070, 2986, 2941, 2838, 10.2 Hz, 2H), 7.87-7.70 (m, 2H), 7.56-7.39 (m, 3H),
1651, 1588, 1552, 1489, 1462, 1446, 1425, 1395, 5.72 (brs, 2H), 3.90 (s, 3H), 3.80 (s, 3H); ESI-MS:
1366, 1349, 1301, 1270, 1229, 1180, 1145, 1104, m/z, 479.0 (M+1).
1065, 1004, 974, 949, 914, 882, 839, 822, 753, 709,
675, 623, 597, 572, 535, 504, 458 cm-1; 1H NMR (400 Antibacterial and antifungal bioassay
MHz, DMSO-d6): d 11.95 (brs, 1H), 8.67 (brs,1H),
The antibacterial activity of all the hydrazone
8.46 (brs, 1H), 8.12 (brs, 1H), 7.97 (d, J = 10.8 Hz, derivatives (8a-j) were examined against a panel of
2H), 7.88 (d, J = 11.2 Hz, 2H), 7.81-7.74 (m, 4H), bacterial culture viz., Staphylococcus.pyogens,
7.16 (brs, 1H), 5.72 (brs, 2H), 3.90 (s, 3H), 3.80 (s, Staphylococcus.aureus (Gram positive) and
3H); ESI-MS: m/z, 521.0 (M+1).
Escherichia.coli, Pseudomonas.aeruginosa (Gram
negative). The antibacterial activity was performed
(E)-N’-(4-(1-((3,4-dimethoxypyridin-2-yl) by agar well diffusion method with reference to
methyl)-1H-1,2,3-triazol-4-yl)benzylidene)-4- Ciprofloxacin (250 µg/mL) as standard drug. Nutrient
chlorobenzohydrazide 8h
agar was used as culture media and DMSO was
Pale yellow solid; Yield: 86%; M.p.: 128– used as solvent control36-38. Similarly, the antifungal
129°C;IR (KBr): Umax 3744, 3461, 3230, 3089, 2985, activity was evaluated Aspergillus niger and
2942, 2838, 1655, 1592, 1566, 1548, 1490, 1457, Candida albicans with reference to Nystatin as the
1427, 1358, 1302, 1272, 1237, 1180, 1144, 1094, standard antifungal drug. Sabouraud dextrose agar
1065, 1012, 977, 946, 915, 842, 752, 728, 677, 602, was used as culture media and DMF was used as
534, 495 cm-1; 1H NMR (400 MHz, DMSO-d6): d 11.95 solvent control39.The results of the antibacterial and
(brs, 1H), 8.72 (brs,1H), 8.46 (brs, 1H), 8.09 (brs, antifungal activity was determined by measuring
1H), 7.95-7.93 (m, 4H), 7.81 (brs, 2H), 7.62 (d, J = zone of inhibition and is tabulated Table 1.
11.2 Hz, 2H), 7.18 (brs, 1H), 5.71 (brs, 2H), 3.90 (s,
3H), 3.80 (s, 3H); ESI-MS: m/z, 477.0 (M+1).
CONCLUSION
(E)-N’-(4-(1-((3,4-dimethoxypyridin-2-yl)
Insummary, thepresentpaperdescribesthe
methyl)-1H-1,2,3-triazol-4-yl)benzylidene)-3,5- synthesisofsomenew1,2,3-triazole-benzohydrazides
dichlorobenzohydrazide 8i 8a-j in six steps involving condensation of the key
Pale yellow solid; Yield: 88%; M.p.: 136– intermediate 4-(1-((3,4-dimethoxypyridin-2-yl)
138°C;IR (KBr): Umax 3452, 3149, 3086, 2947, 2841, methyl)-1H-1,2,3-triazol-4-yl)benzaldehyde 6 with
1670, 1586, 1563, 1490, 1433, 1381, 1351, 1301, various benzohydrazide7a-j in quatitative yields.The
1271, 1231, 1176, 1133, 1100, 1067, 996, 974, 944, antifungal screening of these hydrazones revealed
903, 876, 864, 824, 805, 748, 707, 663, 602, 533, 499 that compounds 8b, 8d, 8i and 8j with R = 4-OH,
cm-1; 1H NMR (400 MHz, DMSO-d6): d 12.04 (brs, 4-SO2Me, 3,5-dichloro and 2,5-difluoro substitution
1H), 8.68 (brs,1H), 8.44 (brs, 1H), 8.11-7.89 (m, 6H), exhibited very good fungal activity and the remaining
7.81 (d, J = 10.4 Hz, 2H), 7.16 (brs, 1H), 5.72 (brs, hydrazone derivatives in the series showed moderate
2H), 3.90 (s, 3H), 3.80 (s, 3H); ESI-MS: m/z, 511.0 antifungal activity.
(M+1).
ACKNOWLEDGEMENTS
(E)-N’-(4-(1-((3,4-dimethoxypyridin-2-yl)
methyl)-1H-1,2,3-triazol-4-yl)benzylidene)-2,5-
difluorobenzohydrazide 8j
The authors are grateful to JNTUH for
providing facilities to carry out the work

SAIDUGARI et al., Orient. J. Chem., Vol. 32(4), 2155-2161 (2016)
2161
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