Hushare VJ et al. IRJP 2013, 4 (1)
INTERNATIONAL RESEARCH JOURNAL OF PHARMACY
www.irjponline.com
ISSN 2230 – 8407
Research Article
SYNTHESIS, CHARACTERIZATION OF SOME NOVEL PYRAZOLES AND THEIR
GROWTH PROMOTING ACTIVITY ON SOME FLOWERING PLANTS
Hushare VJ*, Rajput PRa, Malpani MO a,b, Ghodile NGa
*Department of Chemistry, GVISH Amravati (M.S.), aDepartment of Chemistry, Vidya Bharati Mahavidyalaya, Camp Road,
Amravati (M.S.), India. Department of Chemistry, Shankarlal Khandelwal College, Akola (M.S.), India
Article Received on: 10/11/12 Revised on: 11/12/12 Approved for publication: 31/12/12
*Email: [email protected]
ABSTRACT
A series of chlorosubstituted 4-aroylpyrazoles have been synthesized by refluxing of chlorosubstituted-3-aroylflavones and 3-alkoylchromone with
phenylhydrazine hydrochloride in dioxane medium with 0.5 ml of piperidine. Chlorosubstituted-3-aroylflavones and chlorosubstituted-3-alkoylchromone were
prepared by refluxing them separately with iodine crystal in ethanol. Initially chlorosubstituted-3-aroylflavanones and 3-alkoylchromanone have been prepared
separately by the interaction of different aldehydes with 1(2-hydroxy-3,5-dichlorophenyl)-3-phenyl-1,3-propanedione. Constitutions of synthesized
compounds have been confirmed on the basis of elemental analysis, molecular weight determination, UV-Visible, I.R. and 1H-NMR spectral data. The titled
compounds were evaluated for their growth promoting activity on some flowering plants viz. Papaver rhoeas, Dianthus chinensis, Candy tuft, Calendula
officinalise, Gladiola tristis, Gaillardia.
Key words: Chlorosubstituted-3-aroylflavanones, 3-alkoylchromanone, 3-aroylflavones, 3-alkoylchromone, pyrazoles.
INTRODUCTION
Heterocyclic compounds1 promote the life on earth as they
are widely distributed in nature and essential for the sustains
of life. The azoles containing two nitrogen atoms in the 1, 2
positions are designated as pyrazoles. Pyrazoles is the name
given by Knorr2 to this class of compounds in 1883.
Pyrazoles refers both the class of simple aromatic ring
organic compounds of heterocyclic series characterized by a
5-membered ring structure composed of three carbon atoms
and two nitrogen atoms in adjacent position and the
unsubstituted parent compound. Pyrazoles are extensively
used in the field of medicine and agro chemistry. The
pyrazole unit is a one of the core structure in a number of
natural products. A number of pyrazole derivatives have
been found to possess a broad spectrum of biological
activities
such as antihyperglycemic, analgesic, antiinflammatory, antipyretic, antibacterial,
antifungal,
anticoagulant, anti-tumor, sedative, hypnoticactivity3-6,
anticancer7 ,antidepressant8 , anticonvulsant9, antifungal10,
selective enzyme inhibitory activity11, antiarthritic12, HIV-1
reverse transcriptase inhibitory13, Cox-2 inhebitory14-15,
activator of the nitro oxide receptor, and soluble guanylate
cyclase activity16. The synthesized compounds successfully
screened for their growth promoting impacts on some
flowering plants viz. Papaver rhoeas, Dianthus chinensis,
Candy tuft, Calendula officinalise, Gladiola tristis,
Gaillardia.
EXPERIMENTAL
The melting points of all synthesized compounds were
recorded using hot paraffin bath and are uncorrected.
Chemicals used were of A. R. Grade. 1H NMR spectra using
CDCl3.
I.R. spectra were recorded on Perkin-Elmer
spectrophotometer in the range 4000 – 400 cm-1 in nujol mull
and as KBr pellets. UV-VIS spectrums were recorded in
nujol medium.
Syntheses:
a. Synthesis of 2-benzoyloxy-3, 5-dichloroacetophenone
(3a):
2-Hydroxy-3, 5-dichloroacetophenone (2a) (0.04mol) and
benzoyl chlorides (0.05 mol) were dissolved in 10% NaOH
(30 ml). The reaction mixture was shacked for about half an
hour. The products thus separated was filtered washed with
water followed by sodium bicarbonate (10%) washing and
then again with water. The solid product thus separated was
crystallized from ethanol.
b. Synthesis of 1-(-2-hydroxy-3, 5-dichlorophenyl)-3phenyl-1,3-propanedione (4a):
2-Benzoyloxy-3, 5-dichloroacetophenone (3a) (0.05mol) was
dissolved in dry pyridine (40 ml). The solution was warmed
up to 60°C and pulverized KOH (15 gm) was added slowly
with constant stirring. The reaction mixture was kept for
overnight and then acidified by adding ice cold HCl (10%).
The brownish yellow solid product thus separates was
filtered, washed with sodium bicarbonate solution (10%) and
finally again with water. It was then crystallized from
ethanol to get the compound (4a).
c. Synthesis of 3-benzoyl-2-(4-nitrophenyl-)-6, 8dichloroflavanone (5a):
A mixture of 1-(2-hydroxy-3, 5-dichlorophenyl)-3-phenyl-1,
3-propendione (4a) (0.01 mol) and p-nitrobenzaldehyde
(0.02M) was refluxed in dioxane (25 ml) containing 0.5 ml
piperidine for 15–20 min. After cooling the reaction mixture
was acidified with dil. HCl (10%). The product thus separate
was crystallized from ethanol to get the compound (5a).
Similarly other chlorosubstituted flavanones 3-benzoyl-2-(4chlorophenyl-)-6, 8-dichloroflavanone (5b) and 3-benzoyl-2butyl-6, 8-dichlorochromanone (5c) were synthesized
separately from the compound (4a) by using pchlorobenzaldehyde and valeraldehyde respectively.
d. Synthesis of 3-benzoyl-2-(4-nitrophenyl-)-6, 8dichloroflavone (6a):
3-Benzoyl-2-(4-nitrophenyl)-6, 8-dichloroflavanone (5a)
(0.01 mol) was refluxed for about 10 minutes with crystal of
iodine in ethanol (20ml). After cooling the reaction mixture
was diluted with water. The solid product thus separated was
filtered, washed with sodium bicarbonate solution and then
with water. Finally it was crystallized from ethanol to get the
Similarly compounds 3-benzoyl-2-(4compound (6a).
nitrophenyl-)-6, 8-dichloroflavone (6b) and3-benzoyl-2butyl6, 8-dichlorochromanon (6c) were synthesized
separately from the compounds (5b) and (5c) respectively.
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Hushare VJ et al. IRJP 2013, 4 (1)
e. Synthesis of 3-(2-hydroxy-3, 5-dichlorophenyl)-4benzoly-5-(4-nitrophenyl)-1-phenyl -pyrazoles (7a):
A
mixture
of
3-benzoyl-2-(4-nitrophenyl)-6,
8dichloroflavone (6a) (0.01mol) and phenylhydrazine
hydrochloride (0.02 mol) was refluxed in dioxane (20 ml)
containing 0.5 ml piperidine for two hours. After cooling the
reaction mixture was diluted with water. The product thus
separated was filtered crystallized from ethanol. Similarly
other
compounds3-(2-hydroxy-3,
5-dichlorophenyl)-4benzoly-5-(4-chlorophenyl)-1-phenyl pyrazoles (7b) and 3(2-hydroxy-3,5-dichlorophenyl)-4-benzoly-5-butyl-1-phenylpyrazoles (7c) were synthesized separately from the
compounds (6b) and (6c) respectively.
The synthesized compounds were characterized on the
basis of elemental analysis, molecular weight
determination, and spectral data:
Compound (5a): Yield 75%, M.P. 90°C. Elemental analysis
for C22H13O5NCl2: Found C = 59.68, H = 2.86, N = 3.10.
Calculated C = 59.72, H = 2.94, N = 3.16%. UV spectrum
(EtOH): λmax – 364 nm (n à p*). IR spectrum (thin layer):
ν, cm–1: 3050.5 (C-H stretching in Ar) 1611.4 (C=O), 1473.9
(C-NO2), 1278 (-C-O), 1182.6 (-C-O) 717.7 cm-1 (-C-Cl). 1H
NMR spectrum (400 MHz, CDCl3), δppm 6.75 (1H, d, -CHCH) 6.9 (1H, d, -CH-CH), 6.875 – 8.712 (11H, m, Ar-H).
Compound (5b): Yield 70%, M.P. 120°C. Elemental
analysis for C22H13O3Cl3: Found C = 61.10, H = 2.96,
Calculated C = 61.18, H = 3.01, %. UV spectrum (EtOH),
λmax – 319 nm (n à p*). IR spectrum (thin layer), ν, cm–1:
2928.6 (C-H stretching in Ar) 1612.6 (C=O), 1427.7 (C-H in
Ar), 1086.5 (C-O), 764.6 cm-1 (-C-Cl). 1H NMR spectrum
(400 MHz, CDCl3), δppm 6.76 (1H, d, -CH-CH) 6.79 (1H, d,
-CH-CH), 6.926– 8.315 (11H, m, ArH).
Compound (5c): Yield 75%, M.P. 155°C. Elemental
analysis for C20H18O3Cl2: Found C = 63.54, H = 4.50,
Calculated C = 63.66, H = 4.77, %. UV spectrum (EtOH),
λmax – 363 nm (n à p*). IR spectrum (thin layer), ν, cm–1:
3068.7 (C-H stretching in Ar) 2866.4 (C-H stretching in Ar),
2866.4 (C-H in – (CH2)3- ), 1689.5 (C=O), 1605.8 (C- H
stretching in Ar) 1457.7 (-CH3 Bending), 1286.3 (C – O in
ether), 705.4 cm-1 (-C-Cl). 1H NMR spectrum (400 MHz,
CDCl3), δppm 0.90 (3H, t, (CH2)3-CH3) 1.25 (2H, m (CH2)2CH2 – CH3) 1.50 (2H, t, -CH2-CH2-CH2-CH3) 2.65 (2H, t,
CH2-(CH2)2-CH3) 6.88 (1H, d, C-H), 6.93 (1H, d, C-H) 7.00
– 8.225 (7H, ,m, Ar-H).
Compound (6a): Yield 75%, M.P. 164°C. Elemental
analysis for C22H11O5NCl2: Found C = 59.00, H = 2.30, N =
3.00, Calculated C = 60.00, H = 2.50, N = 3.18, %.
Compound (6b): Yield 80%, M.P. 168oC. Elemental
analysis for C22H11O3Cl3: Found C =61.14, H = 2.20
Calculated C =61.18, H = 2.56%. UV spectrum (EtOH),
λmax —345 nm (n à p*). IR spectrum (thin layer), ν, cm–1:
2917.8 (C-H stretching in Ar), 1639.5 (C=O), 1604.1
(>C=O), 1091.1(-C-O in ether ), 768.2 cm-1 (-C-Cl). 1H
NMR spectrum (400 MHz, acetone), δppm 6.848-8.319(11H,
m, Ar-H).
Compound (6c): Yield 70%, M.P. 162°C. Elemental
analysis for C20H16O3Cl2: Found C = 63.60, H = 4.10,
Calculated C = 64.00, H = 4.27, %. UV spectrum (EtOH),
λmax 301nm (n à p*) , IR spectrum (thin layer), ν, cm–1:,
2942.5 (Ar - CH), 2851.7
(CH str. in alkane),
1637.9(>C=O),1431.7 (-CH2bending),1345.8 (-CH3 bending)
1250.2 (-C-O in ether) 765.5 cm-1 (-C-Cl). 1H NMR
spectrum (400 MHz, acetone), δppm 1.285(3H, s, -(CH2)3CH3),
2.050(2H,qui, (-CH2)2-CH2-CH3),2.808(2H,m, H2-CH2 -CH2CH3),2.839(2H,t, CH2-(CH2)2-CH3)
Compound (7a): Yield 75%, M.P.135°C. Elemental analysis
for C28H17O4N3Cl2: Found C = 63.20. H = 3.00, N = 7.75
Calculated C = 63.39, H = 3.20, N = 7.92 %.
Compound (7b): Yield 80%, M.P. 185oC. Elemental
analysis for C28H17O2N2Cl3 Found C =64.40, H =3.10,
N=5.15, Calculated C =64.67, H =3.27, %. UV spectrum
(EtOH), λmax – 354nm. ( n à p*). IR spectrum (thin layer),
ν, cm–1: 3160.3 (O-H stretching) 1598.2 (C=O),1492.1
(C=N), 1357.2 (C=C), 1254.5(N-N), 767.7cm-1 (-C-Cl). 1H
NMR spectrum (400 MHz, acetone), δppm 6.6 - 8.08(16H,m,
Ar-H).
Compound (7C): Yield 70%, M.P. 190oC. Elemental
analysis for C26H22O2N2Cl2: Found C = 66.95, H = 4.60,
N=5.90 Calculated C = 67.10, H = 4.73, N=6.02, %). UV
spectrum (EtOH), λmax –304nm (n à p*). IR spectrum (thin
layer), ν, cm–1: 3351 (strong intramolecular H- bonded O-H
stretching) 2363.8 (CH in alkane) 1648.9 (>C=O), 1461.9 (CH2-bending) 1355.5(-CH3 stretching ) 1218.6 (N-N
stretching) 771.4 cm-1 (-C-Cl stretching). 1H NMR spectrum
(400 MHz, acetone), δppm 1.283(3H, m, - (CH2)3-CH3),
2.50(2H, qui, (CH2)2-CH2-CH3), 2.813 (CH2-CH2-CH2-CH3),
2.845(2H, s, CH2-(CH2)2-CH3), 6.910-8.119 (12H, m, Ar–
H)17-18.
SCHEME 1: SYNTHESIS OF NOVEL COMPOUNDS
OH
CH 3 COONa
Cl
AlCl 3
o
120 C
Cl
Cl 2 in CH 3 COOH
Cl
Cl
Cl
Cl
OCOC 6 H 5
OH
10% NaOH
C 6 H 5 COCl
Cl
COCH 3
1a
2
1
COCH 3
Cl
COCH 3
OH
KOH/BVT
Pyridine
Cl
R-CHO
Ethanol/Pyridine
Cl
COCH 2 COC 6 H 5
4a
3a
2a
Cl
O
R
Cl
O
Ethanol / I 2 Crystals
Cl
COC 6 H 5
O
5a-c
OH
OCOCH 3
(CH 3 CO) 2 O
Cl
R
COC 6 H 5
6a-c
OH
PhNHNH 2 HCl
Ethanol / Piperidine
COC 6 H 5
Cl
R
O
N
7a-c
Where R= C6H5-NO2, C6H5-Cl, -(CH2)3-CH3
GROWTH PROMOTING ACTIVITIES ON SOME
FLOWERING PLANTS:
The experimental set up of the study was divided into Seed
Treatment and Field Experiment.
Seed Treatment:
With a view to safeguard dormant seed’s potential from
harmful external agencies, the seed of the test plants were
treated by test compounds before sowing.
Field Experiment:
Pre-germinated quality seeds of Poppy, Pink, Candy tuft,
Gaillardia Calendula, Gladiolus were procured from genuine
agricultural agencies.
The beds of black cotton soil, 2.5 x 2.5m size were prepared
on an open field. The sowing of seeds of all six flowering
plants under examination were done in beds and in earthen
pots separately by conventional methods and irrigated as and
when required19.
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NPh
Hushare VJ et al. IRJP 2013, 4 (1)
The plants from each bed and pot were divided into two
groups i.e. A and B which were designated as ‘control’ and
‘treated’ group plants respectively.
The plants from group B were sprayed with the solution of
test compounds at fortnightly intervals. The field experiments
were conducted to compare the treated plants of group B with
untreated plants of controlled group A. In this context, the
observation were recorded on 15, 30, 45, 60, 75 and 90 days
after sowing; corresponding to early vegetative, late
vegetative, flowering, pod filling and pod maturation stages,
with special reference to number of leaves and height of
shoots,
The results of field’s experiments with test compounds are
tabulated in the following table;
Periodicity of
the observation
(in days)
Table 1. Activity of the test compounds (4a), (5a), (6a), (7a)
Calendula
Gladiolus
Pink
Gaillardia
(Calendula
(Gladiola tristis)
(Gaillardia
(Dianthus chinensis)
officinalise)
aristata)
No. of
Shoot
No. of
Shoot
No. of
Shoot
No. of
Shoot
No. of
Shoot
height
leaves
height
leaves
Height
leaves
height
leaves
height
leaves
T
C
T
C
T
C
T
C
T
C
T
C
T
C
T
C
T
C
T
C
Activity of the Test compound 1-(2’-Hydroxy-3’, 5’-dichlorophenyl)-3-phenyl-1, 3-propanedione (4a)
15
3
3
9
10
2
1
9
4
2
1
1
1
4
3
4
5
2
2
4
4
30
7
5
15
15
4
7
18 18
6
5
2
2
6
8
15
8
5
4
10
8
45
10
10 20
25
8
10
30 30
10
9
4
2
8
15
30 20
7
8
15 16
12
12 22
30 10 16
55 55
15 16
5
3
12
18
50 38
10
12 25 29
60
75
16
17 30
47 13 20
80 85
20 20
6
4
16
20
70 60
13
16 34 41
90
20
23 50
78 15 21 100 115 22 21
6
4
20
21 105 95
18
20 50 63
Activity of the Test compound 3-Benzoyl-2-(4’-nitrophenyl)-6, 8-dichloroflavanone (5a)
15
3
3
9
7
2
2
9
12
2
2
1
1
4
2
4
5
2
2
4
2
30
7
6
15
10
4
5
18 28
6
5
2
2
6
5
15
8
5
4
10
6
10
12 20
20
8
11
30 40
10
9
4
2
8
8
30 20
7
7
15 12
45
60
12
18 22
25 10 15
55 60
15 16
5
5
12
10
50 38
10
9
25 18
75
16
22 30
38 13 20
80 100 20 21
6
5
16
12
70 60
13
12 34 26
90
20
26 50
48 15 22 100 130 22 25
6
5
20
18 105 80
18
17 50 45
Activity of the Test compound 3-Benzoyl-2-(4’nitrophenyl)-6, 8-dichloroflavone (6a)
15
3
3
9
8
2
3
9
14
2
2
1
1
4
4
4
6
2
3
4
5
30
7
7
15
15
4
6
18 30
6
5
2
2
6
6
15
8
5
7
10 12
45
10
12 20
38
8
10
30 50
10 11
4
3
8
10
30 27
7
10 15 18
60
12
16 22
50 10 14
55 70
15 15
5
3
12
14
50 50
10
15 25 29
75
16
20 30
60 13 18
80 90
20 21
6
5
16
18
70 80
13
20 34 45
90
20
24 50 100 15 20 100 120 22 23
6
5
20
21 105 140 18 21 50 70
Activity of the Test compound 3-(2’-Hydroxy-3’, 5’-dichlorophenyl)-4-benzoyl-5-(4’’-nitrophenyl)-1-phenylpyrazole (7a)
15
3
3
9
9
2
2
9
6
2
3
1
2
4
6
4
10
2
2
4
3
7
8
15
17
4
6
18 30
6
11
2
3
6
10
15 25
5
4
10
8
30
45
10
15 20
50
8
10
30 50
10 15
4
5
8
12
30 40
7
8
15 20
60
12
18 22
65
10 14
55 70
15 20
5
8
12
16
50 65
10
15 25 29
75
16
22 30
90
13 22
80 110 20 22
6
9
16
20
70 100 13 17 34 50
90
20
28 50 140 15 24 100 140 22 24
6
10
20
24 105 170 18 20 50 85
Poppy
(Papaver rhoeas)
Candytuft (Iberis sp)
Shoot
height
C
T
No of
leaves
C
T
3
6
8
12
15
18
2
4
7
11
15
19
9
15
45
60
100
130
5
20
40
70
105
150
3
6
8
12
15
18
4
8
12
15
19
24
9
15
45
60
100
130
10
27
62
100
145
205
3
6
8
12
15
18
3
7
12
15
19
23
9
15
45
60
100
130
8
18
56
98
135
200
3
6
8
12
15
18
4
10
14
19
21
22
9
15
45
60
100
130
15
37
65
100
150
190
Note: C= Control, T= Treated
Impact of newly synthesized titled compounds on the phytotic growth of some flowering plants:
Before the Treatment
RESULTS AND DISCUSSION
The synthesized compounds were screened for their growth
promoting activity on some flowering plants. The plants
used were Poppy, Pink, Candy tuft, Gaillardia Calendula,
Gladiolus. The efforts have been made to examine and
analyze the morphology of treated plants.
When the comparison of morphological characters was made
between those of treated and control groups plants, it was
interesting to note that all the plants exhibited significant
After the Treatment
shoot growth, and considerable increase in the number of
leaves as compared to those of untreated ones.
ACKNOWLEDGEMENT
The authors are thankful to SAIF, CDRI, Lucknow for providing the spectral
data. I am also thankful to the eminent faculty members of Dr. P. D. K. V.
Akola, Dr. R. M. Gide, Professor, Department of Plant Pathology, Mrs.
M.S. Gaikwad, Senior Research Asst., Department of Plant pathology, Dr.
Paithankar, Asst. Prof., Department of Horticulture, Dr. Ashish U. Nimkar
Page 207
Hushare VJ et al. IRJP 2013, 4 (1)
Asst. Prof., Department of forestry for providing the necessary help for the
completion of interdisciplinary part of the present work.
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