Synthesis, characterization and antimicrobial studies of new bispyrazolines linked via 3-aryl ring with aliphatic chains

Article abstract of DOI:10.1016/j.saa.2012.05.028

The bispyrazolines 4a(a′-f′) and 4b(a′-f′) built around the aliphatic chains of varying lengths have been prepared by refluxing bischalcones 3a(a′-f′) and 3b(a′-f′) with phenyl hydrazine in alcoholic medium. The reactions of chalcones 2a and 2b with suitable 1,ω-dibromoalkanes in the presence of anhydrous K ₂CO₃/dry acetone and Bu₄N⁺I ^- (PTC) provided 3a(a′-f′) and 3b(a′-f′), respectively. The antibacterial and antifungal activities of the synthesized compounds were evaluated against five bacterial and four fungal strains. The compounds 3ba′, 3bc′, 3bd′, 3be′, 3af′, 4aa′ and 4ba′ showed better MIC (μg/mL) against the tested microorganisms.

Full text of DOI:10.1016/j.saa.2012.05.028

Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 96 (2012) 295–304
Contents lists available at SciVerse ScienceDirect
Spectrochimica Acta Part A: Molecular and
Biomolecular Spectroscopy
journal homepage: www.elsevier.com/locate/saa
Synthesis, characterization and antimicrobial studies of new bispyrazolines
linked via 3-aryl ring with aliphatic chains
⇑
Mohamad Yusuf , Payal Jain
Department of Chemistry, Punjabi University, Patiala 147002, Punjab, India
g r a p h i c a l a b s t r a c t
h i g h l i g h t s
Syntheses of new bispyrazolines built around the aliphatic chains of varying length have been described.
The structures of these bisheterocyclics were determined from the rigorous analysis of their spectro-
scopic data. The significant antimicrobial activities were exhibited by the bischalcones and bispyrazolines
built around internal spacer consisting of the even number of methylene groups.
"
The bispyrazolines built around the
aliphatic chains of varying lengths
are synthesized.
These compounds have been
obtained from the cyclization
reactions of the bischalcones with
phenyl hydrazine.
"
"
"
All the products were characterized
by using various spectroscopic
techniques.
The prepared compounds were also
evaluated for their antimicrobial
activities.
a r t i c l e i n f o
a b s t r a c t
The bispyrazolines 4a(a0–f0) and 4b(a0–f0) built around the aliphatic chains of varying lengths have been
prepared by refluxing bischalcones 3a(a0–f0) and 3b(a0–f0) with phenyl hydrazine in alcoholic medium.
Article history:
Received 30 March 2012
Received in revised form 2 May 2012
Accepted 10 May 2012
The reactions of chalcones 2a and 2b with suitable 1,x-dibromoalkanes in the presence of anhydrous
K2CO3/dry acetone and Bu4N+Iꢀ (PTC) provided 3a(a0–f0) and 3b(a0–f0), respectively. The antibacterial
Available online 22 May 2012
and antifungal activities of the synthesized compounds were evaluated against five bacterial and four
fungal strains. The compounds 3ba0, 3bc0, 3bd0, 3be0, 3af0, 4aa0 and 4ba0 showed better MIC (
lg/mL)
against the tested microorganisms.
Keywords:
Aliphatic chains
Chalcones
Ó 2012 Elsevier B.V. All rights reserved.
Bischalcones
Heterocyclic rings
Antimicrobial activity
Introduction
systems [1]. The derivatives of chalcones are the significant com-
pounds which are associated with a wide range of biological activ-
ities [2–11]. Chalcones are the compounds having 1,3-diaryl-2-
propene moiety, containing an olefinic, ketonic and /or hydroxy
group [2,4,6]. Amongst different heteroatomic cycles, pyrazoline
have played a crucial part in the development of the heterocyclic
systems and are also extensively used in the organic synthesis
[12–16]. Pyrazolines are generally prepared from the condensation
The studies of heterocyclic compounds had been remain the
subject of the major attraction in the past due to their occurrence
in nature and numerous applications displayed in the biological
⇑
Corresponding author. Tel.: +91 175 3046409; fax: +91 175 2283073.
E-mail address: yusuf_sah04@yahoo.co.in (M. Yusuf).
1386-1425/$ - see front matter Ó 2012 Elsevier B.V. All rights reserved.
http://dx.doi.org/10.1016/j.saa.2012.05.028

296
M. Yusuf, P. Jain / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 96 (2012) 295–304
reaction of a variety of substituted chalcones with hydrazine and
its derivatives under acidic and basic medium [17–25]. Pyrazoline
compounds have also gained much interest because of their wide
range of applications in biological and pharmaceutical chemistry.
Bispyrazolines are the molecules which are formed by joining
two pyrazoline moieties together through the carbon chains. In
the recent past, we have been actively engaged in the synthesis
of heterocyclic compounds having more than one heteroatom
[26]. In the past some results are reported upon the synthesis of
bispyrazolines [27–31], but very little attention has been paid
upon the compounds linked through the flexible chain of variable
length. This aspect has prompted us to study the synthesis of
bispyrazolines 4a(a0–f0) and 4b(a0–f0) built around the carbon chain
ranging from four to twelve carbon units. The major interest be-
hind this study was to investigate the affect of internal spacer
length upon the formation and antimicrobial behavior of the
bispyrazolines.
from the O-alkylation of 2a and 2b with suitable 1, x-dib-
romoalkanes in the presence of anhydrous K2CO3/dry acetone
and Bu4N+Iꢀ as PTC. In the absence of PTC (Bu4N+Iꢀ), the yields
of bischalcones were very low and also involved long reaction
times. The cyclization reaction [27] of 3a(a0–f0) and 3b(a0–f0)
with phenyl hydrazine under alcoholic condition led to the for-
mation of bispyrazolines 4a(a0–f0) and 4b(a0–f0) which were crys-
tallized from CH3OH to give pure compounds in moderate yields
(Scheme 1). The structures of the prepared compounds 3a(a0–f0),
3b(a0–f0), 4a(a0–f0) and 4b(a0–f0) were determined from the rigor-
ous analysis of their IR, 1H-NMR, 13C-NMR and Mass spectral
data. The purity of these compounds was also very well sup-
ported by their elemental analysis results (see experimental).
IR spectra of bischalcones 3a(a0–f0) and 3b(a0–f0) exhibited car-
bonyl group absorptions in the region at 1665–1652 cmꢀ1 and
bands present in the region at 1603–1590 cmꢀ1 could be ascribed
to C@C stretching. The other significant bands were found in the
region at 2948–2850 (methylene C–H), 1040–1020 and 1240–
1230 (C–O) cmꢀ1. In their 1H-NMR spectra, two broad doublets
resonating at d 7.60–7.11 and 7.41–7.17 could be assigned to H-
3 and H-2, respectively. The coupling value of 15.9 Hz between
these hydrogens describes the trans geometry around the C-2
and C-3 double bond. The doublets in the range of d 7.20–7.02
and 7.45–6.97 may be allotted to aromatic protons H-300, 500 and
H-200, 600, respectively in 3b(a0–f0) while these hydrogens in
Results and discussion
The bispyrazolines 4a(a0–f0) and 4b(a0–f0) needed for the pres-
ent investigations were prepared starting from the Claisen–
Schmidt reaction of o-hydroxy-acetophenone with benzalde-
hyde/tolualdehyde which yielded chalcones 2a and 2b. The bis-
chalcones 3a(a0–f0) and 3b(a0–f0) were obtained in good yields
3
OH
OH
a
Ar
ArCHO
+
CH3
O
O
2a & 2b
1
b
3'
O
CH2
( CH2)n
CH2
O
2'
4'
2
1'
1
3
5'
Ar
Ar
6'
3a(a'-f') & 3b(a'-f')
O
O
c
3'
O
CH2
( CH2)n
CH2
O
2'
4'
H
HM
1'
M
5'
4
3
HA
HA
Ar
2
N
6'
5
N
1
Ar
N
N
HX
HX
1'''
6'''
2'''
3'''
5'''
4'''
4a(a'-f') & 4b(a'-f')
a
b
3''
3''
a'
b' c' d' e'
f'
CH3
4''
5''
4''
5''
2''
1''
2''
1''
n = 2, 3, 4, 6, 8, 10
Ar =
,
;
6' '
6' '
Reaction Conditions: a) NaOH/dry EtOH/0ο C; b) BrCH (CH ) CH Br/K CO /dry acetone/Bu N+I-/ ; c) PhNHNH /dry EtOH/ AcOH/
Δ
Δ
2
2
n
2
2
3
2
4
Scheme 1. Synthesis of bispyrazolines 4a(a’-f’) & 4b(a’-f’).

M. Yusuf, P. Jain / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 96 (2012) 295–304
297
Table 1
13C-NMR data of bischalcone 3a(a0–f0).
Compound C-1
C-20
C-3
C-400
C-10
C-100
C-60
C-
200,600
C-40
C-50
C-
300,500
C-2
C-30
OCH2(CH2)n-
3aa0
3ab0
3ac0
3ad0
3ae0
192.80 157.50 142.62 134.67 133.78 132.34 129.40 128.61 128.24 127.25 120.51 112.71 112.23 67.70, 26.04
192.94 157.58 142.67 134.89 133.60 132.26 129.62 128.70 128.10 127.24 120.50 112.72 112.20 67.73, 29.00, 25.60
192.60 157.61 142.65 135.72 135.85 132.40 129.53 128.50 128.22 127.32 120.31 112.64 112.10 68.29, 29.20, 25.90
192.89 157.82 142.42 135.20 133.04 130.16 129.36 128.85 128.31 127.28 120.68 112.38 112.30 68.54, 30.97, 29.17, 26.16
190.96 158.90 142.70 135.80 132.83 130.50 129.57 128.53 128.35 127.26 120.64 112.61 112.14 68.35, 29.18, 29.00, 26.35,
26.01
3af0
190.98 156.87 142.74 134.09 132.80 130.54 129.51 128.59 128.19 127.38 120.34 112.62 112.19 68.62, 29.53, 29.42, 29.38,
29.28, 26.45
Table 2
13C-NMR data of bischalcone 3b(a0–f0).
Compound C-1
C-20
C-3
C-400
C-10
C-100
C-60
C-
200,600
C-40
C-50
C-
300,500
C-2
C-30
OCH2(CH2)n-
CH3
3ba0
3bb0
3bc0
3bd0
192.96 157.44 142.66 140.68 132.79 132.33 130.40 129.63 129.43 128.32 126.49 120.72 112.25 67.78, 26.10
192.92 157.53 142.74 140.62 132.80 132.36 130.45 129.66 129.48 128.27 126.52 120.75 112.28 67.74, 29.06, 25.80 21.42
192.95 157.66 142.62 140.64 132.83 132.41 130.48 129.64 129.50 128.30 126.38 120.67 112.34 68.32, 29.09, 25.92 21.45
192.99 157.74 142.68 140.58 132.84 132.46 130.50 129.60 129.56 128.34 126.59 120.66 112.41 68.58, 29.29,
29.18, 26.15
192.86 157.78 142.70 140.55 132.89 132.42 130.54 129.61 128.31 128.25 126.56 120.63 112.42 68.50, 29.25,
21.46
21.48
21.40
21.49
3be0
3bf0
29.20, 26.38, 26.12
192.97 157.81 142.67 140.51 132.86 132.51 130.53 129.59 128.35 126.39 126.53 120.64 112.44 68.67, 29.56,
29.48, 29.43,
29.38, 26.28
3a(a0–f0) appeared at d 7.34–6.93 and 7.60–7.47, respectively as
multiplets. Additional sharp singlet was observed due to CH3
group at d 2.37–2.31 in 3b(a0–f0). The OCH2 protons of the internal
spacer were placed at d 4.03–3.89 and the remaining methylene
groups of the flexible chain exhibited signals of appropriate mul-
tiplicities at d 1.88–1.00 (see experimental). In the 13C-NMR spec-
tra of 3a(a0–f0) and 3b(a0–f0), the spacer methylene groups were
resonating at d 68.67–67.70 (OCH2) and d 30.97–25.60 {(CH2)n}
the downfield resonance of the former suggests their placement
near an electronegative oxygen atom. Other noticeable signals
in these compounds were found to be placed at d 192.99–
190.96 (C@O), 120.75–112.38 (C-2) and 142.74–142.42 (C-3)
(see Tables 1 and 2).
significant resonance was observed at d 157.05–155.48 due to C-
20 and the downfield shifting of this carbon was based upon its di-
rect bonding to the oxygen atom of the alkoxy chain (see Tables 3
and 4).
Antimicrobial evaluation
All cultures were obtained from MTCC (Microbial Type Culture
Collection and Gene Bank, Chandigarh 160036, India). The newly
prepared compounds were screened for their antibacterial and
antifungal activity using paper disc method [32] in vitro against
Klubsellia pneumoniae (MTCC 3384), Pseudomonas aeruginosa
(MTCC 424), Escherichia coli (MTCC 443), Staphylococcus aureus
(MTCC 96), Bacillius subtilis (MTCC 441) and Aspergillius janus
(MTCC 2751), Aspergillius niger (MTCC 281), Aspergillius flavus
IR spectra of 4a(a0–f0) and 4b(a0–f0) did not reveal any absorp-
tion in the region of 1665–1652 cmꢀ1 which describes the absence
of C@O group in these derivatives. In the 1H-NMR spectra of these
products, the resonances corresponding to the double bond hydro-
gens (H-3 and 2) at d 7.60–7.11 and 7.41–7.17 of the bischalcones
3a(a0–f0) and 3b(a0–f0) were found missing altogether which indi-
cates the involvement of the enone moiety during the cyclization
reaction. The significant pyrazoline ring protons HX, HM and HA
produced well defined resonances at d 5.25–5.09 (dd), 4.13–3.73
(dd) and 3.35–3.17 (dd), respectively. The vicinal coupling constant
(3J) between HX and HM was found to be 12.0–12.2 Hz which re-
flects that these hydrogens are cis to each other while coupling va-
lue of JXA = 6.7–7.1 Hz and JMA = 17.2–17.8 Hz describes the trans
relationship between HX and HA and HM and HA are geminally
placed at C-40. The most downfield resonance at d 8.02–7.82 may
be attributed to hydrogen (H-60) belonging to the phenyl ring pres-
ent at C-3 position of the pyrazoline moiety. The upfield resonance
of the H-30 at d 6.90–6.62 can be easily ascribed to the +I effect of
the alkoxy group at C-20 position. In the 13C-NMR spectra of 4a(a0–
f0) and 4b(a0–f0), the signal corresponding to C@O group of bischal-
cones at d 193–190 was not present which also corroborates the
involvement of this functionality in the formation of pyrazoline
moiety. The signals resonating at d 147.98–146.53, 46.93–44.35
and 65.87–63.31 could be generated by the C-3, C-4 and C-5,
respectively which are belonging to the pyrazoline ring. Other
(MTCC 277) and Pencillium glabrum (MTCC 4951) at conc. 100 lg/
ml. Amoxicillin and Fluconazole were used as reference drugs for
comparison. In this method, a standard 5 mm diameter sterilized
filter paper disc impregnated with the compound was placed on
an agar plate seeded with the test organism. The plates were incu-
bated for 24 h at 37 °C for bacteria and 48 h at 28 °C for fungi. The
zone of inhibition of bacterial and fungal growth around the disc
was observed. DMSO was used as a control. The control did not
show any activity against the strains of micro-organisms used
and the zone of inhibition (mm) has been recorded as the average
diameters which are given in Figs. 3 and 4. MIC of all the com-
pounds were evaluated by using serial tube dilution methods
[33] at various conc. of 128, 64, 32, 16, 8, 4, 2, 1
All the compounds were also tested for MIC by using serial tube
dilution method at concentration 128, 64, 32, 16, 8, 4, 2, 1 g/mL
against above said microorganisms and observed minimum inhib-
itory concentration (MIC- g/ml) values are given in Tables 5 and 6
lg/mL.
l
l
and observed MIC results have also been depicted in Figs. 1 and 2.
Most of the compounds showed significant activity against tested
microorganisms and the compounds 3ba0, 3bc0, 3bd0, 3be0, 3af0,
4aa0 and 4ba0 showed better MIC against above said microorgan-
isms at conc. of 4 lg/ml (Tables 5 and 6).

298
M. Yusuf, P. Jain / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 96 (2012) 295–304
Table 3
13C-NMR data of bispyrazolines 4a(a0–f0).
Compound C-20
C-3
C-1000, C-100,
C-400
C-40
C-
3000,5000
C-60
C-
300,500
C-
200,600
C-10, C-50,
C-4000
C-30
C-2000
6000
,
OCH2(CH2)n
C-5
C-4
4ba0
4bb0
4bc0
4bd0
4be0
4bf0
156.78 146.61 146.54,
142.79 129.97 128.95 128.52 125.85 122.12,
113.86 112.27 67.75, 26.16
64.35 46.74
64.30 46.70
64.48 46.89
64.55 46.91
63.31 45.75
64.34 44.35
144.95,
140.92
156.06 146.54 146.93,
144.90,
139.91
156.93 146.75 146.72,
120.89,
118.80
142.24 129.25 128.84 128.73 125.54 122.06,
112.97 112.04 67.72, 29.00, 26.51
112.62 112.12 68.27, 29.28, 25.79
120.59,
118.70
142.96 129.70 128.90 128.22 125.90 122.00,
145.07,
120.86,
118.39
140.96
156.53 147.98 145.14,
144.00,
140.30
157.05 146.91 146.82,
144.34,
139.91
155.48 147.89 146.79,
143.35,
142.21 129.94 128.89 128.08 124.78 121.90,
112.98 112.16 68.52, 29.52, 26.43,
18.45
120.00,
118.77
142.91 128.83 128.75 128.00 124.67 121.76,
113.25 112.20 68.48, 29.62, 29.22,
26.38, 25.20
120.62,
118.65
142.88 128.59 128.87 128.26 124.72 121.87,
112.30 112.13 68.40, 29.60, 29.18,
26.40, 26.22, 25.10
120.65,
118.63
139.92
Table 4
13C-NMR data of bispyrazolines 4b(a0–f0).
Compound C-20
C-3
C-1000, C-
100, C-400
C-40
C-3000
C5000
,
C-60
C-300,
C-500
C-
200,600
C-10, C-
50, C-4000
C-30
C-2000
C-6000
,
OCH2(CH2)n-
C-5
C-4
CH3
4aa0
4ab0
4ac0
4ad0
4ae0
4af0
156.86 146.76 145.14,
137.05 129.74 129.69 128.99 125.94 122.18,
113.30 112.25 67.97, 26.28
65.87 45.98 21.20
64.23 46.27 21.18
63.48 45.67 21.14
63.31 45.88 20.22
64.36 46.93 21.12
64.38 46.81 21.32
145.12,
139.99
156.84 146.72 145.11,
145.08,
139.98
156.81 146.53 145.39,
120.82,
118.75
137.00 129.70 129.66 128.95 125.90 122.15,
113.28 112.15 67.75, 29.10,
28.51
120.79,
118.72
137.01 129.68 129.62 128.92 125.88 122.12,
113.23 112.12 67.64, 29.45,
26.48
145.03,
120.76,
118.70
139.92
155.97 147.90 145.78,
144.15,
138.97
155.69 147.95 146.89,
143.38,
138.89
155.82 147.87 146.90,
143.40,
136.87 128.80 128.61 128.09 124.84 121.11,
112.28 111.12 67.25, 28.33,
25.27, 25.13
119.63,
117.67
136.90 128.90 128.88 128.08 124.74 121.90,
113.32 112.17 68.42, 29.64,
29.29, 26.40,
120.65,
118.70
26.24
136.93 128.91 128.83 128.02 124.76 121.91,
113.34 112.19 68.34, 29.62,
29.22, 26.64,
120.68,
118.73
138.77
26.15, 25.12
In vitro MIC of compounds 3aa'-3af' & 4aa'-4af'
18
16
14
12
10
8
E. coli
K. pneumoniae
P. aeruginosa
S. aureus
B. subtillius
Aspergillius janus
Pencillium glabrum
Aspergillius niger
Aspergillius flavus
6
4
2
0
Compounds
g/mL) of compounds 3aa0–3af0 and 4aa0–4af0.
Fig. 1. In vitro MIC (
l

M. Yusuf, P. Jain / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 96 (2012) 295–304
299
In vitro MIC of compounds 3ba'-3bf' & 4ba'-4bf'
18
16
14
12
10
8
E. coli
K. pneumoniae
P. aeruginosa
S. aureus
B. subtillis
Aspergillius janus
Pencillium glabrum
Aspergillius niger
Aspergillius flavus
6
4
2
0
Compounds
Fig. 2. In vitro MIC (
l
g/mL) of compounds 3ba0–3bf0 and 4ba0–4bf0.
In vitro Zone of inhibition of compounds 3aa'-3af' & 4aa'-4af'
30
E. coli
25
20
15
10
5
S. aureus
K. pneumoniae
P. aeruginosa
B. subtillis
Aspergillius janus
Pencillium glabrum
Aspergillius niger
Aspergillius flavus
0
Compounds
Fig. 3. In vitro Zone of Inhibition of compounds 3aa0–3af0 and 4aa0–4af0.
In vitro Zone of inhibition of compounds 3ba'-3bf' & 4ba'-4bf'
30
25
20
15
10
5
E. coli
S. aureus
K. pneumoniae
P.aeruginosa
B. subtillis
Aspergillius janus
Pencillium glabrum
Aspergillius niger
Aspergillius flavus
0
Compounds
Fig. 4. In vitro Zone of inhibition of compounds 3ba0–3bf0 and 4ba0–4bf0.
It may be evaluated that the bischalcone 3af0 showed significant
activity against A. janus whereas the compound 3ba0, 3bc0, 3bd0 and
3be0 showed activity against the strain P. aeruginosa while the
compounds 3bc0, 3bd0 and 3be0 showed significant activity against

300
M. Yusuf, P. Jain / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 96 (2012) 295–304
Table 5
MIC (in l
g/mL) of compounds 3aa0–3af0 and 4aa0–4af0.
Compound No.
Gram (ꢀve) bacteria
Gram (+ve) bacteria
Fungi
E. coli
K. pneumoniae
P. aeruginosa
S. aureus
B. subtilis
A. janus
P. glabrum
A. niger
A. flavus
3aa0
16
16
16
8
8
8
8
16
8
8
8
16
16
8
8
16
8
4
8
8
8
16
16
16
16
8
8
16
8
16
8
16
16
2
16
8
16
16
8
16
16
8
16
8
4
8
8
8
8
8
8
–
16
16
16
16
8
16
8
16
8
16
16
8
–
1
8
8
8
16
16
8
8
8
8
8
8
8
3ab0
3ac0
16
16
16
16
16
16
8
16
16
16
2
16
16
16
16
16
8
3ad0
8
3ae0
16
16
16
16
8
3af0
4aa0
4ab0
4ac0
8
4ad0
8
16
16
16
–
4ae0
8
8
2
–
16
16
2
16
16
–
4af0
16
2
–
Amoxicillin
Fluconazole
–
–
–
1
1
1
Table 6
MIC (in
l
g/mL) of compounds 3ba0–3be0 and 4ba0–4be0.
Compound No.
Gram (ꢀve) bacteria
Gram (+ve) bacteria
Fungi
E. coli
K. pneumoniae
P. aeruginosa
S. aureus
B. subtilis
A. janus
P. glabrum
A. niger
A. flavus
3ba0
16
16
16
8
16
16
16
16
16
16
16
8
8
8
8
8
8
4
16
4
4
4
8
8
8
16
8
8
16
8
8
8
8
8
4
4
4
16
16
16
8
16
16
16
16
16
8
8
16
16
16
16
16
16
8
8
8
16
16
–
8
8
8
4
4
16
16
16
8
16
16
8
16
4
16
16
8
8
8
16
16
–
3bb0
3bc0
3bd0
3be0
3bf0
8
8
8
8
8
4
4ba0
4bb0
16
16
16
8
16
2
16
16
16
8
16
2
16
16
16
16
16
2
4bc0
4bd0
8
4be0
16
16
2
16
16
–
16
16
–
4bf0
Amoxicillin
Fluconazole
2
–
–
–
–
–
1
1
1
1
the microorganism B. subtilis. The compounds 3bd0 and 3be0 also
showed significant antifungal activity against A. niger, A. flavus.
Among the pyrazolines the compounds 4aa0 showed activity
against K. pneumoniae while 4ba0 showed significant activity
against B. subtilis.
It is evident from the above MIC data that bischalcones linked
through the internal chain of four, six, eight and ten carbon atoms
were more active in the present investigations. Similarly, the
bispyrazolines built around four, six and eight methylene spacer
units also provided significant results. Thus, compounds involving
longer internal chain consisting of even number of carbon atoms
seem to be better antimicrobial products. The importance of this
work lies in the possibility that the new compounds might be more
efficacious derivatives against the strains for which investigations
regarding the more biological studies could be helpful in designing
the potent antimicrobial agents.
Experimental
Melting points reported are uncorrected. IR spectra were
scanned in KBr pellets on a Perkin Elmer RXIFT Infrared spectro-
photometer. 1H-NMR spectra were recorded on a 400 MHz Bruker
spectrometer using TMS as the internal standard. The mass spectra
have been scanned on the Waters Micromass Q-T of Micro (ESI)
spectrometer. TLC plates were coated with silica gel suspended
in MeOH–CHCl3 and iodine vapors were used as visualizing agent.
Synthesis of (E)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one (2a)
A solution of O-hydroxyacetophenone (5.0 ml, 0.0070 mol),
benzaldehyde 1a (5.0 ml, 0.0070 mol) and NaOH (5.0 g,
0.024 mol) in EtOH (25.0 ml) was stirred for 10 h at 0 °C. During
the course of reaction, the initially formed creamish mixture chan-
ged to a reddish gummy mass. The resulting mass was poured into
iced-HCl to provide a crude material which was crystallized from
CH3OH to yield a pure yellow compound 2a.
Conclusion
It may be concluded that this study describes the general meth-
od for the synthesis of some bispyrazolines linked through the 3-
aryl ring under the normal conditions. The significant antimicro-
bial activities were provided by the bischalcones and bispyrazo-
lines built around internal spacer consisting of the even number
of methylene groups.
2a: Yellow needles, Yield 82%; m.p.: 55–57 °C [34]. IR (KBr)
cmꢀ1: 3461 (OH), 1695 (C@O), 1604 (C@C); 1H-NMR (400 MHz,
CDCl3): d 12.81 (1H, s, OH), 7.94 (1H, dd, Jp,o = 1.0, 8.4 Hz, H-60),
7.91 (1H, d, Jtrans = 15.5 Hz, H-3), 7.68 (2H, dt, J = 1.0, 2.8, 4.4 Hz,
H-200, 600), 7.65 (1H, d, Jtrans = 15.5 Hz, H-2), 7.51 (1H, td, Jm,o = 1.6,
7.2 Hz, H-40), 7.44 (3H, m, H-300,400,500), 7.04 (1H, dd, Jp,o = 1.0,

M. Yusuf, P. Jain / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 96 (2012) 295–304
301
8.4 Hz, H-50), 6.95 (1H, td, Jp,o = 1.1, 8.1 Hz, H-30). MS(ESI): m/z
3ad0: Brown solid; Yield 73%; m.p.: 70–72 °C. IR (KBr) cmꢀ1
:
1659 (C@O), 1599 (C@C), 2936 and 2858 (methylene C–H), 1240
and 1025 (C–O); 1H-NMR (400 MHz, CDCl3): d 7.59 (2H, dd,
Jm,o = 1.8, 7.6 Hz, H-60), 7.54 (2H, d, Jtrans = 15.9 Hz, H-3), 7.47 (4H,
ddd, Jp,m,o = 0.56, 1.8, 7.8 Hz, H-200,600), 7.35 (2H, d, Jtrans = 15.9 Hz,
H-2), 7.40 (2H, ddd, Jp,m,o = 0.5, 1.9, 7.6 Hz, H-40), 7.27 (6H, m, H-
300,400,500), 6.95 (2H, td, Jm,o = 1.8, 7.5 Hz, H-50), 6.88 (2H, d,
Jo = 8.3 Hz, H-30), 3.91 (4H, t, Jvic = 6.2 Hz, OCH2CH2CH2CH2), 1.86
(4H, quintet, Jvic = 3.5 Hz, OCH2CH2CH2CH2), 1.60 (4H, quintet,
Jvic = 2.3 Hz, OCH2CH2CH2CH2), 1.00 (4H, quintet, Jvic = 3.5 Hz,
OCH2CH2CH2CH2); MS(ESI): m/z (M + H)+ = 559. Anal. Calc. for
(M + 1)+ = 225. Anal. Calc. for C15O2H12: Calc. C, 80.35%; H, 5.36%;
Found: C, 80.43%; H, 5.28%.
Synthesis of (2E, 20E)-1,10-(2,20-(butane-1,4-diylbis(oxy))bis(2,1-
phenylene))bis(3-phenylprop-2-en-1-one) (3aa0)
A suspension of chalcone 2a (2.0 g, 0.00840 mol), K2CO3 (2.0 g),
1,4-dibromobutane (0.90754 g, 0.00420168 mol) and tetrabutyl
ammonium iodide (1.0 g) in dry acetone (25 ml) was refluxed for
6 h with continuous stirring. The progress of reaction was moni-
tored by TLC. After the completion of reaction, the reaction mixture
turned into a colorless mass which was poured over iced-HCl to
provide crude solid which was recrystallized from CH3OH:CHCl3
(3:1) to yield a pure compound 3aa0.
C
38O4H38: Calc. C, 81.72%; H, 6.81%; Found: C, 81.68%; H, 6.85%.
Synthesis of (2E, 20E)-1,10-(2,20-(decane-1,10-diylbis(oxy))bis(2,1-
phenylene))bis(3-phenylprop-2-en-1-one) (3ae0)
3aa0: Yellow solid; Yield 68%; m.p.: 92–94 °C. IR (KBr) cmꢀ1
:
1660 (C@O), 1596 (C@C), 2930 and 2862 (methylene C–H), 1230
and 1025 (C–O); 1H-NMR (400 MHz, CDCl3): d 7.62 (2H, dd,
Jp,o = 1.7, 7.6 Hz, H-60), 7.52 (2H, d, Jtrans = 15.9 Hz, H-3), 7.50 (4H,
m, H-200, 600), 7.42 (2H, ddd, Jp,m,o = 1.0, 1.8, 7.4 Hz, H-40), 7.34 (6H,
m, H-300,400, 500), 7.31 (2H, d, Jtrans = 15.9 Hz, H-2), 7.02 (2H, td,
Jp,o = 0.72, 7.4 Hz, H-50), 6.82 (2H, d, Jo = 8.2 Hz, H-30), 3.90 (4H, t,
Jvic = 2.6 Hz, OCH2CH2), 1.88 (4H, t, Jvic = 2.6 Hz, OCH2CH2); MS(ESI):
m/z (M + Na)+ = 525. Anal. Calc. for C34O4H30: Calc. C, 81.27%; H,
5.97%; Found: C, 81.32%; H, 6.01%.
The bischalcone 3ae0 was prepared by reacting chalcone 2a
(2.0 g,
0.00840 mol)
with
1,10-dibromodecane
(1.260 g,
0.00420168 mol) under similar conditions as described earlier for
3aa0.
3ae0: Brown solid; Yield 75%; m.p.: 58–60 °C. IR (KBr) cmꢀ1
:
1665 (C@O), 1602 (C@C), 2938 and 2870 (methylene C–H), 1240
and 1025 (C–O); 1H-NMR (400 MHz, CDCl3): d 7.59 (2H, dd,
Jm,o = 1.7, 7.9 Hz, H-60), 7.55 (2H, d, Jtrans = 15.9 Hz, H-3), 7.48 (4H,
td, Jm,o = 1.8, 7.8 Hz, H-200, 600), 7.40 (2H, ddd, Jp,m,o = 1.0, 1.9,
7.6 Hz, H-40), 7.36 (2H, d, Jtrans = 15.9 Hz, H-2), 7.28 (6H, m, H-
300,400,500), 6.95 (2H, t, Jo = 7.5 Hz, H-50), 6.90 (2H, d, Jo = 8.3 Hz, H-
30), 3.96 (4H, t, Jvic = 6.1 Hz, OCH2CH2CH2CH2CH2), 1.65 (4H, quintet,
Jvic = 6.1 Hz, OCH2CH2CH2CH2CH2), 1.30 (4H, quintet, Jvic = 6.1 Hz,
OCH2CH2CH2CH2CH2), 1.18 (4H, m, OCH2CH2CH2CH2CH2), 1.07
(4H, m, OCH2CH2CH2CH2CH2); MS(ESI): m/z (M + Na)+ = 609. Anal.
Calc. for C40O4H42: Calc. C, 81.91%; H, 7.16%; Found: C, 81.86%; H,
7.12%.
Synthesis of (2E, 20E)-1,10-(2,20-(pentane-1,5-diylbis(oxy))bis(2,1-
phenylene))bis(3-phenylprop-2-en-1-one) (3ab0)
The bischalcone 3ab0 was prepared from the reaction of chal-
cone 2a (2.0 g, 0.00840 mol) with 1,5-dibromopentane
(0.9661342 g, 0.0042016 mol) under the similar conditions as used
for 3aa0.
3ab0: Yellow solid; Yield 60%; m.p.: 89–91 °C. IR (KBr) cmꢀ1
:
1654 (C@O), 1596 (C@C), 2948 and 2869 (methylene C–H), 1240
and 1025 (C–O); 1H-NMR (400 MHz, CDCl3): d 7.62 (2H, dd,
Jm,o = 1.7, 7.6 Hz, H-60), 7.54 (2H, d, Jtrans = 15.9 Hz, H-3), 7.50 (4H,
dd, Jm,o = 4.1, 7.6 Hz, H-200, 600), 7.40 (2H, ddd, Jp,m,o = 0.56, 1.8,
7.4 Hz, H-40), 7.36 (2H, d, Jtrans = 15.9 Hz, H-2), 7.28 (6H, m, H-
300,400,500), 7.00 (2H, td, Jp,o = 0.56, 7.6 Hz, H-50), 6.82 (2H, d,
Jo = 8.2 Hz, H-30), 3.93 (4H, t, Jvic = 6.2 Hz, OCH2CH2CH2), 1.50 (4H,
t, Jvic = 6.0 Hz, OCH2CH2CH2), 1.30 (2H, quintet, Jvic = 3.7 Hz,
OCH2CH2CH2); MS(ESI): m/z (M + 1)+ = 517. Anal. Calc. for
Synthesis of (2E, 20E)-1,10-(2,20-(dodecane-1,12-diylbis(oxy))bis(2,1-
phenylene))bis(3-phenylprop-2-en-1-one) (3af0)
The bischalcone 3af0 was synthesized by reacting chalcone 2a
(2.0 g, 0.00840 mol) with 1,12-dibromododecane (1.401 g,
0.00420168 mol) as described earlier for 3aa0.
3af0: Yellow solid; Yield 80%; m.p.: 60–64 °C. IR (KBr) cmꢀ1: 1655
(C@O), 1600 (C@C), 2919 and 2852 (methylene C–H), 1238 and
1022 (C–O); 1H-NMR (400 MHz, CDCl3): d 7.59 (6H, dd, Jm,o = 1.8,
7.6 Hz, H-200,400, 600), 7.39 (2H, d, Jtrans = 15.9 Hz, H-2), 7.11 (2H, d,
Jtrans = 15.9 Hz, H-3), 7.00 (4H, d, Jo = 8.0 Hz, H-30, 50), 6.93 (8H, m,
H-20, 60, 300, 500), 4.01 (4H., t, Jvic = 6.3 Hz, OCH2CH2CH2CH2CH2CH2),
1.72 (4H, quintet, Jvic = 6.3 Hz, OCH2CH2CH2CH2CH2CH2), 1.32 (4H,
quintet, Jvic = 7.2 Hz, OCH2CH2CH2CH2CH2CH2), 1.15 (4H, m,
OCH2CH2CH2CH2CH2CH2), 1.00 (8H, m, OCH2CH2CH2CH2CH2CH2);
MS(ESI): m/z (M)+ = 614. Anal. Calc. for C42O4H46: Calc. C, 82.08%;
H, 7.49%; Found: C, 82.13%; H, 7.53%.
C35O4H32: Calc. C, 81.39%; H, 6.20%; Found: C, 81.45%; H, 6.15%.
Synthesis of (2E, 20E)-1,10-(2,20-(hexane-1,6-diylbis(oxy))bis(2,1-
phenylene))bis(3-phenylprop-2-en-1-one) (3ac0)
The bischalcone 3ac0 was obtained from the reaction of chal-
cone 2a (2.0 g, 0.00840 mol) with 1,6-dibromohexane (1.025 g,
0.00420168 mol) under the similar conditions as described earlier
for 3aa0.
3ac0: Yellow solid; Yield 70%; m.p.: 82–84 °C. IR (KBr) cmꢀ1
:
1659 (C@O), 1603 (C@C), 2937 and 2870 (methylene C–H), 1236
and 1040 (C–O); 1H-NMR (400 MHz, CDCl3): d 7.65 (2H, dd,
Jm,o = 1.7, 7.6 Hz, H-60), 7.59 (2H, d, Jtrans = 15.9 Hz, H-3), 7.51 (4H,
dd, Jm,o = 4.1, 7.6 Hz, H-200, 600), 7.43 (2H, ddd, Jp,m,o = 0.6, 1.8,
7.4 Hz, H-40), 7.39 (2H, d, Jtrans = 15.9 Hz, H-2), 7.32 (6H, m, H-300,
400, 500), 7.01 (2H, td, Jp,o = 0.56, 7.6 Hz, H-50), 6.89 (2H, d, Jo = 8.2 Hz,
Synthesis of 1,4-bis-[3-(2-oxy-phenyl)-4,5-dihydro-1,5-diphenyl-1H-
pyrazole] butane (4aa0)
A mixture of bischalcone 3aa0 (1.0 g, 0.001886 mol), phen-
ylhydrazine (0.4080 g, 0.0037735 mol) and glacial AcOH (5 ml) in
dry EtOH (30 ml) was refluxed for 8 h. The progress of reaction
was monitored by TLC. The resulting reaction mixture was concen-
trated to obtain a solid compound which was further crystallized
from methanol to yield bis-pyrazoline 4aa0.
H-30), 3.90 (4H, t, Jvic = 6.2 Hz, OCH2CH2CH2), 1.58 (4H, t, Jvic
=
6.0 Hz, OCH2CH2CH2), 1.33 (4H, quintet, Jvic = 3.7 Hz, OCH2CH2
CH2); MS(ESI): m/z (M)+ = 530. Anal. Calc. for C36O4H34: Calc. C,
81.50%; H, 6.41%; Found: C, 81.46%; H, 6.46%.
4aa0: Yellow solid; Yield 68%; m.p.: 130–132 °C. IR (KBr) cmꢀ1
:
1598 (C@N), 2928 and 2873 (methylene C–H), 1239 and 1022 (C–
O); 1H-NMR (400 MHz, CDCl3): d 7.92 (2H, dd, Jp,o = 1.6, 7.8 Hz, H-
60), 7.28 (10H, m, H-3000,4000,5000,200,600), 7.15 (2H, td, Jm,o = 2.0, 7.8 Hz,
H-40), 6.99 (10H, m, H-2000, 6000,300,400,500), 6.82 (2H, td, Jm,o = 1.8,
7.6 Hz, H-50), 6.63 (2H, d, Jo = 8.4 Hz, H-30), 5.14 (2H, dd,
JXM = 12.1, JXA = 6.7 Hz, HX), 3.71 (4H, brs, OCH2CH2), 3.94 (2H, dd,
JMX = 12.1, JMA = 17.3 Hz, HM), 3.17 (2H, dd, JAX = 6.6, JAM = 17.7 Hz,
Synthesis of (2E, 20E)-1,10-(2,20-(octane-1,8-diylbis(oxy))bis(2,1-
phenylene))bis(3-phenylprop-2-en-1-one) (3ad0)
The bischalcone 3ad0 was obtained from the reaction of chal-
cone 2a (2.0 g, 0.00840 mol) and 1,8-dibromooctane (1.142 g,
0.00420168) under similar conditions as used for 3aa0.

302
M. Yusuf, P. Jain / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 96 (2012) 295–304
HA), 1.70 (4H, brs, OCH2CH2); MS(ESI): m/z (M + 1)+ = 683. Anal.
Calc. for C46O2N4H42: Calc. C, 80.93%; H, 6.15%; N, 8.21%; Found:
C, 80.96%; H, 6.10%; N, 8.16%.
4ae0: Brown solid; Yield 60%; m.p.: 110–112 °C. IR (KBr) cmꢀ1
:
1594 (C@N), 2929 and 2855 (methylene C–H), 1236 and 1020
1
(C–O); H-NMR (400 MHz, CDCl3): d 8.02 (2H, d, Jo = 7.8 Hz, H-60),
7.36 (10H, m, H-3000,5000,40,200,600), 7.05 (2H, td, Jm,o = 2.0, 7.8 Hz, H-
50), 7.10 (2H, d, Jo = 8.0 Hz, H-4000), 7.12 (4H, m, H-2000, 6000), 6.80
(2H, d, Jo = 8.0 Hz, H-30), 5.25 (2H, dd, JXM = 12.1, JXA = 6.9 Hz, HX),
4.13 (2H, dd, JMX = 12.1, JMA = 17.2 Hz, HM), 4.02 (4H, t, Jvic = 6.4 Hz,
OCH2CH2CH2CH2CH2), 3.35 (2H, dd, JAX = 7.0, JAM = 17.2 Hz, HA),
1.78 (4H, quintet, Jvic = 6.3 Hz, OCH2CH2CH2CH2CH2), 1.62 (4H,
quintet, Jvic = 6.2 Hz, OCH2CH2CH2CH2CH2), 1.35 (8H, m,
OCH2CH2CH2CH2CH2); MS(ESI): m/z (M)+ = 766. Anal. Calc. for
Synthesis of 1,5-bis-[3-(2-oxy-phenyl)-4,5-dihydro-1,5-diphenyl-1H-
pyrazole] pentane (4ab0)
The compound 4ab0 was synthesized from the reaction of bis-
chalcone 3ab0 (1.0 g, 0.001838 mol) with phenylhydrazine
(0.3975 g, 0.003676 mol) under similar conditions as described
above for 4aa0.
4ab0: Brown solid; Yield 65%; m.p.: 132–134 °C. IR (KBr) cmꢀ1
:
1592 (C@N), 2932 and 2866 (methylene C–H), 1240 and 1025 (C–
O); 1H-NMR (400 MHz, CDCl3): d 7.82 (2H, dd, Jp,o = 1.5, 7.8 Hz, H-
60), 7.18 (10H, m, H-2000,3000,5000,6000,40), 7.07 (4H, td, Jm,o = 2.1, 7.8 Hz,
H-2000, 600), 6.91 (2H, dd, Jp,o = 1.1, 7.8 Hz, H-50), 6.81 (2H, td,
Jp,o = 1.1, 8.0 Hz, H-4000), 6.72 (4H, td, Jm,o = 2.0, 7.8 Hz, H-300,500), 6.62
(2H, m, H-30), 5.09 (2H, dd, JXM = 12.0, JXA = 7.0 Hz, HX), 3.82 (4H,
m, OCH2CH2CH2), 3.73 (2H, dd, JMX = 12.1, JMA = 17.3 Hz, HM), 3.20
(2H, dd, JAX = 7.0, JAM = 17.3 Hz, HA), 1.60 (4H, quintet, Jvic = 6.8 Hz,
OCH2CH2CH2), 1.41 (2H, quintet, Jvic = 6.8 Hz, OCH2CH2CH2); MS(E-
SI): m/z (M)+ = 696. Anal. Calc. for C47O2N4H44: Calc. C, 81.03%; H,
6.32%; N, 8.04%; Found: C, 81.08%; H, 6.35%; N, 8.09%.
C52O2N4H54: Calc. C, 81.46%; H, 7.04%; N, 7.31%; Found: C,
81.41%; H, 7.02%; N, 7.36%.
Synthesis of 1,12-bis-[3-(2-oxy-phenyl)-4,5-dihydro-1,5-diphenyl-
1H-pyrazole] dodecane (4af0)
The compound 4af0 was synthesized from the reaction of bis-
chalcone 3af0 (1.0 g, 0.001502 mol) with phenylhydrazine
(0.3402 g, 0.003012 mol) under similar conditions as described
above for 4aa0.
4af0: Orange solid; Yield 67%; m.p.: 125–127 °C. IR (KBr) cmꢀ1
:
1599 (C@N), 2931 and 2878 (methylene C–H), 1238 and 1028 (C–
O); 1H-NMR (400 MHz, CDCl3): d 7.90 (2H, dd, Jp,o = 1.5 , 7.8 Hz, H-
60), 7.28 (2H, m, H-40), 7.19 (10H, m, H-2000000,3000,400,5000,6000), 7.05 (4H,
td, Jm,o = 2.0, 7.8 Hz, H-200, 600), 7.00 (2H, td, Jp,o = 1.4, 7.0 Hz, H-4000),
6.92 (2H, td, Jp,o = 1.4, 7.8 Hz, H-50), 6.80 (4H, td, Jm,o = 2.2, 7.8 Hz,
H-300, 500), 6.69 (2H, td, Jp,o = 1.6, 7.8 Hz, H-30), 5.12 (2H, dd,
JXM = 12.1, JXA = 7.08 Hz, HX), 4.00 (2H, dd, JMX = 12.1, JMA = 17.3 Hz,
HM), 3.90 (4H, m, OCH2CH2CH2CH2CH2CH2), 3.30 (2H, dd, JAX = 7.0,
JAM = 17.3 Hz, HA), 1.71 (4H, m, OCH2CH2CH2CH2CH2CH2), 1.30 (4H,
m, OCH2CH2CH2CH2CH2CH2), 1.21 (12H, m, OCH2CH2CH2CH2CH2
CH2); MS(ESI): m/z (M + H)+ = 795. Anal. Calc. for C54O2N4H58: Calc.
C, 81.61%; H, 7.30%; N, 7.05%; Found: C, 81.66%; H, 7.36%;
N, 7.08%.
Synthesis of 1,6-bis-[3-(2-oxy-phenyl)-4,5-dihydro-1,5-diphenyl-1H-
pyrazole] hexane (4ac0)
The compound 4ac0 was obtained from the reaction of bischal-
cone 3ac0 (1.0 g, 0.001792 mol) with phenylhydrazine (0.3875 g,
0.003584 mol) under same conditions as described above for 4aa0.
4ac0: Yellow solid; Yield 75%; m.p.: 150–152 °C. IR (KBr) cmꢀ1
:
1596 (C@N), 2934 and 2878 (methylene C–H), 1236 and 1025 (C–
O); 1H-NMR (400 MHz, CDCl3): d 7.89 (2H, dd, Jm,o = 1.7, 7.4 Hz, H-
60), 7.20 (10H, m, H-3000,5000,40,200,600), 7.09 (8H, m, H-4000, 300, 400, 500),
6.90 (2H, td, Jm,o = 1.9, 7.8 Hz, H-50), 6.67 (4H, td, Jp,o = 0.60,
7.8 Hz, H-2000,6000), 6.77 (2H, d, Jo = 8.0 Hz, H-30), 5.09 (2H, dd,
JXM = 12.1, JXA = 7.0 Hz, HX), 3.84 (6H, m, HM, OCH2CH2CH2), 3.23
(2H, dd, JAX = 7.0, JAM = 17.3 Hz, HA), 1.60 (4H, t, Jvic = 6.4 Hz,
OCH2CH2CH2), 1.32 (4H, quintet, Jvic = 2.8 Hz, OCH2CH2CH2); MS(E-
SI): m/z (M + Na)+ = 733. Anal. Calc. for C48O2N4H46: Calc. C,
81.12%; H, 6.47%; N, 7.88%; Found: C, 81.09%; H, 6.52%; N, 7.83%.
Synthesis of (E)-1-(2-hydroxyphenyl)-3-p-tolylprop-2-en-1-one (2b)
The compound 2b was prepared from o-hydroxyacetophenone
(5.0 ml, 0.0070 mol) and tolualdehyde (5.0 ml, 0.0070 mol) under
similar conditions as used for 2a.
Synthesis of 1,8-bis-[3-(2-oxy-phenyl)-4,5-dihydro-1,5-diphenyl-1H-
pyrazole] octane (4ad0)
2b: Yellow solid; Yield 80%; m.p.: 102–104 °C [34]. IR (KBr)
cmꢀ1: 3467 (OH), 1690 (C@O), 1600 (C@C); 1H-NMR (400 MHz,
CDCl3): d 12.87 (1H, s, OH), 7.93 (1H, ddd, Jp,m,o = 1.7, 3.0, 8.0 Hz,
H-50), 7.89 (1H, d, Jtrans = 15.4 Hz, H-3), 7.57 (2H, d, J = 8.0 Hz, H-
200, 600), 7.62 (1H, d, Jtrans = 15.4 Hz, H-2), 7.50 (1H, td, Jm,o = 1.6,
8.4 Hz, H-40), 7.24 (2H, d, Jo = 8.0 Hz, H-300,500), 7.03 (1H, dd,
Jp,o = 1.0, 8.4 Hz, H-50), 6.94 (1H, td, Jp,o = 1.1, 8.0 Hz, H-30), 2.40
(3H, s, CH3); MS(ESI): m/z (M + 1)+ = 239. Anal. Calc. for
The compound 4ad0 was prepared from the reaction of bischal-
cone 3ad0 (1.0 g, 0.001706 mol) with phenylhydrazine (0.3689 g,
0.003412 mol) under similar conditions as used for 4aa0.
4ad0: Orange solid; Yield 70%; m.p.: 165–167 °C. IR (KBr) cmꢀ1
:
1602 (C@N), 2925 and 2858 (methylene C–H), 1245 and 1028 (C–
O); 1H-NMR (400 MHz, CDCl3): d 7.97 (2H, dd, Jm,o = 1.6, 7.7 Hz, H-
60), 7.17 (2H, td, Jm,o = 1.8, 7.8 Hz, H-40), 7.22 (14H, m, H-
3000,5000,200,300,400,500,600), 7.05 (4H, dd, Jp,o = 0.6, 7.6 Hz, H-2000, 6000), 6.98
(2H, td, Jm,o = 2.0, 8.0 Hz, H-50), 6.87 (2H, d, Jo = 8.4 Hz, H-4000),
6.76 (2H, d, Jo = 7.2 Hz, H-30), 5.18 (2H, dd, JXM = 12.2, JXA = 7.2 Hz,
HX), 3.93 (2H, dd, JMX = 12.2, JMA = 17.8 Hz, HM), 4.08 (4H, t,
Jvic = 6.4 Hz, OCH2CH2CH2CH2), 3.31 (2H, dd, JAX = 7.1, JAM = 17.8 Hz,
HA), 1.72 (4H, quintet, Jvic = 6.6 Hz, OCH2CH2CH2CH2), 1.34 (4H,
quintet, Jvic = 6.2 Hz, OCH2CH2CH2CH2), 1.25 (4H, quintet,
Jvic = 6.2 Hz, OCH2CH2CH2CH2); MS(ESI): m/z (M)+ = 738. Anal. Calc.
for C50O2N4H50: Calc. C, 81.30%; H, 6.77%; N, 7.58%; Found: C,
81.34%; H, 6.80%; N, 7.53%.
C16O2H14: Calc. C, 80.67%; H, 5.88%; Found: C, 80.60%; H, 5.94%.
Synthesis of (2E,20E)-1,10-(2,20-(butane-1,4-diylbis(oxy))bis(2,1-
phenylene))bis(3-p-tolylprop-2-en-1-one) (3ba0)
The bischalcone 3ba0 was obtained from the reaction of chal-
cone 2b (2.0 g, 0.00820 mol) with 1,4-dibromobutane (0.90754 g,
0.00420168 mol) under the similar conditions as used for 3aa0.ꢀ1
3ba0: Yellow solid; Yield 68%; m.p.: 143–145 °C. IR (KBr) cm
:
1656 (C@O), 1598, (C@C), 2936 and 2871 (methylene C–H), 1235
and 1020 (C–O); 1H-NMR (400 MHz, CDCl3): d 7.62 (2H, dd,
Jm,p = 1.8, 3.6 Hz, H-60), 7.54 (2H, d, Jtrans = 15.9 Hz, H-3), 7.41 (6H,
m, H-200, 600, 40), 7.29 (2H, d, Jtrans = 15.9 Hz, H-2), 7.12 (4H, d,
Jo = 7.0 Hz, H-300, 500), 7.01 (2H, td, Jp,o = 0.6, 7.4 Hz, H-50), 6.82
(2H, d, Jo = 8.2 Hz, H-30), 3.89 (4H, t, Jvic = 6.2 Hz, OCH2CH2), 2.31
(6H, s, CH3), 1.88 (4H, quintet, Jvic = 6.2 Hz, OCH2CH2); MS(ESI):
m/z (M + Na)+ = 553. Anal. Calc. for C36O4H34: Calc. C, 81.50%; H,
6.41%; Found: C, 81.44%; H, 6.48%.
Synthesis of 1,10-bis-[3-(2-oxy-phenyl)-4,5-dihydro-1,5-diphenyl-
1H-pyrazole] decane (4ae0)
The compound 4ae0 was prepared from the reaction of bischal-
cone 3ae0 (1.0 g, 0.001628 mol) with phenylhydrazine (0.3522 g,
0.003257 mol) under similar conditions as described above for
4aa0.

M. Yusuf, P. Jain / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 96 (2012) 295–304
303
Synthesis of (2E,20E)-1,10-(2,20-(pentane-1,5-diylbis(oxy))bis(2,1-
phenylene))bis(3-p-tolylprop-2-en-1-one) (3bb0)
m/z (M + H)+ = 615. Anal. Calc. for C42O4H46: Calc. C, 82.08%; H,
7.49%; Found: C, 82.14%; H, 7.54%.
The bischalcone 3bb0 was prepared from the reaction of chalcone
2b (2.0 g, 0.00820 mol) with 1,5-dibromopentane (0.9661342 g,
0.0042016 mol) under the similar conditions as used for 3aa0.
Synthesis of (2E,20E)-1,10-(2,20-(dodecaness-1,12-diylbis(oxy))bis(2,1-
phenylene))bis(3-p-tolylprop-2-en-1-one) (3bf0)
3bb0: Yellow solid; Yield 60%; m.p.: 76–78 °C. IR (KBr) cmꢀ1
:
The bischalcone 3bf0 was prepared from the reaction of 2b
(2.0 g, 0.00840 mol) with 1,12-dibromododecane (1.401 g,
0.00420168 mol) as described for 3aa0.
1654 (C@O), 1599 (C@C), 2938 and 2863 (methylene C–H), 1237
and 1024 (C–O); 1H-NMR (400 MHz, CDCl3): d 7.62 (2H, dd,
Jm,o = 1.8, 3.7 Hz, H-60), 7.60 (2H, d, Jtrans = 15.8 Hz, H-3), 7.42 (6H,
m, H-200, 40, 00), 7.36 (2H, d, Jtrans = 15.8 Hz, H-2), 7.20 (4H, d,
Jo = 7.2 Hz, H-300, 500), 7.01 (2H, td, Jp,o = 0.7, 7.4 Hz, H-50), 6.94
(2H, d, Jo = 8.4 Hz, H-30), 4.03 (4H, t, Jvic = 6.4 Hz, OCH2CH2CH2),
2.37 (6H, s, CH3), 1.78 (4H, m, OCH2CH2CH2), 1.51 (2H, m,
OCH2CH2CH2); MS(ESI): m/z (M + 1)+ = 545. Anal. Calc. for
3bf0: Yellow solid; Yield 80%; m.p.: 93–95 °C. IR (KBr) cmꢀ1: 1653
(C@O), 1599 (C@C), 2917 and 2850 (methylene C–H), 1235 and 1020
(C–O); 1H-NMR (400 MHz, CDCl3): d 7.63 (4H, dd, Jm,o = 1.8, 7.6 Hz,
H-40, 60), 7.43 (2H, d, Jtrans = 15.9 Hz, H-3), 7.17 (2H, d, Jtrans = 15.9 Hz,
H-2), 7.02 (4H, d, Jo = 8.0 Hz, H-300, 500), 6.97 (8H, m, H-200, 600, 30, 50),
4.03 (4H., t, Jvic = 6.3 Hz, OCH2CH2CH2CH2CH2CH2), 2.34 (6H, s,
CH3), 1.76 (4H, quintet, Jvic = 6.3 Hz, OCH2CH2CH2CH2CH2CH2),
1.39 (4H, quintet, Jvic = 7.2 Hz, OCH2CH2CH2CH2CH2CH2),
1.20 (4H, m, OCH2CH2CH2CH2CH2CH2), 1.09 (8H, m, OCH2CH2
CH2CH2CH2CH2); MS(ESI): m/z (M + Na)+ = 665. Anal. Calc. for
C44O4H50: Calc. C, 82.24%; H, 7.78%; Found: C, 82.28%; H, 7.83%.
C37O4H36: Calc. C, 81.61%; H, 6.62%; Found: C, 81.68%; H, 6.69%.
Synthesis of (2E,20E)-1,10-(2,20-(hexane-1,6-diylbis(oxy))bis(2,1-
phenylene))bis(3-p-tolylprop-2-en-1-one) (3bc0)
The bischalcone 3bc0 was obtained from the reaction of chal-
cone 2b (2.0 g, 0.00820 mol) with 1,6 dibromohexane (1.025 g,
0.00420168 mol) under given conditions as used for 3aa0.
Synthesis of 1,4-bis-[3-(2-oxy-phenyl)-4,5-dihydro-1-phenyl-5-p-
tolyl-1H-pyrazole] butane (4ba0)
3bc0: Orange yellow solid; Yield 70%; m.p.:102–104 °C. IR (KBr)
cmꢀ1: 1652 (C@O), 1600 (C@C), 2934 and 2864 (methylene C–H),
1233 and 1025 (C–O); 1H-NMR (400 MHz, CDCl3): d 7.66 (2H, dd,
Jm,o = 1.7, 7.6 Hz, H-60), 7.60 (2H, d, Jtrans = 15.9 Hz, H-3), 7.48 (2H,
dd, Jm,o = 1.8, 7.8 Hz, H-40), 7.45 (4H, d, Jo = 7.0 Hz, H-200, 600), 7.37
(2H, d, Jtrans = 15.9 Hz, H-2), 7.16 (4H, d, Jo = 7.0 Hz, H-300, 500), 7.04
(2H, td, Jp,o = 0.52, 7.3 Hz, H-50), 6.92 (2H, d, Jo = 8.2 Hz, H-30),
3.92 (4H, t, Jvic = 6.2 Hz, OCH2CH2CH2), 2.31 (6H, s, CH3), 1.62 (4H,
quintet, Jvic = 6.2 Hz, OCH2CH2CH2), 1.38 (4H, quintet, Jvic = 7.2 Hz,
OCH2CH2CH2); MS(ESI): m/z (M + Na)+ = 581. Anal. Calc. for
A mixture of bischalcone 3ba0 (1.0 g, 0.001886 mol) was re-
fluxed with phenylhydrazine (0.4080 g, 0.0037735 mol) under
similar conditions as used for 4aa0.
4ba0: Yellow solid; Yield 68%; m.p.: 232–234 °C. IR (KBr) cmꢀ1
:
1595 (C@N), 2920 and 2868 (methylene C–H), 1236 and 1018 (C–
O); 1H-NMR (400 MHz, CDCl3): d 7.92 (2H, dd, Jp,o = 1.6, 7.8 Hz, H-
60), 7.29 (6H, m, H-3000,5000,40), 7.15 (4H, td, Jm,o = 2.1, 7.6 Hz, H-200,
600), 7.05 (4H, dd, Jp,o = 1.1, 9.0 Hz, H-2000, 6000), 6.96 (2H, td,
Jp,o = 1.1, 7.8 Hz, H-50), 6.86 (2H, d, Jo = 7.8 Hz, H-30), 6.80 (4H, dt,
Jm,o = 2.5, 7.8 Hz, H-300, 500), 6.72 (2H, td, Jm,o = 2.2, 8.0 Hz, H-4000),
5.10 (2H, dd, JXM = 12.1, JXA = 7.0 Hz, HX), 3.94 (4H, m, OCH2CH2),
3.89 (2H, dd, JMX = 12.1, JMA = 17.2 Hz, HM), 3.24 (2H, dd, JAX = 7.0,
JAM = 17.2 Hz, HA), 2.23 (6H, s, CH3), 1.82 (4H, t, Jvic = 6.8 Hz,
OCH2CH2); MS(ESI): m/z (M + Na)+ = 733. Anal. Calc. for
C38O4H38: Calc. C, 81.72%; H, 6.81%; Found: C, 81.77%; H, 6.86%.
Synthesis of (2E,20E)-1,10-(2,20-(octane-1,8-diylbis(oxy))bis(2,1-
phenylene))bis(3-p-tolylprop-2-en-1-one) (3bd0)
The bischalcone 3bd0was synthesized from the reaction of chal-
cone 2b (2.0 g, 0.00840 mol) with 1,8 dibromooctane (1.142 g,
0.00420168) as described for 3aa0.
C48O2N4H46: Calc. C, 81.12%; H, 6.47%; N, 7.88%; Found: C,
81.18%; H, 6.41%; N, 7.92%.
3bd0: Orange yellow solid; Yield 73%; m.p.: 110–112 °C. IR (KBr)
cmꢀ1: 1654 (C@O), 1593 (C@C), 2935 and 2852 (methylene C–H),
1234 and 1022 (C–O); 1H-NMR (400 MHz, CDCl3): d 7.63 (2H, dd,
Jm,o = 1.8, 7.6 Hz, H-60), 7.59 (2H, d, Jtrans = 15.9 Hz, H-3), 7.43 (6H,
m, H-200, 600, 40), 7.38 (2H, d, Jtrans = 15.9 Hz, H-2), 7.14 (4H, d,
Jo = 7.9 Hz, H-300, 500), 7.02 (2H, td, Jp,o = 0.84, 7.6 Hz, H-50), 6.94
(2H, d, Jo = 8.3 Hz, H-30), 3.98 (4H, t, Jvic = 6.3 Hz, OCH2CH2CH2CH2),
2.32 (6H, s, CH3), 1.67 (4H, quintet, Jvic = 7.3 Hz, OCH2CH2CH2CH2),
1.31 (4H, m, OCH2CH2CH2CH2), 1.09 (4H, m, OCH2CH2CH2CH2);
MS(ESI): m/z (M + H)+ = 587. Anal. Calc. for C40O4H42: Calc. C,
81.91%; H, 7.16%; Found: C, 81.86%; H, 7.19%.
Synthesis of 1,5-bis-[3-(2-oxy-phenyl)-4,5-dihydro-1-phenyl-5-p-
tolyl-1H-pyrazole] pentane (4bb0)
The compound 4bb0 was obtained from the reaction of bischal-
cone 3bb0 (1.0 g, 0.001838 mol) with phenylhydrazine (0.3975 g,
0.003676 mol) as described above for 4aa0.
4bb0:Brownishyellowsolid;Yield65%;m.p.:140–142 °C.IR(KBr)
cmꢀ1: 1596 (C@N), 2936 and 2864 (methylene C–H), 1239 and 1023
(C–O); 1H-NMR (400 MHz, CDCl3): d 7.88 (2H, dd, Jp,o = 1.5, 7.8 Hz, H-
60), 7.20 (10H, m, H-2000,3000,5000,6000,40), 7.11 (4H, td, Jm,o = 2.1, 7.8 Hz, H-
200, 600), 6.98 (2H, dd, Jp,o = 1.1, 7.8 Hz, H-50), 6.86 (2H, td, Jp,o = 1.1,
8.0 Hz, H-4000), 6.78 (4H, td, Jm,o = 2.0, 7.8 Hz, H-300,500), 6.68 (2H, m, H-
30),5.11(2H,dd,JXM = 12.0,JXA = 7.0 Hz,HX),3.86(4H,m,OCH2CH2CH2),
3.78 (2H, dd, JMX = 12.1, JMA = 17.3 Hz, HM), 3.23 (2H, dd, JAX = 7.0,
JAM = 17.3 Hz, HA), 2.23 (6H, s, CH3), 1.69 (4H, quintet, Jvic = 6.8 Hz,
OCH2CH2CH2),1.44(2H,quintet,Jvic = 6.8 Hz,OCH2CH2CH2);MS(ESI):
m/z (M + H)+ = 725. Anal. Calc. for C49O2N4H48: Calc. C, 81.21%; H,
6.62%;N,7.73%;Found:C,81.26%;H,6.67%;N,7.78%.
Synthesis of (2E,20E)-1,10-(2,20-(decane-1,10-diylbis(oxy))bis(2,1-
phenylene))bis(3-p-tolylprop-2-en-1-one) (3be0)
The bischalcone 3be0 was obtained from the reaction of chal-
cone 2b (2.0 g, 0.00840 mol) with 1,10-dibromodecane (1.260 g,
0.00420168 mol) as the conditions as used for 3aa0.
3be0: Yellow solid; Yield 75%; m.p.: 120–122 °C. IR (KBr) cmꢀ1
:
1659 (C@O), 1599 (C@C), 2935 and 2873 (methylene C–H), 1238
and 1021 (C–O); 1H-NMR (400 MHz, CDCl3): d 7.64 (2H, dd, J = 1.8,
7.6 Hz, H-60), 7.60 (2H, d, Jtrans = 15.9 Hz, H-3), 7.44 (6H, m, H-200,
600, 40), 7.41 (2H, d, Jtrans = 15.9 Hz, H-2), 7.15 (4H, d, Jo = 8.0 Hz, H-
300, 500), 7.01 (2H, td, Jp,o = 0.8, 9.0 Hz, H-50), 6.96 (2H, d, Jo = 8.2 Hz,
H-30), 4.02 (4H., t, Jvic = 6.3 Hz, OCH2CH2CH2CH2CH2), 2.33 (6H, s,
CH3), 1.74 (4H, quintet, Jvic = 6.3 Hz, OCH2CH2CH2CH2CH2), 1.36
(4H, quintet, Jvic = 7.2 Hz, OCH2CH2CH2CH2CH2), 1.15 (4H, m,
OCH2CH2CH2CH2CH2), 1.05 (4H, m, OCH2CH2CH2CH2CH2); MS(ESI):
Synthesis of 1,6-bis-[3-(2-oxy-phenyl)-4,5-dihydro-1-phenyl-5-p-
tolyl-1H-pyrazole] hexane (4bc0)
The compound 4bc0 was prepared from the reaction of bischal-
cone 3bc0 (1.0 g, 0.001792 mol) with phenylhydrazine (0.3875 g,
0.003584 mol) as described above for 4aa0.
4bc0: Yellow solid; Yield 75%; m.p.: 80–82 °C. IR (KBr) cmꢀ1
:
1598 (C@N), 2939 and 2873 (methylene C–H), 1233 and 1022
(C–O); 1H-NMR (400 MHz, CDCl3):
7.99 (2H, dd, Jp,o = 1.8,
7.6 Hz, H-60), 7.29 (6H, m, H-3000,5000,40), 7.20 (4H, td, Jm,o = 2.1,
d

304
M. Yusuf, P. Jain / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 96 (2012) 295–304
7.8 Hz, H-200, 600), 7.15 (2H, td, Jp,o = 1.1, 7.8 Hz, H-50), 7.12 (4H, dd,
Jp,o = 1.1, 8.9 Hz, H-2000,6000), 6.90 (2H, d, Jo = 7.8 Hz, H-30), 6.85 (4H, d,
Jo = 7.8 Hz, H-300, 500), 6.75 (2H, td, Jm,o = 2.2, 8.0 Hz, H-4000), 5.10 (2H,
dd, JXM = 12.0, JXA = 7.1 Hz, HX), 3.99 (4H, m, OCH2CH2CH2), 3.77
(2H, dd, JMX = 12.0, JMA = 17.2 Hz, HM), 3.33 (2H, dd, JAX = 7.0,
JAM = 17.2 Hz, HA), 2.20 (6H, s, CH3), 1.65 (4H, m, OCH2CH2CH2),
1.53 (4H, m, OCH2CH2CH2); MS(ESI): m/z (M + Na)+ = 761. Anal.
Calc. for C50O2N4H50: Calc. C, 81.30%; H, 6.77%; N, 7.58%; Found:
C, 81.25%; H, 6.82%; N, 7.63%.
MS(ESI): m/z (M + H)+ = 823. Anal. Calc. for C56O2N4H62: Calc. C,
81.75%; H, 7.54%; N, 6.81%; Found: C, 81.79%; H, 7.50%; N, 6.87%.
Acknowledgment
Authors are highly thankful to DST (SERC, Fast Track Scheme no.
SR/FT/CS-041/2010), New Delhi for providing the financial support
for this research work.
References
Synthesis of 1,8-bis-[3-(2-oxy-phenyl)-4,5-dihydro-1-phenyl-5-p-
tolyl-1H-pyrazole] octane (4bd0)
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The compound 4bd0 was synthesized from the reaction of
bischalcone 3bd0 (1.0 g, 0.001706 mol) with phenylhydrazine
(0.3689 g, 0.003412 mol) under similar conditions as used for 4aa0.
4bd0: Orange solid; Yield 70%; m.p.: 148–150 °C. IR (KBr) cmꢀ1
:
1596 (C@N), 2922 and 2853 (methylene C–H), 1240 and 1022 (C–
O); 1H-NMR (400 MHz, CDCl3): d 7.95 (2H, dd, Jp,o = 1.1, 7.8 Hz, H-
60), 7.35 (2H, m, H-40), 7.16 (10H, m, H-2000,3000,4000,5000,6000), 7.06 (4H,
td, Jm,o = 2.0, 8.4 Hz, H-200, 600), 6.99 (4H, td, Jm,o = 2.0, 8.4 Hz, H-300,
500), 6.86 (2H, td, Jo = 1.4, 8.0 Hz, H-50), 6.73 (2H, td, Jp,o = 1.0,
7.8 Hz, H-30), 5.16 (2H, dd, JXM = 12.0, JXA = 7.1 Hz, HX), 4.06 (2H,
dd, JMX = 12.0, JMA = 17.2 Hz, HM), 3.88 (4H, m, OCH2CH2CH2CH2),
3.30 (2H, dd, JAX = 7.0, JAM = 17.2 Hz, HA), 2.27 (6H, s, CH3), 1.72
(4H, m, OCH2CH2CH2CH2), 1.38 (4H, m, OCH2CH2CH2CH2), 1.25
(4H, m, OCH2CH2CH2CH2); MS(ESI): m/z (M)+ = 766. Anal. Calc.
for C52O2N4H54: Calc. C, 81.46%; H, 7.04%; N, 7.31%; Found: C,
81.50%; H, 7.08%; N, 7.37%.
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(1989) 161.;
Synthesis of 1,10-bis-[3-(2-oxy-phenyl)-4,5-dihydro-1-phenyl-5-p-
tolyl-1H-pyrazole] decane (4be0)
The compound 4be0 was prepared from the reaction of bischal-
cone 3be0 (1.0 g, 0.001628 mol) with phenylhydrazine (0.3522 g,
0.003257 mol) as described above for 4aa0.
(11b) S.V. Jovanovic, S. Steenken, M. Tosic, B. Marjanovic, M.G. Simic, J. Am.
Chem. Soc. 116 (1994) 4846;
(11c) W. Bors, W. Heller, C. Michel, K. Stettmaier, in: E. Cadenas, L. Packer
(Eds.), Handbook of Antioxidants, vol. 27, Marcel Dekker, New York, 1996, p.
409;
4be0: Orange solid; Yield 60%; m.p.: 98–100 °C. IR (KBr) cmꢀ1
:
1596 (C@N), 2921 and 2851 (methylene C–H), 1237 and 1026
(C–O); 1H-NMR (400 MHz, CDCl3):
d
7.97 (2H, dd, Jp,o = 1.5,
(11d) C.A. Rice-Evans, N.J. Miller, G. Paganga, Free Rad. Biol. Med. 20 (1996)
933.
7.8 Hz, H-60), 7.37 (2H, m, H-40), 7.20 (8H, m, H-2000,3000,5000,6000),
7.15 (4H, td, Jm,o = 2.0, 7.8 Hz, H-20, 60), 7.05 (2H, td, Jp,o = 1.4,
7.0 Hz, H-4000), 6.98 (2H, td, Jo = 1.4, 7.8 Hz, H-50), 6.87 (4H, td,
Jm,o = 2.2, 7.8 Hz, H-300, 500), 6.73 (2H, td, Jm,o = 1.6, 7.8 Hz, H-30),
5.17 (2H, dd, JXM = 12.1, JXA = 7.08 Hz, HX), 4.08 (2H, dd,
JMX = 12.1 Hz, JMA = 17.3 Hz, HM), 3.92 (4H, m, OCH2CH2
CH2CH2CH2), 3.30 (2H, dd, JAX = 7.0, JAM = 17.3 Hz, HA), 2.29 (6H,
s, CH3), 1.73 (4H, m, OCH2CH2CH2CH2CH2), 1.36 (4H, m,
OCH2CH2CH2CH2CH2), 1.23 (8H, m, OCH2CH2CH2CH2CH2); MS(ESI):
m/z (M)+ = 794. Anal. Calc. for C54O2N4H58: Calc. C, 81.61%; H,
7.30%; N, 7.05%; Found: C, 81.57%; H, 7.26%; N, 7.00%.
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Synthesis of 1,12-bis-[3-(2-oxy-phenyl)-4,5-dihydro-1-phenyl-5-p-
tolyl-1H-pyrazole] dodecane (4bf0)
The compound 4bf0 was synthesized from the reaction of
bischalcone 3bf0 (1.0 g, 0.001502 mol) with phenylhydrazine
(0.3402 g, 0.003012 mol) as described above for 4aa0.
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4bf0:Orange solid; Yield 61%; m.p.: 120–122 °C. IR (KBr) cmꢀ1
:
1594, (C@N), 2921 and 2870 (methylene C–H), 1235 and 1023
(C–O); 1H-NMR (400 MHz, CDCl3):
d
7.93 (2H, dd, Jp,o = 1.5,
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7.8 Hz, H-60), 7.32 (2H, m, H-40), 7.22 (8H, m, H-2000,3000,5000,6000),
7.10 (4H, td, Jm,o = 2.0, 7.8 Hz, H-200, 600), 7.08 (2H, td, Jp,o = 1.4,
7.0 Hz, H-4000), 6.99 (2H, td, Jo = 1.4, 7.8 Hz, H-50), 6.88 (4H, td,
Jm,o = 2.2, 7.8 Hz, H-300, 500), 6.74 (2H, td, Jp,o = 1.6, 7.8 Hz, H-30),
5.19 (2H, dd, JXM = 12.1, JXA = 7.08 Hz, HX), 4.05 (2H, dd,
JMX = 12.1, JMA = 17.3 Hz, HM), 3.94 (4H, m, OCH2CH2CH2
CH2CH2CH2), 3.32 (2H, dd, JAX = 7.0, JAM = 17.3 Hz, HA), 2.27 (6H,
s, CH3), 1.75 (4H, m, OCH2CH2CH2CH2CH2CH2), 1.33 (4H, m,
OCH2CH2CH2CH2CH2CH2), 1.28 (12H, m, OCH2CH2CH2CH2CH2CH2);