18
M.H. Malani, B.Z. Dholakiya / Bioorganic Chemistry 51 (2013) 16–23
Table 1
Physico chemical papameter of synthesized compounds.
Sr. no.
Compound code
R1, R2 and R3
% Yield
Color (solid powder)
Melting point
1
2
3
4
5
6
7
8
5a
5b
5c
5d
5e
5f
R
R
R
R
1 = H, R2 = H and R3 = AOCH3
1 = H, R2 = ANO2 and R3 = H
1 = H, R2 = H and R3 = ANO2
1 = H, R2 = H and R3 = ACH3
85%
79%
73%
68%
83%
67%
69%
74%
Cremish to off white
Cremish
Dark brown
Yellow
Light brown
Dark yellow
Light yellow
Dark yellow
Dec.>250 °C
200–201 °C
195–197 °C
168–170 °C
>250 °C
85–87 °C
188–189°c
127–128 °C
R1 = H, R2 = H and R3 = AOH
R
R
R
1 = Cl, R2 = H and R3 = H
1 = H, R2 = H and R3 = ACl
1 = H, R2 = H and R3 = H (Naphthalene ring)
5g
5h
flat bottom reaction flask with stirring at 28–30 °C. Gradually tem-
perature was raised to reflux and maintain it for 3.0 h. Progress of
the reaction was examined by TLC. After completion of reaction
mass was evaporated to dryness to obtain oily sticky mass. 25 ml
water and 25 ml ethyl acetate was charged in flask containing oily
sticky mass and stirred it for 10 min at 25–30 °C. Reaction mass
was transfer from reaction flask to separating funnel to obtain
two layers. Top organic layer was treated with sodium sulfate
and evaporated to dryness. Light yellow solid mass was obtain hav-
ing melting point 90–95 °C (5.2 g, 88% yield).
(100 MHz, DMSO) 22, 80, 126, 130, 132, 134, 142, 144, 190 d
ppm; FTIR (KBr) tmax cm-1: 2918 (C@C), 1650 (C@O), 2234 (CAN,
Nitrile), 862 (p-disubstituted Ar).
2.4.2. 40-4-[3-(3-Nitro-phenyl)-acryloyl]-piperazin-1-ylmethyl-
biphenyl-2-carbonitrile 5b
Yield 79%; m.p. 200–201 °C; 1H NMR (400 MHz, DMSO), 2.51 d
ppm (1H, d, J = 13.1 Hz, ACH@CH), 3.53 d ppm (1H, m, ACH2-
CHOHCH2), 3.39 d ppm (4H,dd, J = 5.1 Hz, Piprazine), 3.57 d ppm
(1H, d, J = 13.2 Hz, ACH@CH), 7.20–7.76 d ppm (8H, m, ArAH),
8.16 d ppm(2H, s, AArACH2); 13C NMR (100 MHz, DMSO) 23, 79,
127, 129, 131, 133, 143, 145, 192 d ppm; FTIR (KBr) tmax cmꢀ1
:
2.4. Preparation of 40-4-[3-(substituted-phenyl)-acryloyl]-piperazin-
1-ylmethyl-biphenyl-2-carbonitrile compounds 5a-5 h
2916 (C@C), 1648 (C@O), 2226 (CAN, Nitrile), 780 (m-
disubstituted Ar).
40-4-[3-(Substituted-phenyl)-acryloyl]-piperazin-1-ylmethyl-
biphenyl-2-carbonitrile (5a–5h) compounds were prepared from
compound-4 and various aldehydes under alkaline conditions in
present of alcohol. Reaction mass was continuously stirred and
temperature was maintain at 55–60 °C for 12 h. Final targeted
compounds were isolated from alcohol by using water at pH 6–7.
Purification of these compounds were carried out by recrystalliza-
tion in present of ethanol. All compounds were characterized by
FTIR, 1HNMR, 13C NMR and screened for their biological activity
viz, bacterial, fungal and malarial.
2.4.3. 40-4-[3-(4-Nitro-phenyl)-acryloyl]-piperazin-1-ylmethyl-
biphenyl-2-carbonitrile 5c
Yield 73%; m.p. 195–197 °C; 1H NMR (400 MHz, DMSO), 2.52 d
ppm (1H, d, J = 13.2 Hz, ACH@CH), 3.55 d ppm (1H, m, ACH2-
CHOHCH2), 3.38 d ppm (4H,dd, J = 5.2 Hz, Piprazine), 3.53 d ppm
(1H, d, J = 13.1 Hz, ACH@CH), 7.16–7.71 d ppm (8H, m, ArAH),
8.12 d ppm(2H, s, AArACH2); 13C NMR (100 MHz, DMSO) 20, 77,
123, 126, 127, 129, 138, 140, 186 d ppm; FTIR (KBr) tmax cmꢀ1
:
2912 (C@C), 1644 (C@O), 2222 (CAN, Nitrile), 840 (p-disubstituted
Ar).
2.4.1. 40-4-[3-(4-Methoxy-phenyl)-acryloyl]-piperazin-1-ylmethyl-
biphenyl-2-carbonitrile 5a
2.4.4. 40-[4-(3-p-Tolyl-acryloyl)-piperazin-1-ylmethyl]-biphenyl-2-
carbonitrile 5d
Yield 85%; m.p. >250 °C; 1H NMR (400 MHz, DMSO), 2.55 d ppm
(1H, d, J = 13.3 Hz, ACH@CH), 3.52 d ppm (1H, m, ACH2CHOHCH2),
3.35 d ppm (4H,dd, J = 5.2 Hz, Piprazine), 3.54 d ppm (1H, d,
J = 13.4 Hz, ACH@CH), 4.1 d ppm (3H, s,Ar-OCH3) 7.17–7.75 d
ppm (8H, m, ArAH), 8.14 d ppm (2H, s, AArACH2); 13C NMR
Yield 68%; m.p. 168–170 °C; 1H NMR (400 MHz, DMSO), 2.37 d
ppm (3H, s, ArACH3), 2.53 d ppm (1H, d, J = 13.3 Hz, ACH@CH),
3.37 d ppm (4H,dd, J = 5.2 Hz, Piprazine), 3.55 d ppm (1H, d,
J = 13.2 Hz, ACH@CH), 7.18–7.73 d ppm (8H, m, ArAH), 8.15 d
Fig. 1. IR Spectrum of synthesized compound.