Page 216 - 80_01

Krishna
Naik&
col.

IXk:
N-­-methyl
piperizinyl,
267oC,
68
%,
C22H21N7O3S,
C:57.01
(56.63),
H:4.53
(4.38),

N:21.16
(21.02),
O:10.36
(10.12),
S:6.91
(6.83).

n.
IR
(KBr)
Spectral
data
(?max
in
cm-­-1)

IXa:
1608
(C=N),
1665
(C=O),
1156
(C=S),
2939
(C-­-HStr),
3140
(NH),
3250
(Ar
–
NH).

IXb:
1620
(C=N),
1660
(C=O),
1150
(C=S),
2925
(C-­-HStr),
3130
(NH),
3240
(Ar
–
NH).

IXc:
1610
(C=N),
1670
(C=O),
1160
(C=S),
2945
(C-­-HStr),
3145
(NH),
3255
(Ar
–
NH).

IXd:
1608
(C=N),
1663
(C=O),
1158
(C=S),
2940
(C-­-HStr),
3172
(NH),
3253
(Ar
–
NH),

IXe:
1609
(C=N),
1665
(C=O),
1155
(C=S),
2943
(C-­-HStr),
3143
(NH),
3254
(Ar
–
NH).

IXf:
1605
(C=N),
1655
(C=O),
1145
(C=S),
2930
(C-­-HStr),
3135
(NH),
3245
(Ar
–
NH).

IXg:
1590
(C=N),
1645
(C=O),
1135
(C=S),
2925
(C-­-HStr),
3125
(NH),
3230
(Ar
–
NH).

IXh:
1593
(C=N),
1667
(C=O),
1107
(C=S),
2940
(C-­-HStr),
3150
(NH),
3250
(Ar
–
NH).

IXi:
1610(C=N),
1675
(C=O),
1165
(C=S),
2955
(C-­-HStr),
3150
(NH),
3265
(Ar
–
NH).

IXj:
1610
(C=N),
1670
(C=O),
1160
(C=S),
2945
(C-­-HStr),
3145
(NH),
3260
(Ar
–
NH).

IXk:
1605
(C=N),
1655
(C=O),
1145
(C=S),
2935
(C-­-HStr),
3140
(NH),
3255
(Ar
–
NH).

o.
1H
NMR
(DMSO-­-d6)
Spectral
data
(d
in
ppm)

IXa:
2.28
(s,
3H,
CH3),

2.36
(s,
3H,
CH3),
5.0
(s,
2H,
NCH2),

5.64
(s,
2H,
N-­-CH2-­-N),

6.8
(s,
H,

Ar-­-NH),
7.1-­-7.3
(m,
9H,
Ar-­-H),
7.4
(d,
2H,
C6H4),
7.7
(d,
2H,
C6H4),
11.2
(s,
H,
Ar-­-NH).

IXb:
2.40
(s,
3H,
CH3),
3.82
(s,
3H,
CH3),
5.06
(s,
2H,
N-­-CH2),

5.62
(s,
2H,
N-­-CH2-­-N),
6.8
(s,
H,

Ar-­-NH),
7.1-­-7.3
(m,
9H,
Ar-­-H),
7.4
(d,
2H,
C6H4),
7.7
(d,
2H,
C6H4),
11.1
(s,
H,
Ar-­-NH).

IXf:
2.50
(s,
3H,
CH3),
4.96
(s,
2H,
N-­-CH2),

5.50
(s,
2H,
N-­-CH2-­-N),

6.8
(s,
1H,
Ar-­-NH),
7.1-­-
7.3
(m,
9H,
Ar-­-H),
7.4
(d,
2H,
C6H4),
7.7
(d,
2H,
C6H4),
10.23
(s,
1H,
NH).

IXi:
2.60
(s,
3H,
CH3),
2.62
(t,
4H
CH2-­-N-­-CH2),
3.70
(t,
4H,
CH2-­-O-­-CH2),

4.50
(s,

2H,
N-­-CH2-­-
N),
5.24
(s,
2H,
N-­-CH2),

5.48
(s,
2H,
N-­-CH2-­-N),

6.8
(s,
H,
Ar-­-NH),
7.1-­-7.3
(m,
9H,
Ar-­-H),
6.8

(s,
H,
Ar-­-NH),
7.4
(d,2H,C6H4),
7.7(d,
2H,
C6H4),
10.20
(s,
1H,
NH).

IXj:
2.56
(t,
4H
CH2-­-N-­-CH2),
2.58
(s,
3H,
CH3),
4.
45
(s,
2H,
N-­-CH2-­-N),

5.20
(s,
2H,
N–CH2),

5.45
(s,
2H,
N-­-CH2-­-N),

4.45
(s,
2H,
N-­-CH2-­-N),
6.8
(s,
H,
Ar-­-NH),
7.1-­-7.3
(m,9H,
Ar-­-H),

7.4(d,2H,C6H4),
7.7
(d,
2H,C6H4),
10.19
(s,
H,
NH).

3.2.
Antimicrobial
activity

All
synthesized
compounds
were
subjected
to
preliminary
antibacterial

screening
by
disc
diffusion
method
against
Staphylococus
aureus
NCCS
2079,

Bacillus
cereus
NCCS
2106,
Escherichia
coli
NCCS
2065
and
Pseudomanas

aeruginosa
NCCS
2200.
As
shown
in
Table
1,
VII
series
showed
moderate
activity

against
tested
organism.
In
this
series
chloro,
bromo
and
nitro
substituted

compounds
showed
more
activity
than
other
compounds.
Whereas
among
the

compounds
of
IX
series,
fluoro,
chloro,
bromo,
nitro,
morphonilyl,
piperizynyl,
N-­-

methylpiperizine
showed
more
activity
than
other
compounds.

All
synthesized
compounds
were
subjected
to
preliminary
antifungal

screening
by
disc
diffusion
method
against
Aspergillus
niger
NCCS
1196
and

Candida
albicans
NCCS
2106.
Among
the
compounds
of
VII
series,
Chloro,
bromo

and
nitro
substituted
compounds
showed
more
activity
against
Aspergillus
niger

NCCS
1196
and
Candida
albicans
NCCS
2106.
The
compounds
of
IX
series
have

demonstrated
good
antifungal
activity
particularly
fluoro,
chloro,
bromo,
nitro,

morphonilyl,
piperizynyl
and
N-­-methyl
piperizine
showed
good
antifungal
activity.

The
details
are
given
in
Table
1
and
2.

2
10