AJANI et al., Orient. J. Chem., Vol. 32(1), 109-120 (2016)
113
1
1
1
34.9, 129.8 (2CH aromatic), 129.6 (2CH aromatic),
28.8 (2CH aromatic), 127.5, 127.2 (2CH aromatic),
19.5, 56.5, 39.0 (CH ), 21.7 (CH ). l in nm (log
of NH , two bands), 3276 (N-H), 3173 (N-H), 3026
2
(C-H aromatic), 2929 (C-H aliphatic of CH ), 2845
2
(C-H aliphatic), 1603 (C=C aromatic), 1583 (C=N),
2
3
max
-
1
+
εmax): 212 (3.4050), 236 (2.9974), 293 (2.6857). IR
742 (Ar-H) cm . MS: in m/z (rel. %): 218.17 (M ,
89.3%), 190.17 (M – N2, 100%), 162.16 (73.5%),
145.03 (41.6%), 106.15 (96.2%), 77.17 (40.7%).
(
KBr): 3384, 3363 (N-H of NH , two bands), 3209
2
(
N-H), 3022 (C=H aromatic), 2889 (C-H aliphatic),
-
1
1
615 (C=C aromatic), 1575 (C=N), 749 (Ar-H) cm .
+
MS:in m/z (rel.%):237.09 (M , 94.5%), 236.08 (M –
H, 67.9%), 217.11 (58.4%), 187.15 (58.1%), 119.14
Synthesis of 2-(1H-benzo[d]imidazol-2-yl)aniline,
10i
(
73.7%), 106.09 (100%), 77.12 (40.7%).
Treatment of o-phenylenediamine (0.54 g, 5
mmol) with anthranilic acid (0.96 g, 7 mmol) afforded
2-(1H-benzo [d]imidazol-2-yl)aniline, 10i. H-NMR
1
Synthesis of 1-(1H-benzo[d]imidazol-2-yl)-3-
(
methylthio)propan-1-amine, 10g
(400 MHz, DMSO-d ) δ: 11.13 (s, 2H, NH ), 8.49
6
2
Treatment of o-phenylenediamine (0.54 g,
mmol) with L-methionine (1.04 g, 7 mmol) afforded
(s, 1H, NH), 7.96-7.94 (d, J = 8.08 Hz, 2H, Ar-H),
7.78-7.76 (d, J = 8.00 Hz, 2H, Ar-H), 7.37-7.34 (m,
2H, Ar-H), 6.87-6.85 (m, 2H, Ar-H). C-NMR (100
5
1
1
8
7
2
13
-(1H-benzo [d]imidazol-2-yl)-3-(methylthio)propan-
1
-amine, 10g. H-NMR (400 MHz, DMSO-d ) d:
MHz, DMSO-d ) d:147.4, 143.2, 139.5, 139.3, 139.1,
6
6
.23 (s, 1H, NH), 7.75-7.73 (d, J = 8 Hz, 2H, Ar-H),
.29-7.27 (m, 2H, Ar-H), 5.68-5.66 (d, J = 7.55 Hz,
128.1, 128.0, 126.7, 126.5, 119.8, 119.7, 119.3,
119.2 ppm. lmax in nm (log εmax): 209 (3.1553), 242
(2.4914), 335 (2.0899).IR (KBr):3384, 3366 (N-H of
H, NH -CH), 2.50-2.48 (m, 1H, CH), 2.35-2.33 (t,
2
J = 8.88 Hz, 2H, CH -CH -S), 1.97 (s, 3H, CH -S),
NH , two bands), 3201 (N-H), 3031 (C-H aromatic),
2
2
3
2
13
-1
1
.82-1.73 (m, 2H, CH-CH -CH ). C-NMR (100 MHz,
1576 (C=N), 748 (Ar-H) cm . MS: in m/z (rel. %):
2
2
+
DMSO-d ) δ: 145.3, 139.3, 139.1, 126.9, 126.9,
209.23 (M , 76.5%), 194.25 (M – NH, 91.4%), 118.
6
1
1
17.3, 117.3, 58.2 (CH), 43.7 (CH ), 31.2 (CH ),
22 (44.24%), 106.15 (100%), 77.25 (38.2%).
2
2
5.9 (CH ). l in nm (log εmax): 209 (3.3181), 236
3
max
(
2.6064), 293 (2.2553). IR (KBr): 3384, 3363 (N-H
Antimicrobial Activity
of NH , two bands), 3276 (N-H), 3173 (N-H), 3029
The antimicrobial properties of the
2
(
(
C-H aromatic), 2921 (C-H aliphatic of CH ), 2885
2-substituted benzimidazole derivatives were
investigated in form of the general sensitivity
testing with respect to six targeted organisms.
The six organisms of interest in this present study
are Staphylococcus aureus, Proteus vulgaris,
Streptococcus faecalis, Klebsiella pneumonia,
Pseudomonas aeruginosa and Escherichia coli
which pose serious threat to life of man and animals
from time to time. They are associated with the
gastrointestinal tract damage in man and animal.
2
C-H aliphatic), 1600 (C=C), 1575 (C=N), 745 (Ar-H)
-1
+
cm .MS:in m/z (rel.%):221.08 (M , 75.9%), 195.07
(51.7%), 182.07 (82.5%), 164.07 (M – SCH 89.3%),
3,
1
06.09 (100%), 77.12 (40.7%).
Synthesis of 1-(1H-benzo[d]imidazol-2-yl)
pentane-1,5-diamine, 10h
Treatment of o-phenylenediamine (0.54
g, 5 mmol) with L-lysine (1.28 g, 7 mmol) afforded
1
-(1H-benzo[d]imidazol-2-yl)pentane-1,5-diamine,
1
10h. H-NMR (400 MHz, DMSO-d ) δ: 8.51 (s, 1H,
Antibacterial Sensitivity Testing of Compounds
Allthesynthesizedbenzimidazoletemplates
6
NH), 7.78-7.76 (d, J = 8 Hz, 2H, Ar-H), 7.37-7.34
m, 2H, Ar-H), 6.23-6.21 (d, J = 7.75 Hz, 2H, NH2-
CH), 5.97-5.94 (t, J = 8.04 Hz, 2H, NH -CH ), 3.91-
(
and gentamicin were screened for antibacterial
activity on the targeted organisms mentioned above
2
2
2
9
3
.94 (m, 1H, CH), 2.35-2.33 (t, J = 8.04 Hz, 2H,
using agar well diffusion method . The medium
employed was diagnostic sensitivity test agar
(Biotech Ltd). With the aid of a sterile 1 mL pipette,
about 0.2 mL of the broth culture of test organism
was added to 18 mL sterile molten diagnostic
sensitivity test agar (Biotech Ltd) which had already
CH -CH -NH ), 2.13-2.11 (quintet, J = 8.17 Hz, 2H,
2
2
2
CH -CH -CH ), 1.92-1.90 (quintet, J = 8.14 Hz, 2H,
2
2
2
13
CH -CH -CH ), 1.82-1.73 (m, 2H, CH-CH -CH ). C-
2
2
2
2
2
NMR (100 MHz, DMSO-d ) δ: 145.3, 139.6, 139.4,
6
1
2
26.7, 126.7, 119.9, 119.9, 55.8, 43.1, 39.6, 32.9,
1.5 ppm. lmax in nm (log εmax): 206 (2.6222), 236
o
cooled down to 45 C. This was well mixed and
(
1.5911), 296 (0.6021). IR (KBr): 3383, 3365 (N-H
poured into previously sterilized petri dishes, which