Convenient one-pot synthesis of novel 2-substituted benzimidazoles, tetrahydrobenzimidazoles and imidazoles and evaluation of their in vitro antibacterial and antifungal activities

Article abstract of DOI:10.1016/j.ejmech.2008.03.026

A series of novel 2-substituted benzimidazoles and imidazoles have been synthesized from long-chain alkenoic acids. The reactions occurred under relatively mild conditions and afforded the desired product in good yields. The structures of these compounds have been elucidated by elemental and spectral (IR, ¹H NMR, ¹³C NMR, mass) analyses. Furthermore, compounds were screened for in vitro antibacterial activity against the representative panel of two Gram-positive and two Gram-negative bacteria. All the synthesized compounds were also tested for their inhibitory action against five strains of fungus. The various compounds show potent inhibitory action against test organisms.

Full text of DOI:10.1016/j.ejmech.2008.03.026

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European Journal of Medicinal Chemistry 44 (2009) 1751e1757
http://www.elsevier.com/locate/ejmech
Short communication
Convenient one-pot synthesis of novel 2-substituted benzimidazoles,
tetrahydrobenzimidazoles and imidazoles and evaluation of
their in vitro antibacterial and antifungal activities
*
Shweta Sharma, Saloni Gangal, Abdul Rauf
Department of Chemistry, Aligarh Muslim University, Aligarh 202002, Uttar Pradesh, India
Received 2 January 2008; received in revised form 27 March 2008; accepted 30 March 2008
Available online 4 April 2008
Abstract
A series of novel 2-substituted benzimidazoles and imidazoles have been synthesized from long-chain alkenoic acids. The reactions occurred
under relatively mild conditions and afforded the desired product in good yields. The structures of these compounds have been elucidated by
elemental and spectral (IR, 1H NMR, 13C NMR, mass) analyses. Furthermore, compounds were screened for in vitro antibacterial activity against
the representative panel of two Gram-positive and two Gram-negative bacteria. All the synthesized compounds were also tested for their
inhibitory action against five strains of fungus. The various compounds show potent inhibitory action against test organisms.
Ó 2008 Elsevier Masson SAS. All rights reserved.
Keywords: 2-Substituted benzimidazoles; Tetrahydrobenzimidazoles; Imidazoles; Antibacterial activity; Antifungal activity
1. Introduction
asetomidate, cimetidine, omeprazole and lansoprazole, in
drug therapy [8]. Therefore the development of facile synthetic
routes to achieve access to these molecules is of prime interest.
In view of the above mentioned pharmacological applications
of benzimidazoles and imidazoles and in continuation of our
research on the synthesis of biologically active molecules
[9], we considered undertaking the design and synthesis of
hitherto unknown benzimidazoles and imidazoles bearing
long alkenyl chain.
Further, the increasing number of multidrug resistant path-
ogens has led us to screen the newly synthesized derivatives
against the representative panel of Gram-positive (gþ) and
Gram-negative (gꢀ) bacteria and fungi.
The benzimidazole has been an important pharmacophore
and privileged structure in medicinal chemistry, encompassing
a diverse range of biological activities including antiarrhyth-
mic, antiulcer, anthelmintical, inotropic, antihistamine, anti-
fungal, antiviral, and cytotoxicity displaying diverse range of
biological activities [1]. Benzimidazoles exhibit significant
activity as potential antitumor agents [2], antimicrobial agents
[3], smooth muscle cell proliferation inhibitors [4], a treatment
for intestinal cystitis [5], and in diverse area of chemistry [6].
The imidazole core is a common moiety in a large number of
natural products and pharmacologically active compounds [7].
Recently, there has been considerable amount of progress in
imidazole chemistry due to the recognition of importance of
the imidazole structure in biological processes and the increas-
ing application of imidazole containing compounds, such as
2. Chemistry
A typical one-pot procedure for the synthesis of 4aAe4dC
involves the addition of 1,2-phenylenediamine derivatives
2Ae2C to the acid chloride 1ae1d (Scheme 1) at 0 ꢁC in
dry dioxane and stirring for 30 min at room temperature to
furnish the corresponding N-acyl-1,2-phenylenediamine
* Corresponding author. Tel.: þ91 9412545345.
E-mail address: abduloafchem@gmail.com (A. Rauf).
0223-5234/$ - see front matter Ó 2008 Elsevier Masson SAS. All rights reserved.
doi:10.1016/j.ejmech.2008.03.026

1752
S. Sharma et al. / European Journal of Medicinal Chemistry 44 (2009) 1751e1757
NH2
R1
NH2
R1
R1
NH2
O
N
BF3.OEt2
2A-C
R
R
NH
N
H
Cl
R
O
2A, R1=H
2B, R1=NO2
2C, R1=Cl
3aA, 3bA, 3cA, 3dA
3aB, 3bB, 3cB, 3dB
3aC, 3bC, 3cC, 3dC
4aA, 4bA, 4cA, 4dA
4aB, 4bB, 4cB, 4dB
4aC, 4bC, 4cC, 4dC
1a-d
1
a
R
zH
CH2
6
HE
CH2
b
c
6
4
5
CH2
5
OH
OH
d
CH2
6
3
Scheme 1. Synthesis of 2-substituted-1H-benzimidazoles 4aAe4dC.
derivatives 3. To the prior, acid chloride 1ae1d was synthe-
sized from olefinic and hydroxy olefinic long-chain acids by
in situ preparation. Since acid chlorides 1ae1d are not com-
mercially available the present method has greatly solved
the problem by facile and efficient in situ preparation. We
have used BF3$OEt2 for cyclization of 3. BF3$OEt2 in dry
dioxane was added to 3 without isolating the product and re-
action mixture refluxed for 1e2 h at 130 ꢁC. The yields of
products 4aAe4dC are excellent and independent of the sub-
stituents present in the precursor. The scope of the reaction
using olefinic (internal and terminal) and hydroxy acids is
found to be good. This strategy was also be used to increase
the structural diversity of the member library through the syn-
thesis of benzimidazole 7aXe7dX (Scheme 2). Similarly
10aYe10dY (Scheme 3) have been prepared by the reaction
of ethylenediamine 8Y to the acid chloride 1ae1d at 0 ꢁC in
dry dioxane and stirring for 30 min at room temperature to
furnish the corresponding 9 which undergo cyclization in pres-
ence of BF3$OEt2 to form 10aYe10dY. The yield of products
was found to be appreciable. The preliminary study of 4aA,
4bA, 10bY has been reported earlier [10]. The newly synthe-
sized compounds were analyzed for C, H and N content and
3. Biological activity
3.1. Antibacterial studies
The newly synthesized compounds were screened in vitro
against an assortment of two Gram-positive bacteria Staphylo-
coccus aureus MSSA 22 and Bacillus subtilis ATCC 6051
and two Gram-negative bacteria Escherichia coli K12 and
Salmonella typhimurium MTCC 98. Screening results are sum-
marized in Table 1. All the synthesized compounds were
dissolved to prepare a stock solution of 1 mg/ml using
DMSO. Stock solution was aseptically transferred and suitably
diluted to have solutions of different concentrations ranging
from 300 to 18.75 mg/ml by two-fold dilution. The antibacte-
rial activity of test compounds and standard chloramphenicol
was done by filter paper disc method [11]. Media with
DMSO was set up as control. All cultures were routinely
maintained on NA (nutrient agar) and incubated at 37 ꢁC.
The inoculums of bacteria were performed by growing the
culture in NA broth at 37 ꢁC for overnight. The culture was
centrifuged at 1000 rpm and pellets was resuspended and
diluted in sterile NSS to obtain viable count 105 cfu/ml.
Approximately 0.1 ml of diluted bacterial culture suspension
was spread with the help of spreader on NA plates uniformly.
1
structures were confirmed by IR, H NMR, 13C NMR and
mass spectral data.
NH2
NH2
NH2
H
N
NH2
NH2
NH
NH2
N
O
O
BF3.OEt2
5 X
R
BF3.OEt2
8 Y
R
R
R
NH
N
H
Cl
Cl
N
R
O
O
R
6aX, 6bX, 6cX, 6dX
7aX, 7bX, 7cX, 7dX
1a-d
9aY, 9bY, 9cY, 9dY
10aY, 10bY, 10cY, 10dY
1a-d
Scheme 2. Synthesis of 2-substituted-tetrahydro-1H-benzimidazoles 7aXe
7dX.
Scheme 3. Synthesis of 2-substituted-1H-imidazoles 10aYe10dY.

S. Sharma et al. / European Journal of Medicinal Chemistry 44 (2009) 1751e1757
1753
were incubated at 28 ꢁC for filamentous fungi for 72 h or
more while for C. albicans plates were incubated at 37 ꢁC
for 18e48 h. Antifungal activity was determined by measuring
the diameters of the inhibition zone (mm).
Table 1
In vitro antibacterial activity of compounds 4aAe10dY
Compound
E. coli
Diameter of zone of inhibition (mm)
S. typhimurium
B. subtilis
S. aureus
4aA
4bA
18(150)
16(150)
17(150)
17(150)
20(75)
16(75)
14(75)
12(75)
12(75)
12(37.5)
11(37.5)
12(37.5)
13(37.5)
14(37.5)
15(37.5)
17(37.5)
17(37.5)
11(75)
10(75)
12(75)
13(75)
14(74)
11(75)
12(75)
12(75)
20(6)
22(75)
21(75)
21(75)
19(75)
19(37.5)
20(37.5)
21(37.5)
22(37.5)
19(75)
18(75)
19(75)
20(75)
18(75)
19(75)
19(75)
23(75)
22(37.5)
19(37.5)
18(37.5)
19(37.5)
24(6)
20(150)
18(150)
19(150)
19(150)
22(150)
21(37.5)
19(37.5)
19(37.5)
22(37.5)
20(37.5)
21(37.5)
21(37.5)
18(75)
4. Results and discussion
4cA
4dA
4aB
4bB
The antibacterial and antifungal screening revealed that all
the tested compounds 4aAe4dA, 7aXe7dX, 10aYe10dY
showed moderate to good inhibition. The antibacterial screen-
ing indicated that among the tested bacterial strains, good
inhibitory results were obtained against S. typhimurium and
E. coli. The structural activity study showed that benzimid-
azoles and their substituted derivatives 4aAe4dC have vary-
ing degrees of microbial inhibition. The antibacterial and
antifungal activity seemed to be dependent on the heterocyclic
moiety as well as on the nature of substituents. Although the
benzimidazoles 4aAe4dA itself are observed active the activ-
ity was further enhanced by the presence of nitro and chloro
substituent on the benzimidazole moiety (Table 1). The nitro
substituted derivatives 4aB, 4bB have shown good activity
against E. coli and S. aureus. The maximum inhibition was
observed in 4dB against B. subtilis. The chloro substituted
derivatives 4aCe4dC have shown maximum inhibition against
S. aureus. The tetrahydrobenzimidazoles 7aXe7dX are moder-
ately active against S. typhimurium and 7aX, 7dX are best
active against E. coli and B. subtilis whereas the imidazoles
10aYe10dY showed moderate activity results against test
bacterial strains. In another set of experiments, the above
mentioned compounds were also examined for antifungal activ-
ity (Table 2). Nystatin was used as standard drug for the
20(75)
4cB
4dB
16(37.5)
18(37.5)
20(75)
4aC
4bC
18(75)
18(75)
4cC
4dC
19(37.5)
17(37.5)
17(150)
15(150)
16(150)
15(150)
11(150)
12(150)
12(150)
25(12.5)
e
7aX
7bX
16(75)
17(75)
16(75)
7cX
7dX
10aY
10bY
16(150)
15(150)
15(150)
15(150)
26(12.5)
e
10cY
10dY
Chloroamphenicol
Control DMSO
e
e
Values in brackets are MIC values (mg/ml).
Sterile 8 mm discs (Hi-media Pvt. Ltd.) were impregnated
with the test compounds. Antibiotic disc, chloroamphenicol
(30 mg/disc Hi-Media) was used as control. The disc was
placed onto the plate. Each plate had one control disc impreg-
nated with solvent. The plates were then incubated for 24 h at
37 ꢁC, and the resulting zones of inhibition (in mm) were
measured. The minimum inhibitory concentration at which
no growth was observed was taken as the MIC values.
Table 2
In vitro antifungal activity of compounds 4aAe10dY
3.2. Antifungal studies
Compound
Diameter of zone of inhibition (mm)
C. albicans H. oryzae A. niger T. viridae Penicillium sp.
The newly synthesized compounds were also screened for
Aspergillus niger (laboratory isolate), Candida albicans IOA-
109, Penicillium sp. (laboratory isolate), Trichoderma viridae
(lab isolate), Helminthosporum oryzae (2537 ICAR, Jaipur).
The synthesized compounds were dissolved in DMSO. Media
with DMSO was set up as control. All cultures were routinely
maintained on SDA and incubated at 28 ꢁC. Spore formation
of filamentous fungi was prepared from 7-day old culture in
sterile normal solution (8% NaCl) and approximately diluted
to obtain 105 cfu/ml. The inoculums of non-sporing fungi,
C. albicans was performed by growing the culture in SD broth
at 37 ꢁC for overnight. The culture was centrifuged at
1000 rpm and pellets was resuspended and diluted in sterile
NSS to obtain viable count 105 cfu/ml. Approximately
0.1 ml of diluted fungal culture suspension was spread with
the help of spreader on SDA plates uniformly. Sterile 8 mm
discs (Hi-media Pvt. Ltd.) were impregnated with test com-
pounds. Antibiotic disc, nystatin (30 mg/disc Hi-Media) was
used as control. The disc was placed onto the plate. Each plate
had one control disc impregnated with solvent. The plates
4aA
19(75)
19(75)
19(75)
18(75)
18(37.5)
19(37.5)
19(37.5)
19(37.5)
18(37.5)
18(37.5)
18(37.5)
18(37.5)
18(75)
18(75)
17(75)
19(75)
19(75)
18(75)
18(75)
18(75)
20(6)
13(150) 14(150) 7(75)
12(150) 16(150) 6(75)
13(150) 16(150) 8(75)
11(150) 14(150) 8(75)
18(75)
18(75)
19(75)
17(75)
4bA
4cA
4dA
4aB
10(75)
12(75)
15(75)
14(75)
15(75)
16(75)
14(75)
14(75)
15(37.5) 8(37.5) 18(37.5)
15(37.5) 8(37.5) 18(37.5)
16(37.5) 9(37.5) 19(37.5)
14(37.5) 9(37.5) 19(37.5)
15(37.5) 10(37.5) 19(37.5)
15(37.5) 9(37.5) 19(37.5)
14(37.5) 9(37.5) 19(37.5)
14(37.5) 8(37.5) 19(37.5)
4bB
4cB
4dB
4aC
4bC
4cC
4dC
7aX
11(150) 12(37.5) 7(37.5) 18(75)
12(150) 13(37.5) 6(37.5) 17(75)
11(150) 12(37.5) 7(37.5) 16(75)
11(150) 12(37.5) 8(37.5) 17(75)
7bX
7cX
7dX
10aY
10bY
10cY
10dY
Nystatin
12(150) 11(150) 6(75)
12(150) 12(150) 4(75)
13(150) 13(150) 6(75)
12(150) 14(150) 6(75)
18(12.5) 18(12.5) 15(6)
16(150)
17(150)
18(150)
19(150)
20(6)
Control DMSO e
e
e
e
e
Values in brackets are MIC values (mg/ml).

1754
S. Sharma et al. / European Journal of Medicinal Chemistry 44 (2009) 1751e1757
comparison of antifungal results. The nitro and chloro
substituted compounds 4aBe4dB and 4aCe4dC showed
same trend in case of fungal strains. The excellent inhibition
results were obtained against C. albicans and Penicillium sp.
by 4aBe4dB. The moderate activity was obtained in H. oryzae
and A. niger. The inhibitory activity against T. viridae was sig-
nificantly lower than the other tested microorganisms. Hence
we conclude that higher activity of compounds 4aBe4dB and
4aCe4dC may be attributed to the presence of nitro and chloro
groups. The inhibition by 4aAe4dA, 7aXe7dX, 10aYe10dY
is due to the presence of benzimidazole, tetrahydrobenzimida-
zole and imidazole, respectively. Thus the nature of substituents
and basic skeleton of molecule have strong influence on the
extent of antibacterial and antifungal activities. Thus the data
revealed that all compounds have produced the marked en-
hancement in the potency of these analogues as antibacterial
and antifungal agents.
were synthesized by utilizing cis cyclohexanediamine and
acid chlorides. BF3$OEt2 (0.015 mol) in dry dioxane (10 ml)
was added dropwise to the above stirred reaction mixtures in
10 min and reaction mixtures further refluxed for 1e2 h at
130 ꢁC. The resulting solution was concentrated in vacuo,
saturated NH4Cl solution added until the pH becomes 6,
extracted with EtOAc, dried over anhydrous Na2SO4 and con-
centrated in vacuo to give the crude products 4aAe4dC,
7aXe7dX, 10aYe10dY which were further purified by
column chromatography.
6.1.1. 2-(Dec-9-enyl)-1H-benzimidazole (4aA)
Colorless oily liquid: yield: 89%; IR (KBr): nmax cmꢀ1
1
3350, 1630, 1585. H NMR d (ppm): 9.01 (s, 1H, NeH),
6.73e6.71 (m, 4H, AreH), 5.82 (tdd, 1H, JHꢀ C
8
¼ 6:6 Hz,
H2
JHꢀH ¼ 10:2 Hz, JHꢀH ¼ 17:1 Hz, CH2]CHe), 5.02 (dd,
Z
E
1H, JH ꢀH ¼ 10:2 Hz, JH ꢀH ¼ 1:2 Hz, HZC]CH), 4.90
Z
Z
E
(dd, 1H, JH ꢀH ¼ 17:1 Hz, JH ꢀH ¼ 1:2 Hz, HEC]CHe),
E
E
Z
5. Conclusion
2.34 (t, 2H, J ¼ 7.12 Hz, a to benzimidazole ring), 2.03 (m,
2H, eCH2eCH]CH2), 1.63 (m, 2H, b to benzimidazole
ring), 1.30 (br s, 10H, chain CH2). 13C NMR d (ppm):
143.44, 139.01, 133.56, 121.45, 118.17, 114.14, 34.25, 33.77,
29.20, 28.88, 24.73. MS (m/z %): 257 (Mþ þ 1, 56), 256
(Mþ, 45), 229 (34), 145 (40), 117 (100). Anal. calcd. for
C17H24N2: C, 79.65; H, 9.43; N, 10.92. Found: C, 79.06; H,
9.49; N, 10.87%.
The fact that readily synthesized starting material, available
reagents along with short reaction time, no additives and sim-
ple work-up and isolation of the product make the current
method a feasible and attractive protocol for generation of
benzimidazoles and imidazoles from long-chain olefinic and
hydroxyl olefinic acids. The antibacterial and antifungal eval-
uation of compounds has proved them potent antibacterial and
antifungal agents. The other biological evaluation may furnish
some other important applications.
6.1.2. 2-(Heptadec-8-enyl)-1H-benzimidazole (4bA)
Pale yellow oily liquid; yield: 89%; IR (KBr): nmax cmꢀ1
1
3360, 1640, 1590. H NMR d (ppm): 9.12 (s, 1H, NeH),
6. Experimental
6.73e6.70 (m, 4H, AreH), 5.38 (m, 2H, eCH]CHe),
2.35 (t, 2H, J ¼ 7.22 Hz, a to benzimidazole ring), 2.02 (m,
4H, eCH2eCH]CHeCH2e), 1.61 (m, 2H, b to benzimid-
azole ring), 1.30 (br s, 20H, chain CH2), 0.89 (dist. t, 3H,
CH3). 13C NMR d (ppm): 143.22, 133.66, 122.77, 118.41,
34.20, 31.81, 29.65, 29.49, 29.09, 27.05, 24.72, 22.56,
22.45, 14.92. MS (m/z %): 355 (Mþ þ 1, 40), 354 (Mþ, 34),
237 (25), 181 (25), 117 (100). Anal. calcd. for C24H38N2:
C, 81.31; H, 10.79; N, 7.90. Found: C, 81.88; H, 10.73; N,
7.94%.
(9Z,12R)-12-Hydroxyoctadec-9-enoic (ricinoleic) and
(9R,12Z )-9-hydroxyoctadec-12-enoic (isoricinoleic) acids were
isolated from the natural sources, i.e. from Ricinus communis
and Wrightia tinctoria seed oils, respectively. The concentrate
of pure hydroxy acids were obtained by Gunstone’s partition-
ing [12] of freshly prepared acids and further purified by
column chromatography. 1H NMR and 13C NMR spectra
were recorded in CDCl3 on a Bruker DRX-400 instrument.
The chemical shifts (d) were measured relative to TMS as
an internal standard. Coupling constants (J ) are expressed in
Hz. Mass spectra were obtained on a Jeol SX-102 (FAB) spec-
trometer. IR spectra were obtained on Shimadzu 8201 PC FT-
6.1.3. 2-[(8Z, 11R)-11-Hydroxyheptadec-8-enyl]-
1H-benzimidazole (4cA)
IR using KBr pellet with absorption given in cmꢀ1
.
Yellow oily liquid; yield: 88%; IR (KBr): nmax cmꢀ1 3390,
1650, 1580. 1H NMR d (ppm): 9.25 (s, 1H, NeH), 6.72e6.70
(m, 4H, AreH), 5.42 (m, 2H, eCH]CHe), 3.66 (m, 1H,
C-11 methine proton), 2.32 (t, 2H, J ¼ 7.19 Hz, a to benz-
imidazole ring), 2.27 (m, 1H, eOH), 2.02 (m, 4H, eCH2e
CH]CHeCH2e), 1.57 (m, 2H, b to benzimidazole ring),
1.39 (br s, 18H, chain CH2), 0.88 (dist. t, 3H, CH3). 13C
NMR d (ppm): 143.44, 134.09, 123.22, 117.81, 34.02,
31.81, 29.56, 29.94, 29.90, 27.51, 24.27, 22.65, 22.54,
14.17. MS (m/z %): 371 (Mþ þ 1, 38), 370 (Mþ, 34), 255
(20), 241 (100), 173 (15). Anal. calcd. for C24H38N2O: C,
77.79; H, 10.33; N, 7.56. Found: C, 77.16; H, 10.39; N,
7.51%.
6.1. Procedure for the preparation of 2-substituted
benzimidazoles and imidazoles
Thionyl chloride (0.015 mol) was added to fatty acid
(0.01 mol) at 80 ꢁC for about 2 h to form the corresponding
acid chloride 1ae1d. The excess of thionyl chloride was dis-
tilled off. A typical reaction procedure involves the addition of
1,2-phenylenediamine derivatives (0.01 mmol) 2Ae2C and
5X to the stirred solution of acid chloride at 0 ꢁC in dry diox-
ane and stirring for 30 min at rt to furnish the corresponding
3aAe3dC and 6aXe6dX, respectively. Similarly 9aYe9dY

S. Sharma et al. / European Journal of Medicinal Chemistry 44 (2009) 1751e1757
1755
6.1.4. 2-[(8R, 11Z )-8-Hydroxyheptadec-11-enyl]-
1H-benzimidazole (4dA)
(Mþ þ 1, 35), 415 (Mþ, 70), 330 (100), 300 (70), 260 (20).
Anal. calcd. for C24H37N3O3: C, 69.37; H, 8.97; N, 10.11.
Found: C, 69.79; H, 8.92; N, 10.16%.
Yellow oily liquid; yield: 88%; IR (KBr): nmax cmꢀ1 3355,
1626, 1596. 1H NMR d (ppm): 9.04 (s, 1H, NeH), 6.78e6.76
(m, 4H, AreH), 5.44 (m, 2H, eCH]CHe), 3.66 (m, 1H, C-8
methine proton), 2.31 (t, 2H, J ¼ 7.20 Hz, a to benzimidazole
ring), 2.11 (m, 1H, eOH), 2.04 (m, 4H, eCH2eCH]CHe
CH2e), 1.61 (m, 2H, b to benzimidazole ring), 1.40 (br s,
18H, chain CH2), 0.88 (dist. t, 3H, CH3). 13C NMR
d (ppm): 143.66, 133.17, 123.22, 118.12, 34.25, 31.41,
29.58, 29.39, 29.23, 27.26, 24.72, 24.22, 14.91. MS (m/z %):
371 (Mþ þ 1, 20), 370 (Mþ, 45), 299 (10), 245 (100), 131
(15). Anal. calcd. for C24H38N2O: C, 77.79; H, 10.33; N,
7.56. Found: C, 77.21; H, 10.27 N, 7.53%.
6.1.8. 2-[(8R, 11Z )-8-Hydroxyheptadec-11-enyl]-
5-nitro-1H-benzimidazole (4dB)
Yellow oily liquid; yield: 80%; IR (KBr): nmax cmꢀ1 3390,
1630, 1584. 1H NMR d (ppm): 9.20 (s, 1H, NeH), 7.16 (d, 1H,
AreH), 7.04 (m, 1H, AreH), 6.93 (m, 1H, AreH), 5.43 (m,
2H, eCH]CHe), 3.67 (m, 1H, C-8 methine proton), 2.36
(t, 2H, J ¼ 7.29 Hz, a to benzimidazole ring), 2.21 (m, 1H,
eOH), 2.04 (m, 4H, eCH2eCH]CHeCH2e), 1.64 (m, 2H,
b to benzimidazole ring), 1.42 (br s, 18H, chain CH2), 0.87
(dist. t, 3H, CH3). 13C NMR 1 d (ppm): 144.23, 135.64,
131.39, 129.41, 123.83, 117.71, 37.51, 34.66, 31.38, 29.51,
27.43, 25.44, 23.11, 22.15, 15.16. MS (m/z %): 416
(Mþ þ 1, 10), 415 (Mþ, 70), 344 (100), 290 (25), 246 (20).
Anal. calcd. for C24H37N3O3: C, 69.37; H, 8.97; N, 10.11.
Found: C, 69.84; H, 8.92; N, 10.13%.
6.1.5. 2-(Dec-9-enyl)-5-nitro-1H-benzimidazole (4aB)
Light yellow oily liquid; yield: 85%; IR (KBr): nmax cmꢀ1
3375, 1660, 1575. 1H NMR d (ppm): 9.22 (s, 1H, NeH), 7.12
(d, 1H, AreH), 7.04 (m, 1H, AreH), 6.91 (m, 1H, AreH),
5.82 (tdd, 1H, JHꢀ C
8
¼ 6:6 Hz, JHꢀH ¼ 10:2 Hz, JHꢀH
¼
H2
Z
E
17:1 Hz, CH2]CHe), 5.02 (dd, 1H, JH ꢀH ¼ 10:2 Hz,
6.1.9. 2-(Dec-9-enyl)-5-chloro-1H-benzimidazole (4aC)
Colorless oily liquid; yield: 88%; IR (KBr): nmax cmꢀ1 3368,
1
1640, 1578. H NMR (CDCl3) (d): 9.01 (s, 1H, NeH), 7.43e
Z
JH ꢀH ¼ 1:2 Hz, HZC]CH), 4.90 (dd, 1H, JH ꢀH ¼ 17:1 Hz,
Z
E
E
JH ꢀH ¼ 1:2 Hz, HEC]CHe), 2.28 (t, 2H, J ¼ 7.17 Hz, a to
E
Z
benzimidazole ring), 2.04 (m, 2H, eCH2eCH]CH2), 1.66
(m, 2H, b to benzimidazole ring), 1.31 (br s, 10H, chain
CH2). 13C NMR d (ppm): 143.12, 139.01, 136.22, 130.12,
131.65, 122.26, 117.31, 33.91, 31.61, 28.22, 27.19, 22.33.
MS (m/z %): 302 (Mþ þ 1, 10), 301 (Mþ, 82), 274 (10), 176
(100), 162 (60). Anal. calcd. for C17H23N3O2: C, 67.76; H,
7.68; N, 13.94. Found: C, 67.30; H, 7.73; N, 13.99%.
7.31 (m, 3H, AreH), 5.82 (tdd, 1H, JHꢀ C
8
¼ 6:6 Hz, JHꢀH
H2
Z
¼ 10:2 Hz, JHꢀH ¼ 17:1 Hz, CH2]CHe), 5.02 (dd, 1H,
E
JH ꢀH ¼ 10:2 Hz, JH ꢀH ¼ 1:2 Hz, HZC]CH), 4.90 (dd,
Z
Z
E
1H, JH ꢀH ¼ 17:1 Hz, JH ꢀH ¼ 1:2 Hz, HEC]CHe), 2.31
E
E
Z
(t, 2H, J ¼ 7.33 Hz, a to benzimidazole ring), 2.04 (m, 2H, e
CH2eCH]CH2), 1.63 (m, 2H, b to benzimidazole ring),
1.33 (br s, 10H, chain CH2). 13C NMR (CDCl3) (d): 142.81,
141.31, 132.91, 131.61, 129.71, 128.91, 124.71, 123.46,
29.71, 28.36, 27.91, 23.91, 22.45, 14.81. MS (m/z %): 291
(Mþ þ 1, 10), 290 (Mþ, 85), 263 (100), 179 (25), 151 (40).
Anal. calcd. for C17H23ClN2: C, 70.22; H, 7.96; N, 9.63. Found:
70.80; H, 7.92; N, 9.58%.
6.1.6. 2-(Heptadec-8-enyl)-5-nitro-1H-benzimidazole (4bB)
Pale yellow oily liquid; yield: 84%; IR (KBr): nmax cmꢀ1
1
3352, 1636, 1580. H NMR d (ppm): 9.21 (s, 1H, NeH),
7.13 (d, 1H, AreH), 7.04 (m, 1H, AreH), 6.90 (m, 1H, Are
H), 5.38 (m, 2H, eCH]CHe), 2.34 (t, 2H, J ¼ 7.24 Hz,
a to benzimidazole ring), 2.02 (m, 4H, eCH2eCH]CHe
CH2e), 1.63 (m, 2H, b to benzimidazole ring), 1.30 (br s,
20 H, chain CH2), 0.89 (dist. t, 3H, CH3). 13C NMR
d (ppm): 143.62, 136.06, 131.33, 129.71, 123.44, 118.13,
34.19, 31.41, 29.53, 28.99, 27.41, 22.32, 22.45, 14.15. MS
(m/z %): 400 (Mþ þ 1, 20), 399 (Mþ, 25), 286 (75), 190
(70), 162 (100). Anal. calcd. for C24H37N3 O2: C, 72.15; H,
9.33; N, 10.51. Found: C, 72.70; H, 9.28; N, 10.56%.
6.1.10. 2-(Heptadec-8-enyl)-5-chloro-1H-
benzimidazole (4bC)
Light yellow oily liquid; yield: 87%; IR (KBr): nmax cmꢀ1
1
3370, 1655, 1589. H NMR d (ppm): 9.12 (s, 1H, NeH),
7.55e7.20 (m, 3H, AreH), 5.44 (m, 2H, eCH]CHe), 2.24
(t, 2H, J ¼ 7.44 Hz, a to benzimidazole ring), 2.04 (m, 4H,
eCH2eCH]CHeCH2e), 1.56 (m, 2H, b to benzimidazole
ring), 1.29 (br s, 20 H, chain CH2), 0.87 (dist. t, 3H, CH3).
13C NMR d (ppm): 143.48, 133.85, 131.24, 129.57, 127.71,
121.61, 117.81, 37.41, 34.21, 33.92, 29.56, 29.13, 25.84,
23.13, 22.35, 14.12. MS (m/z %): 389 (Mþ þ 1, 30), 388
(Mþ, 75), 275 (15), 165 (100), 151 (80). Anal. calcd. for
C24H37ClN2: C, 74.11; H, 9.58; N, 7.20. Found: C, 74.68;
H, 9.63; N, 7.16%.
6.1.7. 2-[(8Z, 11R)-11-Hydroxyheptadec-8-enyl]-
5-nitro-1H-benzimidazole (4cB)
Yellow oily liquid; yield: 82%; IR (KBr): nmax cmꢀ13355,
1
1640, 1580. H NMR d (ppm): 9.25 (s, 1H, NeH), 7.13 (d,
1H, AreH), 7.04 (m, 1H, AreH), 6.91 (m, 1H, AreH), 5.45
(m, 2H, eCH]CHe), 3.68 (m, 1H, C-11 methine proton),
2.33 (t, 2H, J ¼ 7.31 Hz, a to benzimidazole ring), 2.23 (m,
1H, eOH), 2.04 (m, 4H, eCH2eCH]CHeCH2e), 1.61 (m,
2H, b to benzimidazole ring), 1.36 (br s, 18H, chain CH2),
0.88 (dist. t, 3H, CH3). 13C NMR d (ppm): 144.13, 135.44,
131.19, 129.31, 123.33, 117.71, 37.11, 34.26, 31.83, 29.61,
27.10, 25.81, 23.11, 22.15, 15.06. MS (m/z %): 416
6.1.11. 2-[(8Z, 11R)-11-Hydroxyheptadec-8-enyl]-5-chloro-
1H-benzimidazole (4cC)
Yellow oily liquid; yield: 87%; IR (KBr): nmax cmꢀ1 3412,
1648, 1572. 1H NMR d (ppm): 9.25 (s, 1H, NeH), 7.43e7.31
(m, 3H, AreH), 5.46 (m, 2H, eCH]CHe), 3.67 (m, 1H, C-
11 methine proton), 2.33 (t, 2H, J ¼ 7.12 Hz,
a to

1756
S. Sharma et al. / European Journal of Medicinal Chemistry 44 (2009) 1751e1757
benzimidazole ring), 2.27 (m, 1H, eOH), 2.02 (m, 4H, CH2e
CH]CHeCH2), 1.57 (m, 2H, b to benzimidazole ring), 1.39
(br s, 18H, chain CH2), 0.88 (dist. t, 3H, CH3). 13C NMR
d (ppm): 142.98, 133.76, 130.99, 129.76, 127.80, 121.53,
119.01, 37.03, 34.12, 33.57, 29.34, 28.37, 25.71, 23.91,
22.11, 15.17. MS (m/z %): 405 (Mþ þ 1, 15), 404 (Mþ, 70),
319 (100), 249 (85), 207 (90). Anal. calcd. for C24H37ClN2O:
C, 71.18; H, 9.20; N, 6.91. Found: C, 71.66; H, 9.23; N,
6.87%.
6.1.15. 2-[(8Z, 11R)-11-Hydroxyheptadec-8-enyl]-4,5,6,
7-tetrahydro-1H-benzimidazole (7cX)
Yellow oily liquid; yield: 88%; IR (KBr): nmax cmꢀ1 3350,
1
1620, 1592. H NMR d (ppm): 9.25 (s, 1H, NeH), 5.42 (m,
2H, eCH]CHe), 3.66 (m, 1H, C-11 methine proton), 2.32
(t, 2H, J ¼ 7.28 Hz, a to benzimidazole ring), 2.27 (m, 1H,
eOH), 2.02 (m, 4H, eCH2eCH]CHeCH2e), 1.88 (m, 2H,
eCHe ring), 1.67 (m, 2H, b to imidazole ring), 1.50 (m,
8H, eCH2e ring), 1.39 (br s, 18H, chain CH2), 0.88 (dist. t,
3H, CH3). 13C NMR d (ppm): 169.99, 71.72, 63.89, 36.98,
34.22, 33.63, 31.66, 28.61, 27.63, 24.56, 22.91, 22.11,
21.81, 14.73. MS (m/z %): 377 (Mþ þ 1, 15), 376 (Mþ, 70),
291(10), 247 (85), 123 (100). Anal. calcd. for C24H44N2O:
C, 76.55; H, 11.77; N, 7.43. Found: C, 76.01; H, 11.82; N,
7.40%.
6.1.12. 2-[(8R, 11Z )-8-Hydroxyheptadec-11-enyl]-
5-chloro-1H-benzimidazole (4dC)
Yellow oily liquid; yield: 86%; IR (KBr): nmax cmꢀ1 3349,
1629, 1590. 1H NMR d (ppm): 9.29 (s, 1H, NeH), 7.46e7.33
(m, 3H, AreH), 5.45 (m, 2H, eCH]CHe), 3.68 (m, 1H, C-8
methine proton), 2.36 (t, 2H, J ¼ 7.23 Hz, a to benzimidazole
ring), 2.29 (m, 1H, eOH), 2.04 (m, 4H, eCH2eCH]CHe
CH2e), 1.62 (m, 2H, b to benzimidazole ring), 1.28 (br s,
18H, chain CH2), 0.88 (dist. t, 3H, CH3). 13C NMR
d (ppm): 142.68, 133.67, 130.89, 129.67, 127.82, 121.43,
119.01, 37.53, 34.41, 33.51, 29.43, 28.32, 25.17, 23.22,
22.13, 15.19. MS (m/z %): 405 (Mþ þ 1, 10), 404 (Mþ, 80),
333 (40), 279 (85), 179 (65). Anal. calcd. for C24H37ClN2O:
C, 71.18; H, 9.20; N, 6.91. Found: C, 71.71; H, 9.16; N,
6.94% .
6.1.16. 2-[(8R, 11Z )-8-Hydroxyheptadec-11-enyl]-4,5,6,
7-tetrahydro-1H-benzimidazole (7dX)
Yellow oily liquid; yield: 87%; IR (KBr): nmax cmꢀ1 3358,
1
1658, 1577. H NMR d (ppm): 9.72 (s, 1H, NeH), 5.44 (m,
2H, eCH]CHe), 3.68 (m, 1H, C-8 methine proton), 2.28
(t, 2H, J ¼ 7.39 Hz, a to benzimidazole ring), 2.21 (m, 1H,
eOH), 2.03 (m, 4H, eCH2eCH]CHeCH2e), 1.87 (m, 2H,
eCHe ring), 1.69 (m, 2H, b to imidazole ring), 1.52 (m,
2H, eCH2e ring), 1.36 (br s, 18H, chain CH2), 0.88 (dist. t,
3H, CH3). 13C NMR d (ppm): 169.87, 71.73, 64.01, 36.89,
34.32, 33.36, 31.66, 28.64, 27.53, 24.65, 22.98, 22.11,
21.81, 14.69. MS (m/z %): 377 (Mþ þ 1, 30), 376 (Mþ, 50),
305 (10), 251 (75), 123 (100). Anal. calcd. for C24H44N2O:
C, 76.55; H, 11.77; N, 7.43. Found: C, 76.98; H, 11.72; N,
7.47%.
6.1.13. 2-(Dec-9-enyl)-4,5,6,7-tetrahydro-1H-benzimidazole
(7aX)
Pale yellow oily liquid; yield: 90%; IR (KBr): nmax cmꢀ1
3338, 1632, 1580. 1H NMR d (ppm): 9.01(s, 1H, NeH),
5.82 (tdd, 1H, JHꢀ C
8
¼ 6:6 Hz, JHꢀH ¼ 10:2 Hz, JHꢀH
¼
H2
Z
E
17:1 Hz, CH2]CHe), 5.02 (dd, 1H, JH ꢀH ¼ 10:2 Hz,
Z
JH ꢀH ¼ 1:2 Hz, HZC]CH), 4.90 (dd, 1H, JH ꢀH
¼
Z
E
E
6.1.17. 2-(Dec-9-enyl)-1H-imidazole (10aY)
17:1 Hz, JH ꢀH ¼ 1:2 Hz, HEC]CHe), 2.34 (t, 2H,
E
Z
Colorless oily liquid: yield: 89%; IR (KBr): nmax cmꢀ1
3354, 1642, 1598. 1H NMR d (ppm): 9.81(s, 1H, NeH ),
J ¼ 7.36 Hz, a to benzimidazole ring), 2.03 (m, 2H, eCH2e
CH]CH2), 1.87 (m, 2H, eCHe ring), 1.69 (m, 2H, b to im-
idazole ring), 1.50 (m, 8H, eCH2e ring), 1.30 (br s, 10H,
chain CH2). 13C NMR d (ppm): 170.33, 139.81, 117.61,
64.01, 37.62, 31.91, 29.88, 28.35, 24.57, 22.50, 22.21. MS
(m/z %): 263 (Mþ þ 1, 30), 262 (Mþ, 70), 235 (100), 179
(70), 123 (60). Anal. calcd. for C17H30N2: C, 77.82; H,
11.51; N, 10.67. Found: C, 77.30; H, 11.47; N, 10.70%.
5.82 (tdd, 1H, JHꢀ C
8
¼ 6:6 Hz, JHꢀH ¼ 10:2 Hz, JHꢀH
¼
H2
Z
E
17:1 Hz, CH2]CHe), 5.60 (m, 2H, eCH]CHe), 5.02 (dd,
1H, JH ꢀH ¼ 10:2 Hz, JH ꢀH ¼ 1:2 Hz, HZC]CH), 4.90
Z
Z
E
(dd, 1H, JH ꢀH ¼ 17:1 Hz, JH ꢀH ¼ 1:2 Hz, HEC]CHe),
E
E
Z
2.31 (t, 2H, J ¼ 7.16 Hz, a to imidazole ring), 2.04 (m, 2H,
eCH2eCH]CH2), 1.66 (m, b to imidazole ring), 1.36 (br s,
10H, chain CH2). 13C NMR d (ppm): 152.3, 130.9, 125.9,
33.6, 32.8, 30.1, 23.2, 14.3. MS (m/z %): 207 (Mþ þ 1, 20),
206 (Mþ, 22), 176 (36), 109 (100), 81 (100). Anal. calcd.
for C13H22N2: C, 75.69; H, 10.74; N, 13.57. C, 75.22; H,
10.70; N, 13.63%.
6.1.14. 2-(Heptadec-8-enyl)-4,5,6,7-tetrahydro-
1H-benzimidazole (7bX)
Light yellow oily liquid; yield: 89%; IR (KBr): nmax cmꢀ1
3356, 1641, 1593. 1H NMR d (ppm): 9.12 (s, 1H, NeH), 5.38
(m, 2H, eCH]CHe), 2.34 (t, 2H, J ¼ 7.30 Hz, a to benz-
imidazole ring), 2.02 (m, 4H, eCH2eCH]CHeCH2e),
1.86 (m, 2H, eCHe ring), 1.66 (m, 2H, b to imidazole
ring), 1.50 (m, 8H, eCH2e ring), 1.32 (br s, 20 H, chain
CH2), 0.88 (dist. t, 3H, CH3). 13C NMR d (ppm): 169.97,
63.91, 36.92, 31.88, 28.22, 27.36, 24.63, 22.49, 22.12,
21.90, 14.91. MS (m/z %): 361 (Mþ þ 1, 40), 360 (Mþ, 85),
247 (45), 207 (50), 193 (67). Anal. calcd. for C24H44N2: C,
79.95; H, 12.29; N, 7.76. Found: C, 79.40; H, 12.36; N,
7.72%.
6.1.18. 2-(Heptadec-8-enyl)-1H-imidazole (10bY)
Pale yellow oily liquid: yield: 88%; IR (KBr): nmax cmꢀ1
1
3367, 1644, 1590. H NMR d (ppm): 9.77 (s, 1H, NeH),
5.62 (m, 4H, eCH]CHe), 2.33 (t, 2H, J ¼ 7.35 Hz, a to im-
idazole ring), 2.05 (m, 4H, eCH2eCH]CHeCH2e), 1.62
(m, 2H, b to imidazole ring), 1.29 (br s, 20H, chain CH2),
0.87 (dist. t, 3H, CH3). 13C NMR d (ppm): 152.7, 131.7,
126.8, 33.3, 32.2, 30.4, 23.6, 14.3 MS (m/z %): 305
(Mþ þ 1, 40), 304 (Mþ, 22), 191 (31), 165 (31), 67 (100).

S. Sharma et al. / European Journal of Medicinal Chemistry 44 (2009) 1751e1757
1757
Anal. calcd. for C20H36N2: C, 78.89; H, 11.91; N, 9.20. C,
78.35; H, 11.86; N, 9.15%.
References
[1] D.A. Horton, G.T. Bourne, M.L. Smythe, Chem. Rev. 103 (2003) 893e
930 and references cited therein.
6.1.19. 2-[(8Z, 11R)-11-Hydroxyheptadec-8-enyl]-
1H-imidazole (10cY)
[2] W.A. Denny, G.W. Rewcastle, B.C. Baguley, J. Med. Chem. 33 (1990)
814e819.
Yellow oily liquid: yield: 86%; IR (KBr): nmax cmꢀ1 3378,
[3] (a) T. Fonseca, B. Gigante, T.L. Gilchrist, Tetrahedron 57 (2001) 1793e
1799;
1
1655, 1597. H NMR d (ppm): 9.81 (s, 1H, NeH), 5.66 (m,
(b) A.R. Parikh, M.D. Khunt, Abstracts of the American Chemical
Society, Division of Medicinal Chemistry, 222nd ACS National Meet-
ing, Chicago, IL, Aug 2001, vols. 26e29, ACS, Washington, DC,
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4H, eCH]CHe), 3.59 (m, 1H, C-11 methine proton), 2.36
(t, 2H, J ¼ 7.39 Hz, a to imidazole ring), 2.32 (m, 1H, e
OH), 2.03 (m, 4H, eCH2eCH]CHeCH2e), 1.62 (m, 2H,
b to imidazole ring), 1.29 (br s, 18H, chain CH2), 0.88 (dist.
t, 3H, CH3). 13C NMR d (ppm): 152.94, 131.41, 126.53,
71.91, 36.98, 34.22, 33.63, 31.66, 28.54, 27.36, 24.65,
22.19, 22.11, 21.81, 14.34. MS (m/z %): 321 (Mþ þ 1, 40),
320 (Mþ, 22), 235 (100), 191 (31), 165 (100). Anal. calcd.
for C20H36N2O: C, 74.96; H, 11.31; N, 8.74. C, 74.61; H,
11.37; N, 8.70%.
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6.1.20. 2-[(8R, 11Z )-8-Hydroxyheptadec-11-enyl]-
1H-imidazole (10dY)
(c) J.P. Rizzi, A.A. Nagel, T. Rosen, S. McLean, T. Seeger, J. Med.
Chem. 33 (1990) 2721e2725;
Yellow oily liquid: yield: 86%; IR (KBr): nmax cmꢀ1 3354,
(d) G. Shapiro, B. Gomez-Lor, J. Org. Chem. 59 (1994) 5524e5526;
(e) L.J. Adams, J.C. Boehm, S. Kassis, P.D. Gorycki, E.F. Webb, R. Hall,
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Med. Chem. Lett. 8 (1998) 3111e3116.
1
1628, 1578. H NMR d (ppm): 9.81 (s, 1H, NeH), 5.59 (m,
4H, eCH]CHe), 3.61 (m, 1H, C-8 methine proton), 2.41
(t, 2H, J ¼ 7.44 Hz, a to imidazole ring), 2.33 (m, 1H,
eOH), 2.05 (m, 4H, eCH2eCH]CHeCH2e), 1.65 (m, 2H,
b to imidazole ring), 1.30 (br s, 18H, chain CH2), 0.89 (dist.
t, 3H, CH3). 13C NMR d (ppm): 152.88, 131.39, 126.35,
71.68, 36.89, 34.56, 33.34, 31.48, 28.45, 27.63, 24.56,
22.91, 22.18, 21.71, 14.37. MS (m/z %): 321 (Mþ þ 1, 38),
320 (Mþ, 46), 249 (100), 195 (18), 165 (73). Anal. calcd.
for C20H36N2O: C, 74.96; H, 11.31; N, 8.74. C, 74.48; H,
11.26; N, 8.69%.
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1084;
Acknowledgements
(c) P.G. Speranza, Su. Wei Yang, U.S. (1990) 5 pp. CODEN: USXXAM
US 4927942 A 19900522 CAN 113:172019 AN 1990:572019;
(d) C. Graenacher, J. Meyer, (1940), US 2226057 19401224 CAN 35:
14107 AN 1941:14107.
We wish to give special thanks to Dr. Iqbal Ahmad,
Department of Agricultural Microbiology, AMU for perform-
ing antimicrobial activity of our compounds. We are also
grateful to the SAIF Central Drug Research Institute,
Lucknow and Panjab University for providing IR, H NMR,
13C NMR and mass spectra.
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1