Synthesis and antimicrobial activity of some benzimidazole and 2-methylbenzimidazole derivatives

Article abstract of DOI:10.14233/ajchem.2017.20328

In the present work, benzimidazole and 2-methylbenzimidazole derivatives were synthesized and evaluated for antimicrobial activity against Escherichia coli (Gram-negative bacteria), Staphylococcus aureus (Gram-positive bacteria) and Candida albicans (fungal stain). The structure of the synthesized compounds was confirmed by FTIR, ¹H NMR and mass spectroscopy. Antimicrobial activity of all the synthesized compounds was carried out by Broth dilution method to determine MIC value. Compounds P2, P7 and P10 showed better antibacterial activity against Escherichia coli as compared to benzimidazole, 2-methylbenzimidazole and ampicillin. Compounds P8 and P12 showed better antibacterial activity against Staphylococcus aureus as compared to benzimidazole, 2-methylmenzimidazole and ampicillin. Compound P2 and P9 showed better antifungal activity against Candida albicans as compared to benzimidazole, 2-methylbenzimidazole and griseofulvin.

Full text of DOI:10.14233/ajchem.2017.20328

Asian Journal of Chemistry; Vol. 29, No. 4 (2017), 838-842
A
SIAN
J
OURNAL OF HEMISTRY
C
https://doi.org/10.14233/ajchem.2017.20328
Synthesis andAntimicrobialActivity of Some Benzimidazole and 2-Methylbenzimidazole Derivatives
1
2,*
P. JAIN and M. TIWARI
1Department of Pharmacy, Shri G.S. Institute of Technology and Science, 23-Park Road, Indore-452 003, India
2Medicinal Chemistry Research Lab, Department of Pharmacy, Shri G.S. Institute of Technology and Science, 23-Park Road, Indore-452 003
India
*Corresponding author: E-mail: mtiwari@sgsits.ac.in
Received: 5 October 2016;
Accepted: 16 December 2016;
Published online: 31 January 2017;
AJC-18255
In the present work, benzimidazole and 2-methylbenzimidazole derivatives were synthesized and evaluated for antimicrobial activity
against Escherichia coli (Gram-negative bacteria), Staphylococcus aureus (Gram-positive bacteria) and Candida albicans (fungal stain).
The structure of the synthesized compounds was confirmed by FTIR, 1H NMR and mass spectroscopy. Antimicrobial activity of all the
synthesized compounds was carried out by Broth dilution method to determine MIC value. Compounds P2, P7 and P10 showed better
antibacterial activity against Escherichia coli as compared to benzimidazole, 2-methylbenzimidazole and ampicillin. Compounds P8
and P12 showed better antibacterial activity against Staphylococcus aureus as compared to benzimidazole, 2-methylmenzimidazole
and ampicillin. Compound P2 and P9 showed better antifungal activity against Candida albicans as compared to benzimidazole,
2-methylbenzimidazole and griseofulvin.
Keywords: Benzimidazole, 2-Methylbenzimidazole, Antimicrobial activity.
to possess antimicrobial property. So keeping the above
observation in consideration, benzimidazole derivatives with
substituted benzoic acid were prepared.
In the present work, we have synthesized benzimidazole
and 2-methylbenzimidazole derivatives and evaluated anti-
microbial activity against Escherichia coli, Staphylococcus
aureus and Candida albicans [14-16].
INTRODUCTION
Microbial diseases are pressing problem worldwide and
problems of multidrug resistant organisms have reached an
alarming level. Novel drugs are urgently required in the therapy
of microbial infectious diseases. Millions of people are infected
and around 20,000 deaths are reported in the tropical region
every year because of microbial infections. The incidence of
microbial infection has increased at an alarming level all over
the world as a result of antimicrobial resistance in past 25
years [1-4].
Benzimidazole is a heterocyclic aromatic organic compound,
consists of the fused benzene and imidazole. It is important
pharmacophore and a privileged structure in medicinal chemistry.
It shows various pharmacological activities such as anticancer,
antihistaminic, antihypertensive and antiulcer [5-7]. This
has drawn more and more attention to investigate the other
medicinal applications of benzimidazole. Recently, extensive
biochemical and pharmacological studies revealed that
benzimidazole possessed large potential to inhibit the growth
of bacteria and fungi [8-10].
EXPERIMENTAL
o-Phenylenediamine, acetic acid, formic acid and methanol
were purchased from Spectrochem Pvt. Ltd. Mumbai, India.
substituted benzoic acid were purchased from Himedia Pvt. Ltd.
Mumbai, India. Ammonia and sodium bicarbonate were pur-
chased from Lobachemie Pvt. Ltd. Mumbai, India. The melting
point of synthesized compounds was determined by capillary
tube method. The progress of reaction and purity of synthesized
compounds was checked by TLC using pre coated aluminium
sheets with GF-254 silica gel purchased from Merk specialities
Pvt. Ltd. Mumbai, India. using mobile phase chloroform:
methanol (9:1). The spots were visualized in UV light chamber.
The λmax (nm) of the synthesized compounds was determined
by Shimadzu 1700 UV-visible spectrophotometer. The FTIR
spectra of the synthesized compounds was recorded on FTIR
Alpha Bruker by KBr disc in the range of 4000-400 cm-1. The
proton NMR (1H NMR) spectra were recorded using Bruker
Benzimidazole blocks DNA replication, exerting powerful
antimicrobial action, indicating that benzimidazole derivatives
are promising candidates for developing new antimicrobial
agents [11-14]. In literature sodium benzoate has been reported

Vol. 29, No. 4 (2017)
Synthesis and Antimicrobial Activity of Some Benzimidazole and 2-Methylbenzimidazole Derivatives 839
Advance II 400 NMR spectrometer. The Mass spectra of
synthesized compounds were recorded using CIF Mass facility
IISER Bhopal|.
chloroform, 9:1) 0.67, IR (KBr, νmax, cm-1): (-C=O, amide) 1656,
(-C=C, aromatic) 1597, (-C-H, stretch) 2853, (-C-H, bend)
1446, (-C-N) 1229, (-C=N) 1577, (-N= tertiary amine) 3422,
1H NMR (DMSO): 7.19-8.170 (m, 10H,Ar-H), m/z: 222.9 (M+).
(4-Aminophenyl)(1H-benzo[d]imidazole-1-yl)-
methanone (P2): Pale yellow colour, yield 77 %, m.p.: 240-
A series of fifteen 1-sustituted benzimidazole (P1-P8) and
1-substituted 2-methylbenzimidazole (P9-P15) derivatives
were synthesized according to the synthetic route presented
in Fig. 1. On reaction of o-phenylenediamine and substituted
acid under refluxed in the presence of ammonia solution the
two intermediate benzimidazole (1H-benzo[d]imidazole) and
2-methylbenzimidazole (2-methyl-1H-benzo[d]imidazole)
were synthesized. The final products (P1-P15) were obtained
by the reaction between benzimidazole or 2-methylbenzimi-
dazole and the corresponding substituted benzoyl derivatives.
The formation of compound (P1-P15) was confirmed by m.p.,
Rf value, FTIR, 1H NMR and mass spectra.
Synthesis of benzimidazole: A mixture of o-phenylenedi-
amine 0.03 mol (3.24 g), formic acid 0.09 mol (5.05 mL) and
20 mL of water were refluxed for 45 min. The reaction mixture
was cooled and made basic by the gradual addition of concen-
trated ammonia solution. The precipitated product was collected
and recrystallized from 10 % ethanol [18-20].
Synthesis of benzimidazole derivative: 0.025 mol (3 g)
of benzimidazole was dissolved in 30 mL of 10 % sodium
hydrogen carbonate solution, 0.04 mol of substituted benzoyl
chloride was added and the reaction mixture was shaken
vigorously than acidified to congored with dilute HCl, the
precipitate obtained was filtered, the product was recrystallized
from ethanol [21,22].
Synthesis of 2-methylbenzimidazole: A mixture of
o-phenylenediamine 0.03 mol (3.24 g), acetic acid 0.09 mol
(5.67 mL) and 20 mL of water were refluxed for 45 min. The
reaction mixture was cooled and made basic by the gradual
addition of concentrated ammonia solution. The precipitated
product was collected and recrystallized from 10 % ethanol
[17-19].
242 °C, Rf (methanol:chloroform, 9:1) 0.72, IR (KBr, νmax
,
cm-1): (-C=O, amide) 1703, (-C=C, aromatic) 1610, (-C-H,
stretch) 2869, (-C-H, bend) 1449, (-C-N) 1239, (-C=N) 1508,
(-N= tertiary amine, N-H) 3424, 1H NMR (DMSO): 6.35-8.00
(m, 9H, Ar-H), 3.43 (s, 2H, N-H), m/z: 238.0 (M+1).
(1H-Benzo[d]imidazole-1-yl)(4-chlorophenyl)methanone
(P3): Salmon pink colour, yield 85 %, m.p.: 270-272 °C, Rf
(methanol:chloroform, 9:1) 0.73, IR (KBr, νmax, cm-1): (-C=O,
amide) 1682, (-C=C, aromatic) 1494, (-C-H, stretch) 2841,
(-C-H, bend) 1425, (-C-N) 1239, (-C=N) 1652, (-N= tertiary
amine) 3416, (-C-Cl) 607, 1H NMR (DMSO): 7.29-8.36 (m,
9H, Ar-H), m/z: 256.8 (M+).
(1H-Benzo[d]imidazol-1-yl)(4-bromophenyl)methanone
(P4): Pale yellow colour, yield 36 %, m.p.: 266-268 °C, Rf
(methanol:chloroform, 9:1) 0.62, IR (KBr, νmax, cm-1): (-C=O,
amide) 1679, (-C=C, aromatic) 1587, (-C-H, stretch) 3153,
(-C-H, bend) 1399, (-C-N) 1234, (-C=N) 1587, (-N= tertiary
amine) 3492, (-C-Br) 603, 1H NMR (DMSO): 6.62-8.06 (m,
9H, Ar-H), m/z: 301.14 (M+).
(3-Aminophenyl)(1H-benzo[d]imidazol-1-yl)methanone
(P5): Dark brown colour, yield 26 %, m.p.: 265-267 °C, Rf
(methanol:chloroform, 9:1) 0.70, IR (KBr, νmax, cm-1): (-C=O,
amide) 1685, (-C=C, aromatic) 1591, (-C-H, stretch) 2983,
(-C-H, bend) 1456, (-C-N) 1203, (-C=N) 1647, (-N= tertiary
1
amine, N-H) 3423, H NMR (DMSO): 7.28-8.02 (m, 9H,
Ar-H), 3.51 (s, 2H, N-H), m/z: 238.6 (M+1).
(1H-Benzo[d]imidazol-1-yl)(3-chlorophenyl)methanone
(P6): White colour, yield 54 %, m.p.: 251-253 °C, Rf
(methanol:chloroform, 9:1) 0.68, IR (KBr, νmax, cm-1) (-C=O,
amide) 1696, (-C=C, aromatic) 1597, (-C-H, stretch) 2850,
(-C-H, bend) 1450, (-C-N) 1261, (-C=N) 1643, (-N= tertiary
amine) 3391, (-C-Cl) 605, 1H NMR (DMSO): 7.28-8.36 (m,
9H, Ar-H), m/z: 257.3 (M+1).
(1H-Benzo[d]imidazol-1-yl)(2-chlorophenyl)methanone
(P7): White colour, yield 63 %, m.p.: 188-190 °C, Rf (methanol:
chloroform, 9:1) 0.61, IR (KBr, νmax, cm-1): (-C=O, amide)
1685, (-C=C, aromatic) 1475, (-C-H, stretch) 2873, (-C-H,
bend) 1437, (-C-N) 1266, (-C=N) 1591, (-N= tertiary amine)
3426, (-C-Cl) 605, 1H NMR (DMSO): 7.30-8.36 (m, 9H, Ar-
H), m/z: 257.6 (M+1).
Synthesis of 2-methylbenzimidazole derivatives: 0.025
mol (3.30 g) of 2-methylbenzimidazole was dissolved in 30
mL of 10 % sodium hydrogen carbonate solution, 0.04 mol of
substituted benzoyl chloride was added and the reaction
mixture was shaken vigorously than acidified to congored with
dilute HCl, the precipitate obtained was filtered, the product
was recrystallized from ethanol [20,21].
Spectral data of synthesized compounds
(1H-Benzo[d]imidazole-1-yl)(phenyl)methanone (P1):
Off white colour, yield 62 %, m.p.: 236-238 °C, Rf (methanol:
N
R1
O
C Cl
N
C O
(b)
NH2
N
(a)
R2
+
+
R1
R1COOH
R2
N
H
NH2
R3
R4
R3
R4
Reagent and conditions: (a) ammonia solution 45 min, reflux (b) sodium bicarbonate
R1 = H, CH3, R2 = H, Cl, R3 = H, Cl, NH2, R4 = H, Cl, NH2, Br
Fig. 1. Reaction scheme of synthesized compounds

840 Jain et al.
Asian J. Chem.
(1H-Benzo[d]imidazol-1-yl)(2,4-dichlorophenyl)-
methanone (P8): Pale yellow colour, yield 34 %, m.p.: 288-
Antimicrobial activity [22,23]: The antimicrobial
screening was carried out using Broth dilution method:
Serial dilutions were prepared in primary and secondary
screening. The control tube containing no antimicrobial was
immediately sub cultured (before inoculation) by spreading a
loopful evenly over a quarter of plate of medium suitable for
the growth of the test organism and kept for incubation at 37 °C
overnight. The tubes were then incubated overnight. The MIC
of the control organism was read to check the accuracy of
the compounds concentrations. The lowest concentration for
inhibiting growth of the organism was recorded as the MIC.
The amount of growth from the control tube before incubation
(which represents the original inoculums) was compared.
Primary screen: In primary screening solution containing
1000, 500 and 250 µg/mL concentrations of the synthesized
compound were prepared. The active synthesized compounds
found in this primary screening were further tested in a second
set of dilution against all microorganisms.
290 °C, Rf (methanol:chloroform, 9:1) 0.78, IR (KBr, νmax
,
cm-1): (-C=O, amide) 1651, (-C=C, aromatic) 1607, (-C-H,
stretch) 2860, (-C-H, bend) 1378, (-C-N) 1243, (-C=N) 1587,
1
(-N= tertiary amine) 3181, (-C-Cl) 623, H NMR (DMSO):
7.29-8.16 (m, 8H, Ar-H), m/z: 291.1 (M+).
(2-Methyl-1H-benzo[d]imidazol-1-yl)(phenyl)methanone
(P9): Salmon pink colour, yield 61 %, m.p.: 242-244 °C, Rf
(methanol:chloroform, 9:1) 0.66, IR (KBr, νmax, cm-1): (-C=O,
amide) 1656, (-C=C, aromatic) 1597, (-C-H, stretch) 3056,
(-C-H, bend) 1446, (-C-N) 1228, (-C=N) 1578, (-N= tertiary
1
amine) 3444, H NMR (DMSO): 7.28-8.22 (m, 9H, Ar-H),
2.50 (s, 3H, C-H), m/z: 236.9 (M+).
(4-Aminophenyl)(2-methyl-1H-benzo[d]imidazol-1-
yl)methanone (P10): Greenish brown colour, yield 62 %, m.p.:
246-248 °C, Rf (methanol:chloroform, 9:1) 0.64, IR (KBr, νmax
,
cm-1): (-C=O, amide) 1632, (-C=C, aromatic) 1605, (-C-H,
stretch) 2880, (-C-H, bend) 1441, (-C-N) 1268, (-C=N) 1505,
(-N= tertiary amine, N-H) 3422, 1H NMR (DMSO): 6.36- 8.05
(m, 8H, Ar-H), 3.43 (s, 2H, N-H), 2.49 (s, 3H, C-H), m/z: 252.3
(M+1).
Secondary screen:The compounds found active in primary
screening were similarly diluted to obtain solution containing
200, 100, 62.5, 50, 25, 12.5, 6.250 µg/mL of synthesized
compound.
(4-Chlorophenyl)(2-methyl-1H-benzo[d]imidazol-1-
yl)methanone (P11): Salmon pink colour, yield 98 %, m.p.:
Reading result: The highest dilution showing at least
99 % inhibition was taken as MIC.
285-287 °C, Rf (methanol:chloroform, 9:1) 0.69, IR (KBr, νmax
,
cm-1): (-C=O, amide) 1680, (-C=C, aromatic) 1593, (-C-H,
stretch) 2677, (-C-H, bend) 1443, (-C-N) 1237, (-C=N) 1652,
RESULTS AND DISCUSSION
In the present study benzimidazole and 2-methylbenzimi-
dazole derivatives were synthesized. The synthesis of these
compounds involves cyclization reaction between o-phenyl-
enediamine and corresponding carboxylic acid derivatives and
was reacted with the substituted benzoyl chloride to form
the corresponding benzoyl substituted benzimidazole. The
structure of all synthesized compounds confirmed by FTIR,
1H NMR and mass spectroscopy.
Antibacterial activity was carried out by Broth dilution
method.All compounds were screened against E. coli (MTCC
442) and S. aureus (MTCC 96). The compounds were dissolved
in DMSO and ampicillin was taken as the standard drug for the
screening. The result showed that among the tested compounds,
P2, P7, P10, P12, P13 and P14 better antibacterial activity
against E. coli and compounds P2, P4, P6, P8, P10, P11 and
P13 showed better antibacterial activity as compared to
benzimidazole and 2-methyl benzimidazole. The results of the
antibacterial screening are summarized in Table-1.
All compounds were screened for antifungal activity against
C. albicans (MTCC 227). The compounds were dissolved in
DMSO and antifungal activity was determined using the broth
dilution method. Griseofulvin was taken as the standard drug.
Compound P1, P2, P3, P4, P6, P9 and P11 showed better
antifungal activity as compared to benzimidazole and 2-methyl
benzimidazole. The results of the antifungal screening are
summarized in Table-1.
1
(-N= tertiary amine) 3442, (-C-Cl) 628, H NMR (DMSO):
7.27-8.17 (m, 8H,Ar-H), 2.99 (s, 3H, C-H), m/z: 269.6 (M-1).
(3-Aminophenyl) (2-methyl-1H-benzo[d]imidazol-1-
yl)methanone (P12): Dark brown colour, yield 27 %, m.p.:
271-273 °C, Rf (methanol:chloroform, 9:1) 0.63, IR (KBr, νmax
,
cm-1): (-C=O, amide) 1682, (-C=C, aromatic) 1649, (-C-H,
stretch) 2982, (-C-H, bend) 1370, (-C-N) 1210, (-C=N) 1545,
(-N= tertiary amine, N-H) 3443, 1H NMR (DMSO): 6.35-7.97
(m, 8H, Ar-H), 3.43 (s, 2H, N-H), 2.49 (s, 3H, C-H), m/z: 251.3
(M+).
(3-Chlorophenyl)(2-methyl-1H-benzo[d]imidazol-1-
yl)methanone (P13): Salmon pink colour, yield 58 %, m.p.:
263-265 °C, Rf (methanol:chloroform, 9:1) 0.77, (KBr, νmax
,
cm-1): (-C=O, amide) 1694, (-C=C, aromatic) 1608, (-C-H,
stretch) 3066, (-C-H, bend) 1450, (-C-N) 1259, (-C=N) 1597,
1
(-N= tertiary amine) 3391, (-C-Cl) 603, H NMR (DMSO):
6.36-7.89 (m, 8H,Ar-H), 2.49 (s, 3H, C-H), m/z: 269.3 (M-1).
(2-Chlorophenyl) (2-methyl-1H-benzo[d]imidazol-1-
yl)methanone (P14): Salmon pink colour, yield 67 %, m.p.:
222-224 °C, Rf (methanol:chloroform, 9:1) 0.71, (KBr, νmax
,
cm-1): (-C=O, amide) 1691, (-C=C, aromatic) 1477, (-C-H,
stretch) 2988, (-C-H, bend) 1435, (-C-N) 1266, (-C=N) 1691,
1
(-N= tertiary amine) 3442, (-C-Cl) 646, H NMR (DMSO):
7.29-7.99 (m, 8H,Ar-H), 2.51 (s, 3H, C-H), m/z: 269.8 (M-1).
(2,4-Dichlorophenyl)(2-methyl-1H-benzo[d]imidazol-
1-yl)methanone (P15): Salmon pink colour, yield 74 %, m.p.:
Conclusion
294-296 °C, Rf (methanol:chloroform, 9:1) 0.65, (KBr, νmax
,
cm-1): (-C=O, amide) 1651, (-C=C, aromatic) 1606, (-C-H,
stretch) 2926, (-C-H, bend) 1446, (-C-N) 1237, (-C=N) 1586,
In the present work N-1 of benzimidazole and 2-methyl-
benzimidazole derivatives were synthesized. Substitution by
-NH2 group (electron donating group) at para position of
benzoyl moiety at N-1 of benzimidazole and 2-methylbenzimi-
1
(-N= tertiary amine) 3195, (-C-Cl) 595, H NMR (DMSO):
6.62-7.85 (m, 7H,Ar-H), 2.50 (s, 3H, C-H), m/z: 306.3 (M+1).

Vol. 29, No. 4 (2017)
Synthesis and Antimicrobial Activity of Some Benzimidazole and 2-Methylbenzimidazole Derivatives 841
TABLE-1
ANTIBACTERIAL AND ANTIFUNGAL ACTIVITY OF SYNTHESIZED COMPOUNDS P1-P15
N
R
N
R'
Gram-negative
bacteria
Gram-positive
bacteria
S. aureus
Fungal stain
Compd. No.
R
R'
m.f.
E. coli
C. albicans
MTCC442
MTCC96
MTCC227
-H
-H
-H
-H
C14H10N2O
C14H11N3O
200
62.5
200
125
250
200
250
200
500
250
P1
P2
P3
P4
O
NH2
Cl
O
C14H9ClN2O
C14H9BrN2O
1000
1000
O
Br
O
O
NH2
-H
-H
-H
C14H11N3O
C14H9ClN3O
C14H9ClN2O
100
200
62.5
250
200
250
>1000
500
P5
P6
P7
Cl
O
Cl
>1000
O
Cl
-H
C14H8Cl2N2O
100
100
>1000
P8
Cl
O
-CH3
-CH3
-CH3
C15H12N2O
C15H13N3O
250
62.5
200
250
125
125
250
1000
500
P9
O
NH2
P10
P11
O
Cl
C15H11ClN2O
O
NH2
-CH3
-CH3
C15H13ClN3O
C15H11ClN2O
125
125
100
125
1000
500
P12
P13
O
Cl
HO
O
Cl
-CH3
-CH3
C15H11ClN2O
C15H10Cl2N2O
100
200
200
200
500
P14
P15
O
Cl
>1000
Cl
O
Benzimidazole
2-Methy-benzimidazole
Ampicillin
-H
-H
-H
-CH3
C7H6N2
C8H8N2
100
200
100
–
250
125
250
–
>1000
500
–
Griseofulvin
500

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ACKNOWLEDGEMENTS
The authors are thankful to Director, Shri G.S. Institute
of Technology and Science, Indore, India for providing the
facilities to carry out the work.
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