Synthesis of some new nucleosides derived from 2-mercapto benzimidazole with expected biological activity

Article abstract of DOI:10.13005/ojc/330519

2-mercaptobenzimidazole derivatives and their acyclic nucleosides were synthesized. The synthesized compounds were tested for their antibacterial activity against Escherichia coli, Staphylococcus aureus and S. epidermidis. Most of tested compounds showed

Full text of DOI:10.13005/ojc/330519

ISSN: 0970-020 X
CODEN: OJCHEG
2017, Vol. 33, No.(5):
Pg. 2303-2310
ORIENTAL JOURNAL OF CHEMISTRY
An International Open Free Access, Peer Reviewed Research Journal
www.orientjchem.org
Synthesis of Some New Nucleosides Derived From 2-
Mercapto Benzimidazole with Expected Biological Activity.
HAMADA . H. AMER,1,2*, OMAR . M . ALI1,3* and IBRAHIM . KH . EL-KAFAWEEN1
1Department of Chemistry, Faculty of Applied and Medical Sciences, Taif University,
Turbah, Taif, Saudia Arabia.
2Animal Medicine and Infectious Diseases Department, Faculty of Veterinary medicine,
Sadat City University, Egypt.
3Department of Chemistry, Faculty of Science, Menoufia University, Shebin El-Koam, Egypt.
*Corresponding author E-mail: dr.hamada1435@gmail.com
http://dx.doi.org/10.13005/ojc/330519
(Received: July 13, 2017; Accepted: August 01, 2017)
ABSTRACT
2-mercaptobenzimidazole derivatives and their acyclic nucleosides were synthesized.
The synthesized compounds were tested for their antibacterial activity against Escherichia coli,
Staphylococcus aureus and S. epidermidis. Most of tested compounds showed moderate to high
antibacterial activity while few compounds were found to show little or no activity against the tested
microorganisms.
Keywords: Oxadiazolines, Arylidene derivatives, Nucleosides, Antibacterial activity
INTRODUCTION
have been prepared by the general method
described by Van Allan and Deacon10. The
synthized 2-mercaptobenzoimidazole derivatives
exhibit moderate antibacterial and antifungal
activities when compared to ampicillin and
ketoconazole respectively11. 2-mercaptoben-
zimidazole derivatives were screened for their anti-
inflammatory activity by carrageenan induced paw
edema method12.The derivatives of 2-mercaptoben-
zimidazole were prepared using Mannich
reaction showed moderate to high antibacterial
activity13. The benzimidazole moiety is present in
wide antimicrobial, antiprotozoal and analgesic
The chemistry of heterocyclic compounds
was used to prepare 2-mercaptobenzimidazole
and its derivatives for obtaining novel biologically
active ingredients such as anthelmintic1, anti-HIV2,
antifungal3 antibacterial4, CNS depressant5, anti-
inflammatory6, and analgesic7 activities. In the last
years, 2-mercaptobenzimidazole derivatives play
an important role in therapeutic and pharma-
cological fields. It possesses antimicrobial8,
analgesic and anti-inflammatory activities9.A
number of 2-mercaptobezoimidazole derivatives

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AMER & ALI et al., Orient. J. Chem., Vol. 33(5), 2303-2310 (2017)
drugs14-16. The pharmacological and biological the acetylation was carried out in acetic anhydride
evaluating of it is clearly concluded that under reflux at 90°C afforded oxadiazoline
the prepared compounds are promisingly derivatives 7a-d in 70-78% yields. Treatment of
high antimicrobial, anti-inflammatory and hydrazide 4 with different aldehydes to give
analgesic agent17. Benzimidazole derivatives play an arylidene derivatives 8a-d in 88-94 % yields. The
important role in medical field with so many arylidene derivatives were reacted with acetic
Pharmacological activities such as antimicrobial, anhydride to afford oxadiazoline derivatives 9a-d
antiviral, antidiabetic and anticancer activity18. in 80-88 % yields.
Benzimidazole derivatives are considered as a
N
S
O
RCHO, AcOH, EtOH
reflux
4
promising class of biologically active heterocyclic
compounds that show a wide of biological activities like
anti-viral, anti-microbial, anticancer, anti-diabetic,anti-
parasitic,anti-oxidant, anthelmintics,anti-HIV, anti-
proliferative, anti-convulsant,anti-inflammatory,anti-
hypertensive, anti-neoplastic,and anti-trichinellosis19
.Synthesized Schiff base (AMPOHA) showed hight
activity against Bacillus subtilis, Escherichia coli,
Aspergillu and Aspergillus flavus20 .N-phthalimido and
acetomido derivatives has to undergo antimicrobial
activity against Klebsiella, Escherichia coli,
epidermitis, Staphylococcus, Micrococcus leteus,
Bacillus cereus and Staphylococcus aureus21.
N
NHN
CH
H
5(a-d)
R
Ac
N
N
N
N
N
S
O
S
N
R1
O
NHN
CH
H
H
6(a-d)
7(a-d)
R1
R
HO
OH
OH
HO
HO
HO
HO
OH
OH
OH
OH
OH
OH
OH
OH
HO
HO
OH
OH
5a
5b
5c
5d
R1
OAc
AcO
AcO
OAc
AcO
AcO
AcO
AcO
AcO
OAc
OAc
OAc
OAc
OAc
OAc
OAc
OAc
OAc
OAc
6b,7b
6c,7c
6d,7d
6a,7a
RESULTS AND DISCUSSION
Scheme.2
2-mercaptobenzimidazole (2) was
synthized by mannich reaction and allowed to react
with ethylchloroacetate in acetone and dry
potassium carbonate to afford ethoxycarbon-
ylmethyl-2-mercaptobenzimidazole (3) in 87%
yield. Hydrazinolysis of the ethyl ester 3 in etnanol
at reflux temperature affording the corresponding
hydrazide 4 in 92% yield which was allowed to react
with different sugars in ethanol at reflux temperature
and in the presence of acetic acid to afford sugar
hydrazone derivatives 5a-d in 83-88% yields.
Acetylation of 5a-d with acetic anhydride in pyridine
at room temperature afforded acetylated sugar
hydrazone derivatives 6a-d in 75-92% yields. When
Scheme.3
EXPERIMENTAL
Melting points were determined with a
NH2
N
KOH, EtOH
Kofler block apparatus and are uncorrected. The IR
spectra were recorded on a Perkin-Elmer model
1720 FTIR spectrometer for KBr discs. NMR spectra
were recorded on a Varian Gemini 200 NMR
Spectrometer at 300 MHz for 1H NMR withTMS as a
standard. The progress of the reactions was
monitored by TLC using aluminum silica gel plates
60 F 245. Spectroscopic analyses were performed
at the Dr.Ahmed Farag laboratory at Faculty of
science, Cairo University, Egypt.
CS2
SH
+
reflux
N
H
NH2
1
2
ClCH2COOCH2CH3
K2CO3, acetone
reflux
N
N
N
NH2NH2, EtOH
reflux
S
O
S
O
N
O
H
NHNH2
H
3
4
Scheme.1

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AMER & ALI et al., Orient. J. Chem., Vol. 33(5), 2303-2310 (2017)
Ethoxycarbonylmethyl-2-mercaptobenzimidazole
(3)22.
= 3.14-3.92 (m, 5H, H-32, H-42, H-52, H-62, H-622),
3.10 (m, 1H, H-22), 3.42 (brs, 1H, OH), 3.55 (brs,
2H, 2xOH), 3.62 (brs, 2H, 2xOH), 4.15 (s, 2H, CH2),
4.90 (brs, 1H, NH), 6.90 (brs, 1H, NH), 6.93-7.35
(m, 4H, Ar-H), 7.55 (s, 1H, CH).
A mixture of 2-mercaptobenzimidazole 2
(15g, 0.1 mole), dry acetone (300 ml), anhydrous
K2CO3 (13.8 g, 0.1 mole) and ethylchloroacetate
(15.92 g, 0.13 mole) was heated under reflux for 6 h
(TLC). The reaction mixture was filtered of and the
filtrate was evaporated under reduces pressure.The
residue was recrystallized from ethanol to yield
brown oil in 87% yield. Rf = 0.48 (5% MeOH in
CH2Cl2).1H NMR (DMSO-d6): d = 1.26 (t, 3H, J = 8.1
Hz, CH3CH2), 4.15 (q, 2H, J = 8.1 Hz, CH3CH2),
4.55 (s, 2H, CH2), 5.25 (brs, 1H, NH), 7.32 (d, 2H, J
= 5.5Hz, H-2), 7.57 (d, 2H, J = 5.5 Hz, H-3).
D-(-)–Mannose(2-mercaptobenzimidazole-1-1-yl)
acetohydrazide (5c)
White powder (90%), m.p.196-198 °C. Rf
= 0.72 (5% MeOH in CH2Cl2). 1H NMR (DMSO-d6): δ
= 3.16-3.95 (m, 5H, H-3',H-4', H-5',H-6',H-6'', 3.12
(m, 1H, H-2', 3.45 (brs, 1H, OH), 3.60 (brs, 2H,
2xOH), 3.62 (brs, 2H, 2xOH), 4.15 (s, 2H, CH2),
4.90 (brs, 1H, NH), 6.93 (brs, 1H, NH), 6.95-7.40
(m, 4H, Ar-H), 7.55 (s, 1H, CH).
2-((1H-benzo[d]imidazol-2-yl)thio)acetohydrazide
(4)23.
D-(-)–Galactose(2-mercaptobenzimidazole-1-1-
yl) acetohydrazide (5d)
A mixture of 3 (2.36g, 0.01 mole),
hydrazine hydrate (1.5 g, 0.03 mole) and ethanol
(40 ml) was heated under reflux for 3 h. (TLC). The
product was filtered off, recystallized from ethanol
to yield white powder in 92% yield, m.p.143-145
°C Rf = 0.33 (5% MeOH in CH2Cl2). 1H NMR (DMSO-
d6): d = 2.11 (brs, 2H, NH2), 4.50 (s, 2H, CH2), 5.35
(brs, 1H, NH), 7.27 (d, 2H, J= 5.5 Hz, Ar-H), 7.55 (d,
2H, J= 5.5 Hz, Ar-H), 8.35 (brs, 1H, NH).
White powder (90%), m.p.174-176 °C. Rf =
0.72 (5% MeOH in CH2Cl2). 1H NMR (DMSO-d6): d
= 3.13-3.94 (m, 5H, H-32, H-42, H-52, H-62, H-622),
3.13 (m, 1H, H-22), 3.44 (brs, 1H, OH), 3.59 (brs,
2H, 2xOH), 3.61 (brs, 2H, 2xOH), 4.15 (s, 2H, CH2),
4.92 (brs, 1H, NH), 6.92 (brs, 1H, NH), 6.94-7.38
(m, 4H, Ar-H), 7.60 (s, 1H, CH).
General procedure for preparation of sugar of tetra-
O-acetyl- and penta-O-acetyl(2-mercapto-
benzimidazol- 1-yl)acetylhydrazones 6 (a- d).
Reaction of (4) with Different sugars to Afford
the Corresponding sugar hydrazones 5( a-d ).
To solution of 4 (10 mmol) in absolute
A mixture of the sugar hydrazones 5 (a-d)
ethanol, different sugars (10 mmol) were added
and then glacial acetic acid (1 ml) was added to the
reaction mixture which was refluxed for 10h (TLC).
The solvent was evaporated or concentrated under
reduced pressure and the product was filtered off
to afford 5(a-d) (83 - 88%) yields.
(10 mmol), was dissolved in 30 ml of pyridine and
then ( 15 mmol ) of acetic anhydride was added.
The reaction was stirred at room temperature
overnight (TLC). The mixture was cooled and
poured on crushed ice.The precipitate was filtered
off and dried to give 6 (a- d) in 75-92% yields.
L-(-)–Arabinose(2-mercaptobenzimidazole-1-1-
yl) acetohydrazide (5a)
2,3,4,5-Tetra-O-acetyl-L-(-)-arabinose(2-
mercaptobenzimidazol-1-yl)acetylhydrazone ( 6a ).
Yellow gum (75%), Rf = 0.72 (5% MeOH in
Yellow powder (83%), m.p.182-184 °C. Rf
= 0.65 (5% MeOH in CH2Cl2), 1H NMR (DMSO-d6):
δ = 3.12-3.85 (m, 5H, H-22, H-32, H-42, H-52, H-
522), 2.75 (brs, 1H, OH), 3.52-3.61 (brs, 3H, 3xOH),
4.05 (s, 2H, CH2), 4.95 (brs, 1H, NH), 6.95-7.32 (m,
4H, Ar-H), 7.40 (brs, 1H, NH), 7.55 (s, 1H, CH).
CH2Cl2). 1H NMR (DMSO-d6): δ = 1.99, 2.01, 2.10,
2.21 (4s, 12H, 4xCH3CO), 4.15 (s, 2H, CH2),
4.30,4.41 (2m, 2H, H-52, H-522), 4.60 (m, 1H, H-
22), 5.06 ( brs, 1H, NH ), 5.10 (m, 1H, H-42), 5.12
(m, 1H, H-32), 7.12 ( brs, 1H, NH ), 7.52 (d, 1H,
J=2.5 Hz, H-12), 7.25-7.62 (m,4H, Ar-H).
D-(-)–Glucose(2-mercaptobenzimidazole-1-1-yl)
acetohydrazide (5b)
White powder (85%), m.p.202-204 °C. Rf
= 0.65 (5% MeOH in CH2Cl2). 1H NMR (DMSO-d6): δ
2,3,4,5-Tetra-O-acetyl-D-(+)-Glucose(2-
mercaptobenzimidazol-1-yl)acetylhydrazone ( 6b ).
Yellow gum (80%), Rf = 0.72 (5% MeOH in

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AMER & ALI et al., Orient. J. Chem., Vol. 33(5), 2303-2310 (2017)
CH2Cl2). 1H NMR (DMSO-d6): d = 1.97, 2.03, 2.04, 2.06, 1H, J=3.2, 6.2 Hz, H-12), 5.89 (d, 1H, J=8.8 Hz,
2.25 (5s, 15H, 5xCH3CO), 4.13(s, 2H, CH2), 4.25,4.47 oxadiazoline H-5), 7.24-7.59 (m, 4H, Ar-H).
(2m, 2H, H-62,H-622), 4.60 (m, 1H, H-22), 5.00 (m, 1H,
H-32), 5.05 (brs, 1H, NH), 5.10 (m, 1H, H-42), 5.12 (m, 4-Acetyl-5-(1,2,3,4,5-penta-O-acetyl-D-
1H, H-52), 7.12 ( brs, 1H, NH), 7.25-7.58 (m, 4H, Ar-H), glucopentitolyl)-2(2-methylbenzimidazol-1-yl)-
7.60 (d, 1H, J=2.5 Hz, H-12).
1,3,4-oxadiazoline ( 7b )
Brown oil (72%), Rf = 0.72 (5% MeOH in
1
2,3,4,5-Tetra-O-acetyl-D-(+)-Mannose(2- CH2Cl2). H NMR (DMSO-d6): δ =2.04, 2.07, 2.09,
mercaptobenzimidazol-1-yl)acetylhydrazone ( 6c ) 2.12, 2.22, 2.34 (6s, 18H, 6xCH3CO), 4.60 (s, 2H,
Yellow gum (85%), Rf = 0.72 (5% MeOH in CH2), 4.27,4.48 (2m, 2H, H-52,H-522), 5.10 (brs,
CH2Cl2). 1H NMR (DMSO-d6): δ = 2.11, 2.18, 2.20, 1H, NH),, 5.15 (m, 1H, H-42), 5.21 (m, 1H, H-32),
2.22, 2.26 (5s, 15H, 5xCH3CO), 4.11(s, 2H, CH2), 5.28 (m, 1H, H-22), 5.32 (dd, 1H, J=3.2, 6.2 Hz, H-
4.29,4.47 (2m, 2H, H-62,H-622), 4.57 (m, 1H, H- 12),5.93 (d, 1H, J=8.8 Hz, oxadiazoline H-6), 7.25-
22), 5.04 (m, 1H, H-32), 5.09 (brs, 1H, NH), 5.13 (m, 7.60 (m, 4H, Ar-H).
1H, H-42), 5.20 (m, 1H, H-52), 7.19 ( brs, 1H, NH),
7.29-7.59 (m, 4H, Ar-H), 7.65 (d, 1H, J=2.5 Hz, H- 4-Acetyl-5-(1,2,3,4,5-penta-O-acetyl-D-
12).
glucopentitolyl)-2(2-methylbenzimidazol-1-yl)-
1,3,4-oxadiazoline ( 7c )
2,3,4,5-Tetra-O-acetyl-D-(+)-Galactose(2-
mercaptobenzimidazol-1-yl)acetylhydrazone ( 6d )
Brown oil (73%), Rf = 0.72 (5% MeOH in
CH2Cl2). 1H NMR (DMSO-d6): δ = 1.97, 1.99, 2.03,
Brown gum (92%), Rf = 0.72 (5% MeOH in 2.06, 2.10, 2.32 (6s, 18H, 6xCH3CO), 4.60 (s, 2H,
CH2Cl2). 1H NMR (DMSO-d6): δ = 2.16, 2.21, 2.24, CH2), 4.24,4.46 (2m, 2H, H-52,H-522), 5.12 (brs,
2.26, 2.29 (5s, 15H, 5xCH3CO), 4.11(s, 2H, CH2), 1H, NH),, 5.16 (m, 1H, H-42), 5.22 (m, 1H, H-32),
4.27,4.49 (2m, 2H, H-62,H-622), 4.58 (m, 1H, H- 5.26 (m, 1H, H-22), 5.34 (dd, 1H, J=3.2, 6.2 Hz, H-
22), 5.03 (m, 1H, H-32), 5.07 (brs, 1H, NH), 5.12 (m, 12),5.94 (d, 1H, J=8.8 Hz, oxadiazoline H-6), 7.22-
1H, H-42), 5.16 (m, 1H, H-52), 7.17 ( brs, 1H, NH), 7.52 (m, 4H, Ar-H).
7.27-7.57 (m, 4H, Ar-H), 7.63 (d, 1H, J=2.5 Hz, H-
12).
4-Acetyl-5-(1,2,3,4,5-penta-O-acetyl-D-
glucopentitolyl)-2(2-methylbenzimidazol-1-yl)-
General procedure for the synthesis of 4-acetyl- 1,3,4-oxadiazoline ( 7d )
5-(tetra-and penta-O-acetylalditolyl)-2-(2- Brown oil (78%), Rf = 0.72 (5% MeOH in
mercaptobenzimidazol-1-yl)-1, 3, 4-oxadiazoline CH2Cl2). H NMR (DMSO-d6): δ =1.95, 1.97, 1.99,
1
7 ( a-d )
2.04, 2.07, 2.34 (6s, 18H, 6xCH3CO), 4.58 (s, 2H,
A solution of sugar hydrazones 5(a-d) (0. CH2), 4.25,4.47 (2m, 2H, H-52,H-522), 5.11 (brs,
01 mol) in acetic anhydride (10 ml) was heated at 1H, NH),, 5.17 (m, 1H, H-42), 5.21 (m, 1H, H-32),
90 °C for 3 h. The resulting solution was poured 5.26 (m, 1H, H-22), 5.32 (dd, 1H, J=3.2, 6.2 Hz, H-
onto crushed-ice and the product that separated 12),5.90 (d, 1H, J=8.8 Hz, oxadiazoline H-6), 7.20-
out was filtered off, washed with water, and then 7.560 (m, 4H, Ar-H).
dried. The products were recrystallized from
methanol to give 7(a-d) in 70-78 yields.
General procedures for the reaction of (4) with
aromatic aldehydes to afford Schiff2s bases
4 -Acetyl-5-(1, 2, 3, 4-tetra-O-acetyl-L- 8(a-d).
arabinotetritolyl)-2-(2mercaptobenzimidazol-1-
A solution of 4 (0.01 mol), an aromatic
yl)-1,3,4-oxadiazoline (7a)
aldehyde (0.01 mol) in abs. ethanol (30 ml) and
Brown oil (70%), Rf = 0.72 (5% MeOH in glacial acetic acid (1 ml) was refluxed for 6-8 h (TLC).
CH2Cl2). 1H NMR (DMSO-d6): δ = 2.03, 2.05, 2.07, The solvent was evaporated under reduced
2.10, 2.21 (5s, 15H, 5xCH3CO), 4.40 (s, 2H, CH2), pressure and the residue was filtered off and
4.12, 4.45 (2m, 2H, H-42,H-422), 5.05 (brs, 1H, NH), recrystallized from ethanol to afford 8(a-d) in 88-94
5.14 (m, 1H, H-32), 5.19 (m, 1H, H-22), 5.89 (dd, % yields.

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AMER & ALI et al., Orient. J. Chem., Vol. 33(5), 2303-2310 (2017)
2-((1H-benzo[d]imidazol-2-yl)thio)-N’-
benzylideneacetohydrazide (8a)
General procedure for preparation of
oxadiazoline derivatives 9 (a- d).
Yellow gum (88%), Rf = 0.72 (5% MeOH in
CH2Cl2). 1H NMR (DMSO-d6): δ =4.18 (s, 2H, CH2),
5.55 (brs, 1H, NH), 7.23-7.85 (m, 9H, Ar-H),8.13 (s,
1H, CH), 8.45 (brs, 1H, NH).
A mixture of the shiff bases 8(a-d) (10
mmol), were dissolved in acetic anhydride (10 ml)
and the reaction mixture was refluxed at 100 oC 5-
7h (TLC). The mixture was onto crushed-ice and
the product that separated out was filtered off,
washed with water, and then dried. The products
were recrystallized from methanol to give 9(a-d) in
80-88 yields.
2-((1H-benzo[d]imidazol-2-yl)thio)-N’-(2-
hydroxybenzylidene)acetohydrazide ( 8b ).
Yellow gum (90%), Rf = 0.72 (5% MeOH in
CH2Cl2). 1H NMR (DMSO-d6): δ =4.15 (s, 2H, CH2),
5.10 (brs, 1H, NH), 5.34 (s, 1H, OH), 7.05-7.65 (m,
8H, Ar-H), 8.00 (brs, 1H, NH), 8.95(s, 1H, CH).
1-(5-(((1H-benzo[d]imidazol-2-yl)thio)methyl)-2-
phenyl-1,3,4-oxadiazol-3(2H)-yl)ethanone (9a).
Yellow powder (80%) m.p. 152-154 °C. Rf
2-((1H-benzo[d]imidazol-2-yl)thio)-N’-(furan-2-
ylmethylene)acetohydrazide ( 8c ).
= 0.72 (5% MeOH in CH2Cl2). 1H NMR (DMSO-d6): δ
= 2.10 (s, 3H, COCH3), 4.50 (s, 2H, CH2), 5.13 (brs,
1H, NH), 6.55 (s, 1H, CH) 7.24-7.57 (m, 9H, Ar-H).
White crystals (92%), m.p. 160-164 °C. Rf
= 0.72 (5% MeOH in CH2Cl2). 1H NMR (DMSO-d6): δ
= 4.20 (s, 2H, CH2), 5.15 (brs, 1H, NH), 6.50-7.80
(m, 7H, Ar-H), 7.95 (brs, 1H, NH), 8.42 (s, 1H, CH).
1-(5-(((1H-benzo[d]imidazol-2-yl)thio)methyl)-2-
(2-hydroxyphenyl)-1,3,4-oxadiazol-3(2H)-
yl)ethanone (9b).
2-((1H-benzo[d]imidazol-2-yl)thio)-N’-(4-
(dimethylamino)benzylidene)acetohydrazide (8d).
White crystals (94%), m.p. 158-160 ºC. Rf
= 0.72 (5% MeOH in CH2Cl2). 1H NMR (DMSO-
d6): δ = 3.10 (s, 6H, 2CH3), 4.18 (s, 2H, CH2), 5.11
(brs, 1H, NH), 6.58-7.64 (m, 9H, Ar-H), 8.05 (brs,
1H, NH), 8.37 (s, 1H, CH).
Yellow powder (84%) m.p. 136-138 °C. Rf
= 0.72 (5% MeOH in CH2Cl2). 1H NMR (DMSO-d6):
δ= 2.12 (s, 3H, COCH3), 4.35 (s, 2H, CH2), 5.11(brs,
1H, NH), 5.37 (s, 1H, OH), 6.95 (s, 1H, CH) 6.85-
7.56 (m, 8H, Ar-H).
Table : 1 Antibacterial activity of different synthesized compounds.
E.coli
S.e
S.aureus
Zone of inhibition (mm)
Synthesized
compounds
30
60
90
30
60
90
30
60
90
mg/mL mg/mL mg/mL mg/mL mg/mL mg/mL mg/mL mg/mL mg/mL
8b
6c
6a
8a
7a
5c
5a
7a
40
13
13
15
11
15
11
8
45
15
17
18
12
20
13
11
19
18
13
S.a
8
50
22
20
22
20
22
17
13
21
17
12
10
8
20
15
14
17
10
-
25
17
15
20
12
-
-
-
-
-
-
-
-
-
-
-
-
12
18
11
18
-
-
15
22
13
20
8
-
-
17
23
14
22
8
-
-
-
-
-
-
-
10
8
-
-
9b
18
-
Amoxicillin
tetracycline 30
6
E.coli
18
13
s.e
10
8
Amoxicillin
tetracycline
6

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1-(5-(((1H-benzo[d]imidazol-2-yl)thio)methyl)- Microbiological investigation of compounds.
AMER & ALI et al., Orient. J. Chem., Vol. 33(5), 2303-2310 (2017)
2-(furan-2-yl)-1, 3, 4-oxadiazol-3(2H)-
Antibacterial of compounds are carried out
yl)ethanone (9c).
against the (Gram –ve) as E.coli and ( Gram +ve)
o
Yellow powder (85%) m.p. 142-144 C. Rf as S.aureus and (S. epidermidis) , the antimicrobial
= 0.72 (5% MeOH in CH2Cl2). 1H NMR (DMSO- activity was estimated based on size of inhibition
d6): δ= 2.09 (s, 3H, COCH3), 4.40 (s, 2H, CH2), zone around dishes against Gram+v the 7a fig. 1
5.14(brs, 1H, NH), 6.87 (s, 1H, CH), 6.35-7.69 (m, 5a , 5c, 9a fig. 2, 3, 4 and 9b are varied degree of
7H, Ar-H).
inhibitory effect against S.aureus and 8a,bc and
8a varied degree of inhibitory effect against
1-(5-(((1H-benzo[d]imidazol-2-yl)thio)methyl)-2- S.epidermidis ,also in Gram-v the 8b, 6c, 6a, 8a, 7a
(4-(dimethylamino)phenyl)-1,3,4-oxadiazol-3(2H)- fig. 5, 5c and 9b are varied degree of inhibitory
yl)ethanone (9d).
effect against E.coli. The antibacterial activities of
White crystals (88%), m.p. 170-172 oC. Rf compounds against E. coli ,S. aureus and
= 0.72 (5% MeOH in CH2Cl2). 1H NMR (DMSO- S.epidermids tested and compared to known
d6): δ= 3.12 (s, 6H, 2CH3), 2.10 (s, 3h, COCH3), 4.50 antibiotics Tables. The results showed that
(s, 2H, CH2), 5.14 (brs, 1H, NH), 6.65 (s, 1H, CH) increasing the zone of inhibition in compared
6.27-7.66 (m, 8H, Ar-H).
with
known antibiotic Amoxicillin and
tetracycline. the data showed in Table1.
MATERIALS AND METHODS
Antibacterial sensitivity test:
Microbiological investigation hole well
method the investigated isolates of bacteria were
seeded in tubes with nutrient broth (NB) two
different bacteria species were used Escherichia
coli (E.coli) ,Staphylococcus epidermidis (S.
epidermidis) and Staphylococcus aureus (S.aureus).
antimicrobial activity of chemical compounds was
evaluated by Hole well method , Briefly ,inoculum
containing approx. cell density (1.5 * 108 CFU/ml )
was spread on Mueller-Hinton agar (MHA) plates
the holes diameter( 0.5 cm ) were done in the cool
medium after that 50µ from different concentration
of compounds 10,20 and 30 was applied using a
micropipette. After incubation for 24h in an incubator
Fig.2. influence of the synthesized compound 9a
on Staphylococcus aureus.
o
at 37 C for bacteria the inhibition zone diameters
were measured and expressed in cm. The previous
procedure was repeated with 30 μg/disc of
tetracycline and with ampicillin at 10 μg/disc24.
Fig. 3. influence of the synthesized compound 9a
on Staphylococcus aureus.
Fig. 1. influence of the synthesized compound 7a
on Staphylococcus aureus.
Fig. 4. influence of the synthesized compound 9a
on Staphylococcus aureus.

2309
AMER & ALI et al., Orient. J. Chem., Vol. 33(5), 2303-2310 (2017)
different sugars ( arabinose, glucose, mannose and
arabinose ) and aromatic aldehydes to give the
corresponding sugar hydrazones and arylidene
derivatives respectively.The synthized compounds were
showed high to moderate activity against the (Gram –
ve) as E.coli and ( Gram +ve) as S.aureus and (S.
epidermidis).
ACKNOWLEDGMENTS
Fig. 5. influence of the synthesized compound 7a
on E.coli.
The authors are pleased to acknowledge
Taif University for providing the facilities for the
research.
CONCLUSION
In this research the 2-mercaptobenzimidazole
derivatives were synthized and then were coupled with
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