Aboul-Enein and El Rashedy. Med chem 2015, 5:7
DOI: 10.4172/2161-0444.1000280
Review Article Open Access
Med chem
ISSN: 2161-0444 Med chem, an open access journal
Volume 5(7): 318-325 (2015) - 318
Benzimidazole Derivatives as Antidiabetic Agents
Hassan Y Aboul-Enein
1
* and Ahemd A El Rashedy
2
1
Pharmaceutical and Medicinal Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, Cairo 12311, Egypt
2
Natural and Microbial Department, National Research Centre, Dokki, Giza 12622, Egypt
*Corresponding author: Hassan Y. Aboul-Enein, Pharmaceutical and Medicinal
Chemistry Department, National Research Centre, Dokki, Cairo 12311, Egypt, Tel:
+201003678948; Fax: +20233370931; E-mail: haboulenein@yahoo.com
Received June 01, 2015; Accepted July 17, 2015; Published July 25, 2015
Citation: Aboul-Enein HY, El Rashedy AA (2015) Benzimidazole Derivatives as
Antidiabetic Agents. Med chem 5: 318-325. doi: 10.4172/2161-0444.1000280
Copyright: © 2015 Aboul-Enein HY, et al. This is an open-access article
distributed under the terms of the Creative Commons Attribution License, which
permits unrestricted use, distribution, and reproduction in any medium, provided
the original author and source are credited.
Keywords: Benzimidazole derivatives; Antidiabetic agents;
Pharmacological activity; Mechanism of action; Synthesis
Diabetes mellitus (DM) is a chronic metabolic disease which
result due to no production of insulin causing type 1 DM or due to
partial and/or insufcient production of insulin causing type 2 DM.
Furthermore , insulin resistance cause hyperglycemia and diabetes
due to the inability of the cells to use insulin properly and efciently.
Some to the serious complication of diabetes include nephropathy,
retinopathy, neuropathy, foot ulcers among other symptoms [1]. One
of the most widely used antidiabetic agents are the sulfonylureas which
act through the stimulation of the pancreatic β-cells for the secretion
of insulin. Another class of antidiabetic agents are thiazolidinediones
e.g. glibenclamide, ciglitazone and troglitazone. Tese drugs stimulate
insulin secretion and therefore are efective in treatment of in a type-2
diabetic patients. Metformin which belongs to the biguanides group
which enhance insulin action at the post receptor level in peripheral
tissues such as muscle [2].
“Shingalapur et al. [3] synthesized a series of 1,3,4-oxadiazoles
derivatives containing 2-mercapto benzimidazole moiety and screened
for in vivo antidiabetic activity using oral glucose tolerance test
(OGTT)”. Some of these derivatives showed improved reduction in
blood–glucose levels compared with glibenclamide (Scheme 1).
N
H
N
S
O
N
N
R
1
1
R= 4-OH,2-OH,Fufurayl, naphthalen-2-ol
Some new benzimidazole containing thiazolidinone 2, 3 were also
reported for anti-diabetic activity. Both compounds were found to be
more potent in hyperglycemic and normoglycemic models at a dose of
50 mg/kg [4].
N
H
N
N
S
H3CO
O
COOH
N
H
N
N
S
H3CO
O
2
3
A series of bis-benzimidazole derivatives were synthesized and
found that compound 4 has showed signifcant antidiabetic activity
when compared to glibenclamide as standard drug [5] (Scheme 2).
N
H
N
(CH
2
)n
H
3
C
N
N
H
CH
3
n=2, 3,6 ,7
4
Type 2 diabetes mellitus (T2DM) is characterized by defects in
insulin secretion and insulin sensitivity [6,7]. Insulin resistance by itself
will not result in T2DM unless β-cell secretion of insulin is decreased.
Based on the Centers for Disease Control and Prevention National
Diabetes Fact Sheet in 2007 [8], there were 23.6 million Americans with
diabetes, of whom 90% to 95% have T2DM.
Peroxisome Proliferator Activated Receptors (PPARs) act as
regulators of lipid and glucose metabolism. Tis resulted in the
development of synthetic drugs which represent a potential tool for
Abstract
Benzimidazole is an important pharmacophore which was included in several biologically active compounds
resulted in the development of several classes of drugs. This review discusses the synthesis of benzimidazole
derivatives as a target agents for antidiabetic by different mechanism such as peroxisome proliferator – activated
receptor α transcriptional activity, glycosidases receptor, dipeptidyl peptidase IV, glucokinase, human glucagon
receptor (hGCGR) antagonist , aldose reductase enzyme and stearoyl- CoA desaturase .
NH
2
NH
2
N
H
N
SH + ClCH
2
COOC
2
H
5
a
b
N
H
N
SCH
2
COOC
2
H
5
d
N
H
N
SCH
2
N
N
O
Ar
Scheme 1: Reagent and condition: (a) CS
2
, NaOH, EtOH; (b) EtOH (c) EtOH,
NH
2
NH
2
.H
2
O (d) Ar -COOH , POCl
3
Scheme 2: Benzimidazole as Peroxisome proliferator
N
H
N
(CH2)n
H3C
N
N
H
CH3
NH2
NH2
+ COOH (CH2)n COOH
70-90 C ,20hr
phosphotungstic acid(PTA)
M
e
d
i
c
i
n
a
l
c
h
e
m
i
s
t
r
y
ISSN: 2161-0444
Medicinal chemistry