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Original Research Article
Evaluation of Sulfonamide
Derivatives of Dagenan Chloride as Lipoxygenase and
α-Glucosidase Inhibitors
Muhammad A Abbasi1*,
Saima Najm1, Aziz-ur-Rehman1,
Shahid Rasool1, Khalid M Khan2,
Muhammad Ashraf3, Rumana Nasar3
and Umber Alam3
1Department of Chemistry,
Government College University, Lahore-54000, 2HEJ
Research Institute of Chemistry, International Center
for Chemical and Biological Sciences, University of
Karachi, Karachi-75270, 3Department of
Biochemistry and Biotechnology, The Islamia University
of Bahawalpur, Bahawalpur-63100, Pakistan
*For correspondence:
Email:
atrabbasi@yahoo.com; Tel:
(+92)-42-111000010 ext.266
Received: 6 January 2014
Revised accepted: 14
November 2014
Tropical Journal of Pharmaceutical Research,
January 2015;
14(1):
47-54
http://dx.doi.org/10.4314/tjpr.v14i1.8
Abstract
Purpose: To study the enzyme
inhibition activity of various sulfonamides derived from
dagenan chloride.
Methods: The synthesis of
N-(naphthalen-1-yl)-4-acetamidobenzenesulfonamide (3)
was carried out by gearing up 1-naphthylamine (1) with
dagenan chloride (2) in water in the presence of Na2CO3
solution. Further, compound 3 was treated with various
alkyl/aralkyl halides (4a-o) to yield 5a-o in an aprotic
polar solvent, DMF (dimethylformamide), using LiH as
activator. The structures of all the synthesized
molecules were corroborated by infra red spectroscopy (IR),
proton nuclear magnetic resonance (1H-NMR) and electron
impact mass spectrometry (EI-MS) and screened against
lipoxygenase and α-glucosidase using baicalein and
acarbose as reference standards, respectively.
Results: Molecules 5e and 5j showed
good lipoxygenase inhibition activity with IC50
(50 % inhibition concentration) value of 132.21 ± 0.73
and 133.33 ± 0.87 μmol/L, respectively, relative to
reference, while 5m was the most active inhibitor of
α-glucosidase with IC50 of 19.41 ± 0.55 μmol/L
relative to reference.
Conclusion: Most of the synthesized
compounds are good inhibitors of lipoxygenase but
moderate inhibitors of α-glucosidase enzyme. These
molecules should be evaluated for their in vivo activity
to determine their potentials as anti-inflammatory and
anti-diabetic drugs.
Keywords: 1-Naphthylamine,
Sulfonamide, Lipoxygenase, α-Glucosidase, Dagenan
chloride, Enzyme inhibitor, Anti-inflammatory,
Anti-diabetic |
