International Journal of Drug Development & Research | April-June 2011 | Vol. 3 | Issue 2 | ISSN 0975-9344 | Available online http://www.ijddr.in Covered in Official Product of Elsevier, The Netherlands ©2010 IJDDR NOVEL PIPERIDONE DERIVATIVES: SYNTHESIS, SPECTRAL AND EVALUATION OF ANTIOXIDANT ACTIVITY N. KARTHIK*1, S. NITHIYA 2, J. JAYABHARATHI 3 1
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Department of Chemistry, Rajalakshmi Engineering College, Chennai-602 105, India. 2 Department of Chemistry, Periyar University,Salem -636 011,India. 3 Department of Chemistry, Annamalai University, Annamalai Nagar-608 002, India.
N. Karthik et al.
Abstract
Copyright © 2010 IJDDR,
The present study was designed to synthesize
This is an open access paper distributed under the
isomeric alcohols from corresponding piperidone 1
copyright agreement with Serials Publication, which
by sodium ethoxide reduction and the alcohols
permits
were separated by column chromatography. The
reproduction in any medium, provided the original
synthesized compounds were characterized by IR,
work is properly cited.
1H
&
vitro
13C
unrestricted
use,
distribution,
and
spectral studies. In addition to that in
potential
antioxidant
activity
of
the
Article History:------------------------
compounds were analyzed via DPPH assay and
Date of Submission: 16-02-2011
compared with standard antioxidant such as α-
Date of Acceptance: 26-03-2011
tocopherol and proposed suitable mechanism of
Conflict of Interest: NIL
antiradical
Source of Support: NONE
piperidone
action.
It
has
1demonstrated
been
found
excellent
that
radical
scavenging activity, much better than its isomeric alcohols 2 and 3.
1. INTRODUCTION During a fairly recent 10-year period, several
Key words:
thousand
Piperidone, Isomeric Alcohols, NMR, DPPH.
piperidine
compounds
have
been
mentioned in clinical and preclinical studies [1]. Besides the interesting structural features, these
How to Cite this Paper:
compounds are also of pharmaceutical interest as
N. Karthik*, S Nithiya, J. Jayabharathi “Novel
they exhibit a wide range of biological activities [2].
Piperidone Derivatives: Synthesis, Spectral and
Nevertheless,
Evaluation of Antioxidant activity”, Int. J. Drug Dev.
substitution patterns found in piperidine targets and
& Res., April-June 2011, 3(2): 122-127
the widely accepted concept that the biological
the
variety
of
functionality
and
properties of piperidines are highly dependent on the type and location of substituents on the heterocyclic ring [3]. Piperidine derivatives are found to possess *Corresponding author, Mailing address: Phone: 91-9952443523 Fax: 044-27156750, 51 Email:
[email protected]
pharmacological activity and form an essential part of the molecular structures of important drugs such as raloxifene and minoxidil [4].Selective inhibition of
Int. J. Drug Dev. & Res., April-June 2011, 3 (2): 122-127 Covered in Scopus & Embase, Elsevier
122
N. Karthik et al: Novel Piperidone Derivatives: Synthesis, Spectral and Evaluation of Antioxidant activity
Full Length Research Paper Covered in Official Product of Elsevier, The Netherlands
a number of enzymes involved in the binding and
damages play a significantly pathological role in
processing of glycoproteins has rendered piperidine
human diseases. Cancer, emphysema, cirrhosis,
alkaloids as important tools in the study of
atherosclerosis and arthritis have all been correlated
biochemical pathways [5]. Piperidones are somewhat
with oxidative damage. Also, excessive generation of
less prominent, but often they serve a role as
reactive oxygen species (ROS) induced by various
advanced intermediates prior to their conversion to
stimuli and which exceeds the antioxidant capacity of
piperidines [6]. Hydroxylated piperidine alkaloids
the organism leads to variety of pathophysiological
are frequently found in living systems and display a
processes
wide range of biological activities due to their ability
genotoxicity and cancer[9].In the present study wide
to imitate carbohydrates in a variety of enzymatic
range
processes
antioxidant
[7].
antioxidants
In
become
many
different
more
disciplines
interested
in
new
such
as
applications
inflammation,
of
radical
activities
of
diabetes,
scavenging
newly
and
synthesized
compounds were investigated using DPPH method.
compounds, either synthesized or obtained from natural sources that could provide active components
2. CHEMISTRY
to prevent or reduce the impact of oxidative stress on
Synthesis and isomerization of piperidine-4-ols have
cell [8]. Antioxidants are extensively studied for their
been described by Noller and Balasubramanian [10,
capacity to protect organism and cell from damage
17].
that are induced by oxidative stress. Oxidative
O
CH3
C
CH3
C
H 3C H O
O H 3C
+
C
C
CH
3
H
H H
H N H -2H2O
Ethanol
O CH 3 CH3
N H H 3C
CH
30
3
Sodium ethoxide reduction
H
H 3C
OH
H 3C
OH H HN HN
CH
CH CH3
CH3 H 3C
H 3C
3
3
32
31
123
Int. J. Drug Dev. & Res., April-June 2011, 3 (2): 122-127 Covered in Scopus & Embase, Elsevier
N. Karthik et al: Novel Piperidone Derivatives: Synthesis, Spectral and Evaluation of Antioxidant activity
3. BIOLOGY
of DPPH radicals was determined by decrease in its
The in vitro antioxidant activity of the synthesized
absorbance at 517 nm induced by antioxidants. The
compounds was evaluated by DPPH assay method.
absorption maximum of a stable DPPH radical in
[11]
ethanol was at 517 nm. The decrease in absorbance of DPPH radical caused by antioxidants, because of
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4. STATISTICAL ANALYSIS
reaction between antioxidant molecules and radical,
Statistical significance of difference between the
progresses, which result in the scavenging of the
mean activities of the subgroups of compounds was
radical by hydrogen donation. It is visually noticeable
determined by utilizing ANOVA for variables with
as a discoloration from purple to yellow. Hence,
normal distributions.
DPPH is usually used as a substrate to evaluate antioxidative activity of antioxidants [14].Data of
5. RESULT AND DISCUSSION
antioxidant evaluation were expressed as mean ±
5.1 IR spectra
standard error of the mean (n=3) and independent
The prominent peaks around 3376, 3425 cm-1 in the
student’s t-test was used to determine the level of
IR spectra are attributed to υOH, mode in 2and 3
significance (P 3>2.
concludes that piperidone exhibit strong antioxidant activity by electron donating mechanism (i.e.) it
ACKNOWLEDGEMENT
donate unshared pair of electrons on carbonyl oxygen
One of the author N.Karthik convey his sincere
atom. Reduction of C=O into –OH resulted in a
thanks to Dr.P.Rajasekar, Senior Lecturer and Dr.
decreased scavenging activity of isomeric alcohols
Johanna Rajkumar, Professor & Head, Department
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126
N. Karthik et al: Novel Piperidone Derivatives: Synthesis, Spectral and Evaluation of Antioxidant activity
of Biotechnology, Rajalakshmi Engineering College,
10) C.R.Noller and V.Baliah. The Preparation of Some
Chennai, India for providing necessary chemicals and
Piperidine Derivatives by the Mannich Reaction.J
instruments to evaluate Antioxidant Activity.
Am Chem Soc.1948; 70:3853. 11)
of a Stable Free Radical .Nature. 1958; 181: 1199.
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