NOVEL PIPERIDONE DERIVATIVES - Semantic Scholar

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

Full Length Research Paper Covered in Official Product of Elsevier, The Netherlands

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


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



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


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


126


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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