Keywords

derivatives of podocarpic acid, amide derivatives of podocarpic acid

Abstract

As a class, amides are of great interest in biological studies and pharmaceutical application. In this work, podocarpic acid, a natural tricyclic diterpene, derived from Podocarpus species, has been employed to form a novel family of amide derivatives which will later be studied for their potential as new drug leads. Novel amide derivatives of podocarpic acid were synthesized from podocarpic acid in three steps. The first step involved methylation with dimethylsulfate to form methyl-O-methylpodocarpate. This step was followed by iodination with iodine to give iodomethyl-O-methylpodocarpate. Finally amidation with various aliphatic amides using a copper catalyst yielded four amide derivatives of podocarpic acid. However, iodomethyl-O-methylpodocarpate did not react with aromatic amides. This is perhaps because of the reduction in electrophilicity of an aromatic amide versus an aliphatic amide. Thus this research had led to the discovery of a method that is selective for the synthesis of aliphatic amide derivatives of podocarpic acid. Furthermore, five novel derivatives of podocarpic acid have been synthesized. Therefore a small library of novel compounds has been synthesized by utilizing selective methodology, that are now available for future examination of their anticancer and anti-tuberculosis properties.

Notes

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Graduation Date

2004

Semester

Fall

Advisor

Miles, Howard

Degree

Master of Science (M.S.)

College

College of Arts and Sciences

Department

Chemistry

Degree Program

Industrial Chemistry

Format

application/pdf

Identifier

CFE0000213

URL

http://purl.fcla.edu/fcla/etd/CFE0000213

Language

English

Release Date

January 2014

Length of Campus-only Access

None

Access Status

Masters Thesis (Open Access)

Restricted to the UCF community until January 2014; it will then be open access.

Included in

Chemistry Commons

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