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Synthesis and antimicrobial screening of some C-4- hydroxybenzo[c]pyranquinones
Author(s)
Masenya, Tebogo
Date Issued
2001
Type
Thesis
Publisher
Cape Technikon
Abstract
Many naturally occurring antibiotics have been identified and their synthesis
successfully carried out in laboratories. It was envisaged by our group that by
preparing a variety of, for example, quinoid compounds and then comparing
their biological properties and activities, a better insight would be gained into a
molecular structure - activity relationship.
Chapter 1 deals with the attempted synthesis of 2-(1 '-hydroxyethyl)-3-(prop-2'enyl)-
1,4-benzoquinone (17) which may be converted by known methods into
benzopyran derivatives.
The second chapter describes a synthetic route to (±)(3R, 4R)-3,4-dihydro-3methyl-
4-hydroxy-l H-benzo[c]pyran-5,8-dione (42) and its (±)(45) diastereomer
(43), both of which were found to be active against Gram negative
and Gram positive organisms. The trans-l,3-dimethyl-4-hydroxypyranquinones
(45) and (46) were also successfully synthesised.
A different route of synthesis for the compounds (53), (54), (55) and (56) was
also investigated.
Several compounds were evaluated for biological activity. It was found that the
quinones synthesised during this study were active against Gram negative and
Gram positive bacteria, with the exception of compound (25) which had an
acetate group in place of a hydroxy group. It was found that this trend was
carried through all of the quinone derivatives tested.
successfully carried out in laboratories. It was envisaged by our group that by
preparing a variety of, for example, quinoid compounds and then comparing
their biological properties and activities, a better insight would be gained into a
molecular structure - activity relationship.
Chapter 1 deals with the attempted synthesis of 2-(1 '-hydroxyethyl)-3-(prop-2'enyl)-
1,4-benzoquinone (17) which may be converted by known methods into
benzopyran derivatives.
The second chapter describes a synthetic route to (±)(3R, 4R)-3,4-dihydro-3methyl-
4-hydroxy-l H-benzo[c]pyran-5,8-dione (42) and its (±)(45) diastereomer
(43), both of which were found to be active against Gram negative
and Gram positive organisms. The trans-l,3-dimethyl-4-hydroxypyranquinones
(45) and (46) were also successfully synthesised.
A different route of synthesis for the compounds (53), (54), (55) and (56) was
also investigated.
Several compounds were evaluated for biological activity. It was found that the
quinones synthesised during this study were active against Gram negative and
Gram positive bacteria, with the exception of compound (25) which had an
acetate group in place of a hydroxy group. It was found that this trend was
carried through all of the quinone derivatives tested.
Additional information
Thesis (MTech(Chemistry))--Cape Technikon, Cape Town, 2001
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