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Synthesis of some potential antimicrobial carbocyclic compounds
Author(s)
Van Eeden, Nestor
Date Issued
1994
Type
Thesis
Publisher
Cape Technikon
Abstract
Some naturally occurring compounds containing the naphtho [2,3 - c] pyran ring system
have been found to be useful antibiotic agents and thus the laboratory synthesis ofthese
compounds and their derivatives are of importance in the medical field. Their antibiotic and
even antineoplastic activities are attributed to their potential to act as alkylating agents, via
a bioreductive process.
This thesis deals with studies directed towards the synthesis of some benzo [c] pyrans as
these compounds also possess the correct structural configuration to undergo the
bioreductive process, and act as alkylating agents to cellular nucleic acids.
Chapter Two describes the synthesis 00,4 dihydro - 1,3 - dimethyl- IH - benzo - [cl pyran
- 5,8 - quinone (13) by employing a base induced cyclization with potassium tertiary
butoxide. This compound was proven to be biologically active against both Gram positive
and Gram negative organisms.
(±) (1R, 3R, 4R) - 3,4 - Dihydro - 4 - hyroxy -1,3 - dimethyl- 1H - benzo [e] pyran - 5,8quinone
(17) and its 4 S diastereomer (18) were synthesized with cerium (IV) ammonium
nitrate as the cyclizing reagent. Antimicrobial evaluation ofcompound (17)
displayed inhibitory activity against both Gram positive and Gram negative organism
growth. This is discussed in Chapter Three.
In Chapter Four, the synthesis ofthe benzo analogue ofthe naturally occurring
naphthopyran antibiotic, hongconin, is discussed. The synthetic route used for this synthesis
could well be applied to synthesise hongconin.
have been found to be useful antibiotic agents and thus the laboratory synthesis ofthese
compounds and their derivatives are of importance in the medical field. Their antibiotic and
even antineoplastic activities are attributed to their potential to act as alkylating agents, via
a bioreductive process.
This thesis deals with studies directed towards the synthesis of some benzo [c] pyrans as
these compounds also possess the correct structural configuration to undergo the
bioreductive process, and act as alkylating agents to cellular nucleic acids.
Chapter Two describes the synthesis 00,4 dihydro - 1,3 - dimethyl- IH - benzo - [cl pyran
- 5,8 - quinone (13) by employing a base induced cyclization with potassium tertiary
butoxide. This compound was proven to be biologically active against both Gram positive
and Gram negative organisms.
(±) (1R, 3R, 4R) - 3,4 - Dihydro - 4 - hyroxy -1,3 - dimethyl- 1H - benzo [e] pyran - 5,8quinone
(17) and its 4 S diastereomer (18) were synthesized with cerium (IV) ammonium
nitrate as the cyclizing reagent. Antimicrobial evaluation ofcompound (17)
displayed inhibitory activity against both Gram positive and Gram negative organism
growth. This is discussed in Chapter Three.
In Chapter Four, the synthesis ofthe benzo analogue ofthe naturally occurring
naphthopyran antibiotic, hongconin, is discussed. The synthetic route used for this synthesis
could well be applied to synthesise hongconin.
Additional information
Thesis (M. Diploma in Technology (Chemistry))--Cape Technikon, 1994
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