Degree Name

Doctor of Philosophy


School of Chemistry and Molecular Bioscience


The application of medicinal chemistry drug design and development principles has been undertaken in the current thesis towards the development of antivirals, fluorescent anion transporters and carbonic anhydrase inhibitors.

Chikungunya viral infection is an increasing concern with no current treatments available beyond supportive measures. In the absence of detailed viral molecular information, phenotypic screening of compounds has provided leads for anti-chikungunya agents. Chapter 2 discusses the application of hybridization of two fragments, namely pyrimidine and thiazolidine, with reported anti-CHIKV activity. Convergent and convenient regioselective synthesis of novel thiazolo[2,3-a]pyrimidine derivatives was accomplished using the one-pot reaction of 6-ethylthiouracil, bromoacetic acid, anhydrous sodium acetate, acetic anhydride, acetic acid and a suitable aldehyde. X-ray crystallographic studies reveal the presence of the Z configuration of only one regioisomer confirmed by computational studies as being the most likely isomer present. Anti-CHIKV activity evaluation showed the tailed thiazolopyrimidine (Z)-7-ethyl-2-((4'-methyl-[1,1'-biphenyl]-4-yl)methylene)-5H-thiazolo[3,2-a]pyrimidine-3,5(2H)-dione as a candidate for future development with EC50 = 42 μM, and IC50 > 250 μM against the breast cancer cell line MCF-7 and the endothelial human sapiens cell line EA.hy926...


Thesis by publication.



Unless otherwise indicated, the views expressed in this thesis are those of the author and do not necessarily represent the views of the University of Wollongong.