The chalcone motif is a privileged structure present in an extensive range of biologically active molecules. The chalcone structure can also serve as a versatile starting material for more complex molecules in medicinal chemistry. Eleutherobin, isolated from the Australian coral Eleutherobia and sarcodictyin, isolated from the Mediterranean coral Sarcodictyon roseum are natural products displaying nanomolar cytotoxicity against a range of cancer cell lines including Taxol®-resistant cell lines. Both natural products act as microtubule stabilising agents and will be valuable additions to the clinic, however their limited availability and lengthy total syntheses prevent further development. The urocanic ester side chain present in eleutherobin and sarcodictyin was identified as being critical for biological activity. We discuss the design, synthesis and biological evaluation of fourteen chalcone analogues based on this urocanic motif with the lead chalcone displaying promising antiproliferative activity in a range of cancer cell lines. Combretastatin A-4 is a promising microtubule destabiliser under clinical development. The Z configuration is vital for biological activity, however it can isomerise to the inactive E configuration. We report a library of twenty pyrazolines synthesised from chalcones as “Z restricted” combretastatin analogues with the lead pyrazoline displaying potent antiproliferative activity in cancer cell lines due to the disruption of tubulin. Tissue engineering is a diverse interdisciplinary field that applies engineering principles to the biological sciences with the aim of maintaining or replacing tissue function. Recent developments have revealed metal chelation to be a valuable tool to control the architecture of tissue engineering scaffolds. We report a library of ten novel pyrazolines and their potential as metal chelators. Maltol is a well established Fe3+ chelator with a low toxicity profile. We report a novel maltol hydrazide which can be attached to the cell surface which upon addition of Fe3+ results in cellular aggregation due to metal chelation. Further studies revealed that this process can be applied to form heterocellular aggregates composed of two different cancer types with valuable applications in tissue engineering and cancer research.