The Ipomossieasn family is a unique class of natural products that contain a carbohydrate macrocyclic ring framework. It has been shown that they possess potent anticancer properties. Among this group, ipomossiean F has a single-digit IC<sub>50</sub> value against many cancer cell lines. Through implementation of medicinal chemistry studies, vital parts of the natural product in terms of their impact on biological activities have been identified. Based on the data, the cinnamate moiety is found to be the most crucial. Removal of the cinnamate almost completely abolished the biological activities of Ipomossiean F. Also, by applying structure-relationship testing it has been demonstrated that the ring part of the natural product is not crucial for the activity of the drug. In this work, based on our understanding of the structure-activity relationship of the molecule, we report the design and current progress in synthesis of open-ring analogs containing 2-cyanocinnamic acid derivatives, aiming 1) simplify the total synthesis and 2) improve the biological activities of the natural product.

Design and synthesis of ipomoeassin F analogues containing α-cyano cinnamates

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