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Spring Symposium on UR and Community Engagement has ended
Tuesday, April 24 • 12:00pm - 1:30pm
Synthesis Of β-Lactam Analogues Of CA-4

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This research examines the synthesis of β-lactams as combretastatin A-4 (CA-4) analogues and their ability to target and bind to tubulin within cancer cells. Tubulin is an α, β heterodimeric protein and is an important and promising target for cancer research because cell division relies on tubulin and without it, cell division cannot occur. CA-4 is a naturally occurring compound, isolated from the South African bush willow Combretum Caffrum, and is an important molecule to study because CA-4 can bind to tubulin within cells. A problem with CA-4 is that for it to be biologically active it needs to be in the cis conformation but is more stable in the trans conformation. Creating a β-lactam analogue of CA-4 is beneficial because the β-lactam replaces the ethylene bridge in CA-4 and makes the molecule more rigid, keeping it more aligned in the cis conformation. To synthesize the β-lactams, imines will first be synthesized, which will then be reacted with ketenes using a Staudinger [2+2] cycloaddition. The imines will be synthesized with 3,4,5-trimethoxybenzaldehyde and a variety of different anilines. The synthesis of an imine has already been conducted where 3,4,5-trimethoxybenzalehayde was reacted with aniline. The imine was synthesized with quantitative yield. Throughout the project, the substituent on the benzene ring of the aniline will be changed to see if different substituents affect the β-lactams ability to target and bind to tubulin. Specific ketenes will be synthesized from different acid chlorides, based on the desired substituents to be placed in the alpha position of the β-lactam ring.

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Tuesday April 24, 2018 12:00pm - 1:30pm
Sherrill Center Concourse