Using multi-step Chemical Synthesis to Form Covalent Protease Inhibitors

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2020-09-29

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Covalent bonding drugs have been rising recently in drug discovery. With handfuls being approved in the past century for various ailments such as cancers and viruses. Using conversion of compounds and multi-step synthesis through the summer, and applying concepts learned from organic chemistry such as the hydrolysis of esters into acids, boc protection, amide bond formation, carbamate formation, and Wittig-Horner reactions we have been able to start with a diol and end with an amide. This amide will be paired with a library of acids in house to form structures which haven’t been sought after, and to be further screened in cells against enzymes. Ramifications that arose during this project were mostly due to reactions not working in time, having to make adjustments to get higher yields, and needed reactants being on back order. During COVID limiting the amount of persons allowed in lab at a time also slowed down the process quite a bit. Persevering through these challenges we have successfully been able to produce a compound (In good yield ~3g) which will be used as the building block to pair with our acids in house. This compound arose from a series of six reactions which have been carefully manipulated to obtain a pure product. Sending out 50+ unique compounds to institutions and hospitals (which we will form using our products from the summer), they are to be tested in rare diseases such as osteosarcoma cancer cells and eventually in animals.

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