Event Title

A Concise Synthesis Of BRL-37959 and Several Analogs

Mentor 1

M. Mahmun Hossain

Location

Union Wisconsin Room

Start Date

28-4-2017 1:30 PM

End Date

28-4-2017 4:00 PM

Description

The replacement of opioids for post operationalpain is a necessity in modern medicine.Opiate based drugs have many problems:addiction and gastric irritancyare two of the main complications that arise from their use. BRL-37959 isa compound, which was first synthesized in 1986 and was shown to have great promise as a pain killer. It is classified as a non-steroidal anti-inflammatory drug, which work by inhibiting the COX enzyme to reduce pain and inflammation. One potential benefit of the compound is that in initial studies, it did not affect the stomach lining, unlike most COX inhibitors. However, the original synthesis of BRL-37959 was extremely inefficient, particularly during the formation of the benzofuran backbone, obtaining the final compound in yields of less than one percent. Because of this, research on the compound came to a halt. In 2006, the Hossain lab approached the synthesis of BRL-37959 after developing a reaction which formed benzofuran rings in high yield. Our main goal of this study was to synthesize BRL-37959 and variousanalogsin the most efficient and environmentally friendly way possible. We have now completed the synthesis of several of the target compounds, in greater yields than previously obtained, using a new application of a bismuth catalyst. These compounds will be sent to a collaborator at Vanderbilt University for COX inhibition testing.

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Apr 28th, 1:30 PM Apr 28th, 4:00 PM

A Concise Synthesis Of BRL-37959 and Several Analogs

Union Wisconsin Room

The replacement of opioids for post operationalpain is a necessity in modern medicine.Opiate based drugs have many problems:addiction and gastric irritancyare two of the main complications that arise from their use. BRL-37959 isa compound, which was first synthesized in 1986 and was shown to have great promise as a pain killer. It is classified as a non-steroidal anti-inflammatory drug, which work by inhibiting the COX enzyme to reduce pain and inflammation. One potential benefit of the compound is that in initial studies, it did not affect the stomach lining, unlike most COX inhibitors. However, the original synthesis of BRL-37959 was extremely inefficient, particularly during the formation of the benzofuran backbone, obtaining the final compound in yields of less than one percent. Because of this, research on the compound came to a halt. In 2006, the Hossain lab approached the synthesis of BRL-37959 after developing a reaction which formed benzofuran rings in high yield. Our main goal of this study was to synthesize BRL-37959 and variousanalogsin the most efficient and environmentally friendly way possible. We have now completed the synthesis of several of the target compounds, in greater yields than previously obtained, using a new application of a bismuth catalyst. These compounds will be sent to a collaborator at Vanderbilt University for COX inhibition testing.