Synthesis of BRL-37959 and Analogues
Mentor 1
Dr. Hossain
Location
Union Wisconsin Room
Start Date
29-4-2016 1:30 PM
End Date
29-4-2016 3:30 PM
Description
The replacement of opiates for post operational pain is a necessity in modern medicine, opiate based drugs have many problems: addiction and gastric irritancy are two of the main complications that arise from their use. BRL 37959 is a compound, which was first synthesized in 1986 and was shown to have great promise as a pain killer, being classified as a non-steroidal anti-inflammatory drug, which work by inhibiting the COX enzyme. A study performed in 2004 has shown that the over expression of the COX enzyme is also linked to several types of cancer, making this compound a likely candidate for cancer therapy. The original synthesis of BRL-37959 was extremely inefficient, particularly during the formation of the benzofuran backbone, causing the compound not to be further studied. In 2006, the Hossain lab approached the synthesis of BRL-37959 after developing a reaction which formed benzofuran rings in high yield. My main goal of this study was to synthesize BRL-37959 and various analogs in the most efficient and greenest way possible. We have now completed the synthesis of the main compound using a new catalyst and microwave reactions, improving one step from a 10% to a 70% yield, giving a 60-70% yield over the course of the synthesis. The compound, and several more analogs are now being prepared in greater quantities and more quickly. These compounds will be sent to a collaborator at Vanderbilt University for COX inhibition testing, as well as the biology department here at the University of Milwaukee for screening against cancer cell lines.
Synthesis of BRL-37959 and Analogues
Union Wisconsin Room
The replacement of opiates for post operational pain is a necessity in modern medicine, opiate based drugs have many problems: addiction and gastric irritancy are two of the main complications that arise from their use. BRL 37959 is a compound, which was first synthesized in 1986 and was shown to have great promise as a pain killer, being classified as a non-steroidal anti-inflammatory drug, which work by inhibiting the COX enzyme. A study performed in 2004 has shown that the over expression of the COX enzyme is also linked to several types of cancer, making this compound a likely candidate for cancer therapy. The original synthesis of BRL-37959 was extremely inefficient, particularly during the formation of the benzofuran backbone, causing the compound not to be further studied. In 2006, the Hossain lab approached the synthesis of BRL-37959 after developing a reaction which formed benzofuran rings in high yield. My main goal of this study was to synthesize BRL-37959 and various analogs in the most efficient and greenest way possible. We have now completed the synthesis of the main compound using a new catalyst and microwave reactions, improving one step from a 10% to a 70% yield, giving a 60-70% yield over the course of the synthesis. The compound, and several more analogs are now being prepared in greater quantities and more quickly. These compounds will be sent to a collaborator at Vanderbilt University for COX inhibition testing, as well as the biology department here at the University of Milwaukee for screening against cancer cell lines.
