Event Title

Synthesis of 5-[5-(5-Formyi-2-thienyI)-2-furyl]-2-thiophenecarbaIdehyde

Location

CSU 255A/B

Start Date

23-4-2007 10:00 AM

End Date

23-4-2007 12:00 PM

Student's Major

Chemistry and Geology

Student's College

Science, Engineering and Technology

Mentor's Name

Brian L. Groh

Mentor's Department

Chemistry and Geology

Mentor's College

Science, Engineering and Technology

Description

5-[5-(5-Formyl-2-thienyl)-2-furyl]-2-thiophenecarbaldehyde (NSC 629035) has been found to possess antitumor properties in the NCI Anticancer Drug Screen. A similar compound, 2,5-bis(5-hydroxymethyl-2- thienyl)furan (NSC 652287), has also been found to possess anti-tumor properties. A correlation between the ability to metabolize NSC 652287, hypothesized as NSC 629035, and its cytotoxicity has been demonstrated. The mechanism by which these compounds act is not fully understood. Approximately 3 g of commercially available NSC 629035 ($3,850/250 mg) is required for mechanistic studies. The prohibitive cost demanded the development of a viable synthetic approach to this compound. Two routes for the synthesis of NSC 629035 will be presented.

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Apr 23rd, 10:00 AM Apr 23rd, 12:00 PM

Synthesis of 5-[5-(5-Formyi-2-thienyI)-2-furyl]-2-thiophenecarbaIdehyde

CSU 255A/B

5-[5-(5-Formyl-2-thienyl)-2-furyl]-2-thiophenecarbaldehyde (NSC 629035) has been found to possess antitumor properties in the NCI Anticancer Drug Screen. A similar compound, 2,5-bis(5-hydroxymethyl-2- thienyl)furan (NSC 652287), has also been found to possess anti-tumor properties. A correlation between the ability to metabolize NSC 652287, hypothesized as NSC 629035, and its cytotoxicity has been demonstrated. The mechanism by which these compounds act is not fully understood. Approximately 3 g of commercially available NSC 629035 ($3,850/250 mg) is required for mechanistic studies. The prohibitive cost demanded the development of a viable synthetic approach to this compound. Two routes for the synthesis of NSC 629035 will be presented.

Recommended Citation

Bequette, Joseph P.. "Synthesis of 5-[5-(5-Formyi-2-thienyI)-2-furyl]-2-thiophenecarbaIdehyde." Undergraduate Research Symposium, Mankato, MN, April 23, 2007.
https://cornerstone.lib.mnsu.edu/urs/2007/oral-session-05/3