fairfolio
Saved Projects

Increasing the Bioefficacy of Artemisinin through Trifluoromethylation

CSEF · 2013 Chemistry

Shreya S. Ramayya · Palos Verdes Peninsula High School, Rolling Hills Estates, Los Angeles County

Overview

Objectives/Goals The application of fluorine in pharmaceuticals has been widely recognized. Due to its structural similarity to hydrogen and high electronegativity, fluorine has been extensively employed to modulate such biological properties of drug molecules as acidity, basicity, protein binding affinity, and lipophilicity. There is an urgent need for capable protocols to efficiently incorporate fluorine into complex organic molecules. This study has specifically focused building the process to trifluoromethylate artemisinin to increase its bioefficacy and make the currently available drugs for malaria even more potent and cost effective. Methods/Materials TMS-CF(3), the Ruppert- Prakash reagent, has become very popular for nucleophilic trifluoromethylation of carbonyl compounds. Before attempting trifluoromethylation of a complex molecule like artemisinin, aldehydes, esters, and ketones were used as substrates to devise a possible reaction mechanism for the process. The reactions required a simple catalyst, such as potassium carbonate to achieve the maximum yield. Results Using NMR (Nuclear Magnetic Resonance) analysis, the results show that the trifluoromethylation of the substrates produced high yields of the desired products with the Ruppert- Prakash reagent. With yields of products ranging from 80-94%, the method of trifluoromethylation proved successful. Conclusions/Discussion The results of this study suggest that it is possible to include fluorine and the trifluoromethyl group into substrates with structures similar to that of artemisinin by using the Ruppert-Prakash reagent. Therefore, it is possible that trifluoromethylation may increase the bioefficacy of artemisinin to treat a variety of diseases, including malaria and cancer, in the future.

Summary statement

This main goal of my experiments was to create a practical reaction procedure that could be followed for the trifluoromethylation of artemisinin.

Help received

I worked at Loker Hydrocarbon Research Institute at USC and was supervised by Drs. Surya Prakash, Parag Jog, and Hema Krishnan. My parents took me to and from the lab.

Competition history

  • CSEF 2013 Chemistry · Entry S0620

Resources

Related projects

Closest projects by meaning, across every fair and year in the corpus.

Browse more like this

Source: California Science & Engineering Fair public projects

Save projects to your library

Sign in with Google to keep track of projects you find interesting, organized into folders. An account also raises your daily allowance for “Has this been done?”, and lets you create a key for the MCP server with a much higher limit than anonymous use. Browsing stays public.

Continue with Google