The design and synthesis of antimicrofilaria and anticancer compounds

Author

Roy Franklin Thompson

Date of Award

12-1994

Degree Type

Thesis

Degree Name

Master of Science

Major

Chemistry

Major Professor

David C. Baker

Committee Members

David J.A. Schedler, Stephen C. Johnson

Abstract

The research described herein covers two separate projects. The first project was the synthesis of 1-amidino-4-(o-chlorobenzoyl)piperazine (9). The second project was the synthesis of 5-amino-5-deoxy-myo-inositol (36).

The synthesis of 1-amidino-4-(,i>o-chlorobenzoyl)piperazine (9) was accomplished using previously reported methods. Slight modification and more detailed characterizations were preformed to assist the World Health Organization in the search for antimicrofilarial compounds. 1-Amidino-4-(o-chlorobenzoyl)piperazine (9) showed an 18% reduction of target organisms in their respective hosts.

The synthesis of 5-amino-5-deoxy-myo-inositol (36) explored various protection protocols in an effort to maximize yield. Among the various strategies studied were the following: (1) preparation of various cyclohexylidene derivatives, (2) reparation of benzyl ether derivatives, (3) di silyl ethers, (4) double displacement reactions, and (5) Mitsunobu inversion. In spite of these efforts, only one synthetic route proved to be useful in obtaining the desired target.

Recommended Citation

Thompson, Roy Franklin, "The design and synthesis of antimicrofilaria and anticancer compounds. " Master's Thesis, University of Tennessee, 1994.
https://trace.tennessee.edu/utk_gradthes/11709