1. Synthesis of Biologically Active Thiadiazole Analogs Lillian Nordahl 2006

2. Background: Auxin - Causes cell growth and development in plants - Role in cell growth not fully understood on a molecular level because of unidentified receptor proteins Auxin (indole-3-acetic acid)

3. Background: Use of Auxin Inhibitors to Study Auxin -Structure-activity relationship testing to identify chemical group(s) that bind to receptor proteins of auxin Furyl acrylate ester of a thiadiazole heterocycle: identified in 2004 as an inhibitor of auxin by Armstrong et al.

4. Background: Use of Auxin Inhibitors to Study Auxin -Structure-activity relationship testing to identify chemical group(s) that bind to receptor proteins of auxin Furyl acrylate ester of a thiadiazole heterocycle: identified in 2004 as an inhibitor of auxin by Armstrong et al.

5. Background: Use of Auxin Inhibitors to Study Auxin -Structure-activity relationship testing to identify chemical group(s) that bind to receptor proteins of auxin Furyl acrylate ester of a thiadiazole heterocycle: identified in 2004 as an inhibitor of auxin by Armstrong et al.

6. Background: Use of Auxin Inhibitors to Study Auxin -Structure-activity relationship testing to identify chemical group(s) that bind to receptor proteins of auxin Furyl acrylate ester of a thiadiazole heterocycle: identified in 2004 as an inhibitor of auxin by Armstrong et al.

7. Goal - Synthesize derivatives of a furyl acrylate ester to determine which chemical groups of the furyl acrylate ester bind to a target protein of auxin

8. Acylation: Furoyl Chloride Derivative Ethyl-amino thiadiazole + furoyl chloride

9. Acylation: Furoyl Chloride Derivative furoyl chloride derivative

10. Acylation: Furoyl Chloride Derivative Ethyl-amino thiadiazole + furoyl chloride  furoyl chloride derivative

11. Acylation: Furoyl Chloride Derivative Ethyl-amino thiadiazole + furoyl chloride  furoyl chloride derivative

12. Acylation: Thiophenecarbonyl Chloride Derivative Ethyl-amino thiadiazole + thiophenecarbonyl chloride

13. Acylation: Thiophenecarbonyl Chloride Derivative thiophenecarbonyl chloride derivative

14. Acylation Set-up

15. Purification - Aqueous rinses -Flash chromatography -Medium pressure liquid chromatography Aqueous rinsing

16. Identification - Silica gel thin-layer chromatography (TLC) - 1 H and 13 C nuclear magnetic resonance (NMR) spectroscopy - Infrared (IR) spectroscopy

17. 1 H NMR Spectrum of Furoyl Chloride Derivative

21. 13 C NMR Spectrum of Furoyl Chloride Derivative

22. IR Spectrum of Furoyl Chloride Derivative

26. 1 H NMR Spectrum of Thiophenecarbonyl Chloride Derivative

27. 13 C NMR Spectrum of Thiophenecarbonyl Chloride Derivative

28. IR Spectrum of Thiophene-carbonyl Chloride Derivative

29. Conclusions - Correct number and arrangement of hydrogen and carbon atoms - Desired hybridization and bonding present - Pure products - DMAP improves yield for thiophenecarbonyl chloride derivative

30. Conclusions - Correct number and arrangement of hydrogen and carbon atoms - Desired hybridization and bonding present - Pure products - DMAP improves yield for thiophenecarbonyl chloride derivative

31. Future Studies - Structure-activity relationship studies - Isolation of receptor protein - Applications in processes involving the control of plant growth

32. Acknowledgements - Dr. Rebecca C. Hoye at Macalester College - Minnesota Academy of Science and Academy of Applied Sciences - Ms. Lois Fruen - Team Research

33. Synthesis of Biologically Active Thiadiazole Analogs Lillian Nordahl 2006