Synthesis of Biologically Active Thiadiazole Analogs

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

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

17. 1H NMR Spectrumof Furoyl Chloride Derivative

18. 1H NMR Spectrumof Furoyl Chloride Derivative

19. 1H NMR Spectrumof Furoyl Chloride Derivative

20. 1H NMR Spectrumof Furoyl Chloride Derivative

21. 13C NMR Spectrumof Furoyl Chloride Derivative

22. IR Spectrum of Furoyl Chloride Derivative

23. IR Spectrum of Furoyl Chloride Derivative

24. IR Spectrum of Furoyl Chloride Derivative

25. IR Spectrum of Furoyl Chloride Derivative

26. 1H NMR Spectrum of Thiophenecarbonyl Chloride Derivative

27. 13C 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