Synthesis of Biologically Active Thiadiazole Analogs

Lillian Nordahl

2006

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

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Auxin (indole-3-acetic acid)

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.

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.

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.

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.

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

Acylation: Furoyl Chloride Derivative

Ethyl-amino thiadiazole + furoyl chloride

Acylation: Furoyl Chloride Derivative

furoyl chloride derivative

Acylation: Furoyl Chloride Derivative

Ethyl-amino thiadiazole + furoyl chloride furoyl chloride derivative

Acylation: Furoyl Chloride Derivative

Ethyl-amino thiadiazole + furoyl chloride furoyl chloride derivative

Acylation: Thiophenecarbonyl Chloride Derivative

Ethyl-amino thiadiazole + thiophenecarbonyl chloride

Acylation: Thiophenecarbonyl Chloride Derivative

thiophenecarbonyl chloride derivative

Acylation Set-up

Purification

- Aqueous rinses

- Flash chromatography- Medium pressure liquid

chromatography

Aqueous rinsing

Identification

- Silica gel thin-layer chromatography (TLC)

- 1H and 13C nuclear magnetic resonance (NMR) spectroscopy

- Infrared (IR) spectroscopy

1H NMR Spectrum of Furoyl Chloride Derivative

1H NMR Spectrum of Furoyl Chloride Derivative

1H NMR Spectrum of Furoyl Chloride Derivative

1H NMR Spectrum of Furoyl Chloride Derivative

13C NMR Spectrum of Furoyl Chloride Derivative

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IR Spectrum of Furoyl Chloride Derivative

IR Spectrum of Furoyl Chloride Derivative

IR Spectrum of Furoyl Chloride Derivative

IR Spectrum of Furoyl Chloride Derivative

1H NMR Spectrum of Thiophenecarbonyl Chloride Derivative

13C NMR Spectrum of Thiophenecarbonyl Chloride Derivative

IR Spectrum of Thiophene-carbonyl Chloride Derivative

Conclusions

- Correct number and arrangement of hydrogen and carbon

atoms

- Desired hybridization and bonding present

- Pure products

- DMAP improves yield for thiophenecarbonyl chloride derivative

Conclusions

- Correct number and arrangement of hydrogen and carbon

atoms

- Desired hybridization and bonding present

- Pure products

- DMAP improves yield for thiophenecarbonyl chloride derivative

Future Studies

- Structure-activity relationship studies

- Isolation of receptor protein

- Applications in processes involving the control of plant growth

Acknowledgements

- Dr. Rebecca C. Hoye at Macalester College

- Minnesota Academy of Science and Academy of Applied

Sciences

- Ms. Lois Fruen

- Team Research

Synthesis of Biologically Active Thiadiazole Analogs

Lillian Nordahl

2006