synthesis of biologically active thiadiazole analogs lillian nordahl 2006
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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
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