Chemistry
Event Title
Synthesis of 5-Methyl-4-phthalimido-1,2,3-thiadiazole and 4-Phthalimidomethyl-1,2,3-thiadiazole
Document Type
Poster Presentation
Location
Indianapolis, IN
Subject Area
Chemistry
Start Date
11-4-2014 8:30 AM
End Date
11-4-2014 9:30 AM
Sponsor
Nazir Khatri (Franklin College)
Description
Biologically, 1,2,3-thiadizoles have inhibitory effects on necroptosis, a mechanism that regulates cell death. The mechanism is involved in illnesses including stroke, myocardial infarction, and trauma. Molecules that can inhibit necroptosis could reveal the role of necroptosis in these diseases, and potentially lead to synthesis of compounds for therapeutic use.
N-acetonylphthalimide and carboethoxyhydrazine were reacted to form acetonyl-phthalimidecarboethoxyhydrazone (APCH). This compound was obtained in 88.4% yield and it was reacted with thionyl chloride to give two 1,2,3-thiadizole isomers (A and B). The isomers were identified by NMR Spectroscopy to be a mixture 5-Methyl-4-phthalimido-1,2,3-thiadiazole (A) and 4-Phthalimidomethyl-1,2,3-thiadiazole (B) in a 40:60 ratio. The mixture of isomers A and B was isolated in 46.2% yield.
Synthesis of 5-Methyl-4-phthalimido-1,2,3-thiadiazole and 4-Phthalimidomethyl-1,2,3-thiadiazole
Indianapolis, IN
Biologically, 1,2,3-thiadizoles have inhibitory effects on necroptosis, a mechanism that regulates cell death. The mechanism is involved in illnesses including stroke, myocardial infarction, and trauma. Molecules that can inhibit necroptosis could reveal the role of necroptosis in these diseases, and potentially lead to synthesis of compounds for therapeutic use.
N-acetonylphthalimide and carboethoxyhydrazine were reacted to form acetonyl-phthalimidecarboethoxyhydrazone (APCH). This compound was obtained in 88.4% yield and it was reacted with thionyl chloride to give two 1,2,3-thiadizole isomers (A and B). The isomers were identified by NMR Spectroscopy to be a mixture 5-Methyl-4-phthalimido-1,2,3-thiadiazole (A) and 4-Phthalimidomethyl-1,2,3-thiadiazole (B) in a 40:60 ratio. The mixture of isomers A and B was isolated in 46.2% yield.