86634-64-2

Basic information

• Product Name: 3-phenyl-4-oxo-7-thia-1,3-diazabicyclo<3.3.0>octane-2-thione
• CAS NO: 86634-64-2
• Molecular Weight: 250.345
• Mol File: 86634-64-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3-phenyl-4-oxo-7-thia-1,3-diazabicyclo<3.3.0>octane-2-thione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyl-4-oxo-7-thia-1,3-diazabicyclo<3.3.0>octane-2-thione(86634-64-2)
• EPA Substance Registry System: 3-phenyl-4-oxo-7-thia-1,3-diazabicyclo<3.3.0>octane-2-thione(86634-64-2)

Safety Data

• Hazardous Substances Data: 86634-64-2(Hazardous Substances Data)

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 60664-15-5 ethyl (4R)-1,3-thiazolidine-4-carboxylate 
• 137941-34-5 ethyl (S)-1,3-thiazolidine-4-carboxylate 
• 444-27-9 (RS)-4-thiazolidinecarboxylic acid 
• 34592-47-7 L-thioproline 
• 42258-90-2 (R)-thiazolidine-4-carboxylic acid methyl ester 

Relevant articles and documents

New aspects of the formation of 2-substituted thiazolidine-4-carboxylic acids and their thiohydantoin derivatives

Aromatic aldehydes reacted readily with (R)-cysteine in boiling acidified methanol to give diastereomeric mixtures of the corresponding 2-(aryl substituted) thiazolidine-4-carboxylic acids. 4-Nitrobenzaldehyde under similar conditions afforded one isomer of 2-(4-nitrophenyl)-thiazolidine-4-carboxylic acid, which epimerized in the NMR solvents into a diastereomeric mixture. 2-Nitrobenzaldehyde reacted with (R)-cysteine to afford 3,5-bis-(2-nitrophenyl)-tetrahydro-1H-thiazolo[3,4-c]oxazol-1-one as the sole product, which collapsed in the NMR solvent into a diastereomeric mixture of the thiazolidine-4-carboxylic acids. The thiazolidine derivatives reacted smoothly with phenyl isothiocyanate to give single isomers of the corresponding thiohydantoins.

Immunomodulatory agents: Dioxothiadiazabicyclo[3.3.0]octanes and their 2- spiro derivatives

A series of 6,8-dioxo-3-thia-1,7-diazabicyclo[3.3.0]octanes and a series of 6,8-dioxo-3-thia-1,7-diazabicyclo[3.3.0]octane 2-spiro derivatives were synthesized from L-(-)-R-cysteine ethyl ester in two steps. The synthetic route involved condensation of the amino acid with an appropriate aldehyde or ketone, then a further condensation of the resultant ethyl thiazolidine-4- carboxylate with an isocyanate or an isothiocyanate. The proliferative response to human lymphocyte mitogen (phytohemagglutinin) was used as a primary screening assay for most of the thiadiazabicyclic compounds in comparison with levamisole. Furthermore, the most active compounds were tested for ability to release soluble receptors (sRIL-2) after mitogenic stimulation of T cells and for ability to activate macrophage oxidative metabolism measured by chemiluminescence. Most compounds were active in all three tests and some showed dose-dependent activity.

Synthesis of 1H,3H-Imidazothiazole-5,7--dione and 7,8-Dihydro-5H-imidazothiazine-1,3--dione and Derivatives

1H,3H-Imidazothiazole-5,7--dione and the corresponding 7-thione derivatives as well as 7,8-dihydro-5H-imidazothiazine-1,3--dione and the corresponding 3-thione derivatives were synthesized starting from L-cysteine and DL