389850-23-1

Basic information

• Product Name: 2-[2-imino-4,5,6,7-tetrahydro-1,3-benzothiazol-3(2H)-yl]-1-phenyl-1-ethanone hydrobromide
• Synonyms: 2-[2-imino-4,5,6,7-tetrahydro-1,3-benzothiazol-3(2H)-yl]-1-phenyl-1-ethanone hydrobromide
• CAS NO: 389850-23-1
• Molecular Formula: C15H17BrN2OS
• Molecular Weight: 353.29
• Mol File: 389850-23-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-[2-imino-4,5,6,7-tetrahydro-1,3-benzothiazol-3(2H)-yl]-1-phenyl-1-ethanone hydrobromide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[2-imino-4,5,6,7-tetrahydro-1,3-benzothiazol-3(2H)-yl]-1-phenyl-1-ethanone hydrobromide(389850-23-1)
• EPA Substance Registry System: 2-[2-imino-4,5,6,7-tetrahydro-1,3-benzothiazol-3(2H)-yl]-1-phenyl-1-ethanone hydrobromide(389850-23-1)

Safety Data

• Hazardous Substances Data: 389850-23-1(Hazardous Substances Data)

Upstream product

• 55895-83-5 2-amino-4,5-tetramethylenethiazole hydrobromide 
• 70-11-1 α-bromoacetophenone 
• 2933-29-1 2-Amino-4,5,6,7-tetrahydrobenzothiazole 

Relevant articles and documents

A convenient one-pot synthesis of thiazol-2-imines: application in the construction of pifithrin analogues

For the first time a reaction intermediate has been isolated giving further insight into the mechanism of thiazol-2-imine formation. The first step of the reaction requires a basic medium, while the second step is an acid mediated E1 elimination reaction. An efficient one-pot synthesis of substituted thiazol-2-imines have been achieved by the condensation of carbonyl compounds with thioureas and 1,3-disubstituted thioureas using 1,1′-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT). Unsymmetrical 1,3-disubstituted thioureas give regioselective products with symmetrical ketones, which are mainly governed by the pKas of NH protons of thiourea, whereas symmetrical 1,3-disubstituted thioureas give regioselective products with symmetrical carbonyl compounds owing to the regioselective bromination of ketones. The methodology is extended to access novel neurodegenerative drug candidate pifithrin-α analogues in good yields in shorter reaction time. This method is simple, versatile and is applicable for different 1,3-disubstituted thioureas as well as a range of carbonyl compounds.

Novel p53 inactivators with neuroprotective action: Syntheses and pharmacological evaluation of 2-imino-2,3,4,5,6,7-hexahydrobenzothiazole and 2-imino-2,3,4,5,6,7-hexahydrobenzoxazole derivatives

Tumor suppressor protein, p53, is an intracellular protein that is critical within the biochemical cascade that leads to cell death via apoptosis. Recent studies identified the tetrahydrobenzothiazole analogue, pifithrin-α (2), as a p53 inhibitor that was effective in protecting neuronal cells against a variety of lethal insults and reducing the side effects of anticancer drugs. As up-regulation of p53 has been described as a common feature of several neurodegenerative disorders, including Alzheimer's disease, 2 and novel analogues (3-16) were synthesized to (i) assess the value of tetrahydrobenzothiazole analogues as neuroprotective agents and (ii) define the structural requirements for p53 inactivation. Not only did 2 exhibit neuroprotective activity in both tissue culture and in vivo stroke models but also compounds 6, 7, 10, 13, 15, and 16 proved to be highly potent in protecting PC12 cells and compounds 3, 4, and 6 were highly potent in protecting primary hippocampal cells against death induced by the DNA-damaging agent, camptothecin.