106006-80-8

Basic information

• Product Name: 6-AcetaMido-2-aMino-4,5,6,7-tetrahydrobenzothiazole
• Synonyms: Acetyl prasol;Acetyl Pramipexole;(6S) - 2-amino-6-acetyl tetrahydrobenzothiazole
• CAS NO: 106006-80-8
• Molecular Formula: C₉H₁₃N₃OS
• Molecular Weight: 211.28402
• Mol File: 106006-80-8.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-AcetaMido-2-aMino-4,5,6,7-tetrahydrobenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AcetaMido-2-aMino-4,5,6,7-tetrahydrobenzothiazole(106006-80-8)
• EPA Substance Registry System: 6-AcetaMido-2-aMino-4,5,6,7-tetrahydrobenzothiazole(106006-80-8)

Safety Data

• Hazardous Substances Data: 106006-80-8(Hazardous Substances Data)

Upstream product

• 27514-08-5 N-(4-oxocyclohexyl)acetamide 
• 17356-08-0 thiourea 
• 23363-88-4 trans-N-acetyl-4-hydroxycyclohexylamine 
• 1071-86-9 bis(formamidine)disulphide dihydrobromide 
• 687639-03-8 2-bromo-4-acetamidocyclohexanone 

Downstream Products

• 104617-97-2 6-acetylamino-2-benzoylamino-4,5,6,7-tetrahydro-benzthiazole 
• 106092-11-9 (R)-4,5,6,7-tetrahydrobenzo[1,2-d]thiazole-2,6-diamine 
• 104632-26-0 pramipexole 
• 106092-09-5 (S)-4,5,6,7-tetrahydrobenzo[d]thiazol-2,6-diamine 
• 106006-83-1 2,6-diamino-4,5,6,7-tetrahydro-benzthiazole 
• 1262552-31-7 1-((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-3-(2-fluorophenyl)thiourea 
• 1262552-30-6 1-((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-3-(3-methoxyphenyl)thiourea 
• 1262552-29-3 1-((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-3-(3-chlorophenyl)thiourea 
• 1262552-28-2 1-((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-3-(4-fluorophenyl)thiourea 
• 1262552-27-1 1-((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-3-(4-methoxyphenyl)thiourea 
• 1262552-35-1 1-((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-3-phenylthiourea 
• 1262552-34-0 1-((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-3-(4-chlorophenyl)thiourea 
• 1262552-33-9 1-((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-3-(2,4-dichlorophenyl)thiourea 
• 1262552-32-8 1-((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-3-(2-chlorophenyl)thiourea 

Relevant articles and documents

Preparation method of pramipexole intermediate 2, 6-diamino-4, 5, 6, 7-tetrahydrobenzothiazole

The invention discloses a preparation method of pramipexole intermediate 2, 6-diamino-4, 5, 6, 7-tetrahydrobenzothiazole. According to the method, 4-acetamido cyclohexanol is taken as a starting material, hydrobromic acid is taken as an oxidizing agent an

Discovery of 4,5,6,7-Tetrahydrobenzo[1,2- d ]thiazoles as Novel DNA Gyrase Inhibitors Targeting the ATP-Binding Site

Bacterial DNA gyrase and topoisomerase IV are essential enzymes that control the topological state of DNA during replication and validated antibacterial drug targets. Starting from a library of marine alkaloid oroidin analogues, we identified low micromolar inhibitors of Escherichia coli DNA gyrase based on the 5,6,7,8-tetrahydroquinazoline and 4,5,6,7-tetrahydrobenzo[1,2-d]thiazole scaffolds. Structure-based optimization of the initial hits resulted in low nanomolar E. coli DNA gyrase inhibitors, some of which exhibited micromolar inhibition of E. coli topoisomerase IV and of Staphylococcus aureus homologues. Some of the compounds possessed modest antibacterial activity against Gram positive bacterial strains, while their evaluation against wild-type, impA and ΔtolC E. coli strains suggests that they are efflux pump substrates and/or do not possess the physicochemical properties necessary for cell wall penetration. Our study provides a rationale for optimization of this class of compounds toward balanced dual DNA gyrase and topoisomerase IV inhibitors with antibacterial activity.

Synthesis and identification of a new class of (S)-2,6-diamino-4,5,6,7- tetrahydrobenzo[d]thiazole derivatives as potent antileukemic agents

Benzothiazoles are multitarget agents with broad spectrum of biological activity. Among the antitumor agents discovered in recent years, the identification of various 2-(4-aminophenyl) benzothiazoles as potent and selective antitumor drugs against different cancer cell lines has stimulated remarkable interest. Some of the benzothiazoles are known to induce cell cycle arrest, activation of caspases and interaction with DNA molecule. Based on these interesting properties of benzothiazoles and to obtain new biologically active agents, a series of novel 4,5,6,7-tetrahydrobenzo[d]thiazole derivatives 5(a-i) were synthesized and evaluated for their efficacy as antileukemic agents in human leukemia cells (K562 and Reh). The chemical structures of the synthesized compounds were confirmed by 1H NMR, LCMS and IR analysis. The cytotoxicity of these compounds were determined using trypan blue exclusion, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) and lactate dehydrogenase (LDH) assays. Results showed that, these compounds mediate a significant cytotoxic response to cancer cell lines tested. We found that the compounds having electron withdrawing groups at different positions of the phenyl ring of the thiourea moiety displayed significant cytotoxic effect with IC50 value less than 60 μM. To rationalize the role of electron withdrawing group in the induction of cytotoxicity, we have chosen molecule 5g (IC 50 ～15 μM) which is having chloro substitution at ortho and para positions. Flow cytometric analysis of annexin V-FITC/propidium iodide (PI) double staining and DNA fragmentation suggest that 5g can induce apoptosis. Springer Science + Business Media, LLC 2009.