106092-11-9

Basic information

• Product Name: (+)-(6R)-2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole
• Synonyms: (R)-4,5,6,7-TETRAHYDRO-BENZOTHIAZOLE-2,6-DIAMINE;(+)-(6R)-2,6-DIAMINO-4,5,6,7-TETRAHYDROBENZOTHIAZOLE;(+)-2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole（intermidiate of Pramipexole）;(6R)-4,5,6,7-Tetrahydro-2,6-benzothiazolediamine;(R)-2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole;(R)-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine;REF DUPL: (R)-4,5,6,7-Tetrahydro-benzothiazole-2,6-diamine;(R)-N-Despropyl PraMipexole
• CAS NO: 106092-11-9
• Molecular Formula: C₇H₁₁N₃S
• Molecular Weight: 169.25
• EINECS: 1806241-263-5
• Product Categories: intermidiate of Pramipexole;All Inhibitors;Inhibitors;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 106092-11-9.mol

Chemical Properties

• Melting Point: 228-230°C
• Boiling Point: 359 °C at 760 mmHg
• Flash Point: 170.9 °C
• Appearance: off-white solid
• Density: 1.313 g/cm³
• Vapor Pressure: 2.45E-05mmHg at 25°C
• Refractive Index: 1.655
• Storage Temp.: Refrigerator
• Solubility: Methanol (Sparingly), Water (Slightly)
• PKA: 9.18±0.20(Predicted)
• CAS DataBase Reference: (+)-(6R)-2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(6R)-2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole(106092-11-9)
• EPA Substance Registry System: (+)-(6R)-2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole(106092-11-9)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 106092-11-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(+)-(6R)-2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole is used as an intermediate in the synthesis of (R)-Pramipexole, a dopamine autoreceptor agonist. This application is significant because (R)-Pramipexole is a crucial component in the development of medications for the treatment of Parkinson's disease and other movement disorders. As a chiral intermediate, it plays a vital role in ensuring the correct stereochemistry of the final drug product, which is essential for its therapeutic efficacy and safety.
Additionally, due to its unique chemical structure and properties, (+)-(6R)-2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole may have potential applications in other areas of the pharmaceutical industry, such as the development of new drugs or as a building block for the synthesis of complex organic molecules. However, further research and development would be required to explore and validate these potential uses.

InChI:InChI=1/C7H11N3S/c8-4-1-2-5-6(3-4)11-7(9)10-5/h4H,1-3,8H2,(H2,9,10)/t4-/m1/s1

Upstream product

• 106006-83-1 2,6-diamino-4,5,6,7-tetrahydro-benzthiazole 
• 27514-08-5 N-(4-oxocyclohexyl)acetamide 
• 687639-03-8 2-bromo-4-acetamidocyclohexanone 
• 106006-80-8 N-(2-amino-4,5,6,7-tetrahydrobenzo[1,2-d]thiazol-6-yl)acetamide 

Downstream Products

• 106006-85-3 (+)-2-amino-6-propionamidotetrahydrobenzothiazole 
• 104632-27-1 (R)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine dihydrochloride 
• 1332723-78-0 (R)-(+)-2-amino-4,5,6,7-tetrahydro-6-(n-propylamino)benzothiazole p-toluenesulfonic acid 
• 104632-28-2 (R)-(+)-pramipexole 

Relevant articles and documents

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.

PROCESS FOR PREPARING CHIRALLY PURE 2-AMINO-6-(ALKYL)AMINO-4,5,6,7-TETRAHYDROBENZOTHIAZOLES BY LIQUID CHROMATOGRAPHIC RESOLUTION

Processes for obtaining single enantiomers of 2-amino-6-(alkyl)amino-4,5,6,7-tetrahydrobenzothiazoles by liquid chromatography are disclosed.

Novel thrombin inhibitors incorporating weakly basic heterobicyclic P1-arginine mimetics: optimization via modification of P1 and P3 moieties.

Optimization of lead compounds 1 and 2 resulted in novel, selective, and potent thrombin inhibitors incorporating weakly basic heterobicyclic P(1)-arginine mimetics. The design, synthesis, and biological activity of racemic thrombin inhibitors 17-29 and enantiomerically pure thrombin inhibitors 30-33 are described. The arginine side-chain mimetics used in this study are 4,5,6,7-tetrahydro-1,3-benzothiazol-2-amine, 4,5,6,7-tetrahydro-2H-indazole, and 2-imino-4,5,6,7-tetrahydro-1,3-benzothiazol-3(2H)-ylamine.

Dopamine autoreceptor agonists: Resolution and pharmacological activity of 2,6-diaminotetrahydrobenzothiazole and an aminothiazole analogue of apomorphine

The enantiomers of the aminothiazole analogues of the known dopaminergic agonists apomorphine (1) and 2-aminohydroxytetralin (2) have been prepared. The absolute configurations of the enantiomers of 2,6-diaminotetrahydrobenzothiazole have been established by X-ray crystallographic analysis. Dopamine (DA) autoreceptor agonist activities of the compounds were evaluated. Testing revealed (-)-5, the S enantiomer, to be the most active compound tested (inhibition of GBL accelerated dopamine synthesis and inhibition of α-methyltyrosine-induced decline of DA). In addition (-)-5 does not exhibit stereotyped behavior, suggesting a pronounced selectivity for DA autoreceptors.