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
• Article Data: 4

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

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 106092-11-9 differently. You can refer to the following data:
1. (R)-Pramipexole intermediate as dopamine autoreceptor agonist.
2. (R)-Pramipexole (P700745) intermediate as dopamine autoreceptor agonist.

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

Downstream Products

• 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 
• 106006-85-3 (+)-2-amino-6-propionamidotetrahydrobenzothiazole 

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.

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.