106006-83-1

Basic information

• Product Name: 2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole
• Synonyms: ()-2,6-DIAMINO-4,5,6,7-TETRA-HYDROBENZOTHIAZOL;4,5,6,7-tetrahydrothieno[3,4-c]pyridine-1,3-diamine;R,S-2,6-DiaMino-4,5,6,7- tetrahydrobenzothiazole
• CAS NO: 106006-83-1
• Molecular Formula: C₇H₁₁N₃S
• Molecular Weight: 169.25
• Mol File: 106006-83-1.mol

Chemical Properties

• Boiling Point: 359 °C at 760 mmHg
• Flash Point: 170.9 °C
• Appearance: off-white powder
• Density: 1.313 g/cm³
• Vapor Pressure: 2.45E-05mmHg at 25°C
• Refractive Index: 1.655
• CAS DataBase Reference: 2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole(106006-83-1)
• EPA Substance Registry System: 2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole(106006-83-1)

Safety Data

• Hazardous Substances Data: 106006-83-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole is used as a precursor or intermediate in the synthesis of pharmaceuticals and organic compounds. Its unique structure and functional groups allow for the development of new drugs with potential therapeutic applications.
Used in Chemistry and Materials Science:
In the field of chemistry and materials science, 2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole is utilized for its potential applications in the development of new materials and chemical processes. Its versatile structure and reactivity make it a valuable component in the creation of advanced materials with specific properties.
Used in Industrial Applications:
2,6-Diamino-4,5,6,7-tetrahydrobenzothiazole has been the subject of research due to its potential use in various industrial applications. Its unique chemical and biological properties make it a valuable compound for exploring new possibilities in different industries, such as chemical manufacturing, coatings, and other specialized applications.

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

Upstream product

• 17356-08-0 thiourea 
• 27489-62-9 trans-4-aminocyclohexan-1-ol 
• 766508-72-9 2-bromo-4-aminocyclohexanone 
• 27514-08-5 N-(4-oxocyclohexyl)acetamide 
• 687639-03-8 2-bromo-4-acetamidocyclohexanone 
• 202058-46-6 2-(3-bromo-4-oxocyclohexyl)isoindoline-1,3-dione 
• 27489-62-9 trans-4-hydroxycyclohexylamine 
• 104618-32-8 2-(4-oxocyclohexyl)-1H-isoindole-1,3(2H)-dione 
• 99337-98-1 2-((1R,4R)-4-hydroxycyclohexyl) isoindoline-1,3-dione 
• 23363-88-4 trans-N-acetyl-4-hydroxycyclohexylamine 
• 106006-80-8 N-(2-amino-4,5,6,7-tetrahydrobenzo[1,2-d]thiazol-6-yl)acetamide 
• 113030-24-3 2-amino-6-oxo-4,5,6,7-tetrahydrobenzothiazole 
• 916334-22-0 2-Amino-6-phthalimido-4,5,6,7-tetrahydrobenzothiazole hydroiodide 
• 104618-33-9 2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)isoindoline-1,3-dione 

Downstream Products

• 106092-11-9 (R)-4,5,6,7-tetrahydrobenzo[1,2-d]thiazole-2,6-diamine 
• 106092-09-5 (S)-4,5,6,7-tetrahydrobenzo[d]thiazol-2,6-diamine 
• 104632-25-9 pramipexole dihydrochloride 
• 1262552-32-8 1-((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-3-(2-chlorophenyl)thiourea 
• 1262552-33-9 1-((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-3-(2,4-dichlorophenyl)thiourea 
• 1262552-34-0 1-((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-3-(4-chlorophenyl)thiourea 
• 1262552-35-1 1-((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-3-phenylthiourea 
• 1262552-27-1 1-((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-3-(4-methoxyphenyl)thiourea 
• 1262552-28-2 1-((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-3-(4-fluorophenyl)thiourea 
• 1262552-29-3 1-((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-3-(3-chlorophenyl)thiourea 
• 1262552-30-6 1-((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-3-(3-methoxyphenyl)thiourea 
• 1262552-31-7 1-((S)-2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)-3-(2-fluorophenyl)thiourea 

Relevant articles and documents

Pharmacological characterization of a new series of carbamoylguanidines reveals potent agonism at the H2R and D3R

Even today, the role of the histamine H2 receptor (H2R) in the central nervous system (CNS) is widely unknown. In previous research, many dimeric, high-affinity and subtype-selective carbamoylguanidine-type ligands such as UR-NK22 (5, pKi = 8.07) were reported as H2R agonists. However, their applicability to the study of the H2R in the CNS is compromised by their molecular and pharmacokinetic properties, such as high molecular weight and, consequently, a limited bioavailability. To address the need for more drug-like H2R agonists with high affinity, we synthesized a series of monomeric (thio)carbamoylguanidine-type ligands containing various spacers and side-chain moieties. This structural simplification resulted in potent (partial) agonists (guinea pig right atrium, [35S]GTPγS and β-arrestin2 recruitment assays) with human (h) H2R affinities in the one-digit nanomolar range (pKi (139, UR-KAT523): 8.35; pKi (157, UR-MB-69): 8.69). Most of the compounds presented here exhibited an excellent selectivity profile towards the hH2R, e.g. 157 being at least 3800-fold selective within the histamine receptor family. The structural similarities of our monomeric ligands to pramipexole (6), a dopamine receptor agonist, suggested an investigation of the binding behavior at those receptors. The target compounds were (partial) agonists with moderate affinity at the hD2longR and agonists with high affinity at the hD3R (e.g. pKi (139, UR-KAT523): 7.80; pKi (157, UR-MB-69): 8.06). In summary, we developed a series of novel, more drug-like H2R and D3R agonists for the application in recombinant systems in which either the H2R or the D3R is solely expressed. Furthermore, our ligands are promising lead compounds in the development of selective H2R agonists for future in vivo studies or experiments utilizing primary tissue to unravel the role and function of the H2R in the CNS.

Industrial preparation method of 2,6-diamino-4,5,6,7-tetrahydro-benzothiazole

The invention discloses a preparation method of 2,6-diamino-4,5,6,7-tetrahydro-benzothiazole suitable for industrial production, wherein 2,6-diamino-4,5,6,7-tetrahydro-benzothiazole is prepared by using p-acetamido cyclohexanone as a raw material through a one-pot method. According to the method, liquid bromine and acetic acid are not used in the production and preparation process, the 6-acetamido-2-amino-4,5,6,7-tetrahydro-benzothiazole can be prepared through a one-pot method, post-treatment operation is easy and convenient, the labor cost is saved, and the production cost is greatly reduced. The 2,6-diamino-4,5,6,7-tetrahydro-benzothiazole prepared by the method is high in yield, good in purity and suitable for industrial production.

Crystallization process of diamino -4, 5, 6, 7- tetrahydrobenzothiazole

Reaction and formation, of the product, with acetone as a reaction solvent, takes place in acetone as a reaction solvent to give the product, as a raw material, with acetone as a reaction solvent to obtain the mixed rotation product, and then recrystallize the reaction solvent with water: to obtain the reaction . Example, shows that the reaction time, is greatly shortened by taking the product, as a reaction solvent by taking acetone as a reaction solvent as a raw material A; dropwise to obtain the reaction and the reaction of the reaction, solvent with water and dissolving: dropwise with acetone as a reaction solvent in step A as a reaction solvent in an existing production process by, acetone, L - taking acetone as a, reaction solvent to prepare a reaction solvent for, the whole process, to prepare a crystal, by taking acetone as, a reaction solvent to prepare a reaction solvent by taking acetone as a reaction solvent to prepare a. reaction solvent by taking acetone as a reaction solvent.

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

Preparation method of pramipexole dihydrochloride and intermediate thereof

The invention discloses a preparation method of pramipexole dihydrochloride and an intermediate thereof. The invention provides a preparation of pramipexole II. The preparation method of the pramipexole II comprises the following steps: performing condensation reaction and reduction reaction on a pramipexole intermediate III, propylamine and hydrogen in an organic solvent and under the existence of a chiral catalyst, and performing one-pot method to obtain the pramipexole II. According to the preparation method provided by the invention, the route step is short, chiral resolution is not neededand the total molar yield is high; furthermore, the prepared product has high purity, can reach to the standard of raw material medicines and is suitable for industrialized production. (The formula is shown in the description).

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.

IMPROVED PROCESS FOR THE PREPARATION OF (S)-2-AMINO-4,5,6,7-TETRAHYDRO-6 - (PROPYLAMINO) BENZOTHIAZOLE AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS

The present invention relates to an improved process for the preparation of of (S)-2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole and its pharmaceutically acceptable salts. Specifically relates to the compound represented by the following structural formula- Ia.

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.

PROCESSES FOR THE PREPARATION OF PRAMIPEXOLE AND SALTS THEREOF

The invention relates to processes for the preparation of pramipexole or pharmaceutically acceptable salts thereof. More particularly, it relates to a process for the preparation of pramipexole dihydrochloride monohydrate. The invention also relates to a novel compound, 2-bromo-4-aminocyclohexanone and processes for its preparation. The 2- bromo-4-aminocyclohexanone is a useful intermediate in the preparation of pramipexole or salts thereof. The invention further relates to a single step process for the preparation of 2,6-diamino-4,5,6,7-tetrahydrobenzathiazole, an intermediate useful in the preparation of pramipexole or salts thereof.

PROCESS FOR PREPARING (S)-PRAMIPEXOLE AND ITS INTERMEDIATES

The present invention relates to an improved process for the preparation of (S)- 2,6-diamino-4,5,6,7-tetrahydrobenzothiazole of formula (II) useful in the preparation of pramipexole or (S)-2,6-amino-6-(n-propylamino)-4,5,6,7-tetrahydrobenzothiazole of formula (I) and its pharmaceutically acceptable salts or solvates thereof. The present invention further provides a process for the preparation of Pramipexole and its pharmaceutically acceptable salts, hydrates, solvates thereof.