104618-33-9

Basic information

• Product Name: 2-Amino-6-phthalimido-4,5,6,7-tetrahydro benzothiazole
• Synonyms: 2-(2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)isoindoline-1,3-dione;1H-Isoindole-1,3(2H)-dione, 2-(2-amino-4,5,6,7-tetrahydro-6-benzothiazolyl)-
• CAS NO: 104618-33-9
• Molecular Formula: C15H13N3O2S
• Molecular Weight: 299.3476
• Mol File: 104618-33-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 526.459 °C at 760 mmHg
• Flash Point: 272.193 °C
• Appearance: /
• Density: 1.516 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.737
• Storage Temp.: 2-8°C
• PKA: 5.41±0.40(Predicted)
• CAS DataBase Reference: 2-Amino-6-phthalimido-4,5,6,7-tetrahydro benzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-6-phthalimido-4,5,6,7-tetrahydro benzothiazole(104618-33-9)
• EPA Substance Registry System: 2-Amino-6-phthalimido-4,5,6,7-tetrahydro benzothiazole(104618-33-9)

Safety Data

• Hazardous Substances Data: 104618-33-9(Hazardous Substances Data)

Usage

Description

2-Amino-6-phthalimido-4,5,6,7-tetrahydro benzothiazole is a chemical compound with a unique molecular structure that features a benzothiazole core, a phthalimido group, and an amino group. 2-Amino-6-phthalimido-4,5,6,7-tetrahydro benzothiazole is known for its potential applications in various industries, particularly in pharmaceuticals and chemical synthesis.

Uses

Used in Pharmaceutical Industry:
2-Amino-6-phthalimido-4,5,6,7-tetrahydro benzothiazole is used as an intermediate in the improved synthesis of pramipexole, an anti-Parkinson drug. Its unique structure allows for the efficient production of pramipexole, which is crucial in the treatment of Parkinson's disease and other movement disorders.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Amino-6-phthalimido-4,5,6,7-tetrahydro benzothiazole serves as a valuable building block for the development of new compounds with potential applications in various industries. Its versatile structure enables the creation of a wide range of derivatives, making it a promising candidate for further research and development.

InChI:InChI=1/C15H13N3O2S/c16-15-17-11-6-5-8(7-12(11)21-15)18-13(19)9-3-1-2-4-10(9)14(18)20/h1-4,8H,5-7H2,(H2,16,17)

Upstream product

• 202058-46-6 2-(3-bromo-4-oxocyclohexyl)isoindoline-1,3-dione 
• 17356-08-0 thiourea 
• 22509-74-6 N-ethoxycarbonylphthalimide 
• 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 

Downstream Products

• 106006-83-1 2,6-diamino-4,5,6,7-tetrahydro-benzthiazole 

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.

IMPROVED PROCESS FOR THE PREPARATION OF BIOLOGICALLY ACTIVE TETRAHYDROBENZTHIAZOLE DERIVATIVE

Improved process for the preparation of the intermediate compound of formula II for formation pramipezole of formula (I) as well as the biological active tetrahydrobenzothiazole compound of formula (I) and/or its pharmaceutically acceptable salts or solvates.