53440-32-7

Basic information

• Product Name: 2-(1,4,5,6-TETRAHYDRO-2-PYRIMIDINYL)BENZENETHIOL
• Synonyms: 2-(1,4,5,6-TETRAHYDRO-2-PYRIMIDINYL)BENZENETHIOL;2-(1,4,5,6-TETRAHYDRO-2-PYRIMIDYL)THIOPHENOL;2-(1,4,5,6-TETRAHYDROPYRIMIDIN-2-YL)BENZENE-1-THIOL;2-(1,4,5,6-Tetrahydro-2-pyridinyl)benzenethiol;2-(1,4,5,6-TETRAHYDROPYRIMIDIN-2-YL)BENZENE THIOL
• CAS NO: 53440-32-7
• Molecular Formula: C₁₀H₁₂N₂S
• Molecular Weight: 192.28
• Mol File: 53440-32-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 235-237°C
• Boiling Point: 372°Cat760mmHg
• Flash Point: 178.8°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.658
• CAS DataBase Reference: 2-(1,4,5,6-TETRAHYDRO-2-PYRIMIDINYL)BENZENETHIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1,4,5,6-TETRAHYDRO-2-PYRIMIDINYL)BENZENETHIOL(53440-32-7)
• EPA Substance Registry System: 2-(1,4,5,6-TETRAHYDRO-2-PYRIMIDINYL)BENZENETHIOL(53440-32-7)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 53440-32-7(Hazardous Substances Data)

Usage

General Description

2-(1,4,5,6-Tetrahydro-2-pyrimidinyl)benzenethiol, also known as BzATP, is a chemical compound that belongs to the class of thioethers. It has a molecular formula of C14H17N3S and a molecular weight of 259.37 g/mol. BzATP is commonly used as a P2X7 receptor agonist, which is involved in various cellular functions including inflammation and apoptosis. It has been studied for its potential therapeutic applications in conditions such as chronic pain, neurodegenerative diseases, and cancer. Additionally, BzATP has also been investigated for its role in regulating the immune response and as a tool in neurobiological research.

InChI:InChI=1/C10H12N2S/c13-9-5-2-1-4-8(9)10-11-6-3-7-12-10/h1-2,4-5,13H,3,6-7H2,(H,11,12)

Upstream product

• 147-93-3 Thiosalicylic acid 
• 109-76-2 Trimethylenediamine 
• 72596-74-8 6H-6-imino-(2,3,4,5-tetrahydropyrimido)[1,2-c]-[1,3]benzothiazine 
• 1202518-94-2 3,4-dihydro-2H,6H-pyrimido[1,2-c][1,3]benzothiazine-6-thione 
• 70-18-8 GLUTATHIONE 

Downstream Products

• 325959-09-9 2-[2-(2-chloro-6-fluoro-benzylsulfanyl)-phenyl]-1,4,5,6-tetrahydro-pyrimidine; hydrochloride 
• 325798-41-2 C₁₈H₁₉N₃O₃S 

Relevant articles and documents

Covalent inhibition of histone deacetylase 8 by 3,4-dihydro-2H-pyrimido[1,2-c][1,3]benzothiazin-6-imine

Background: HDAC8 is an established target for T-cell lymphoma and childhood neuroblastoma. Benzothiazine-imines are promising HDAC8 inhibitors with unknown binding mechanism lacking a usual zinc binding group. Methods: In this study high-resolution and quantitative HPLC-coupled ESI-MS/MS techniques are combined with crystal structure determination and a variety of biochemical and computational methods to elucidate the reaction mechanism between benzothiazine-imine 1 and HDAC8. Results: 1) 1 is a covalent inhibitor of HDAC8; 2) inhibition is reversible in the presence of reducing agents; 3) C153 in the active site and C102 are involved in the inhibition mechanism; 4) 1 modifies various cysteines in HDAC8 forming either thiocyanates or mixed disulfides with 3; 5) 1 and 5 dock in close proximity to C153 within the active site. This is supposed to accelerate covalent inactivation particularly in HDAC8 and suggested as major determinant for the observed nanomolar potency and selectivity of 1. Conclusions: 1 and its analogs are interesting model compounds but unsuitable for therapeutic treatment due to their high unselective reactivity towards thiol groups. However, the postulated preceding non-covalent binding mode of 1 opens a door to optimized next generation compounds that combine potent and selective non-covalent recognition with low reactivity towards C153 at the active site of HDAC8. General significance: 1 represents a completely new class of inhibitors for HDAC8. Initial non-covalent interaction at the bottom of the active site is suggested to be the key for its selectivity. Further optimization of non-covalent interaction and thiol-reactivity provides opportunities to develop therapeutic useful covalent HDAC8 inhibitors.

PHARMACOLOGICAL CHAPERONES FOR TREATING OBESITY

The invention relates to methods of enhancing normal melanocortin-4 receptor (MC4R) activity, and to enhancing activity of an MC4R having a mutation which affects protein folding and/or processing of the MC4R. The invention provides a method of treating an individual having a condition in which increased activity of an MC4R at the cell surface would be beneficial, for example in obesity, by administering an effective amount of a pharmacological chaperone for the MC4R. The invention provides MC4R pharmacological chaperones which enhance the activity of MC4R. The invention further provides a method of screening to identify pharmacological chaperones which enhance folding of an MC4R in the endoplasmic reticulum (ER), in order to enhance the activity of the MC4R at the cell surface.