5871-68-1

Basic information

• Product Name: 2-(2-THIENYL)-2,3-DIHYDRO-1,5-BENZOTHIAZEPIN-4(5H)-ONE
• Synonyms: 2-(2-THIENYL)-2,3-DIHYDRO-1,5-BENZOTHIAZEPIN-4(5H)-ONE
• CAS NO: 5871-68-1
• Molecular Formula: C₁₃H₁₁NOS₂
• Molecular Weight: 261.36
• Mol File: 5871-68-1.mol

Chemical Properties

• Melting Point: 159-161°
• Boiling Point: 475.3°Cat760mmHg
• Flash Point: 241.3°C
• Appearance: /
• Density: 1.308g/cm³
• Vapor Pressure: 3.35E-09mmHg at 25°C
• Refractive Index: 1.65
• CAS DataBase Reference: 2-(2-THIENYL)-2,3-DIHYDRO-1,5-BENZOTHIAZEPIN-4(5H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-THIENYL)-2,3-DIHYDRO-1,5-BENZOTHIAZEPIN-4(5H)-ONE(5871-68-1)
• EPA Substance Registry System: 2-(2-THIENYL)-2,3-DIHYDRO-1,5-BENZOTHIAZEPIN-4(5H)-ONE(5871-68-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5871-68-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(2-Thienyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one is used as a potential antifungal agent for targeting the enzyme sterol 14-alpha-demethylase, which is crucial in the biosynthesis of ergosterol in fungi. This inhibition can lead to the disruption of fungal cell membrane integrity and function, offering a novel approach to combat fungal infections.
Used in Pain Management:
Due to its potential analgesic properties, 2-(2-thienyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one may be utilized in the development of new pain management therapies. Its ability to modulate pain pathways could provide an alternative or complementary treatment option for various types of pain conditions.
Used in Anti-Inflammatory Applications:
2-(2-THIENYL)-2,3-DIHYDRO-1,5-BENZOTHIAZEPIN-4(5H)-ONE's potential anti-inflammatory properties suggest that it could be used in the development of treatments for inflammatory conditions. By reducing inflammation, it may help alleviate symptoms and improve the quality of life for individuals suffering from such conditions.
Further research is necessary to fully understand the pharmacological and therapeutic potential of 2-(2-thienyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, as well as to determine its safety and efficacy in various applications.

InChI:InChI=1/C13H11NOS2/c15-13-8-12(11-6-3-7-16-11)17-10-5-2-1-4-9(10)14-13/h1-7,12H,8H2,(H,14,15)

Upstream product

• 15690-25-2 3-(2-thienyl)acrylic acid 
• 137-07-5 2-amino-benzenethiol 
• 1124-65-8 3-(2-thienyl)-2-propenoic acid 

Downstream Products

• 1414861-64-5 C₂₀H₁₇NOS₂ 
• 1428258-26-7 C₂₀H₂₃NOS₂ 
• 1428258-27-8 C₂₀H₁₅NO₂S₂ 

Relevant articles and documents

Discovery of Novel Benzothiazepinones as Irreversible Covalent Glycogen Synthase Kinase 3β Inhibitors for the Treatment of Acute Promyelocytic Leukemia

Recently, irreversible inhibitors have attracted great interest in antitumors due to their advantages of forming covalent bonds to target proteins. Herein, some benzothiazepinone compounds (BTZs) have been designed and synthesized as novel covalent GSK-3β inhibitors with high selectivity for the kinase panel. The irreversible covalent binding mode was identified by kinetics and mass spectrometry, and the main labeled residue was confirmed to be the unique Cys14 that exists only in GSK-3β. The candidate 4-3 (IC50 = 6.6 μM) showed good proliferation inhibition and apoptosis-inducing ability to leukemia cell lines, low cytotoxicity on normal cell lines, and no hERG inhibition, which hinted the potential efficacy and safety. Furthermore, 4-3 exhibited decent pharmacokinetic properties in vivo and remarkably inhibited tumor growth in the acute promyelocytic leukemia (APL) mouse model. All the results suggest that these newly irreversible BTZ compounds might be useful in the treatment of cancer such as APL.

Catalytic Enantioselective Synthesis of Protecting-Group-Free 1,5-Benzothiazepines

A one-pot enantioselective route to N-unprotected 2,3-dihydro-1,5-benzothiazepinones, by an organocatalyzed sulfa-Michael reaction of readily available α,β-unsaturated N-acyl pyrazoles with 2-aminothiophenols followed by silica-gel-catalyzed lactamization

An efficient one-pot procedure for the synthesis of 1,5-benzothiazepinones catalyzed by tetrabutylammonium fluoride (TBAF)

A practical and efficient method for the preparation of 1,5-benzothiazepinone derivatives in good yields has been developed using tetrabutylammonium fluoride (TBAF) as a catalyst. This study not only expands the previous work on the substrate scope and al

Design, synthesis and biological evaluation of benzothiazepinones (BTZs) as novel non-ATP competitive inhibitors of glycogen synthase kinase-3β (GSK-3β)

Glycogen synthase kinase-3β (GSK-3β) plays a key role in type II diabetes and Alzheimer's diseases, to which non-ATP competitive inhibitors represent an effectively therapeutical approach due to their good specificity. Herein, a series of small molecules benzothiazepinones (BTZs) as novel non-ATP competitive inhibitors of GSK-3β have been designed and synthesized. The in vitro evaluation performed by luminescent assay showed most BTZ derivatives have inhibitory effects in micromolar scale. Among them compounds 6l, 6t and 6v have the IC50 values of 25.0 μM, 27.8 μM and 23.0 μM, respectively. Moreover 6v is devoid of any inhibitory activity in the assays to other thirteen protein kinases. Besides, SAR is analyzed and a hypothetical enzymatic binding mode is proposed by molecular docking study, which would be useful for new candidates design.

Identification of novel scaffold of benzothiazepinones as non-ATP competitive glycogen synthase kinase-3β inhibitors through virtual screening

Glycogen synthase kinase-3β (GSK-3β) is an important serine/threonine kinase that has been proved as a key target for neurodegenerative diseases and diabetes. Up to date, most of known inhibitors are bound to the ATP-binding pocket of GSK-3β, which might lead widespread effects due to the high homology between kinases. Recently, some of its non-ATP competitive inhibitors had been confirmed having therapeutical effects owing to their high selectivity. This finding opens a new pathway to study hopeful drugs for treatment of these diseases. However, it is still a challenge nowadays on how to efficiently find non-ATP competitors. Here, we successfully discovered a novel scaffold of benzothiazepinones (BTZs) as selective non-ATP competitive GSK-3β inhibitors through virtual screening approach. A 3D receptor model of substrate binding site of GSK-3β was constructed and applied to screen against drug-like Maybridge database through Autodock program. BTZ compounds were top ranked as efficient hits and were then synthesized for further screening. Among them, the representative compound 4j showed activity to GSK-3β (IC50: 25 μM) in non-ATP competitive mechanism, and nearly no inhibitory effect on other 10 related protein kinases. Overall, the results point out that BTZ compounds might be useful in treatment of Alzheimer's disease and diabetes mellitus as novel GSK-3β inhibitors. It also suggests, on the other hand, that virtual screening would provide a valuable tool in combination with in vitro assays for the identification of novel selective and potent inhibitors.