77261-93-9

Basic information

• Product Name: 1,5-Benzothiazepin-4(5H)-one, 2-(4-chlorophenyl)-2,3-dihydro-
• Synonyms: 4-Oxo-2-<4-chlor-phenyl>-2,3,4,5-tetrahydro-1,5-benzothiazepin;4T-0660
• CAS NO: 77261-93-9
• Molecular Formula: C15H12ClNOS
• Molecular Weight: 289.785
• Mol File: 77261-93-9.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 1,5-Benzothiazepin-4(5H)-one, 2-(4-chlorophenyl)-2,3-dihydro-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-Benzothiazepin-4(5H)-one, 2-(4-chlorophenyl)-2,3-dihydro-(77261-93-9)
• EPA Substance Registry System: 1,5-Benzothiazepin-4(5H)-one, 2-(4-chlorophenyl)-2,3-dihydro-(77261-93-9)

Safety Data

• Hazardous Substances Data: 77261-93-9(Hazardous Substances Data)

Upstream product

• 1615-02-7 p-chlorocinnamic acid 
• 137-07-5 2-amino-benzenethiol 
• 6586-36-3 2-(4-chlorophenyl)-2,3-dihydro-4H-1-benzopyran-4-one 
• 104-88-1 4-chlorobenzaldehyde 
• 519054-04-7 (E)-1-(1H-benzo[d][1,2,3]triazol-1-yl)-3-(4-chlorophenyl)prop-2-en-1-one 
• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 

Downstream Products

• 1448990-67-7 5-(2-nitrobenzyl)-2-(4-chlorophenyl)-dihydrobenzo-1,5-thiazepin-4(5H)-one 
• 89813-75-2 [2-(4-Chloro-phenyl)-4-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazepin-5-yl]-acetic acid 
• 77262-03-4 3-[2-(4-Chloro-phenyl)-4-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazepin-5-yl]-propionic acid 

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

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.