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Usage

Uses

Used in Pharmaceutical Research:
2-(4-nitrophenyl)-4-phenyl-2,3-dihydro-1,5-benzothiazepine is utilized as a research compound for its potential pharmacological applications. Its presence in the benzothiazepine class suggests it may possess properties that could be harnessed for the development of new drugs, particularly in the areas of inflammation, cancer treatment, and microbial infections.
Used in Drug Development:
In the pharmaceutical industry, 2-(4-nitrophenyl)-4-phenyl-2,3-dihydro-1,5-benzothiazepine is employed as a lead compound in the discovery and optimization of new therapeutic agents. Its structural features, including the nitrophenyl and phenyl groups, may offer specific binding affinities or interactions with biological targets, making it a valuable starting point for the design of novel medications.
Used in Medicinal Chemistry:
2-(4-nitrophenyl)-4-phenyl-2,3-dihydro-1,5-benzothiazepine serves as a subject of study in medicinal chemistry to understand its chemical properties and how they may influence biological activity. Researchers are interested in its potential to interact with various biological targets, which could lead to the development of drugs with improved efficacy and selectivity.

Upstream product

• 1222-98-6 4-nitrochalcone 
• 137-07-5 2-amino-benzenethiol 
• 555-16-8 4-nitrobenzaldehdye 
• 98-86-2 acetophenone 
• 2960-55-6 (E)-3-(4-nitrophenyl)-1-phenylprop-2-en-1-one 
• 636-98-6 p-nitrobenzene iodide 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 

Downstream Products

• 1307301-64-9 ethyl 3a,4-dihydro-3-(4-methylphenyl)-3a-phenyl-5-(4-nitrophenyl)-5H-[1,2,4]triazolo[5,4-d][1,5]benzothiazepine-1-carboxylate 
• 1307301-63-8 ethyl 3a,4-dihydro-3-(4-chlorophenyl)-3a-phenyl-5-(4-nitrophenyl)-5H-[1,2,4]triazolo[5,4-d][1,5]benzothiazepine-1-carboxylate 

Relevant academic research and scientific papers

Catalyst-free synthesis of 2,3-dihydro-1,5-benzothiazepines in a renewable and biodegradable reaction medium

A clean and efficient strategy for the synthesis of benzothiazepines from chalcone and ortho-aminothiophenol has been reported. Here, glycerol, a biodegradable and reusable promoting medium, has been utilized under acid, base or metal-free conditions. The

A practical synthesis of 2,3-dihydro-1,5-benzothiazepines

2,3-Dihydro-1,5-benzothiazepines have been obtained through a domino process involving a Michael addition of 2-aminothiophenols to chalcones, followed by in situ cyclization. Up to 98% chemical yields have been obtained at room temperature under essential

In silico studies on 2,3-dihydro-1,5-benzothiazepines as cholinesterase inhibitors

In vitro studies on cholinesterase inhibitory potential on the three sets of 2,3-dihydro-1,5-benzothiazepines have been carried out. The compounds in Set 1 were unsubstituted on ring A, while those in Sets 2 and 3 had a 2′- and 3′-hydoxy substituent, respectively, in ring A. These studies revealed that they are mixed inhibitors of both AChE and BChE as reflected from their IC50 values. It was further observed that 3′-hydroxy substituted benzothiazepines (Set 3) were found to have stronger affinity for both AChE and BChE compared with those of Sets 1 and 2. Moreover, all the compounds in Set 3 were found to be stronger BChE inhibitors than AChE. These experimental observations were rationalized by conducting in silico studies using molecular docking tool of Molecular Operating Environment (MOE) software, thereby, a good correlation was observed between IC50 values and their binding interactions within the enzyme active site. We have observed that these interactions were electrostatic and hydrophobic in nature besides hydrogen bonding. The high BChE inhibitory potential of 3′-hydroxy substituted benzothiazepines was found to be cumulative effect of hydrogen bonding and π-π interactions between the ligand and BChE. These findings may serve as a guideline for synthesizing more potent ChE inhibitors for the treatment of Alzheimer's disease and related dementias. Springer Science+Business Media, LLC 2011.

Synthesis and structure characterization of new [1,2,4]triazolo[5,4-d][1,5] benzothiazepine derivatives through 1,3-dipolar cycloaddition reaction

Reaction of 1,5-benzothiazepines 3, obtained from chalcones 2 and o-aminobenzenthiol, with the (phenylhydrazino) chloromethylenecarboxylates 4 in the presence of Et3N leads to a series of new [1,2,4]triazolo[5,4-d] [1,5]benzothiazepine derivatives 5. Their structures were established using spectroscopic methods and that of compound 5d was confirmed using X-ray diffraction analysis.

Syntheses of potentially bioactive [1,2,4]oxadiazolo[5,4-d]benzothiazepines by 1,3-dipolar cycloaddition

The chalcones, 2a-2l reacted with o-aminobenzenthiol to give a series of 1,5-benzothiazepines, 3a-3l. The [3+2] 1, 3-dipolar cycloaddition reactions of 3a-3l with ethyl chlorooximidoacetate in the presence of Et3N afforded the target compounds, 4a-4l possessing an additional 1,2,4-oxadiazole ring fused to the heptaatomic nucleus. The structures have been elucidated by spectral methods and X-ray crystallographic analysis.

Green protocol for synthesis of 1,5-benzodiazepines and 1,5-benzothiazepines in the presence of nanocrystalline aluminum oxide

An efficient protocol associated with readily available starting materials, mild conditions, excellent yields, and a broad range of the products in synthetic chemistry was established for synthesis of 1,5-benzodiazepine and 1,5-benzothiazepine derivatives

Fluoroboric acid adsorbed on silica-gel (HBF4-SiO2) as a new, highly efficient and reusable heterogeneous catalyst for thia-Michael addition to α,β-unsaturated carbonyl compounds

Fluoroboric acid adsorbed on silica-gel (HBF4-SiO2) has been found to be a new and highly efficient heterogeneous catalyst for thia-Michael addition to α,β-unsaturated carbonyl compounds under solvent-free conditions. In the case of

'On water' synthesis of 2,4-diaryl-2,3-dihydro-1,5-benzothiazepines catalysed by sodium dodecyl sulfate (SDS)

An efficient synthesis of 1,3-diaryl-2,3-dihydro-1,5-benzothiazepines has been developed by the reaction of various 1,3-diaryl-2-propenones with 2-aminothiophenol in water under neutral conditions catalysed by SDS. Excellent chemoselectivity was observed for substrates possessing halogen atoms or nitro/alkoxy/thioalkyl groups which did not undergo competitive aromatic nucleophilic substitution of the halogen atoms or the nitro group, reduction of the nitro or the α,β-unsaturated carbonyl group, or dealkylation of the alkoxy/thioalkoxy groups.

Scope and limitations of HClO4-SiO2 as an extremely efficient, inexpensive, and reusable catalyst for chemoselective carbon-sulfur bond formation

The scope and limitations of perchloric acid adsorbed on silica gel (HClO4-SiO2) as a highly efficient, inexpensive, and reusable catalyst for chemoselective carbon-sulfur bond formation by conjugate addition of thiols to α,β-unsatur

Magnesium perchlorate as a new and highly efficient catalyst for the synthesis of 2,3-dihydro-1,5-benzothiazepines

Commercially available magnesium perchlorate has been found to be a highly efficient catalyst for the reaction of 1,3-diarylprop-2-enones with 2-aminothiophenol leading to the synthesis of 2,3-dihydro-1,5-benzothiazepines in high yields and in short times. Georg Thieme Verlag Stuttgart.