5325-20-2

Basic information

• Product Name: (2H)1,4-BENZOTHIAZIN-3(4H)-ONE
• Synonyms: 4H-1,4-benzothiazin-3-one;BenzothiazinHone;(2H)-1,4-Benzothiazin-3-(4H)-one 98%;2H-1,4-BENZOTHIAZIN-3(4H)-ONE, 99+%;2H-1,4-Benzothiazine-3-ol;3,4-Dihydro-2H-1,4-benzothiazine-3-one;1,4-Benzothiazin-3(4H)-one;3,4-Dihydro-2H-1,4-benzothiazin-3-one
• CAS NO: 5325-20-2
• Molecular Formula: C₈H₇NOS
• Molecular Weight: 165.21
• EINECS: 226-197-5
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Thiazines
• Mol File: 5325-20-2.mol

Chemical Properties

• Melting Point: 176-178 °C(lit.)
• Boiling Point: 272.25°C (rough estimate)
• Flash Point: 169.5 °C
• Appearance: almost white to light beige-grey crystalline powder
• Density: 1.1979 (rough estimate)
• Vapor Pressure: 3.36E-09mmHg at 25°C
• Refractive Index: 1.6458 (estimate)
• Storage Temp.: 2-8°C
• PKA: 12.90±0.20(Predicted)
• BRN: 131642
• CAS DataBase Reference: (2H)1,4-BENZOTHIAZIN-3(4H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (2H)1,4-BENZOTHIAZIN-3(4H)-ONE(5325-20-2)
• EPA Substance Registry System: (2H)1,4-BENZOTHIAZIN-3(4H)-ONE(5325-20-2)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 5325-20-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2H)1,4-Benzothiazin-3(4H)-one is used as a chemical compound for its calcium antagonistic and calmodulin antagonistic activities. These properties make it a potential candidate for the development of drugs targeting conditions related to calcium and calmodulin dysregulation, such as hypertension, certain types of cancer, and neurological disorders.
Used in Chemical Research:
In the field of chemical research, (2H)1,4-Benzothiazin-3(4H)-one serves as a valuable compound for studying the structure-activity relationships of benzothiazine derivatives. This knowledge can be applied to design and synthesize new molecules with improved or novel biological activities, potentially leading to the discovery of new drugs and therapeutic agents.
Used in Material Science:
The crystalline nature of (2H)1,4-Benzothiazin-3(4H)-one may also find applications in material science, particularly in the development of new materials with unique optical, electronic, or mechanical properties. Further research and development in this area could lead to innovative applications in various industries, such as electronics, aerospace, and automotive.

InChI:InChI=1/C16H20ClNO5/c1-4-22-14(20)16(18-11(3)19,15(21)23-5-2)10-12-8-6-7-9-13(12)17/h6-9H,4-5,10H2,1-3H3,(H,18,19)

Upstream product

• 79-08-3 bromoacetic acid 
• 137-07-5 2-amino-benzenethiol 
• 105-39-5 chloroacetic acid ethyl ester 
• 1141-88-4 2-Aminophenyl disulfide 
• 21201-23-0 4-acetoxy-4H-benzo[1,4]thiazin-3-one 
• 50693-98-6 methyl 2-((2-nitrophenyl)thio)acetate 
• 1155-00-6 bis(2-nitrophenyl)disulfide 
• 105-36-2 ethyl bromoacetate 
• 79-11-8 chloroacetic acid 
• 88-73-3 2-Chloronitrobenzene 
• 1208006-08-9 2-chloro-N-(2-mercaptophenyl)acetamide 
• 2044-64-6 N,N-Dimethylacetoacetamid 
• 70685-30-2 2H-1,4-benzothiazine-3,4-dihydro-3-oxo-2-carboxylic acid 
• 24231-81-0 4-(2-chloro-acetylamino)-2-imino-3-phenyl-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester 

Downstream Products

• 37012-79-6 3-(3-oxo-2H-benzo[b][1,4]thiazin-4(3H)-yl)propanoic acid 
• 95476-30-5 2-(4-methyl-benzylidene)-4H-benzo[1,4]thiazin-3-one 
• 54874-85-0 2-(4-chloro-benzylidene)-4H-benzo[1,4]thiazin-3-one 
• 24545-07-1 2-benzylidene-2H-1,4-benzothiazin-3(4H)-one 
• 95476-37-2 2-(4-methoxy-benzylidene)-4H-benzo[1,4]thiazin-3-one 
• 54874-84-9 2-[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-4H-benzo[1,4]thiazin-3-one 
• 6431-73-8 4-benzyl-2H-benzo[b][1,4]thiazin-3(4H)-one 

Relevant articles and documents

Design, synthesis and in vitro anticancer evaluation of new 2h-benzo[b][1,4]thiazin-3(4h)-one based 1,2,3-Triazoles

A series of novel 2H-benzo[b][1,4]thiazin-3(4H)-one derived from 1,4-disubstituted 1,2,3-triazole derivatives (4a-j and 5a-j) were synthesized using Cu(I) catalyzed azide alkyne cyclization (CuAAC) reaction of the compounds 2 and 3 with various aromatic azides. The examination of in vitro anticancer activity revealed that the compounds 4d and 5d were found to possess a broad spectrum of anticancer activity against three cell lines MCF-7, HeLa and IMR-32 with IC50 values ranging from 26. 28 ± 1. 5 to 32. 06 ± 0. 3 M mL-1, respectively. The remaining compounds have shown good to moderate activity against the tested cell lines.

Direct access to α-sulfenylated amides/esters: Via sequential oxidative sulfenylation and C-C bond cleavage of 3-oxobutyric amides/esters

An efficient, environmentally benign and unprecedented synthesis of various α-sulfenylated amides/esters has been developed under oxygen atmosphere. The reaction shows good functional group tolerance and excellent chemo/regioselectivity. All the desired products were obtained in moderate to excellent yields, even on the gram scale. Practically, the related α-thiol Weinreb amide can be readily transferred to a series of prospective compounds, and selenium atom can be introduced to the α-sites of the amides in high yields.

Novel benzothiazine-piperazine derivatives by peptide-coupling as potential anti-proliferative agents

In an attempt to develop potential and selective anti-proliferative agents, a series of novel benzothiazine-piperazine derivatives 8a–i and 10a–g were synthesized by coupling of 2H-1,4-benzothiazin-3(4H)-one with various amines 7a–i and 9a–g in excellent yields and evaluated for their in vitro anti-proliferative activity against four cancer cell lines, HeLa (cervical), MIAPACA (pancreatic), MDA-MB-231 (breast) and IMR32 (neuroblastoma). In vitro inhibitory activity indicated that compounds 8a, 8d, 8g, 10a, 10b, 10e, 10f were found to be good anti-proliferative agents. Among them the derivatives 8g, 10e and 10f were found to be the most active members exhibiting remarkable growth inhibitory activity. Molecular docking was undertaken to investigate the probable binding mode and key active site interactions in HDAC8 and EHMT2 proteins. The docking results are complementary to the experimental results.

HETEROCYCLIC DERIVATIVES FOR THE THRATMENT OF RSV

Disclosed herein are compounds and compositions for treating or inhibiting RSV and related members of the pneumovirus and paramyxovirus families such as human metapneumovirus, mumps virus, human parainfluenzaviruses, and Nipah and hendra virus, and methods of treatment or prevention thereof.

Efficient synthesis of benzene-fused 6/7-membered amides: Via Xphos Pd G2 catalyzed intramolecular C-N bond formation

An efficient approach for benzene-fused 6/7-membered amides via intramolecular amidation of aryl chlorides catalyzed by a Buchwald-Hartwig second generation Pd catalyst (Xphos Pd G2) has been successfully developed. This catalyst system allows the primary amides which have only modest nucleophilicity to be coupled successfully even with electron rich aryl chlorides in short reaction time. The intramolecular amidation reaction also has good chemoselectivity and excellent functional group compatibility.

Synthesis and bioactivity of novel triazole incorporated benzothiazinone derivatives as antitubercular and antioxidant agent

In search of new active molecules against Mycobacterium tuberculosis (MTB) H37Ra and M. bovis BCG, a small focused library of benzothiazinone based 1,2,3-triazoles has been efficiently prepared via click chemistry approach. Several derivatives were found to be promising inhibitors of MTB and M. bovis BCG characterized by lower MIC values (27.34-29.37 μg/mL). Among all the synthesized compounds, 6c and 6e is the most active compound against MTB and M. bovis BCG. The compounds were further tested for anti-proliferative activity against HeLa, A549 and A431 cell lines using MTT assay and showed no significant cytotoxic activity at the maximum concentration evaluated. Further, the synthesized compounds were found to have potential antioxidant activity with IC50 range = 14.14-47.11 μg/mL. Furthermore, to rationalize the observed biological activity data, the molecular docking study also been carried out against a potential target MTB DprE1, which revealed a significant correlation between the binding score and biological activity for these compounds. The results of the in vitro and in silico study suggest that the triazole incorporated benzothiazinone may possess the ideal structural requirements for further development of novel therapeutic agents.

gSK - 3 beta inhibitor or its salt and its pharmaceutical use

The invention belongs to the pharmaceutical chemistry field, and discloses a compound for inhibiting glycogen synthase kinase-3beta (GSK-3beta) in a formula I, its pharmaceutically acceptable salt, or an application of its pharmaceutical composition for preventing and treating the GSK-3beta-related diseases. The compound is a GSK-3beta small-molecule inhibitor, its action mode is non-ATP-competitive competition, and can be used for preparing the medicines for preventing and treating the GSK-3beta-related diseases, and the GSK-3beta-related diseases can be diabetes, Alzheimer's disease, stomach cancer, colorectal cancer, pancreas cancer, liver cancer or mixed acute leukemia. According to the compound, R1, R2, R3, X, Y are consistent with detailed description in the invention.

Synergistic promoting effect of ball milling and KF-alumina support for the green synthesis of benzothiazinones

A solvent-free procedure was developed for the reaction of 2-aminothiophenols with 2-bromoalkanoates, where KF-Al2O3 support and ball milling cooperatively lead to a green and efficient synthesis of several benzothiazinone derivatives in good to excellent yields. The catalyst could be recycled in further reactions while maintaining its activity.

Facile synthesis of 1,4-benzothiazin-3-ones from Cu-catalyzed coupling of 2-iodoanilines and 2-mercaptoacetate

A novel synthesis of 1,4-benzothiazin-3-ones was developed from Cu-catalyzed coupling of readily available substituted 2-iodoanilines with 2-mercaptoacetate. The new method offers clear advantages over existing approaches for its one-step simple operation, wider reaction scope, and moderate to excellent isolated yields.

[NO3], a green and base-free medium for one-pot synthesis of benzothiazinones at room temperature

A general and efficient room-temperature procedure is developed for high-yield synthesis of 2H-benzo[b][1,4]thiazin-3(4H)-one derivatives in one pot from the reaction of 2-aminothiophenols with 2-bromoalkanoates in ionic liquid [bmim]NO3 without the use of any catalyst, base, or additive. Products were obtained in good yields by simple extraction with Et2O followed by evaporation of the volatile contents and recrystallization from Et2O. The ionic liquid was recycled and reused in the next reaction without the loss of its activity.