75908-14-4

Basic information

• Product Name: chromeno[3,4-b][1,4]benzothiazin-6(12H)-one
• Synonyms: 6,12-Dihydrobenzo[b]chromeno[4,3-E][1,4]thiazin-6-one; Chromeno(3,4-b)(1,4)benzothiazin-6(12H)-one; Chromeno[3,4-b][1,4]benzothiazin-6(12H)-one
• CAS NO: 75908-14-4
• Molecular Formula: C₁₅H₉NO₂S
• Molecular Weight: 267.3025
• Mol File: 75908-14-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 452.1°C at 760 mmHg
• Flash Point: 227.2°C
• Density: 1.49g/cm³
• Vapor Pressure: 2.31E-08mmHg at 25°C
• Refractive Index: 1.767
• CAS DataBase Reference: chromeno[3,4-b][1,4]benzothiazin-6(12H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: chromeno[3,4-b][1,4]benzothiazin-6(12H)-one(75908-14-4)
• EPA Substance Registry System: chromeno[3,4-b][1,4]benzothiazin-6(12H)-one(75908-14-4)

Safety Data

• Hazardous Substances Data: 75908-14-4(Hazardous Substances Data)

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 137-07-5 2-amino-benzenethiol 
• 38464-20-9 4-chloro-3-nitro-chromen-2-one 

Relevant articles and documents

Substituted benzopyranobenzothiazinones. Synthesis and estrogenic activity on MCF-7 breast carcinoma cells

In the search for new agents with estrogenic activity mediated by estrogen receptors (ER), six 6,12-dihydro-1-benzopyrano[3,4-b][1,4]benzothiazin-6-ones 3a-f were synthesized. These compounds were readily prepared by the addition of 2-aminothiophenol 2 to substituted 4-hydroxycoumarin derivatives 1a-e. The estrogenic effect has been evaluated on the proliferation of MCF-7 breast adenocarcinoma cells and the specificity of described compounds was evaluated by the inhibition of their effect by ICI 182,780, an antiestrogenic compound. Among the compounds tested, 6,12-dihydro-3-methoxy-1-benzopyrano[3,4-b][1,4]benzothiazin-6-one 3e and 6,12-dihydro-3-hydroxy-1-benzopyrano[3,4-b][1,4]benzothiazin-6-one 3f exhibited an ER-dependent proliferation and a high binding affinity to ER, but a moderate capacity to activate the transcription of a reporter gene. Their pharmacological profiles are defined by their binding properties and their mechanism of action by computational modelling studies.

Synthesis and Electrochemical Study of Benzothiazine and Phenothiazine Derivatives

A number of benzothiazine and phenothiazine derivatives are prepared by reaction of 2-mercaptoaniline and cyclic β-diketo compounds or by reaction of bidentate nucleophiles on 4-chloro-3-nitrocoumarin by using the HSAB principle.The topological resonance energies per ?-electron (TREPE's) are calculated for nine benzothiazine and phenothiazine derivatives and correlated with the first reversible peak potentials.The analysis of the data shows a good correlation between the TREPE values and the oxidation potentials.The chemical behavior of the electrochemically generated radical cations of the two related heterocyclic systems: 6,12-dihydrobenzopyrranobenzothiazin-6-one (1) and 2,3-dihydro-2,2-dimethylphenothiazin-6(1H)-one (2) are examined by using the electroanalytical techniques and preparative controlled potential electrolysis.HMO calculations are used to predict the most reactive sites toward the nucleophilic attack.

Synthesis and Desulphurisation of Substituted 12H--Benzopyranolbenzothiazin-6-ones

Nine substituted 12H--benzopyranobenzothiazin-6-ones have been prepared by condensation of the corresponding 4-hydroxycoumarins with 2-aminothiophenol in dimethyl sulphoxide and one of these subjected to desulphurisation reaction with Raney nickel forming 4-anilinocoumarin.Their spectral properties and physiological activity have been evaluated.