Dibenzo-[B,F][1,4]-Thiazepin-11(10H)- one

Product Description

Dibenzobf14thiazepin1110Hone is a heterocyclic compound that forms the core structure for various biologically active molecules It is particularly notable as a key scaffold in pharmaceuticals including antipsychotic and antidepressant drugs

 Chemical Details

 IUPAC Name Dibenzobf14thiazepin1110Hone  

 Molecular Formula C14H9NOS  

 Molecular Weight 23929 gmol  

 Structure

   A fused bicyclic ring system with

     Two benzene rings

     A sevenmembered thiazepine ring containing sulfur S and nitrogen N atoms

     A ketone group CO at the 11th position

 Physical Properties

 Appearance Pale yellow to offwhite solid depending on purity

 Solubility Moderately soluble in organic solvents like dichloromethane chloroform and ethanol low water solubility

 Melting Point Approximately 160180C varies depending on substitution and purity

 Pharmacological Significance

The dibenzobf14thiazepine scaffold is an important pharmacophore in medicinal chemistry For instance

1 Antipsychotic Drugs

    Quetiapine Seroquel A derivative of this core structure used to treat schizophrenia bipolar disorder and major depressive disorder

    The structure contributes to activity at serotonin 5HT2A and dopamine D2 receptors

2 Potential Therapeutic Uses

    CNS Disorders Modifications of this scaffold are being studied for use in treating anxiety epilepsy and other neurological conditions

    Antiinflammatory Activity Some derivatives show antiinflammatory or analgesic properties

 Synthetic Pathways

The synthesis of dibenzobf14thiazepin1110Hone typically involves

1 Cyclization Reactions

    Reaction of a 2aminobenzophenone derivative with a sulfur source eg Lawessons reagent or sulfur chloride to form the thiazepine ring

2 Oxidation

    Ketone formation at the 11th position often involves selective oxidation steps

3 Functionalization

    Derivatization to introduce substituents at various positions for tuning biological activity

 Chemical Reactivity

1 Ketone Reactivity

    The carbonyl group can undergo standard aldehydeketone reactions eg condensation reduction

2 Thiazepine Reactivity

    The nitrogen and sulfur atoms in the sevenmembered ring can participate in nucleophilic or electrophilic reactions enabling diverse derivatizations

 Safety and Handling

 Toxicity The parent compounds safety profile is largely dependent on its derivatives Precautions should be taken when handling intermediates or precursors

 Storage Store in a cool dry place away from light and oxidizing agents

Would you like more detailed information on the synthesis its derivatives or a specific drug example based on this scaffold