230615-59-5 | 2,3,4,5-Tetrahydro-7,8-dinitro-3-(trifluoroacetyl)-1,5-methano-1H-3-benzazepine

CAS:230615-59-5 | 2,3,4,5-Tetrahydro-7,8-dinitro-3-(trifluoroacetyl)-1,5-methano-1H-3-benzazepine,Description

The compound of interest, 2,3,4,5-Tetrahydro-7,8-dinitro-3-(trifluoroacetyl)-1,5-methano-1H-3-benzazepine, is a derivative of the 2,3,4,5-tetrahydro-1H-3-benzazepine class. These compounds are of significant interest due to their potential pharmacological properties and their use as intermediates in the synthesis of various therapeutic agents.

Synthesis Analysis

The synthesis of 2,3,4,5-tetrahydro-1H-3-benzazepines can be achieved through various methods. One approach involves the oxidative cleavage and reductive amination strategies starting from benzonorbornadiene, yielding the desired product in moderate to good overall yield. Another method utilizes a tandem Michael addition and Pd-catalyzed cyclization to afford an intermediate, which upon further reactions, yields the benzazepine. Additionally, photochemical reactions and domino processes have been employed to synthesize novel hexacyclic benzazepine derivatives.

Molecular Structure Analysis

The molecular structure of benzazepine derivatives is characterized by spectroscopic methods and X-ray analysis. The hexacyclic benzazepine derivative mentioned in one study represents the first example of a complex skeleton, showcasing the diversity of structures achievable within this class of compounds.

Chemical Reactions Analysis

Chemical reactions involving 2,3,4,5-tetrahydro-1H-3-benzazepines include nitration, which yields nitro derivatives that can be further transformed using classical procedures. Cyclization reactions are also common, as seen in the synthesis of various benzazepine derivatives, which can involve intramolecular Friedel–Crafts alkylation or Heck cyclization.

Physical and Chemical Properties Analysis

The physical and chemical properties of 2,3,4,5-tetrahydro-1H-3-benzazepines are influenced by their molecular structure and substituents. For instance, the introduction of nitro groups and trifluoroacetyl groups can significantly alter the compound's reactivity and physical properties. The presence of substituents like methoxy and methylenedioxy groups can also affect the compound's chemical behavior and potential pharmacological activity.

Scientific Research Applications

Chemistry and Biological Activity of 3-Benzazepines

Research on 3-benzazepines, a related chemical family, reveals significant biological activities that include cytotoxicity against leukemia cells, radical production, and interactions with DNA and P-glycoprotein efflux pumps. These properties suggest their potential in developing cancer treatments and understanding cellular mechanisms (Kawase, Saito, & Motohashi, 2000).

1,5-Benzoxazepines as Pharmacological Scaffolds

The 1,5-benzoxazepine derivatives have been identified for their pharmacological properties, including anticancer, antibacterial, and antifungal activities. These compounds' ability to interact with G-protein-coupled receptors highlights their potential as bases for drugs targeting neurological disorders like Alzheimer's and Parkinson's disease (Stefaniak & Olszewska, 2021) .

Synthetic Utilities of Benzodiazepines

The synthesis and biological applications of benzodiazepines, closely related to the query compound, indicate their widespread use in treating anxiety, depression, and other conditions. This research underlines the importance of heterocyclic compounds in developing new medications, suggesting a potential research application for novel compounds like 2,3,4,5-Tetrahydro-7,8-dinitro-3-(trifluoroacetyl)-1,5-methano-1H-3-benzazepine (Ibrahim, 2011).

Heterocyclic Compounds in Drug Development

Heterocyclic compounds, including triazoles and quinoxalines, have been extensively studied for their antimicrobial, antifungal, anticancer, and antiviral activities. The versatility of these compounds in drug development suggests potential research applications for similarly structured compounds in discovering new therapeutic agents (Verma, Sinha, & Bansal, 2019).

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