1408282-26-7 | 8-fluoro-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one

CAS:1408282-26-7 | 8-fluoro-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one,Description

“8-Fluoro-4,5-dihydro-1H-azepino[5,4,3-CD]indol-6(3H)-one” is a chemical compound with the molecular formula C18H13FN2O2. It is also known as "4-(8-fluoro-6-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-2-yl)benzaldehyde".

Synthesis Analysis

The synthesis of this compound involves novel heteroaryl fused indole ring systems. Three synthetic approaches have been developed that allow efficient access to these ring systems. Each strategy is fully exemplified, and the relative merits and limitations of the approaches are discussed.

Molecular Structure Analysis

The molecular structure of this compound is characterized by an azepino[5,4,3-CD]indol-6(3H)-one ring system, which is fused with a heteroaryl group. The presence of the 5-hydroxy group on the indole nucleus is suggested to be essential.

Chemical Reactions Analysis

In the synthesis of this compound, serotonins were found to produce 3, 4, 5, 6-tetrahydro-7-hydroxy-1H-azepino[5, 4, 3-cd]indoles by simple heating with amines under an oxygen atmosphere. Serotonins also reacted with various aldehydes to provide 3, 4, 5, 6-tetrahydro-7-hydroxy-1H-azepino[5, 4, 3-cd]indoles rather than β-carbolines under basic conditions.

Physical And Chemical Properties Analysis

The predicted boiling point of this compound is 667.2±55.0 °C, and its predicted density is 1.386±0.06 g/cm3. The predicted acidity coefficient (pKa) is 13.98±0.20.

Scientific Research Applications

• Fluorescence, DNA Interaction and Cytotoxicity Studies

  • Field : Medicinal Chemistry
  • Application : This research involves the synthesis and characterization of compounds based on 4,5-Dihydro-1H-Pyrazol-1-Yl Moiety. These compounds are evaluated for their fluorescence, DNA interaction, and cytotoxicity.
  • Methods : The compounds were synthesized and characterized using various techniques such as heteronuclear NMR spectroscopy, elemental analysis, IR spectroscopy, and liquid crystal mass spectroscopy. Their binding with HS-DNA was evaluated using viscosity measurements, absorption titration, fluorescence quenching, and molecular docking.
  • Results : The compounds showed effective intercalation mode with DNA. The binding constant of the complexes was found to be 8.1 to 9.2 × 10^4 M^−1. The compounds also underwent bacteriostatic screening and showed MIC of 72.5–100 μM.

• Synthesis of Heteroaryl Fused Indole Ring Systems

  • Field : Organic Chemistry
  • Application : This research involves the development of synthetic approaches for creating novel heteroaryl fused indole ring systems. These include 7,8,9,10-tetrahydro-6H-azepino[1,2-a]indoles, 4-oxo-2,3-dihydro-1H-[1,4]diazepino[1,7-a]indoles, and 1,2,4,5-tetrahydro-[1,4]oxazepino[4,5-a]indoles.
  • Methods : The research presents three different synthetic approaches, each fully exemplified, and discusses the relative merits and limitations of these approaches.
  • Results : The synthetic approaches developed allow efficient access to these novel heteroaryl fused indole ring systems.

• Development of a Positron Emission Tomography (PET) Tracer

  • Field : Radiopharmaceutical Chemistry
  • Application : This research involves the synthesis of a novel compound and its labeling with fluorine-18 (18F) to develop a PET tracer for in vivo visualization of leucine-rich repeat kinase 2 (LRRK2) in the brain. LRRK2 activity in the brain is associated with Parkinson’s disease.
  • Methods : The compound was synthesized and labeled with fluorine-18 (18F).
  • Results : The compound showed high in vitro binding affinity for LRRK2.

• Design and Synthesis of Pyrrolopyridine Derivatives

  • Field : Medicinal Chemistry
  • Application : This research involves the design and synthesis of a series of 1H-pyrrolo[2,3-b]pyridine derivatives with potent activities against fibroblast growth factor receptors (FGFR1, 2, and 3). Abnormal activation of FGFR signaling pathway plays an essential role in various types of tumors.
  • Methods : The compounds were synthesized and their inhibitory activities against FGFR1, 2, and 3 were evaluated.
  • Results : Among the synthesized compounds, compound 4h exhibited potent FGFR inhibitory activity (FGFR1–4 IC50 values of 7, 9, 25 and 712 nM, respectively). In vitro, 4h inhibited breast cancer 4T1 cell proliferation and induced its apoptosis.

• Synthesis of Compounds for Anticancer Agents

  • Field : Medicinal Chemistry
  • Application : This research involves the synthesis of a series of novel compounds containing 1-methylindol and 1-(4,5-dihydro-1H-pyrazol-1-yl)ethanone skeletons. These compounds were designed and synthesized as potential tubulin polymerization inhibitors and anticancer agents.
  • Methods : The compounds were synthesized and their inhibitory activities against tubulin polymerization were evaluated.
  • Results : Among the synthesized compounds, compound 6q showed the most potent tubulin polymerization inhibitory activity.

Future Directions

The development of efficient synthetic approaches to this compound and related heteroaryl fused indole ring systems could have significant implications for the field of medicinal chemistry. These compounds could potentially serve as effective inhibitors of HCV NS5B polymerase.

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