1003858-69-2 | 1H-Indole, 4-fluoro-5-nitro-

CAS:1003858-69-2 | 1H-Indole, 4-fluoro-5-nitro-,Description

Synthesis Analysis

The synthesis of heterocycles derived from 4-fluoro-5-nitro-1H-indole has been explored in the context of developing compounds with potential antimicrobial, anti-inflammatory, and antiproliferative activities. The process involves the reaction of ethyl or methyl indole-2-carboxylates with hydrazine hydrate to yield nitroindole-2-carbohydrazides and fluoroindole-2-carbohydrazides. These intermediates are then treated with acetyl acetone in methanol to produce a series of 2-((3,5-dimethyl-1H-pyrazol-1-yl)carbonyl)-nitro and fluoro-1H-indoles. Additionally, nitroindole-2-carbohydrazides can react with CS2/KOH in methanol to form 1,3,4-oxadiazole-2-thiol and with cyanogen bromide to yield 1,3,4-oxadiazol-2-amines. These reactions demonstrate the versatility of nitroindole derivatives in synthesizing a variety of heterocyclic compounds with potential biological activities.

Molecular Structure Analysis

The molecular structure of 5-nitro-1H-indole-2-acid (NIA), a related compound to 4-fluoro-5-nitro-1H-indole, has been optimized using B3LYP/6-31G level calculations. This optimized structure serves as a basis for understanding the interactions between NIA and biomolecules such as bovine hemoglobin (BHb). The study reveals that NIA forms hydrogen bonds with specific amino acids in BHb and interacts with hydrophobic residues, including tyrosine, which can lead to fluorescence quenching. These findings suggest that the molecular structure of nitroindole derivatives plays a significant role in their biological interactions.

Chemical Reactions Analysis

The reactivity of 4-fluoro-5-nitro-1H-indole can be inferred from studies on similar nitroindole derivatives. These compounds are shown to undergo various chemical reactions, including cyclization and substitution, to form diverse heterocyclic structures. For instance, 4-chloro-2-fluoro-5-nitrobenzoic acid, a compound with similar substitution patterns, has been used as a building block for solid-phase synthesis of heterocycles. The reactivity of the nitro group and halogen substituents allows for the construction of benzimidazoles, benzotriazoles, quinoxalinones, and other nitrogenous cycles, highlighting the potential of nitroindole derivatives in heterocyclic chemistry.

Physical and Chemical Properties Analysis

While the specific physical and chemical properties of 4-fluoro-5-nitro-1H-indole are not directly reported, the properties of related nitroindole compounds provide insights. These compounds typically exhibit moderate to good antiproliferative activity, suggesting their potential use in antitumor applications. The presence of nitro and fluoro substituents is likely to influence the electronic properties and reactivity of the indole core, affecting its interactions with biological targets. The spectroscopic studies of NIA indicate that nitroindole derivatives can interact with proteins and influence their fluorescence properties, which could be leveraged in bioanalytical applications.

Scientific Research Applications

Antituberculosis Activity

4-Fluoro-5-nitro-1H-indole derivatives have shown significant potential in antituberculosis activity. Specifically, compounds related to 5-nitro-1H-indole-2,3-dione derivatives have been tested for their effectiveness against Mycobacterium tuberculosis. Research indicates that certain derivatives exhibit significant inhibitory activity, highlighting the potential of 4-fluoro-5-nitro-1H-indole in tuberculosis treatment research (Karalı et al., 2007) .

Antimicrobial, Antiinflammatory, and Antiproliferative Activities

Studies have been conducted on heterocycles derived from 4-fluoro-5-nitro-1H-indole, exploring their antimicrobial, antiinflammatory, and antiproliferative properties. The research suggests that these derivatives possess a range of biological activities, potentially beneficial for various therapeutic applications (Narayana et al., 2009).

Catalytic Activity in Synthesis of Derivatives

The catalytic activity of nickel ferrite nanoparticles in the synthesis of certain derivatives of 4-fluoro-5-nitro-1H-indole has been examined. This research provides insights into the synthesis processes of these compounds, which could be important for pharmaceutical applications (Rao et al., 2019).

Fluorescent Nanoparticles

Fluorescent organic nanoparticles of 3-styrylindoles, which include derivatives of 4-fluoro-5-nitro-1H-indole, have been synthesized. These nanoparticles exhibit unique properties such as enhanced fluorescence emission, potentially useful in material science and bioimaging applications (Singh & Ansari, 2017).

Pharmaceutical Process Development

Research has also focused on the process development for synthesizing pharmaceutical derivatives of 4-fluoro-5-nitro-1H-indole. These studies involve optimizing synthesis processes, which is crucial for the efficient production of pharmaceutical compounds (Anderson et al., 1997).

Safety And Hazards

While specific safety and hazard information for 4-fluoro-5-nitro-1H-indole is not available, it’s generally recommended to avoid breathing dust and contact with skin and eyes when handling similar chemical compounds.

Future Directions

Indole derivatives, including 4-fluoro-5-nitro-1H-indole, have diverse biological activities and also have an immeasurable potential to be explored for newer therapeutic possibilities. They are considered “privileged structures” in pharmaceutical chemistry due to their high-affinity binding to many receptors. This makes them a valuable area of research for the development of new therapeutic agents.

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