76384-48-0

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Molecular structure

2-[(E)-2-(1H-indol-3-yl)ethenyl]-1-methyl-1,2-dihydroquinoline is a heterocyclic compound containing a quinoline ring and a substituted indole ring connected by a double bond.

Quinoline derivative

The compound is derived from the quinoline core, which is a tricyclic aromatic compound with a pyridine ring fused to a benzene ring.

Indole group

The compound features a 1H-indol-3-yl group, which is a core structure of the compound, consisting of a benzene ring fused to a pyrrole ring.

Ethenyl bond

The compound has a double bond (E) between the indole group and the quinoline backbone, which is responsible for its chemical reactivity and properties.

Saturated six-membered ring

As a 1,2-dihydroquinoline, the compound has a saturated six-membered ring, which contributes to its stability and structure.

Potential pharmaceutical applications

Due to its unique structure and potential biological activity, the compound may have applications in pharmaceutical and medicinal chemistry.

Chemical synthesis and compound development

The compound's structure may be of interest for further chemical synthesis and development, leading to the creation of new compounds with various applications.

Upstream product

• 22948-94-3 1-acetyl-3-indolylcarbaldehyde 
• 876-87-9 N-methylquinaldinium iodide 
• 487-89-8 Indole-3-carboxaldehyde 
• 91-63-4 2-methylquinoline 
• 703-80-0 3-acetylindole 

Relevant academic research and scientific papers

PH triggered dye chemosensor: Design, synthesis and optical switching properties

A novel dye chemosensor based on indole as a donor unit and quinaldium as an acceptor unit have caused promising optical changes when used as a reversible, pH-induced, molecular switching in the presence of alkali/acid stimulus. The dye chemosensor also exhibited marked fluorescence quenching in the presence of alkali addition, which are based on intramolecular charge transfer (ICT) system. The level of energy potential and the electron flowing of this dye chemosensor such as HOMO and LUMO values were calculated by computational calculation approaches. Copyright Taylor and Francis Group, LLC.

Antibacterial activity of indolyl-quinolinium derivatives and study their mode of action

Filamenting temperature-sensitive mutant Z (FtsZ) is recognized as a promising target for new antibiotics development because of its high conservatism and pivotal role in the bacteria cell division. The aromatic heterocyclic scaffold of indole is known showing merit medical functions in antiviral and antimicrobial. In the present study, a series of 1-methylquinolinium derivatives, which were integrated with an indole fragment at its 2-position and a variety of amino groups (cyclic or linear, mono- or di-amine) at the 4-position were synthesized and their antibacterial activities were evaluated. The results of antibacterial study show that the representative compounds can effectively inhibit the growth of testing strains including MRSA and VRE, with MIC values of 1–4 μg/mL by bactericidal mode. The mode of action assays revealed that c2 can effectively disrupt the rate of GTP hydrolysis and dynamic polymerization of FtsZ, and thus inhibits bacterial cell division and then causes bacterial cell death. In addition, the result of resistance generation experiment reveals that c2 is not likely to induce resistance in S. aureus.

Selective visualization of DNA G-quadruplex structures in live cells with 1-methylquinolinium-based molecular probes: The importance of indolyl moiety position towards specificity

A class of small 1-methylquinolinium-based molecular fluorescent probes with high specificity in DNA G-quadruplex structures imaging in live cells was developed through the structural inclusion with an indolyl moiety. The study reveals that the scaffold of 1-methylquinolinium and indole ring is a distinctive combination for molecular design of new probes with effective and sensitive fluorescent signal switch-on functionality, particularly for identifying telomeric DNA, recognizing G-quadruplexes in promoters, and imaging or visualization of DNA G-quadruplex from other DNA structures. In addition, the experimental results demonstrate a rarely investigated factor on the importance of the indolyl moiety and its position when conjugating with a 1-methylquinolinium scaffold though a ethylene bridge in molecular probe design and synthesis; and these factors are determined as the crucial root leading to the excellent fluorescent signal switch-on property for the specific discrimination of DNA G-quadruplexes against other nucleic acids in live human prostate cancer cells (PC-3?cells) experiments. The characteristics of the new probes were comprehensively investigated with fluorescence titration, native PAGE experiments, and CD analysis to validate the selectivity, sensitivity, and stability while interacting with DNA G-quadruplex structures.

Synthesis, spectral properties of cell-permeant dimethine cyanine dyes and their application as fluorescent probes in living cell imaging and flow cytometry

A series of dimethine cyanine dyes, used as fluorescent probes, were synthesized under microwave irradiation, and identified by 1H NMR, IR, elemental analysis and HRMS. The investigation of their spectral properties in phosphate-buffer saline (PBS) showed that the absorption and emission maxima of the dyes were in the region 370-480 nm and 471-569 nm, respectively. The properties of the dyes as fluorescent probes for living cells imaging and flow cytometry were investigated. The results showed that dyes 1, 2, 8 or 9 could penetrate an intact cell membrane, stained the cell nuclear and exhibited bright fluorescence. Little background interference, low cell cytotoxicity and little photobleaching were showed during the imaging tests. The dyes 1, 8 and 9 could be applied in flow cytometry and dye 1/PI, dye 8/PI or dye 9/PI couple could be proposed as double staining agents to measure sperm cell viability. Thus the dyes represented the cell-permeant fluorescent probes.

PH triggered dye chemosensor: Design, synthesis and optical switching properties

A novel dye chemosensor based on indole as a donor unit and quinaldium as an acceptor unit have caused promising optical changes when used as a reversible, pH-induced, molecular switching in the presence of alkali/acid stimulus. The dye chemosensor also exhibited marked fluorescence quenching in the presence of alkali addition, which are based on intramolecular charge transfer (ICT) system.The level of energy potential and the electron flowing of this dye chemosensor such as HOMO and LUMO values were calculated by computational calculation approaches.

RNA-selective probes for live cell imaging of nuclear structure and function

The present invention is directed to fluorescent compounds and methods of making said compounds that selectively bind to cellular RNA. The fluorescent compounds of the present invention are useful for live cell imaging applications.

Simple synthesis of carbon-11 labeled styryl dyes as new potential PET RNA-specific, living cell imaging probes

A new type of styryl dyes have been developed as RNA-specific, live cell imaging probes for fluorescent microscopy technology to study nuclear structure and function. This study was designed to develop carbon-11 labeled styryl dyes as new probes for biome

Combinatorial approach to organelle-targeted fluorescent library based on the styryl scaffold

The first fluorescent styryl dye library with a broad color range was synthesized by combinatorial condensation of various aldehydes and methyl pyridinium compounds, and their applications as organelle specific staining probes were demonstrated. Copyright