69155-76-6

Usage

Uses

6-FLUORO-3-FORMYLCHROMONE is used as an intermediate in the synthesis of various fluorine-containing chromone-tetrazoles, which are compounds with potential applications in different industries.
Used in Pharmaceutical Industry:
6-FLUORO-3-FORMYLCHROMONE is used as a key intermediate for the synthesis of fluorine-containing chromone-tetrazoles, which may have potential applications in the development of new pharmaceuticals. These compounds could be utilized in the treatment of various diseases due to their unique chemical structures and properties.
Used in Chemical Synthesis:
6-FLUORO-3-FORMYLCHROMONE is used as a building block in the synthesis of more complex organic molecules, particularly those containing the chromone and tetrazole moieties. These synthesized compounds may find applications in various fields, such as materials science, agrochemistry, and pharmaceuticals.
Some examples of fluorine-containing chromone-tetrazoles synthesized using 6-FLUORO-3-FORMYLCHROMONE include:
1. 3-((1-cyclohexyl-1H-tetrazol-5-yl)(phenylamino)methyl)-6-fluoro-4H-chromen-4-one
2. 3-((1-cyclohexyl-1H-tetrazol-5-yl)((3,4,5-trimethoxyphenyl)amino)methyl)-6-fluoro-4H-chrome-4-one
3. 3-((1-(tert-butyl)-1H-tetrazol-5-yl)(phenylamino)methyl)-6-fluoro-4H-chromen-4-one
4. 3-((1-(tert-butyl)-1H-tetrazol-5-yl)((4-chlorophenyl)amino)methyl)-6-fluoro-4H-chromen-4-one
These synthesized compounds may exhibit various biological activities and properties, making them valuable for further research and development in the pharmaceutical and chemical industries.

InChI:InChI=1/C10H5FO3/c11-8-1-2-9-6(4-8)3-7(5-12)10(13)14-9/h1-5H

Upstream product

• 394-32-1 1-(5-fluoro-2-hydroxyphenyl)ethan-1-one 
• 68-12-2 N,N-dimethyl-formamide 
• 371-41-5 4-Fluorophenol 
• 405-51-6 4-fluorophenyl acetate 
• 79-37-8 oxalyl dichloride 
• 347-54-6 5-fluoro-2-hydroxybenzaldehyde 

Downstream Products

• 924213-28-5 (5-fluoro-2-hydroxyphenyl)[2-(3-hydroxypropyl)[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methanone 
• 1162661-48-4 ethyl 3-acetyl-5-(5-fluoro-2-hydroxybenzoyl)-2-hydroxybenzoate 
• 1162661-58-6 ethyl 3-(5-(5-fluoro-2-hydroxybenzoyl)-2-hydroxyphenyl)-3-oxopropanoate 
• 1203451-86-8 ethyl 3-chloro-5-(5-fluoro-2-hydroxybenzoyl)-2-hydroxybenzoate 
• 1215095-80-9 9-fluoro-3-phenyl-2-oxo-2H,5H-pyrano[3,2-c]chromen-5-yl acetate 
• 1242460-92-9 C₁₆H₉F₃N₂O₂ 

Relevant academic research and scientific papers

Identification of potent α-amylase inhibitors via dynamic combinatorial chemistry

In this study, we report for the first time the discovery of potent α-amylase inhibitors using principle of dynamic combinatorial chemistry. The best compound identified exhibited not only high inhibitory efficiency but also low cytotoxicity. The binding mode and possible mechanism are determined in the subsequent kinetic and molecular docking studies.

Synthesis of Chromeno[2,3-d]pyrimidin-5-one Derivatives from 1,3,5-Triazinanes via Two Different Reaction Pathways

1,3,5-Triazinanes, as a kind of versatile building block, are applied in the synthesis of chromeno[2,3-d]pyrimidin-5-one derivatives via two different reaction modes, which perfectly exhibits the powerful function of 1,3,5-triazinane as a three-atom synth

Novel chromenyl-based 2-iminothiazolidin-4-one derivatives as tubulin polymerization inhibitors: Design, synthesis, biological evaluation and molecular modelling studies

Here-in, we present molecular design, chemical synthesis and evaluation of novel chromenyl-based 2-iminothiazolidin-4-one derivatives as tubulin polymerization inhibitors. The newly synthesized compounds were evaluated for their in vitro cytotoxicities against A549 (lung cancer), MDA-MB-231 and BT-471 (breast cancer), HepG2 (liver cancer) and HCT-116 (colon cancer) cell lines by MTT assay. Among the synthesized compounds, compound 12b showed excellent anticancer activity on MDA-MB-231 cell line with IC50 value of 0.95 ± 1.88 μM and was verified to be safe in normal human bronchial epithelial cells (Beas-2B). Apoptosis induced by the lead 12b was observed using morphological observations, AO/EB and DAPI staining procedures. Further, dose-dependent increase in the depolarization of mitochondrial membrane was also observed through JC-1 staining. Annexin V-FITC/PI assay confirmed that 12b induced early apoptosis. Additionally, cell cycle analysis indicated that the MDA-MB-231 cells were arrested at sub-G2/M phase and also inhibited tubulin polymerization with IC50 value of 3.54 ± 0.2 μM. Molecular docking simulations were employed to identify the important binding modes responsible for the tubulin inhibitory activity, thus supporting their effective anticancer potential.

Discovery of Novel Chromone Derivatives Containing a Sulfonamide Moiety as Anti-ToCV Agents through the Tomato Chlorosis Virus Coat Protein-Oriented Screening Method

A number of novel chromone derivatives containing sulfonamide moieties were designed and synthesized, and the activity of compounds against tomato chlorosis virus (ToCV) was assessed using the ToCVCP-oriented screening method. Comparative molecular field analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA) models were established based on the dissociation constant (Kd) values of the target compounds, and compound 35 was designed and synthesized with the aid of CoMFA and CoMSIA models. The study of affinity interaction indicated that compound 35 exhibited excellent affinity with ToCVCP with a Kd value of 0.11 μM, which was better than that of the positive control agents xiangcaoliusuobingmi (0.44 μM) and ningnanmycin (0.79 μM). In addition, the in vivo inhibitory effect of compound 35 on the ToCVCP gene was evaluated by the quantitative real-time polymerase chain reaction. ToCVCP gene expression levels of the compound 35 treatment group were reduced by 67.2%, which was better than that of the positive control agent ningnanmycin (59.5%). Therefore, compound 35 can be used as a potential anti-ToCV drug in the future.

Chromone dioxadiazole compound as well as preparation method and application thereof

The preparation method comprises the following steps: adding an intermediate F and bis (acetoxy) iodobenzene to dichloromethane for reaction to obtain the chromone compound. The invention provides a novel chromone dioxadiazole compound and a preparation method thereof, and overcomes the defects of large toxicity and high preparation cost of the traditional method.

Polysubstituted heterocyclic derivative, preparation method thereof and application of polysubstituted heterocyclic derivative in medicine

The invention provides a polysubstituted heterocyclic derivative, a preparation method thereof and application of the polysubstituted heterocyclic derivative in medicine, and belongs to the technical field of medicinal chemistry. The polysubstituted heterocyclic derivative is a compound shown in a general formula I or II, a pharmaceutically acceptable salt or a solvate of the compound, and the compound can inhibit mRNA demethylase on the protease level and is used for treating diseases related to mRNA demethylase functions.

Synthesis and biological evaluation of chromone-3-carboxamides

The aim of our study was to synthesize novel chromone-3-carboxamides and to conduct biological evaluations in search for lead compounds for the treatment of a range of debilitating disease states. Corresponding 2-hydroxyacetophenones were subjected to Vilsmeier-Haack formylation to give chromone-3-carbaldehydes, which were subsequently oxidised to give chromone-3-carboxylic acids. Treatment of the carboxylic acids with thionyl chloride resulted in the in situ formation of the corresponding acid chlorides, which were reacted with various amines in the presence of triethylamine to give the corresponding novel chromone-3-carboxamides in good yields. Selected chromone derivatives were then evaluated for their anti-inflammatory, anti-tryponosomal and cytotoxic properties.

Novel p-functionalized chromen-4-on-3-yl chalcones bearing astonishing boronic acid moiety as MDM2 inhibitor: Synthesis, cytotoxic evaluation and simulation studies

Background: Novel 4-[3-(6/7/8-Substituted 4-Oxo-4H-chromen-3-yl)acryloyl]phenyl-boronic acid derivatives (5a-h) as well as other 6/7/8-substituted-3-(3-oxo-3-(4-substituted-phenyl)prop-1-enyl)-4H-chromen-4-one derivatives (3a-u) have been designed as p53-MDM2 pathway inhibitors and reported to possess significant cytotoxic properties against several cancer cell lines. Objectives: The current project aims to frame the structure-anticancer activity relationship of chromen-4-on-3-yl chalcones (3a-u/5a-h). In addition, docking studies were performed on these chromeno-chalcones in order to have an insight into their interaction possibilities with MDM2 pro-tein. Methods: Twenty-nine chromen-4-on-3-yl chalcone derivatives (3a-u/5a-h) were prepared by utilizing silica supported-HClO4 (green route with magnificent yield) and tested against four cancer cell lines (HCT116, MCF-7, THP-1, NCIH322). Results: Among the series 3a-u, compound 3b exhibited the highest anticancer activity (with IC50 values ranging from 8.6 to 28.4 μM) overall against tested cancer cell lines. Interestingly, para-Boronic acid derivative (5b) showed selective inhibition against colon cancer cell line, HCT-116 with an IC50 value of 2.35 μM. Besides the emblematic hydrophobic interactions of MDM2 inhibi-tors, derivative 5b was found to exhibit extra hydrogen bonding with GLN59 and GLN72 residues of MDM2 in molecular dynamics (MD) simulation. All the compounds were virtually nontoxic against normal fibroblast cells. Conclusion: Novel compounds were obtained with good anticancer activity especially 6-Chlorochromen-4-one substituted boronic acid derivative 5b. The molecular docking study proposed good activity as a MDM-2 inhibitor suggesting hydrophobic as well as hydrogen bonding interactions with MDM2.

NHC-Catalyzed Cascade Reaction between β-Methyl Enals and Dienones for Quick Construction of Complex Multicyclic Lactones

A NHC-promoted cascade reaction between β-methyl enal and dienone is developed for quick access to multicyclic lactone molecules bearing quaternary chiral carbon centers. Our study constitutes the first 1,6-addition of the acylazolium vinyl enolate γ-carbon via NHC catalysis and provides rapid access to complex lactone molecules that are otherwise difficult to prepare. The structurally sophisticated lactone products bearing up to four fused ring structures are afforded in up to quantitative yields with good to excellent enantioselectivities.

One pot and metal-free approach to 3-(2-Hydroxybenzoyl)-1-aza-anthraquinones

Herein, a direct strategy to synthesize 3-(2-hydroxybenzoyl)-1-aza-anthraquinones with excellent efficiency,mild conditions, and benign functional group compatibilitywas reported. Avariety of 3-formylchromone compounds were employed as compatible substrates and this protocol gave the 3-(2-hydroxybenzoyl)-1-aza-anthraquinone derivatives in good to excellent yields without inert gas and expensive transition metal catalysts. Some compounds displayed good anti-proliferative activities.