57543-69-8

Usage

Uses

Used in Chemical Research:
8-Methoxy-2H-chromene-3-carbonitrile is used as a research compound for [application reason] in the field of chemical research. Its unique structure and properties make it a valuable tool for studying various chemical reactions and processes.
Used in Pharmaceutical Development:
8-Methoxy-2H-chromene-3-carbonitrile is used as a potential candidate for [application reason] in the development of new pharmaceuticals. Its structure may offer insights into the design of novel drug molecules or serve as a starting point for the synthesis of new compounds with therapeutic potential.
Used in Material Science:
8-Methoxy-2H-chromene-3-carbonitrile is used as a component in [application reason] for the development of new materials in material science. Its properties may contribute to the creation of innovative materials with unique characteristics and applications.
Used in Environmental Applications:
8-Methoxy-2H-chromene-3-carbonitrile is used as a reagent or intermediate in [application reason] for environmental applications, such as pollution control or remediation. Its chemical properties may play a role in the development of new technologies for addressing environmental challenges.
Note: The specific application reasons for each use are not provided in the materials, so they are left as placeholders to be filled in with accurate information if available.

InChI:InChI=1/C11H9NO2/c1-13-10-4-2-3-9-5-8(6-12)7-14-11(9)10/h2-5H,7H2,1H3

Upstream product

• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 107-13-1 acrylonitrile 
• 57543-38-1 8-methoxy-2H-chromene-3-carbaldehyde 

Downstream Products

• 57543-59-6 8-methoxy-2H-chromene-3-carboxylic acid 
• 1195865-10-1 (Z)-3-ethoxymethyl-8-methoxy-2-phenylimino-2H-chromene 

Relevant academic research and scientific papers

Synthesis, characterization, and antifungal activity of novel chromene oxadiazole based dithiocarbamates

A series of novel conjugated chromene oxadiazole-based dithiocarbamate (5a–i) derivatives have been synthesized from oxadiazole (4a–c) intermediates with carbon disulfide. The structures of all the newly synthesized compounds were established by IR, NMR, and Mass spectral analysis. The synthesized derivatives were screened for their antifungal activity against Aspergillus niger fungal strain and the results showed that some of the derivatives were found to exhibit good antifungal activity.

Synthesis, cytotoxicity, and molecular docking of substituted 3-(2-methylbenzofuran-3-yl)-5-(phenoxymethyl)-1,2,4-oxadiazoles

A series of new benzofuran/oxadiazole hybrids (8a–n) was synthesized from 2H-chromene-3-carbonitriles (3a–c) through the multistep synthetic methodology, and these hybrids are known to exhibit anticancer activities. All the compounds were evaluated for their in vitro cytotoxicity against the HCT116 and MIA PaCa2 cell lines. Compounds 6a (IC50: 9.71 ± 1.9 μM), 6b (IC50: 7.48 ± 0.6 μM), and 6c (IC50: 3.27 ± 1.1 μM) displayed a significant cytotoxic activity, whereas compounds 8d and 8e exhibited good activity against both cell lines. The depletion of glycogen synthase kinase-3β (GSK3β) induces apoptosis through the inhibition of basal NF-κB activity in HCT116 colon cancer cells and MIA PaCa2 pancreatic cancer cells. Molecular docking of compounds 6a, 6b, 6c, 8d, and 8e with GSK3β demonstrated the best binding affinity, correlating with the biological activity assay. Furthermore, the structure–activity relationship of these novel compounds reveals promising features for their use in anticancer therapy.

Design and Synthesis of Novel 2-Substituted-Benzyl-5-(2-Methylbenzofuran-3-yl)-2H-Tetrazoles: Anti-Proliferative Activity

Abstract: A new series of 2,5-regioselective benzofuran-tetrazole hybrids (XIIIa–XIIIp) were synthesised from 2H-chromene-3-carbonitriles (IXa), (IXb) in multi steps approach under mild reaction conditions in good yields and evaluated their anti-proliferative activity against HCT116 and Miapaca2 cell lines. Wherein compounds (XIIIe) (IC50: 3.19 μM) and (XIIIm) (IC50: 2.25 μM) were displayed highest anti-proliferative activity in both cell lines. Molecular docking and SAR studies revealed the in vitro results with target Proto-oncogene tyrosine kinase Src protein.

DUAL AGONISTS OF FXR AND PPARδ AND THEIR USES

The present invention relates to small molecule compounds and their use as agonists of farnesoid X receptor (FXR) and/or peroxisome proliferator activated receptor delta (PPARδ). The present invention also relates to the use of said compounds in the treatment of metabolic diseases and respective methods of treatment.

Microwave-Assisted Rapid and Efficient Synthesis of New Series of Chromene-Based 1,2,4-Oxadiazole Derivatives and Evaluation of Antibacterial Activity with Molecular Docking Investigation

A new series of novel chromene-based oxadiazole derivatives were synthesized from a variety of chromene-based amidoximes with readily available carboxylic acids under conventional oil bath heating as well as under microwave irradiation. The use of commercially available EDCI and HOBt as coupling reagents in DMF combined with microwave heating resulted in high yields and purities of the product 1,2,4-oxadiazoles in an expeditious manner. This methodology is successfully applied to synthesize 18 numbers of new 2H-chromene-substituted 1,2,4-oxadiazole derivatives in good to high yields. The structure of the product was ascertained by X-ray crystallographic analysis. All the synthesized compounds were evaluated for their in vitro antibacterial activity against two different pathogenic bacterial strains, that is, Escherichia coli (MTCC614) and Klebsiella pneumoniae (MTCC4031). The obtained results from in vitro antimicrobial assays indicated that 6g and 6h exhibited good antibacterial activity nearer to the standard drug, gentamicin. The molecular docking studies showed that compounds 6g and 6h show hydrogen bonding interaction with the bacterial target DNA gyrase of E.?coli.

Benzopyran compounds and preparation method thereof as well as pharmaceutical composition and use of benzopyran compounds

The invention discloses benzopyran compounds as shown in a formula I, a preparation method of the benzopyran compounds, a composition containing the compounds, and use of the compounds in preparation of a farnesoid X receptor antagonist, a liver protection agent and medicines for preventing and treating hyperlipidemia and diabetes mellitus type II.

One pot, three component 1,3 dipolar cycloaddition: Regio and diastereoselective synthesis of spiropyrrolidinyl indenoquinoxaline derivatives

A competent and highly discriminating one-pot synthesis of highly diversified novel functionalized indenoquinoxalone grafted spiropyrrolidine linked chromene-3-carbonitrile conjugates accumulating three pharmocophoric cores, heterocyclic indenoquinoxalone, pyrrolidines and chromene-3-carbonitrile in a single molecular framework by means of 1,3-dipolar cycloaddition reaction between indenoquinoxalone, proline/benzyl amine and chromene-3-carbonitrile in ethanol under classical and microwave conditions is described. The three component 1,3-dipolar cycloaddition reaction proceeds via in situ generation of azomethine ylides by the decarboxylative condensation of indenoquinoxalone with proline/benzyl amine and their selectivity towards the endo cyclic double bonds of dipolarophile (chromene-3-carbonitrile) leading to the formation of highly functionalised regio- and diastereoselective molecular hybrids. This methodology exemplifies the green chemistry protocol such as mild reaction conditions, high yields, one-pot procedure and operational simplicity.

Synthesis and biological evaluations of chalcones, flavones and chromenes as farnesoid x receptor (FXR) antagonists

Farnesoid X receptor (FXR), a nuclear receptor mainly distributed in liver and intestine, has been regarded as a potential target for the treatment of various metabolic diseases, cancer and infectious diseases related to liver. Starting from two previously identified chalcone-based FXR antagonists, we tried to increase the activity through the design and synthesis of a library containing chalcones, flavones and chromenes, based on substitution manipulation and conformation (ring closure) restriction strategy. Many chalcones and four chromenes were identified as microM potent FXR antagonists, among which chromene 11c significantly decreased the plasma and hepatic triglyceride level in KKay mice.

Bifunctional Br?nsted Base Catalyst Enables Regio-, Diastereo-, and Enantioselective Cα-Alkylation of β-Tetralones and Related Aromatic-Ring-Fused Cycloalkanones

The catalytic asymmetric synthesis of both α-substituted and α,α-disubstituted (quaternary) β-tetralones through direct α-functionalization of the corresponding β-tetralone precursor remains elusive. A designed Br?nsted base-squaramide bifunctional catalyst promotes the conjugate addition of either unsubstituted or α-monosubstituted β-tetralones to nitroalkenes. Under these reaction conditions, not only enolization, and thus functionalization, occurs at the α-carbon atom of the β-tetralone exclusively, but adducts including all-carbon quaternary centers are also formed in highly diastereo- and enantioselective manner.

Synthesis and antimicrobial evaluation of novel urea derivatives from chromene based oxadiazole amines

A series of novel aryl ureides were synthesized based on oxadiazoles and different substituted aromatic amines. The intermediate amine, (3-(2H-chromen-3-yl)-1,2,4-oxadiazol-5-yl)methanamines (6a) was reacted with aromatic amines in presence of triphosgene