938-40-9

Basic information

• Product Name: 2H-1-Benzopyran-2-one, 4-bromo-
• CAS NO: 938-40-9
• Molecular Formula: C9H5BrO2
• Molecular Weight: 225.041
• Mol File: 938-40-9.mol

Chemical Properties

• CAS DataBase Reference: 2H-1-Benzopyran-2-one, 4-bromo-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1-Benzopyran-2-one, 4-bromo-(938-40-9)
• EPA Substance Registry System: 2H-1-Benzopyran-2-one, 4-bromo-(938-40-9)

Safety Data

• Hazardous Substances Data: 938-40-9(Hazardous Substances Data)

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 42974-18-5 3,4-dibromo-3,4-dihydrocoumarin 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 

Downstream Products

• 139300-90-6 (2-Oxo-2H-chromen-4-yl)-phosphonic acid diethyl ester 
• 100914-71-4 3-chloro-4-phenoxy-2-coumarin 
• 112632-77-6 4-((2-hydroxyphenyl)amino)-2H-chromen-2-one 
• 21315-53-7 4-[(2-hydroxyethyl)amino]-2H-chromen-2-one 

Relevant articles and documents

Indane-Fused Spiropentadiene Chromanones: A Pd-Catalyzed Spiroannulation Followed by Cyclization via C-H Activation Strategy

Pd-catalyzed spiroannulation of 4-bromocoumarin with alkynes has been illustrated. The reaction highlights an interesting process for cascade formation of two five-membered rings through spiroannulation followed by cyclization via C-H activation. This method offers an attractive platform for the synthesis of a broad range of indane-fused spiropentadiene chromanones in good yields.

Amino acid-sensitive reagents with coumarin moiety for latent prints examination

Abstract: New ninhydrin derivatives were designed for the development of latent fingerprints on paper surfaces. The target compounds combine the selectivity of an amino acid-sensitive reagent with the variability of spectral characteristics of a fluorescent probe. These ninhydrin analogues, 2,2-dihydroxy-5-(2-oxo-2H-chromen-4-yloxy)-2H-indane-1,3-diones, prepared by multistep synthesis show enhanced fluorogenic properties compared with the commonly used ninhydrin. These types of derivatives can be potentially used for development of the latent prints on the dark surfaces, because their ninhydrin reaction products provide fluorescent prints under the UV light. The prints developed using these compounds are stable, visible and do not vanish from paper for a relatively long time (5?months). Graphical abstract: [Figure not available: see fulltext.].

Fragment-type 4-azolylcoumarin derivatives with anticancer properties

Several coumarin derivatives with a directly attached azole substituent at C-4 were synthesized and biologically studied for their anticancer properties. The cell lines used for this investigation (HeLa, K-562, MDA-MB-53, and MCF-7) demonstrated different sensitivities. The best response in the MTT (3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide) assay was shown by K-562 cells, with compounds displaying activity (3c, IC50 3.06 μM; 4a, IC50 5.24 μM; 4c, IC50 4.7 μM) similar to that of cisplatin (IC50 ~6 μM), which was used as the standard. The studied azole-substituted coumarins demonstrated weaker activity toward other cell lines, except for compound 4c, which was equally potent in the case of MCF-7 cells. Additional biological evaluations supported interference with the cell cycle as a potential mechanism of action and confirmed the absence of toxicity in zebrafish embryos. On the basis of these initial results, 4-azole coumarins should be explored further. Although their activity would need additional optimization, the fact that these compounds are fragment-like structures with MW 300 and clog P 3 offers enough flexibility to fine-tune their drug-like properties.

Design, Synthesis, and Antiviral Activities of Coumarin Derivatives Containing Dithioacetal Structures

In this study, a series of coumarin derivatives containing dithioacetals were synthesized, characterized, and assessed for their anti-tobacco mosaic virus (TMV) activities. Biological tests showed that most of the title compounds exhibited significant anti-TMV biological activities; in particular, compound b21 showed good inactivating activity anti-TMV, with an EC50 of 54.2 mg/L, superior to that of ribavirin (134.2 mg/L). Transmission electron microscopy analyses showed that compound 21 severely ruptured TMV particles. The interaction of compound b21 with TMV coat protein (TMV CP) was investigated using microscale thermophoresis and molecular docking. Compound b21 exhibited a strong binding ability to TMV CP, with a value of 2.9 μM, superior to ribavirin.

Coumarin derivative and analogue, preparation method and application thereof

The invention relates to a coumarin derivative and analogue, a preparation method and application thereof, belongs to the field of chemical medicines, and provides a compound shown as a formula I or apharmaceutically acceptable salt thereof, and a preparation method and application of the compound. According to the invention, biological experiments show that the compound has a strong in-vitro anti-fibrosis effect, can obviously reduce deposition of intercellular collagenous fibers on TGF-beta induced NRK-49F cells, and has inhibition on migration of HUVEC cells; and the compound with the structure has a certain curative effect on carbon tetrachloride induced hepatic fibrosis and bleomycin induced pulmonary fibrosis mouse models, is relatively low in toxicity, and provides a new choice forclinical treatment of tissue fibrosis diseases including hepatic fibrosis, pulmonary fibrosis and renal fibrosis.

CHIRALITY SENSING WITH MOLECULAR CLICK CHEMISTRY PROBES

The present invention relates to an analytical method that includes providing a sample potentially containing a chiral analyte that can exist in stereoisomeric forms, and providing a probe selected from the group consisting of coumarin-derived Michael acceptors, dinitrofluoroarenes and analogs thereof, arylsulfonyl chlorides and analogs thereof, arylchlorophosphines and analogs thereof, aryl halophosphites, and halodiazaphosphites. The sample is contacted with the probe under conditions to permit covalent binding of the probe to the analyte, if present in the sample; and, based on any binding that occurs, the absolute configuration of the analyte in the sample, and/or the concentration of the analyte in the sample, and/or the enantiomeric composition of the analyte in the sample is/are determined. The probe may be a coumarin-derived Michael acceptor, a di nitrofluoroarene or analog thereof, an arylsulfonyl chloride or analog thereof, an arylchlorophosphine or analog thereof, an aryl halophosphite, or a halodiazaphosphite.

Synthesis and discovery of new compounds bearing coumarin scaffold for the treatment of pulmonary fibrosis

Idiopathic pulmonary fibrosis, characterized by excess accumulation of extracellular matrix, involved in many chronic diseases or injuries, threatens human health greatly. We have reported a series of compounds bearing coumarin scaffold which potently inhibited TGF-β-induced total collagen accumulation in NRK-49F cell line and migration of macrophages. Compound 9d also suppressed the TGF-β-induced protein expression of COL1A1, α-SMA, and p-Smad3 in vitro. Meanwhile, 9d at a dose of 100 mg/kg/day through oral administrations for 4 weeks effectively alleviated infiltration of inflammatory cells in lung tissue and fibrotic degree in bleomycin-induced pulmonary fibrosis model, which may related to its inhibition of TGF-β/Smad3 pathway and anti-inflammation efficacy. In addition, 9d demonstrated decent bioavailability (F = 39.88%) and suitable eliminated half-life time (T1/2 = 13.09 h), suggesting that 9d could be a potential drug candidate for the treatment of fibrotic diseases.

The design, synthesis and evaluation of selenium-containing 4-anilinoquinazoline hybrids as anticancer agents and a study of their mechanism

Inhibition of tubulin polymerization is one of the significant strategies in the treatment of cancer. Inspired by the excellent antitumor activity of EP128495 and the beneficial biological activities of selenium compounds, a series of new selenium-containing 4-anilinoquinazoline hybrids were synthesized and evaluated as tubulin polymerization inhibitors. An anti-proliferative activity assay showed that most of the compounds inhibited human sensitive cancer cells at low nanomolar concentrations. A mechanism study revealed that the optimal compound 5a disrupted microtubule dynamics, decreased the mitochondrial membrane potential and arrested HeLa cells in the G2/M phase, finally resulting in cellular apoptosis.

Mechanistic studies on the palladium-catalyzed cross-dehydrogenative coupling of 4-phenoxy-2-coumarins: Experimental and computational insights

Delineating the mechanistic features of C-H activation in aryl-heteroaryl coupling is an important step in the design of selective, catalytic processes. Herein we use the intramolecular dehydrogenative coupling of 4-phenoxy-2-coumarins as a model study. Computational results and experimental studies suggest that CMD is operative in the cleavage of both C-H bonds, and that the heteroaryl C-H is cleaved initially.

Unexpected C-N bond formation via Smiles rearrangement: One pot synthesis of N -arylated coumarin/pyran derivatives

A conceptually new and one-pot method for the synthesis of N-arylated coumarin/pyran derivatives via Smiles rearrangement. The reaction of 4-bromocoumarin/pyran with 2-amino phenols affords O-arylated coumarin/pyran which subsequently rearranges into N-arylated coumarin/pyran under mild reaction conditions in good yields.