25392-41-0

Basic information

• Product Name: 4-(CHLOROMETHYL)-7-HYDROXY-2H-CHROMEN-2-ONE
• Synonyms: OTAVA-BB BB7014350028;4-(CHLOROMETHYL)-7-HYDROXY-2H-CHROMEN-2-ONE;4-CHLOROMETHYL-7-HYDROXY-CHROMEN-2-ONE;4-(CHLOROMETHYL)-7-HYDROXYCOUMARIN;AKOS BBS-00000158;CELLTRACKER(TM) BLUE CMHC;BlueCMHC;2H-1-Benzopyran-2-one, 4-(chloroMethyl)-7-hydroxy-
• CAS NO: 25392-41-0
• Molecular Formula: C₁₀H₇ClO₃
• Molecular Weight: 210.61
• Mol File: 25392-41-0.mol
• Article Data: 92

Chemical Properties

• Melting Point: 180-183°C
• Boiling Point: 409.6 °C at 760 mmHg
• Flash Point: 201.5 °C
• Appearance: /
• Density: 1.442 g/cm³
• Vapor Pressure: 2.72E-07mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 7.72±0.20(Predicted)
• CAS DataBase Reference: 4-(CHLOROMETHYL)-7-HYDROXY-2H-CHROMEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(CHLOROMETHYL)-7-HYDROXY-2H-CHROMEN-2-ONE(25392-41-0)
• EPA Substance Registry System: 4-(CHLOROMETHYL)-7-HYDROXY-2H-CHROMEN-2-ONE(25392-41-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 25392-41-0(Hazardous Substances Data)

Usage

Uses

Fluorescent Thiol-Reactive cell permeant probe

InChI:InChI=1/C10H7ClO3/c11-5-6-3-10(13)14-9-4-7(12)1-2-8(6)9/h1-4,12H,5H2

Upstream product

• 108-46-3 recorcinol 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 32807-28-6 Methyl 4-chloroacetoacetate 

Downstream Products

• 151889-83-7 7-hydroxy-4-(hydroxylmethyl)-2H-chromen-2-one 
• 69716-04-7 2-(6-hydroxy-1-benzofuran-3-yl)acetic acid 
• 926927-63-1 N-(tert-butyloxycarbonyl)-L-phenylalanine (6-hydroxy-3-oxo-3H-benzopyran-1-yl) methyl ester 
• 1427203-78-8 C₁₇H₁₄ClNO₅S 
• 1427203-94-8 C₁₈H₁₆ClNO₅S 
• 1427203-95-9 C₁₉H₁₈ClNO₅S 
• 1427203-96-0 C₁₈H₁₆ClNO₅S 
• 1427203-99-3 C₁₈H₁₆ClNO₃ 
• 1427204-00-9 C₁₈H₁₆ClNO₃ 
• 1427204-05-4 4-{[(diphenylmethyl)(methyl)amino]methyl}-2-oxo-2H-chromen-7-yl 3-chlorobenzenesulfonate 
• 1427204-06-5 C₁₇H₁₄ClNO₅S 
• 1427203-77-7 C₁₇H₁₅NO₅S 
• 1427203-60-8 4-(chloromethyl)-2-oxo-2H-chromen-7-yl benzenesulfonate 
• 1427203-61-9 4-(chloromethyl)-2-oxo-2H-chromen-7-yl 3-chlorobenzenesulfonate 

Relevant articles and documents

1,2,3-Triazole pharmacophore-based benzofused nitrogen/sulfur heterocycles with potential anti-Moraxella catarrhalis activity

Versatile 1,2,3-triazole pharmacophore-based benzofused heterocycles containing halogen-substituted aromatic (9-17 and 25-28), 7-substituted coumarin (18-23 and 29-30) or penciclovir-like subunit (31a,b-38a) were designed and synthesized to evaluate their

Synthesis and biological evaluation of morpholines linked coumarin–triazole hybrids as anticancer agents

A series of novel morpholines linked coumarin–triazole hybrids (6a–6v) has been synthesized and evaluated for their anti-proliferative potential on a panel of five human cancer cell lines, namely bone (MG-63), lung (A549), breast (MDA-MB-231), colon (HCT-15) and liver (HepG2), using MTT assay. Among all, the compound 6n {7-((1-(2,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl) methoxy)-4-((2,6-dimethylmorpholino) methyl)-2H-chromen-2-one} showed significant growth inhibition against MG-63 cells with an IC50 value of 0.80 ± 0.22 μM. Further, induction of apoptosis by 6n of MG-63 cells confirmed as a result of morphological changes, the sub-G1 phase arrest, increased percentage of apoptotic cells, and decrease in mitochondrial membrane potential and increase in reactive oxygen species levels. The in vitro Gal-1 expression in cell culture supernatant of MG-63 cells treated with compound 6n showed dose-dependent reduction. The binding constant (Ka) of 6n with Gal-1 was calculated from the intercept value which was observed as 3.0 × 105 M?1 by fluorescence spectroscopy. Surface plasmon resonance showed that 6n binds to Gal-1 with binding constant (Ka) of 1.29E+04 1/Ms and equilibrium constant KD value of 7.54E?07 M, respectively. Molecular docking studies revealed the binding interactions of 6n with Gal-1.

Novel chalcone-conjugated, multi-flexible end-group coumarin thiazole hybrids as potential antibacterial repressors against methicillin-resistant Staphylococcus aureus

The increasing resistance of methicillin-resistant Staphylococcus aureus (MRSA) to antibiotics has led to a growing effort to design and synthesize novel structural candidates of chalcone-conjugated, multi-flexible end-group coumarin thiazole hybrids with

Synthesis, 18F-radiolabeling and apoptosis inducing studies of novel 4, 7-disubstituted coumarins

In present study, a new series of 4, 7-disubstituted coumarin derivatives (7a-y) have been synthesized as galectin-1 targeting apoptosis inducing agents and evaluated for their in vitro cytotoxic potentials against a panel of selected human cancer cell lines namely, Brest (MCF7), Ovarian (SKOV3), Prostate (PC-3 & DU145) and normal embryonic kidney (HEK293T) cells, using MTT assay. Most of the compounds exhibited potent growth inhibitory action against the treated cancer cell lines with an IC50 range of 10–30 μM. Compound 7q exhibited a significant growth inhibition against prostate cancer (PC-3 & DU145) cell lines with an IC50 value of 7.45 ± 0.03 μM, 8.95 ± 0.17 μM respectively. Further, the target compound 7q was radiolabeled with fluorine-18 [18F] to be used as a novel PET radiotracer for imaging of tumors via targeting galectin-1, using appropriate reaction conditions in the GE Tracer-lab FX2N synthesis module. The purification of the [18F] radiolabeled compound [18F]-7q was successfully achieved with 60% ethanol. The radiochemical purity was>85% and residual solvent limits of DMF was 65 ± 3 ppm as analysed by HPLC, TLC & GC analytical methods. The apoptosis studies confirm the inhibition of cell proliferation with morphological changes like cell shrinkage, blebbing and cell wall deformation, increasing the ROS levels, and loss of mitochondrial membrane potential by Acridine orange/Ethidium bromide staining, Hoechst-33342 staining, H2DCFDA staining, annexin V-FITC/PI, and JC-1 staining methods. In flow cytometric analysis, 7q selectively arrested the sub-G1 phase of the cell cycle in a dose-dependent manner. In Gal-1 ELISA studies, compound 7q efficiently reduced the levels of Gal-1 protein in dose-dependent manner with an IC50 value of 100 μM. The binding constant (Ka) of 7q with Gal-1 was observed as 1.3 × 104 M?1 by fluorescence spectroscopy. The molecular docking studies clearly showed possible interactions and the pharmacokinetic (ADMET) properties of compound 7q with Gal-1. Hence, the novel 4, 7-disubstituted coumarins could be a potential cytotoxic and PET imaging agents via Gal-1.

B(C6F5)3-catalyzed synthesis of coumarins via Pechmann condensation under solvent-free conditions

Tris(pentafluorophenyl)borane [B(C6F5)3] catalyzed simple, efficient and environmentally benign protocol has been developed for the Pechmann condensation using variety of phenols and β-ketoesters under solvent-free conditions to afford coumarin derivatives. The present protocol displayed significant advantages such as low catalyst loading, short reaction time, mild reaction conditions, low toxicity, easy work-up, high yields, and compatibility with other functional groups. In addition, it is a convenient, clean, and fast alternative approach for synthesizing variety of coumarin derivatives. Moreover, the applicability of this method towards large-scale synthesis demonstrated its suitability for the industrial application. Graphic abstract: [Figure not available: see fulltext.]

Design, synthesis and biological evaluation of potential anti-AD hybrids with monoamine oxidase B inhibitory and iron-chelating effects

A series of active hybrids combining 3-hydroxypyridin-4(1H)-one and coumarin pharmacophores were designed and synthesized as potential agents for the treatment of Alzheimer's disease (AD). All the compounds exhibited excellent iron-chelating activities (p