155272-55-2

Basic information

• Product Name: 7-(2-bromoethoxy)-2H-chromen-2-one
• CAS NO: 155272-55-2
• Molecular Formula: C₁₁H₉BrO₃
• Molecular Weight: 269.0914
• Mol File: 155272-55-2.mol

Chemical Properties

• Boiling Point: 412.3°C at 760 mmHg
• Flash Point: 203.1°C
• Density: 1.575g/cm³
• Vapor Pressure: 5.24E-07mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: 7-(2-bromoethoxy)-2H-chromen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-(2-bromoethoxy)-2H-chromen-2-one(155272-55-2)
• EPA Substance Registry System: 7-(2-bromoethoxy)-2H-chromen-2-one(155272-55-2)

Safety Data

• Hazardous Substances Data: 155272-55-2(Hazardous Substances Data)

Upstream product

• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 106-93-4 ethylene dibromide 
• 17575-15-4 4-hydroxy-7-methoxycoumarine 
• 540-51-2 2-bromoethanol 
• 1530-45-6 (carbethoxymethyl)triphenylphosphonium bromide 
• 74-96-4 ethyl bromide 
• 108-46-3 recorcinol 
• 603-35-0 triphenylphosphine 

Downstream Products

• 1580506-76-8 2-nitro-N-(2-(2-oxo-2H-chromen-7-yloxy)ethyl)-N-(prop-2-ynyl)benzenesulfonamide 

Relevant articles and documents

1,3,5-triazaspiro[5.5]undeca-2,4-dienes as selective Mycobacterium tuberculosis dihydrofolate reductase inhibitors with potent whole cell activity

The emergence of multi- and extensively-drug resistant tubercular (MDR- and XDR-TB) strains of mycobacteria has limited the use of existing therapies, therefore new drugs are needed. Dihydrofolate reductase (DHFR) has recently attracted much attention as

Reversible photoreduction of Cu(II)-coumarin metal-organic polyhedra

We report a new approach for photoinduced reduction of Cu2+ that will enrich the structural diversity of coordination complexes and be a valuable contributor to the development of Cu+/Cu0-based catalysts. To realize controlled Cu2+ reduction, coumarin as a triplet quencher of excited benzophenone was tethered to Cu(ii)-metal-organic polyhedra (MOPs). The photoinduced catalytic activity of the coumarin-MOPs was also examined in a Cu(i)-catalyzed azide-alkyne cycloaddition (CuAAC).

Synthesis and bioactivity of novel coumarin derivatives

[Figure not available: see fulltext.] A series of novel coumarin derivatives were synthesized from commercially available chemical agents. All prepared compounds were evaluated for their in vitro antiproliferative activity against five selected human cancer cell lines (EC109, MGC-803, PC-3, MCF-7, and EC9706) and their in vitro antimicrobial activity against E. coli and M. albicans. 4-(3-Bromopropoxy)-2H-chromen-2-one exhibited the highest growth inhibition against MGC-803 cell line (IC50 47.7 μM) and 7-(2-bromoethoxy)-2H-chromen-2-one exhibited the highest growth inhibition against MCF-7 cell line (IC50 48.3 μM). The latter compound was also the most active against E. coli (MIC50 0.27 μg/ml).

Synthesis and evaluation of 7-substituted coumarin derivatives as multimodal monoamine oxidase-B and cholinesterase inhibitors for the treatment of Alzheimer's disease

A series of 7-substituted coumarin derivatives were designed and synthesised to display ChE and MAO-B inhibitory activity. The compounds consisted out of a coumarin structure (MAO-B inhibitor) and benzyl-, piperidine-, N-benzylpiperidine- or p-bromo-N-benzylpiperizine moiety, resembling the N-benzylpiperidine function of donepezil (ChE inhibitor), connected via an alkyl ether linkage at the 7 position. The biological assay results indicated that all the compounds (1–25) displayed selective inhibition to hMAO-B over hMAO-A, with the benzyloxy series (1–8, 10–13) showing nano-molar hMAO-B inhibition (IC50: 0.5–73?nM). Limited ChE inhibitory activity was however observed for the benzyloxy series with the exception of 2 and especially 3 showing selective BuChE inhibition. From this series 3 showed the best multifunctional activity (eqBuChE IC50?=?0.96?μM, hMAO-A IC50?=?2.13?μM, hMAO-B IC50?=?0.0021?μM). Within the N-benzylpiperidine (16–19) and p-bromo-N-benzylpiperizine (21–24) series the compounds in general showed moderate ChE and MAO-B inhibitory activity. Of these compounds 19 was the most potent multifunctional agent showing good eeAChE and eqBuChE inhibition (IC50?=?9.10?μM and 5.90?μM, respectively), and relatively potent and selective hMAO-B inhibition (IC50?=?0.30?μM, SI?= >33). Molecular modeling revealed that 19 was able to bind simultaneously to the CAS, mid-gorge and PAS sites of AChE and BuChE suggesting that it will be able to inhibit AChE induced Aβ aggregation. From this study, compounds that 3 and 19 can be considered as promising multifunctional lead compounds.

Design, synthesis and evaluation of coumarin-pargyline hybrids as novel dual inhibitors of monoamine oxidases and amyloid-β aggregation for the treatment of Alzheimer's disease

A series of coumarin-pargyline hybrids (4a-x) have been designed, synthesized and evaluated as novel dual inhibitors of Alzheimer's disease (AD). Most of the compounds exhibited a potent ability to inhibit amyloid-β (Aβ) aggregation and monoamine oxidases

Synthesis and biological evaluation of coumarin derivatives containing imidazole skeleton as potential antibacterial agents

Emergence of multidrug-resistant bacteria causes an urgent need for new generation of antibiotics, which may have a different mechanism of inhibition or killing action from the existing. Here, we report on the design, synthesis, and biological evaluation of thirty-nine coumarin derivatives in order to solve the antibacterial resistance by targeting at the inhibition of biosynthesis pathway of fatty acids. Their antibacterial activities against Escherichia coli, Staphylococcus aureus, Streptococcus agalactiae, and Flavobacterium cloumnare are tested and action mechanism against the key enzyme in bacterial fatty acid synthesis pathway are studied. The results show that compounds 13 and 18 have potent and broad spectrum antimicrobial activity. In addition, 9, 14 and 19 show eminent antimicrobial efficacy toward S. aureus, S. agalactiae, and F. cloumnare. Mechanistically, coumarin derivatives display the antibacterial activity via the control of FabI and FabK function. The structure-activity relationship analysis indicate that the length of linker and imidazole substitute group could significantly influence the antimicrobial activity, as well as the inhibitory activity against FabI and FabK. The structural optimization analysis of coumarin suggest that derivatives 9, 13, 14, 18 and 19 could be a viable way of preventing and controlling bacteria and considered as promising lead compounds for the development of commercial drugs.

Chiral recognition by hemicarcerand-like host in aqueous solution

The synthesis and binding properties of a hydrophilic hemicarcerand-like host with three chiral linker groups and one enlarged opening, that is partially blocked by two appending coumarin moieties, are reported. The complexation behavior towards three ach

Discovery of novel dual-active 3-(4-(dimethylamino)phenyl)-7-aminoalcoxy-coumarin as potent and selective acetylcholinesterase inhibitor and antioxidant

A series of 3-substituted-7-aminoalcoxy-coumarin was designed and evaluated as cholinesterase inhibitors and antioxidants. All compounds were effective in inhibiting AChE with potencies in the nanomolar range. The 3-(4-(dimethylamino)phenyl)-7-aminoethoxy-coumarin (6a) was considered a hit, showing good AChE inhibition potency (IC50 = 20 nM) and selectivity (IC50 BuChE/AChE = 354), quite similar to the reference drug donepezil (IC50 = 6 nM; IC50 BuChE/AChE = 365), also presenting antioxidant properties, low citotoxicity and good-predicted ADMET properties. The mode of action (mixed-type) and SAR analysis for this series of compounds were described by means of kinetic and molecular modeling evaluations.

Synthesis of N-substituted indole derivatives as potential antimicrobial and antileishmanial agents

Leishmaniasis and microbial infections are two of the major contributors to global mortality and morbidity rates. Hence, development of novel, effective and safer antileishmanial and antimicrobial agents having reduced side effects are major priority for researchers. Two series of N-substituted indole derivatives i.e. N-substituted indole based chalcones (12a-g) and N-substituted indole based hydrazide-hydrazones (18a-g, 19a-f, 21 a-g) were synthesized. The synthesized compounds were characterized by 1H NMR, 13C NMR, Mass and FT-IR spectral data. Further these derivatives were evaluated for their antimicrobial potential against Escherichia coli, Bacillus subtilis, Pseudomonas putida and Candida viswanathii, and antileishmanial potential against promastigotes of Leishmania donovani. Compounds 18b, 18d and 19d exhibited significant activity with an IC50 of 0.19 ± 0.03 μM, 0.14 ± 0.02 μM and 0.16 ± 0.06 μM against B. subtilis which was comparable to chloramphenicol (IC50 of 0.25 ± 0.03 μM). Compounds 12b and 12c exhibited an IC50 of 24.2 ± 3.5 μM and 21.5 ± 2.1 μM in the antileishmanial assay. Binding interactions of indole based hydrazide-hydrazones were studied with nitric oxide synthase in silico in order to understand the structural features responsible for activity.

Synthesis, biological activity and multiscale molecular modeling studies of bis-coumarins as selective carbonic anhydrase IX and XII inhibitors with effective cytotoxicity against hepatocellular carcinoma

A series of novel bis-coumarin derivatives containing triazole moiety as a linker between the alkyl chains was synthesized and their inhibitory activity against the human carbonic anhydrase (hCA) isoforms I, II, IX and XII were evaluated. In addition, cytotoxic effects of the synthesized compounds on renal adenocarcinoma (769P), hepatocellular carcinoma (HepG2) and breast adeno carcinoma (MDA-MB-231) cell lines were examined. While the hCA I and II isoforms were inhibited in the micromolar range, the tumor-associated isoform hCA IX and XII were inhibited in the high nanomolar range. 4-methyl-7-((1-(12-((2-oxo-2H-chromen-7-yl)oxy)dodecyl)-1H-1,2,3-triazol-4-yl)methoxy)-2H-chromen-2-one (5p) showed the strongest inhibitory activity against hCA IX with the Ki of 144.6 nM and 4-methyl-7-((1-(10-((2-oxo-2H-chromen-7-yl)oxy)decyl)-1H-1,2,3-triazol-4-yl)methoxy)-2H-chromen-2-one (5n) exhibited the highest hCA XII inhibition with the Ki of 71.5 nM. In order to better understand the inhibitory profiles of studied molecules, multiscale molecular modelling approaches were applied. Low energy docking poses of studied molecules at the binding sites of targets have been predicted. In addition, electrostatic potential surfaces (ESP) for binding sites were also generated to understand interactions between proteins and active ligands.