10387-49-2

Usage

InChI:InChI=1/C11H8O4/c1-7(12)14-9-4-2-8-3-5-11(13)15-10(8)6-9/h2-6H,1H3

Upstream product

• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 75-36-5 acetyl chloride 
• 507-09-5 tiolacetic acid 
• 64-19-7 acetic acid 
• 52924-53-5 acetic acid 4-formyl-3-hydroxyphenyl ester 
• 122-59-8 2-phenoxyacetic acid 
• 27542-85-4 4-acetoxycinnamic acid 
• 878-00-2 4-formylphenyl acetate 
• 102-29-4 Resorcinol monoacetate 
• 108-46-3 recorcinol 
• 471-25-0 Propiolic acid 

Downstream Products

• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 6748-68-1 8-acetyl-7-hydroxycoumarin 
• 2555-29-5 8-acetyl-7-hydroxy-4-methyl-2H-chromen-2-one 
• 90104-85-1 8-Benzoyl-7-hydroxycoumarin 
• 20312-83-8 8-Benzoyl-7-hydroxy-4-methylcoumarin 
• 99699-42-0 3-(2,4-dihydroxyphenyl)prop-2-enoic acid 
• 2009-24-7 8-hydroxypsoralen 
• 65535-50-4 7-Benzyloxy-8-hydroxycoumarin 
• 65535-49-1 8-acetyl-7-benzyloxycoumarin 
• 65535-51-5 8-acetoxy-7-benzyloxycoumarin 
• 477770-78-8 daphneticin 
• 83327-22-4 (2R,3R)-daphneticin 
• 83327-22-4 (2S,3S)-daphneticin 
• 477770-86-8 (1S,2R)-7-hydroxy-8-[2,3-epoxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]coumarin 

Relevant academic research and scientific papers

A fluorescent probe for a lewisite simulant

Herein, we report for the first time a highly sensitive fluorescent probe for the detection of an organoarsenic blister agent simulant, arsenic trichloride (AsCl3). This probe showed high selectivity to AsCl3, in the presence of other metal ions, even at low concentrations. Moreover, quantitative determination of AsCl3 in soil was achieved with a detection limit of 61.2 μmol kg-1 that is sufficiently lower than the reported LD50 of lewisite.

Coumarin-based fluorescent 'AND' logic gate probes for the detection of homocysteine and a chosen biological analyte

With this research we set out to develop a number of coumarin-based 'AND' logic fluorescence probes that were capable of detecting a chosen analyte in the presence of HCys. Probe JEG-CAB was constructed by attaching the ONOO- reactive unit, benzyl boronate ester, to a HCys/Cys reactive fluorescent probe, CAH. Similarly, the core unit CAH was functionalised with the nitroreductase (NTR) reactive p-nitrobenzyl unit to produce probe JEG-CAN. Both, JEG-CAB and JEG-CAN exhibited a significant fluorescence increase when exposed to either HCys and ONOO- (JEG-CAB) or HCys and NTR (JEG-CAN) thus demonstrating their effectiveness to function as AND logic gates for HCys and a chosen analyte.

Total Synthesis of the Major Metabolite of Methoxsalen

The total synthesis of the 6-coumarinylacetic acid (15), the major metabolic isolate of methoxsalen (1), starting from umbelliferone (5) is described.Several derivatives of a second metabolite, 4, were also prepared from the common intermediate aldehyde 13.This preparation involves a novel rearrangement of the bromoacetate 20 to the acetoxyphenol 21.A mechanism for the displacement reactions of the metabolite 4 and its derivative 21 implicating the transient enone 24 is presented.

Semisynthesis, ex vivo evaluation, and SAR studies of coumarin derivatives as potential antiasthmatic drugs

Asthma is a chronic inflammatory disorder that causes contraction in the smooth muscle of the airway and blocking of airflow. Reversal the contractile process is a strategy for the search of new drugs that could be used for the treatment of asthma. This work reports the semisynthesis, ex vivo relaxing evaluation and SAR studies of a series of 18 coumarins. The results pointed that the ether derivatives 1-3, 7-9 and 13-15 showed the best activity (E max = 100%), where compound 2 (42 μM) was the most potent, being 4-times more active than theophylline (positive control). The ether homologation (methyl, ethyl and propyl) in position 7 or positions 6 and 7 of coumarins lead to relaxing effect, meanwhile formation of esters generated less active compounds than ethers. The SAR analysis showed that it is necessary the presence of two small ether groups and the methyl group at position 4 (site 3) encourage biological activity through soft hydrophobic changes in the molecule, without drastically affecting the cLogP.

Optimisation of two-photon induced cleavage of molecular linker systems for drug delivery

Photoreactive linker systems for drug delivery in modern ophthalmology are crucial for the efficiency of such applications. We compare 5 different linker molecule candidates (truxillic acid and 4 dimers of coumarin derivates) in solution regarding their chemical stability and two-photon induced cleavage efficiency, and shed light into the role of molecular structure in the cleavage reaction. Dimers of the coumarin family showed much higher two-photon induced cleavage efficiency, achieving the highest reaction cross-section when tert-Butyldimethylsilyl (TBS) was used as a substituent, being almost 5-times higher than the unsubstituted coumarin dimer. Coumarin-based linker systems react promptly with nucleophilic solvents, in particular with short chain alcohols. The polarity of such solvents which do not cause a lactone ring opening seems not to influence the cleavage of the cyclobutane ring in coumarin dimers.

Fluorescent chemodosimeter for selective detection of cyanide in water

A coumarin-based fluorescent chemodosimeter with a salicylaldehyde functionality as a binding site has been developed for selective detection of cyanide anions over other anions in water at biological pH.

Rational design of a highly selective fluorescent sensor for l-histidine detection in aqueous solution

Computational studies in combination with experimental research were used to design a new rapid, selective and sensitive "turn-on" fluorescent sensor (H3) for l-histidine, which can be first quenched by Ni2+ and then recovered upon addition of His.

5-Phenylcoumarin Derivatives: Design, Synthesis, and Vasodilatory Activity

In continuation of our previous efforts towards the development of coumarin derivatives with potential vasodilatory activity, 5-phenylcoumarin derivatives were designed and synthesized. Target compounds and their precursors exhibited moderately vasodilato

Facile total synthesis of xanthotoxol

Xanthotoxol, a biologically active linear furocoumarin, has been efficiently synthesized from 7-hydroxycoumarin in six steps. The key steps included two efficient rearrangements - Fries rearrangement and Claisen rearrangement - and a Baeyer-Villiger oxidation process. The overall yield of xanthotoxol was 29%. This approach also provided a new strategy to furnish easily furocoumarins with a hydroxyl group in the framework. Copyright Taylor & Francis Group, LLC.

The behavior of certain coumarins and furocoumarins toward sulfur reagents

The behavior of 4-hydroxycoumarin (1), 7-hydroxycoumarin (2), 4-hydroxy-bergapten (3), and 4-hydroxyisopimpinellin (4) toward sulfur reagents, namely, thionyl chloride, phosphorus pentasulfide, thiolacetic acid, and Lawesson's reagent (5), was studied. The nature of products in each case depended upon the type of reactants and reaction conditions. Possible reaction mechanisms were considered, and structural elucidations of the new products were based upon compatible elementary and spectroscopic evidences. Copyright Taylor & Francis Group, LLC.