14386-66-4Relevant articles and documents
Synthesis, docking study and relaxant effect of 2-alkyl and 2-naphthylchromones on rat aorta and guinea-pig trachea through phosphodiesterase inhibition
Rodriguez-Ramos, Fernando,Navarrete, Andres,Gonzalez-Andrade, Martin,Alarcon, Carlos,Aguilera-Cruz, Alejandro,Reyes-Ramirez, Adelfo
, p. 17 - 25 (2013)
Chromone (4), which form the base structure of various flavonoids isolated as natural products, is capable of relaxing smooth muscle. This is relevant to the treatment of high blood pressure, asthma and chronic obstructive pulmonary disease. The former disorder involves the contraction of vascular smooth muscle (VSM), and the latter two bronchoconstriction of airway smooth muscle (ASM). One of the principal mechanisms by which flavonoids relax muscle tissue is the inhibition of phosphodiesterases (PDEs), present in both VSM and ASM. Therefore, a study was designed to analyze the structure-activity relationship of chromone derivatives in vaso- and bronchorelaxation through the inhibition of PDE. Docking studies showed that these chromones bind at the catalytic site of PDEs. Consequently, we synthesized analogs of chromones substituted at position C-2 with alkyl and naphthyl groups. These compounds were synthesized from 2-hydroxyacetophenone and acyl chlorides in the presence of DBU and pyridine, modifying the methodology reported for the synthesis of 3-acylchromones by changing the reaction temperature from 80 to 30°C and using methylene chloride as solvent, yielding the corresponding phenolic esters 10a-10h. These compounds were cyclized with an equivalent of DBU, pyridine as solvent, and heated at reflux temperature, yielding the chromones 11a-11h. Evaluation of the vasorelaxant effect of 4, 11a-11h on rat aorta demonstrated that potency decreases with branched alkyl groups. Whereas the EC50 of compound 11d (substituted by an n-hexyl group) was 8.64 ± 0.39 μM, that of 11f (substituted by an isobutyl group) was 14.58 ± 0.64 μM. Contrarily, the effectiveness of the compound is directly proportional to the length of the alkyl chain, as evidenced by the increase in maximal effect of compound 11c versus 11d (66% versus 100%) and 11e versus 11f (60% versus 96%). With an aromatic group like naphthyl as the C-2 substituent, the effectiveness was only 43%. All compounds tested on guinea pig trachea showed less than 55% effectiveness. Compounds 4, 11a-11h were evaluated as PDE inhibitors in vitro, with 11d showing the greatest effect (73%), corroborating the importance of a long alkyl chain, which inhibits the decomposition of cGMP. Docking studies showed that the compound 11d was selective for the inhibition of PDE-5.
Photosensitizers: Comprehensive Photophysics/Photochemistry and Theory of Coumarins, Chromones, their Homologues and Thione Analogues
Becker, Ralph S.,Chakravorti, Sankar,Gartner, Carlos A.,Miguel, Maria de Graca
, p. 1007 - 1020 (1993)
The photophysical-photochemical behaviour, including absorption spectra, flourescence spectra and lifetimes, phosphorescence spectra, triplet-triplet transient spectra, triplet lifetimes and quantum yields and sensitized singlet oxygen formation and yields, has been determined for many of a group of 22 carbonyl and thione compounds.These includes coumarins, psoralens, chromones and furochromone and their thiones.Many of the thiones were synthesized for the first time.Two types of theoretical calculations were carried out on the majority of the compounds.The principal goals of the research for the thiones, were (1) to produce or improve the photosensitizer capability of the compounds in vivo, (2) to shift the spectra of the compounds to significantly longer wavelength and (3) to increase the triplet and singlet oxygen quantum yields.Most of these have been largely achieved.The photosensitizing abilities of the two thiones have been evaluated using a unique testing technique employing a series of genitically engineered bacteria.
One-pot synthesis of 3-(furan-2-yl)-4: H -chromen-4-ones from 1-(2-hydroxyphenyl)butane-1,3-diones and 2,5-dimethoxy-2,5-dihydrofuran catalyzed via K10 montmorillonite under solvent-free conditions
Han, Jie,Wang, Tao,Feng, Siqi,Li, Chenchen,Zhang, Zunting
supporting information, p. 4092 - 4097 (2016/07/21)
A new, concise and efficient method of one-pot synthesis of 3-(furan-2-yl)-4H-chromen-4-ones was developed using K10 montmorillonite catalysis under solvent-free conditions. The procedure of the synthesis of 3-(furan-2-yl)-4H-chromen-4-ones was that 1-(2-hydroxyphenyl)butane-1,3-diones and 2,5-dimethoxy-2,5-dihydrofuran underwent a process of α-alkoxyalkylation in the presence of K10 montmorillonite at 80 °C for 0.5 h and continuously at 120 °C for another 0.5 h. The advantages of this method were that it was solvent-free, the K10 montmorillonite was recyclable and it had an easy work-up.
Dioxomolybdenum(VI) complexes with pyrazole based aryloxide ligands: Synthesis, characterization and application in epoxidation of olefins
Schachner, J?rg A.,Traar, Pedro,Sala, Chris,Melcher, Michaela,Harum, Bastian N.,Sax, Alexander F.,Volpe, Manuel,Belaj, Ferdinand,M?sch-Zanetti, Nadia C.
body text, p. 7642 - 7649 (2012/09/05)
Synthesis, characterization, and epoxidation chemistry of four new dioxomolybdenum(VI) complexes [MoO2(L)2] (1-4) with aryloxide-pyrazole ligands L = L1-L4 is described. Catalysts 1-4 are air and moisture stable and easy to synthesize in only three steps in good yields. All four complexes are coordinated by the two bidentate ligands in an asymmetric fashion with one phenoxide and one pyrazole being trans to oxo atoms, respectively. This is in contrast to the structure found for the related aryloxide-oxazoline coordinated Mo(VI) dioxo complex 5. This was confirmed by the determination of the molecular structures of complexes 1-3 by X-ray diffraction analyses. Compounds 1-4 show high catalytic activities in the epoxidation of various olefins. Cyclooctene (S1) is converted to its epoxide with high activity, whereas the epoxidation of styrene (S2) is unselective. Internal olefins (S3 and S4) are also acceptable substrates, as well as the very challenging olefin 1-octene (S5). Catalyst loading can be reduced to 0.02 mol % and the catalyst can be recycled up to ten times without significant loss of activity. Supportive DFT calculations have been carried out in order to obtain deeper insights into the electronic situation around the Mo atom.
