5751-49-5Relevant academic research and scientific papers
Synthesis of chiral chromanols: Via a RuPHOX-Ru catalyzed asymmetric hydrogenation of chromones
Ma, Yujie,Li, Jing,Ye, Jianxun,Liu, Delong,Zhang, Wanbin
supporting information, p. 13571 - 13574 (2019/01/05)
Chiral chromanols and their derivatives have been synthesized via a RuPHOX-Ru catalyzed asymmetric hydrogenation of chromones in high yields, >20:1 drs and with up to 99.9% ee. Control experiments show that the reaction undergoes two sequential asymmetric hydrogenation steps of the CC and CO double bonds. The reaction could be performed on a gram-scale with a relatively low catalyst loading (up to 1000 S/C), and the resulting products can be transformed to several biologically active compounds.
Carbonylative Sonogashira annulation sequence: One-pot synthesis of 4-quinolone and 4H-chromen-4-one derivatives
Ghosh, Prasanjit,Nandi, Aritra Kumar,Das, Sajal
, p. 2025 - 2029 (2018/04/25)
Carbonylative Sonogashira annulation sequence for one pot synthesis of 4-quinolone and 4H-chromen-4-one has been developed in presence of Pd-NHC catalyst. Substituted 2-iodoaniline and 2-iodophenol independently underwent in the carbonylative Sonogashira
Synthesis of functionalized chromones via organocatalysis
Wen, Sai-Shuai,Wang, Jing,Luo, Yi-Ming,Yang, Hua
, p. 9314 - 9320 (2015/03/05)
A facile and versatile organocatalytic approach to access 2-substituted and 2,3-disubstituted chromone derivatives under mild conditions was developed, which was effectively catalyzed by novel proline phenylsulphonylhydrazide or pyrrolidine. As a result, diversely functionalized chromones were obtained in up to 99% yield. In addition, further modification of the corresponding chromones afforded novel polycyclic chromones.
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 (2013/10/22)
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.
Ruthenium-NHC-catalyzed asymmetric hydrogenation of flavones and chromones: General access to enantiomerically enriched flavanones, flavanols, chromanones, and chromanols
Zhao, Dongbing,Beiring, Bernhard,Glorius, Frank
supporting information, p. 8454 - 8458 (2013/09/02)
Two to four! Readily available flavones and chromones were efficiently converted into four valuable chiral classes of O-heterocycles - flavanones, chromanones, flavanols, and chromanols - by means of an enantioselective Ru/NHC-catalyzed hydrogenation process (see scheme; NHC=N-heterocyclic carbene, PCC=pyridinium chlorochromate). Copyright
A new metal complex promoted system for highly selective synthesis of 4H-chromen-4-ones (chromones)
Nishinaga,Ando,Maruyama,Mashino
, p. 839 - 841 (2007/10/02)
Co(III)(salpr)(OH), a six coordinate cobalt Schiff base complex, promotes the highly selective conversion of 1-(o-hydroxyaryl)-1,3-diketones to 4H-chromen-4-ones under neutral conditions.
Homolytic Alkylation of Chromones in Micellar Solution
Engbersen, J. F. J.,Koudijs, A.,Plas, H. C. van der
, p. 1281 - 1283 (2007/10/02)
Treatment of an aqueous solution of chromone, the detergent sodium dodecylbenzenesulfonate, silver nitrate and an alkanoic acid, with ammonium peroxydisulfate gives 2-R-chromone .In addition 2-R-4-chromanone is formed.It is proposed that the reaction involves as intermediate the relatively stable 2-R-4-chromanon-3-yl radical and that the detergent has a micellar catalytic activity on the free radical alkylation process.
