1211944-10-3Relevant academic research and scientific papers
Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: Experimental and computational evidence for intramolecular and intermolecular C-F?H-C bonds
Grimmer, Craig,Mzozoyana, Vuyisa,Van Heerden, Fanie R.
, p. 190 - 199 (2020)
4-(2-Fluorophenyl)-7-methoxycoumarin (6) was synthesized by Pechmann reaction under mild conditions via a three-step reaction. The solution-state 1H NMR spectra of 6 showed a strong intramolecular interaction between F and H5 (JFH = 2.6 Hz) and 13C NMR suggested that this C-F?H-C coupling is a through-space interaction. The 2D 19F-{1H} HOESY and 1H-{19F} 1D experiments were done to confirm this F?H interaction. The single crystal X-ray structure and the DFT-optimized structure showed that the fluorinated phenyl ring favors the orientation with the fluorine atom closer to H5 than H3. The X-ray structure also showed the existence of the intermolecular C-F?H-C interaction.
Synthesis of Novel Anti-inflammatory Psoralen Derivatives?-?Structures?with?Distinct?Anti-Inflammatory?Activities
Timonen, Juri M.,Vuolteenaho, Katriina,Lepp?nen, Tiina,Nieminen, Riina M.,Aulaskari, Paula,J?nis, Janne,Vainiotalo, Pirjo,Moilanen, Eeva
, p. 2590 - 2597 (2018/09/25)
As a continuum to our work with coumarins, 12 psoralens were synthesized and evaluated for their anti-inflammatory activity. Psoralens were prepared in three steps; at first, 7-hydroxycoumarins were synthesized by von Pechmann condensation and then converted to 7-(2-oxopropoxy)coumarins. In the final step, a fused furan ring was introduced in an intramolecular ring-formation reaction. Based on a SciFinder search, two out of the 12 synthesized psoralen derivatives (compounds 9 and 12) were found to be novel. The derivatives displayed anti-inflammatory activity by suppressing iNOS and IL-6 expression, but their mechanism of action seemed to be dependent on the substitution. Compound 6 with propyl side chain inhibited NF-κB mediated transcription, while compound 10 with a phenyl substituent down-regulated iNOS expression in a posttranscriptional manner. The results introduce psoralen derivatives as promising anti-inflammatory compounds with potential for treatment of conditions involving iNOS and/or IL-6-mediated adverse responses.
Inhibitory effects and structural insights for a novel series of coumarin-based compounds that selectively target human CA IX and CA XII carbonic anhydrases
De Luca, Laura,Mancuso, Francesca,Ferro, Stefania,Buemi, Maria Rosa,Angeli, Andrea,Del Prete, Sonia,Capasso, Clemente,Supuran, Claudiu T.,Gitto, Rosaria
, p. 276 - 282 (2017/12/07)
Coumarin derivatives are a peculiar class of inhibitors of the family of metalloenzymes carbonic anhydrases (CA, EC 4.2.1.1). Several coumarins display higher affinity and selectivity toward most relevant and druggable CA isoforms. By decorating the natur
Synthesis and anti-inflammatory effects of a series of novel 7-hydroxycoumarin derivatives
Timonen, Juri M.,Nieminen, Riina M.,Sareila, Outi,Goulas, Antonis,Moilanen, Lauri J.,Haukka, Matti,Vainiotalo, Pirjo,Moilanen, Eeva,Aulaskari, Paula H.
experimental part, p. 3845 - 3850 (2011/11/13)
A number of 7-hydroxycoumarins have been synthesised by Pechmann cyclisation using differently substituted resorcinols employing perchloric acid as the condensing agent. All the compounds have been characterised by analytical and spectroscopic methods. The anti-inflammatory properties were tested with LPS-induced inflammation in J774 macrophages. Expression of iNOS and COX-2 was determined by Western blot, NO by nitrite assay and IL-6 by ELISA analyses. Fifteen of the tested 7-hydroxycoumarins also inhibited IL-6 production but none of them had any major inhibitory effect on COX-2 expression.
