10549-62-9

Usage

InChI:InChI=1/C16H19NO3/c1-11-9-15(19)20-16-12(11)5-6-14(18)13(16)10-17-7-3-2-4-8-17/h5-6,9,18H,2-4,7-8,10H2,1H3

Upstream product

• 110-89-4 piperidine 
• 50-00-0 formaldehyd 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 108-46-3 recorcinol 

Relevant academic research and scientific papers

Inhibition of neutrophil O2- production by unsymmetrical methylene derivatives of benzopyrans: Their use as potential antiinflammatory agents

Some unsymmetrical derivatives of benzopyrans 9 were synthesized and tested to verify their PKC inhibitory activity. For this purpose, the Mannich bases of 7-hydroxycoumarins 6 were treated with 2-(dialkylamino)benzopyran-4-ones or 3-(dialkylamino)naphtho[2,1-b]pyran-1-ones 8 in the presence of acetic or propionic anhydride, yielding compounds 9. Human neutrophils stimulated with either PMA and f-MLF were used as the cellular model. The efficiency of the compounds 9 was established on their capacity to reduce the O2- production by activated human neutrophils. Compounds 9d and 9f, bearing an acetoxy group in position 7 of the chromone moiety, seem to counteract the neutrophil activation efficiently.

Piperazine and piperidine-substituted 7-hydroxy coumarins for the development of anti-inflammatory agents

Coumarins (2H-1-benzopyran-2-one), derivatives that can be isolated from several plants, have been reported for their anticoagulant, antimicrobial, anti-inflammatory, or anticancer activity. Some of these structures are currently approved for the treatment of cardiovascular diseases, as antibiotics or as an anticancer drug. Given the great potential of this structure and the limited number of studies that focus on molecules derived from carbon 8 of the benzopyranone heterocycle, we synthesized in this project 38 coumarin derivatives by substituting carbon 8 of the benzopyran ring with some aromatic and aliphatically substituted piperidines and piperazines. As a few of these structures were already shown to exhibit some carbonic anhydrase (CA) inhibition and as CA enzymes are reported to be closely related to inflammation, the synthesized derivatives were evaluated for their anti-inflammatory activity in vitro. The results indicated that compounds 20 and 31 revealed promising anti-inflammatory activity, as they demonstrated better activity than the reference drugs.

Mannich bases of hydroxycoumarins: Synthesis, DFT/QTAIM computational study and assessment of biological activity

The synthesis of six Mannich bases derived from hydroxycoumarins was carried out in moderate yields, two of these derivatives were described for the first time. Conformational analysis was performed through DFT theoretical calculations explaining the formation of stable six membered rings based on intramolecular hydrogen bonds within the structure. These findings were correlated with the antiproliferative activity. The biological activity of the Mannich bases through their antiproliferative activity in the HeLa cancer cell line is described for the first time, showing that the compounds were able to inhibit proliferation in cervical cancer by more than 60%. Likewise, the theoretical modeling of the photophysical properties was realized with promising results, showing that the HOMO-LUMO energies of the new compounds present the lowest electronic gap values for those with donor groups in their structure, which makes them potential fluorophores. This journal is

Activity of Mannich bases of 7-hydroxycoumarin against Flaviviridae

Some Mannich bases of 7-hydroxycoumarin (2) and their simple derivatives (3 and 4) were prepared and tested against viruses containing single-stranded, positive-sense RNA genomes (ssRNA+). This study was directed toward Flaviviridae and, in particular, HCV surrogate viruses (BVDV, YFV). The 7-hydroxy derivatives 2 were generally devoid of activity, but when position 7 was propylated, the resulting 7-propyloxy derivatives 3 were in some cases endowed with an interesting activity against BVDV. The formation of 7-benzoyl derivatives 4 gave compounds generally lacking in activity against Flaviviridae, whereas the appearance of activity against RSV has been observed. Also some unsymmetrical methylene derivatives 5-7 (namely coumarins bridged to chromones or indoles) were found moderately active in antiviral tests. Derivatives 3 were submitted to a molecular modeling study using DNA polymerase of HCV as a target. The good correlation between calculated molecular modeling IC50 and experimental EC50 indicates that DNA polymerase is potentially involved in the inhibition of surrogate HCV viruses.

Claisen rearrangement of 3-bromo-, 3,6-dibromo-, 3,8-dibromo- and 8- iodo/aminomethyl/acetyl-7-allyloxy-4-methylcoumarins

7-Hydroxy-4-methylcoumarin 1 has been brominated under different conditions to obtain the corresponding 3-bromo-2; 3,6-dibromo- 4; 3,8- dibromo- 3; and 3,6,8-tribromo- 8 derivatives. The 24 are allylated and subjected to Claisen rearrangement in N,N-DMA when only 8-allyl-7-hydroxy-4- methylcoumarin 13 is obtained. The Claisen rearrangement of 8-iodo and 8- aminomethyl coumarins also give 13. In all these rearrangements the 8- substituent is removed and the migration takes place at the 8-position. The N,N-DMA serves as the scavenger for the substituent lost. The Claisen rearrangement of 8-acetyl-7-allyloxy-4-methylcoumarin gives 8-acetyl-6-allyl- 7-hydroxy-4-methylcoumarin, in which the acetyl group remains intact.