2555-20-6Relevant articles and documents
O-prenylated 3-carboxycoumarins as a novel class of 15-LOX-1 inhibitors
Jabbari, Atena,Mousavian, Mina,Seyedi, Seyed Mohamad,Bakavoli, Mehdi,Sadeghian, Hamid
, (2017)
Allyloxy, Isopentenyloxy, geranyloxy and farnesyloxy derivatives of 3-carboxycoumarin, at position 5, 6, 7, and 8, were synthesized and their inhibitory potency against human 15- lipoxygenase-1 (human 15-LOX-1) were determined. Among the synthetic coumarins, Oallyl and O-isopentenyl derivatives demonstrated no considerable lipoxygenase inhibition while O-geranyl and O-farnesyl derivatives demonstrated potent inhibitory activity. 5-farnesyloxy- 3-carboxycoumarin demonstrated the most potent inhibitory activity by IC50 = 0.74 μM while 6-farnesyloxy-3-carboxycoumarin was the weakest inhibitor among farnesyl analogs (IC50 = 10.4 μM). Bonding affinity of the designed molecular structures toward 15- LOX-1 3D structure complexed with RS75091, as potent 15-LOX-1 inhibitor, was studied by utilizing docking analysis. There was a direct relationship between lipoxygenase inhibitory potency and prenyl length chain. The ability of the prenyl portion to fill the lipophilic pocket which is formed by Ile663, Ala404, Arg403, Ile400, Ile173 and Phe167 side chains can explain the observed relationship. Similarity rate between the docked models and complexed form of RS75091, from point of view of configuration and conformation, could explain inhibitory potency variation between each prenyloxy substitution of 3-carboxycoumarins.
Solid state synthesis of substituted coumarin-3-carboxylic acids via the knoevenagel condensation under microwave irradiation
Heravi, Majid M.,Hekmatshoar, Rahim,Emamgholizadeh, Maryam
, p. 1893 - 1896 (2004)
Synthesis of substituted coumarin-3-carboxylic acids using the Knovenagel reaction of malonic acid and O-hydroxyaryl aldehydes supported onto HZSM-5 zeolite under microwave irradiation is described.
Green synthesis method of coumarin-3-carboxylic acid compound
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Paragraph 0053-0061; 0074, (2021/06/26)
The invention relates to a green synthesis method of a coumarin-3-carboxylic acid compound. The synthesis process of the coumarin-3-carboxylic acid compound is as follows: R1 is H, Cl, Br, NO2, CH3 and HO. A series of coumarin-3-carboxylic acid compounds are synthesized in one step without a catalyst by taking R1-substituted salicylaldehyde and Meldrum's acid as raw materials and water as a reaction medium, the process steps are simple, the method has universality, reaction liquid can be repeatedly added for reaction, no waste or waste liquid is generated, the yield of a target product is greater than 54.3%, and the method is an environment-friendly green synthesis method.
Synthesis of xanthene and coumarin derivatives in water by using β-Cyclodextrin
Kamat, Siddharth R.,Mane, Ananda H.,Patil, Audumbar D.,Lohar, Trushant R.,Salunkhe, Rajashri S.
, p. 911 - 924 (2020/11/09)
Simple and green procedure was developed for the synthesis of various xanthene and coumarin derivatives using beta-cyclodextrin (β-CD) as reusable catalyst at 70?°C in water. Condensation of salicylaldehyde (1?mmol) and dimedone (2?mmol) or 1,3 cyclohexadione (2?mmol) gave corresponding xanthene derivatives, while condensation of salicylaldehyde (1?mmol) with Meldrum’s acid (1?mmol) or 4-Hydroxy-6-methyl-2H-pyran-2-one (1?mmol) gave respective coumarin derivatives in impressive yields. Involvement of β-CD as catalyst was ascertained by inclusion complex evaluation of β-CD-salicylaldehyde with 1H NMR analysis at 70?°C. Graphic abstract: [Figure not available: see fulltext.].
