52591-14-7Relevant academic research and scientific papers
Study of plant coumarins 1. Transformations of peucedanin
Osadchii,Shul'ts,Shakirov,Tolstikov
, p. 375 - 379 (2006)
The structure of 2-bromooreoselon, which was prepared by bromination of peucedanin or oreoselon with molecular bromine, was established. The compositions and structures of the reaction products of this bromide with amines, such as pyridine, triethylamine, and morpholine, as well as with sodium acetate and potassium hydroxide were studied. The reaction of peucedanin with m-chloroperoxybenzoic acid affords peuruthenicin isobutyrate.
Secondary metabolites of Peucedanum tauricum fruits
Tesso, Hailemichael,Koenig, Wilfried A.,Kubeczka, Karl-Heinz,Bartnik, Magdalena,Glowniak, Kazimierz
, p. 707 - 713 (2005)
From the essential oil of fruits of Peucedanum tauricum Bieb., two guaiane type sesquiterpene hydrocarbons guaia-1(10),11-diene (1) and guaia-9,11-diene (2) were identified. The structures of 1 and 2 were assigned by 1D and 2D NMR analysis. The relative configurations of the compounds were established by 2D-NOESY experiments while the absolute configurations were deduced through chemical correlations with (+)-γ-gurjunene (9) and capillary GC analysis using modified cyclodextrins as the stationary phases. From the dichloromethane extract of the less volatile fraction of the fruits, coumarins, viz. peucedanin (3), oxypeucedanin hydrate (4) and officinalin isobutyrate (5) were isolated. Compound 5 was confirmed to be 6-carbomethoxy-7-isobutyroxycoumarin by its 1D and 2D NMR data as well as by conversion into officinalin (7) by alkaline hydrolysis. Peuruthenicin, a positional isomer of officinalin, is assigned structure 8 on spectral basis. Bergapten (6) was identified by its mass spectrum. This is the first report on the isolation of compounds 4 and 5 from P. tauricum.
Synthesis, in vivo anticoagulant evaluation and molecular docking studies of bicoumarins obtained from furocoumarin peucedanin
Lipeeva, Alla V.,Khvostov, Mikhail V.,Baev, Dmitry S.,Shakirov, Makhmut M.,Tolstikova, Tatijana G.,Shults, Elvira E.
, p. 674 - 683 (2016/10/18)
Background: Synthesis of 7,7-linked bicoumarins, 3,3-linked bi(2-isopropyl)psoralens as well as 1H-1,2,3-triazole linked coumarin-2,3-dihydrofurocoumarin and furocoumarin-2,3-dihydrofurocoumarin hybrids was performed by two alternative pathways, either involving a catalyzed transformations of the ethynyl derivatives of plant coumarins -peucedanin or peuruthenicin. Objective and Methods: The Sonogashira reaction of 7-ethynyl coumarins or 3-ethynyl-2-isopropylpsoralen with the subsequent coumarin triflates led to 7,7-linked bicoumarins or 3,3-linked bipsoralens. 1,2,3-Triazole linked coumarin-2,3-dihydrofurocoumarin or furocoumarin-2,3-dihydrofurocoumarin hybrids were synthesized by a regioselective Cu-catalyzed cycloaddition reaction of 2-azidooreoselone with 7-alkynylcoumarins or 3-ethynyl-2-isopropylpsoralen. Results: Pharmacological screening of synthesized bicoumarins for anticoagulant activity in vivo revealed that coumarin-dihydrofurocoumarin hybrids linked with a 1,2,3-triazole ring 20 and 22 were the most active compounds. The presented prothrombin time (PT) values comparable to the reference drug warfarin in a dose 100 mg/kg. Docking studies were undertaken to gain insight into the possible binding mode of these compounds with the coagulation factor Xa (FXa) binding site. Conclusion: The moderate toxicity of compounds 20 and 22 (LD50 valuewas more than 3000 mg/kg) encouraged the further design of therapeutically relevant analogues based on these novel type of coumarin hybrids.
Study of plant coumarins: X*.peurutenicin trifl ate in cross-coupling reactions
Makhneva,Lipeeva,Shults,Shakirov,Tolstikov
, p. 1094 - 1102 (2013/01/15)
By Suzuki cross-coupling reaction of peurutenicin trifl ate with arylboric, furanylboric, pyridinylboric, and indolylboric acids the corresponding 7-aryl(hetaryl)coumarins were synthesized. The high activity of hetarylsubstituted boric acids in the Suzuki
