Synthesis and biological evaluation of glycosylated psoralen derivatives

Chen, Chao-Yue; Sun, Jianguo; Liu, Fei-Yan; Fung, Kwok‐Pui; Wu, Ping; Huang, Zhi‐Zhen

doi:10.1016/j.tet.2012.01.090

Cited by 21 publications

(16 citation statements)

References 44 publications

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“…The reaction is well known to occur for coumarins in basic solutions. [37] Compound 4 showed the most intense H 2 O loss (41% relative abundance in the MS 2 spectrum), followed by elimination of CO, providing the base peak in its MS 3 spectrum. Further MS 4 and MS 5 spectra showed two more CO eliminations (see Supporting Information).…”

Section: Primary Eliminations From the Acetonyloxy Groupmentioning

confidence: 98%

Low‐energy collision‐induced dissociation tandem mass spectrometry of 7‐acetonyloxycoumarins

Timonen

Romppanen

Aulaskari

et al. 2013

Rapid Comm Mass Spectrometry

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The studied coumarins showed interesting characteristics in low-energy CID due to the presence of a 7-acetonyloxy group, leading to both even- and odd-electron product ions. The main dissociation channels observed for each compound were highly dependent on the substituents in the benzopyranone ring. The present results will advance our knowledge on the dissociation characteristics of both synthetic and natural coumarins.

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Section: Primary Eliminations From the Acetonyloxy Groupmentioning

confidence: 98%

Low‐energy collision‐induced dissociation tandem mass spectrometry of 7‐acetonyloxycoumarins

Timonen

Romppanen

Aulaskari

et al. 2013

Rapid Comm Mass Spectrometry

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“…Another example is the synthesis of target psoralen moiety 4-4’-dimethylxanthotoxol ( 31 ) [ 33 ]. Initially, commercial pyrogallol ( 27 ) was employ-yed as a starting material to undergo Pechmann reaction with ethylacetoacetate in the solution of 12 M sulfuric acid.…”

Section: Formation Of Furan Ring Onto Furocoumarinmentioning

confidence: 99%

Psoralen Derivatives: Recent Advances of Synthetic Strategy and Pharmacological Properties

Jamalis

Yusof

Chander³

et al. 2020

AIAAMC

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Introduction: Psoralen or furocoumarin is a linear three ring heterocyclic compound. Psoralens are planar, tricyclic compounds, consisting of a furan ring fused to a coumarin moiety. Psoralen has been known for a wide spectrum of biological activities, spanning from cytotoxic, photosensitizing, insecticidal, antibacterial to antifungal effect. Thus, several structural changes were introduced to explore the role of specific positions with respect to the biological activity. Convenient approaches utilized for the synthesis of psoralen skeleton can be categorized into two parts: (i) the preparation of the tricyclic ring system from resorcinol, (ii) the exocyclic modification of the intact ring system. Conclusion: Furthermore, although psoralens have been used in diverse ways, we mainly focus in this work on their clinical utility for the treatment of psioraisis, vitiligo and skin-related disorder.

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“…13 Therefore, direct O-glycosidation of 2 was performed with peracetyl glycosyl bromide 18 under Koennigs-Knorr conditions in a biphasic media (CH 2 Cl 2 /H 2 O) using tetrabutylammonium bromide (TBAB) as phase-transfer catalyst and NaOH as a base (Scheme 5). 19 Again, this stage was troublesome owing to the aquatic basic conditions, which caused deacetylation of the sugar moiety and the product couldn't be confirmed clearly. At this juncture, we decided to avoid this aquatic environment by using quinoline and silver oxide as insoluble halophile promotor.…”

Section: Letter Syn Lettmentioning

confidence: 99%

Total Synthesis of Eleuthoside A; Application of Rh-Catalyzed Intramolecular Cyclization of Diazonaphthoquinone

Othman

Otsuka

Takahashi

et al. 2017

Synlett

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The first total synthesis of (±)-eleutherol and eleuthoside A, the natural cytotoxic substances extracted from medicinal Indonesian plant, is described. First, the synthesis of (±)-eleutherol has been accomplished in nine steps starting from bromo methoxy aldehyde with the aid of diazo-transfer chemistry approach. Second, a metal-catalyzed intramolecular cyclization reaction of the corresponding diazonaphthoquinone led to the desired eleuotherol, which served as a precursor to eleuthoside A. Then, several glycosidation routes, using different glucosyl donors, were experimented to reach effective O-glycosidation of eleutherol. The only successful strategy involved Koenigs–Knorr glycosidation using peracetyl glycosyl bromide in the presence of Ag2O and quinoline. This strategy furnished our desired acetylated glycoside of β-configuration, regioselectively. Finally, deacetylation and successive separation of diastereomers were conducted to give eleuthoside A.

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Synthesis and biological evaluation of glycosylated psoralen derivatives

Cited by 21 publications

References 44 publications

Low‐energy collision‐induced dissociation tandem mass spectrometry of 7‐acetonyloxycoumarins

Low‐energy collision‐induced dissociation tandem mass spectrometry of 7‐acetonyloxycoumarins

Psoralen Derivatives: Recent Advances of Synthetic Strategy and Pharmacological Properties

Total Synthesis of Eleuthoside A; Application of Rh-Catalyzed Intramolecular Cyclization of Diazonaphthoquinone

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