Studies on the Total Synthesis of Hirtellanine A: Regioselective Synthesis of Benzopyran

Zheng, Shuyan; Li, Xiaoping; Tan, Hongsheng; Yu, Chunhui; Zhang, Jinghua; Shen, Zifei

doi:10.1002/ejoc.201201339

Cited by 21 publications

(15 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The synthesis of 6 began with acylation of phloroglucinol (14) with acetic anhydride in the presence of boron trifluoride etherate. [25] Condensationo fa cetophenone (15)w ith DMF in the presence of MsCl and boron trifluoride etherate led to 6 in moderate yield [26] (Scheme 2).…”

Section: Synthesismentioning

confidence: 99%

Natural and Synthetic Flavonoids as Potent Mycobacterium tuberculosis UGM Inhibitors

Villaume

N’Go

et al. 2017

Chemistry A European J

View full text Add to dashboard Cite

This study reports a novel class of inhibitors of uridine 5'-diphosphate (UDP) galactopyranose mutase (UGM) derived from a screening of natural products. This enzyme is an essential biocatalyst involved in the cell wall biosynthesis of Mycobacterium tuberculosis. Flavonoids are potent inhibitors of UGM. The synthesis of novel methylated flavonoids allowed a structure-activity relationship analysis to be performed and which functional groups and structural elements were required for UGM inhibition could be determined. The binding mode of one of the best inhibitors was found to be noncompetitive. Docking simulations indicated that this molecule was likely to bind UGM in its open conformation, in a cavity recently identified as a "druggable" pocket. Importantly, two of the best inhibitors of the M. tuberculosis UGM displayed moderate activity against whole M. tuberculosis cells. This study reports the first natural products that act as inhibitor of UGM. Given the importance of natural products in medicinal chemistry, these results create new opportunities for the discovery of new antitubercular agents.

show abstract

Section: Synthesismentioning

confidence: 99%

Natural and Synthetic Flavonoids as Potent Mycobacterium tuberculosis UGM Inhibitors

Villaume

N’Go

et al. 2017

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…The synthetic route employed in preparing isolaxifolin ( 1 ) is shown in Scheme and started with the direct prenylation of apigenin ( 3 ) using 3-methyl-2-butenal in the presence of Ca(OH) 2 . The regioisomeric and chromatographically separable 2,2-dimethylated chromenes 4 (15%) and 5 (42%) were thus obtained.…”

Section: Results and Discussionmentioning

confidence: 99%

Cytotoxicity and Anti-inflammatory Properties of Apigenin-Derived Isolaxifolin

Chen

et al. 2019

J. Nat. Prod.

View full text Add to dashboard Cite

The rare flavonoid isolaxifolin, a potent insecticide, has been touted as a potential grain-protecting agent. In order to assess any impact of this natural product on human health and to explore its various other biological properties, we have established a semisynthesis from the simpler but structurally related and more abundant natural product apigenin. The five-step reaction sequence has provided, for the first time, sufficient material for an indepth evaluation of the cytotoxic properties of the title natural product. The impact of isolaxifolin on certain pro-inflammatory cytokines in murine macrophage RAW 264.7 cells has also been examined. Such studies have revealed that isolaxifolin displays no toxic effects toward normal cells while displaying greater cytotoxicities against certain cancer cell lines than its synthetic precursor apigenin. Furthermore, unlike apigenin, isolaxifolin only reduced NO, TNF-α, and IL-6 secretions in LPS-induced RAW 264.7 cells in a rather modest and dose-independent manner.

show abstract

“…Additionally, 54 previously reported compounds were identified as dicycloeuchrestaflavanone B ( 22 ), cudraflavone A ( 23 ), 5,7-dihydroxychromone ( 24 ), isoimperatorin ( 25 ), xanthyletin ( 26 ), 4-hydroxybenzaldehyde ( 27 ), glutinol ( 28 ), achilleol A ( 29 ), oleic acid ( 30 ), demethylsuberosin ( 31 ), 5-dehydroxybavachinone A ( 32 ), imperatorin ( 33 ), isoencecalin ( 34 ), 2,4-dihydroxymethylbenzoate ( 35 ), 4-(methoxymethyl)phenol ( 36 ), α-amyrin ( 37 ), gentisein, toxyloxanthone B, 2-deprenylrheediaxanthone B, 4′- O -demethylcrotaramin, brosimine B, pinocembrin, euchrestaflavanone C, 4′-hydroxyisolonchocarpin, naringenin, 6-prenylnaringenin, tomentosanol D, dalenin, parvisoflavone A, alpinumisoflavone, 8-hydroxygenistein, laburnetin, biochanin A, erythrinins B, C, and G, , cudracuspiphenone A, eriosematin A, decursinol angelate, cis -3′,4′-diisovalerylkhellactone, 7-hydroxycoumarin, 8-methoxypsoralen, bergapten, hyuganin C, 4-hydroxy-3-(4-hydroxybenzyl)benzyl methyl ether, 2,4-bis(4-hydroxybenzyl)phenol, 4-hydroxymethylbenzoate, vanillin, 3-methoxycarbonylindole, 4-hydroxybenzalacetone, lanosterol, γ-hexadecanolactone, hexadecanoic acid, and 9,12-octadecadienoic acid, by comparing their spectroscopic data with published literature values.…”

Section: Resultsmentioning

confidence: 99%

Chemical Constituents Isolated from the Root Bark of Cudrania tricuspidata and Their Potential Neuroprotective Effects

Kwon¹,

Hiep²,

Kim

et al. 2016

J. Nat. Prod.

View full text Add to dashboard Cite

Seventy-five compounds, including 21 new compounds (1-21), were isolated from the root bark of Cudrania tricuspidata. The structures of the isolated compounds were elucidated by interpretation of their spectroscopic data. All isolated compounds were evaluated for their neuroprotective effects against 6-hydroxydopamine (6-OHDA)-induced cell death, and nine compounds had activities with EC50 values of 1.9-30.2 μM. The 75 isolated compounds along with 34 previously reported xanthones were tested also for neuroprotective effects against the 1-methyl-4-phenylpyridinium ion (MPP(+)) and oxygen glucose deprivation (OGD)-induced cell death. Three compounds were active against MPP(+)-induced cell death with EC50 values of 0.2-10.3 μM, and 23 compounds were active in the OGD model with EC50 values of 2.9-35.5 μM.

show abstract

Studies on the Total Synthesis of Hirtellanine A: Regioselective Synthesis of Benzopyran

Cited by 21 publications

References 32 publications

Natural and Synthetic Flavonoids as Potent Mycobacterium tuberculosis UGM Inhibitors

Natural and Synthetic Flavonoids as Potent Mycobacterium tuberculosis UGM Inhibitors

Cytotoxicity and Anti-inflammatory Properties of Apigenin-Derived Isolaxifolin

Chemical Constituents Isolated from the Root Bark of Cudrania tricuspidata and Their Potential Neuroprotective Effects

Contact Info

Product

Resources

About