Antitumor agents 287. Substituted 4-amino-2H-pyran-2-one (APO) analogs reveal a new scaffold from neo-tanshinlactone with in vitro anticancer activity

Dong, Yizhou; Nakagawa‐Goto, Kyoko; Lai, Chin Yu; Morris‐Natschke, Susan L.; Bastow, Kenneth F.; Lee, Kuo Hsiung̀

doi:10.1016/j.bmcl.2011.02.084

Cited by 34 publications

(14 citation statements)

References 9 publications

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“…In the literature, a variety of 2,2-dimethyl-6-(2-oxoalkyl)-1,3-dioxin-4-ones 10 have been reported to undergo thermal cyclization smoothly to afford 6-substituted 4-hydroxy-2-pyrones 11 under conditions originally reported by Sato and coworkers ( Fig 5 ), [ 71 , 62 , 65 – 67 , 69 , 70 ]. The reaction proceeds through an acyl ketene intermediate, which is generated by a retro-Diels-Alder reaction upon heating.…”

Section: Resultsmentioning

confidence: 90%

Novel, male-produced aggregation pheromone of the cerambycid beetle Rosalia alpina, a priority species of European conservation concern

et al. 2017

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Several recent studies have demonstrated the great potential for exploiting semiochemicals in ecology and conservation studies. The cerambycid beetle Rosalia alpina represents one of the flagship species of saproxylic insect biodiversity in Europe. In recent years its populations appear to have declined substantially, and its range has shrunk considerably as a result of forest management and urbanization. Here, we collected volatile chemicals released by males and females of R. alpina. Analyses of the resulting extracts revealed the presence of a single male-specific compound, identified as a novel alkylated pyrone structure. In field bioassays in Slovenia, traps baited with the synthesized pyrone captured both sexes of R. alpina, indicating that the pyrone functions as an aggregation pheromone. Our results represent the first example of a new structural class of pheromones within the Cerambycidae, and demonstrate that pheromone-baited traps can provide a useful tool for sampling R. alpina. This tool could be particularly useful in the ongoing development of conservation strategies for the iconic but endangered Alpine longicorn.

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Section: Resultsmentioning

confidence: 90%

Novel, male-produced aggregation pheromone of the cerambycid beetle Rosalia alpina, a priority species of European conservation concern

et al. 2017

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“…Our research on the development of a novel synthetic route toward 3-aryl-5-azaisocoumarin commenced with the preparation of cycloisomerization precursors. As shown in Scheme 1 , N -pyranonyl propargylamine precursors ( 3a – 3k ) were prepared according to literature procedures with slight modifications (Dong et al, 2011 ). The known hydroxy-2-pyrone 1 (Prasad et al, 1995 ) was treated with tosyl chloride and triethylamine to afford tosylate 2 in 92% yield.…”

Section: Resultsmentioning

confidence: 99%

Preliminary Study on Novel Expedient Synthesis of 5-Azaisocoumarins by Transition Metal-Catalyzed Cycloisomerization

2020

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A preliminary study to develop a novel synthetic method for 3-aryl-5-azaisocoumarins was performed herein. The cycloisomerization of N -pyranonyl propargylamines in the AgOTf-catalyzed system efficiently afforded the desired 3-aryl-5-azaisocoumarins in a highly regioselective manner. This unprecedented method is expected as an expedient alternative synthetic route to 5-azaisocoumarins because the regioselectivity problem is circumvented, and it is easier to introduce substituents on the pyridine ring compared to previously reported intramolecular lactonization approaches.

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“…antibacterial, antifungal, antitumor, anti‐trypanosomal, antioxidant, and insecticidal –. Some natural furo‐benzochromenones (Figure , III–IV ), mainly tanshinones, tanshinlactone and neo‐tanshinlactone, isolated from Salvia miltiorrhiza are regarded as anticancer agents.…”

Section: Introductionmentioning

confidence: 99%

Urea‐Catalysed Access to Novel Spirooxindole Benzopyrans via Domino Multicomponent Cascade: Approach Towards Sustainability

Bagchi¹,

Hussen²,

Deeksha³

et al. 2019

ChemistrySelect

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A multicomponent one-pot domino reaction of 1-hydroxy-3Hbenzo[f]chromen-3-one, isatin and malononitrile/ethyl cyanoacetate is herein investigated. The methodology concludes to synthesize diversified novel spiro-benzo[f]pyranochromene derivatives in good to excellent yields. This method is compatible with different unsubstituted and substituted isatins bearing electron-donating and electron-withdrawing groups. The operational simplicity, short reaction time along with the gram scale up protocol make this synthetic process suitable for both academia as well as industry.

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Antitumor agents 287. Substituted 4-amino-2H-pyran-2-one (APO) analogs reveal a new scaffold from neo-tanshinlactone with in vitro anticancer activity

Cited by 34 publications

References 9 publications

Novel, male-produced aggregation pheromone of the cerambycid beetle Rosalia alpina, a priority species of European conservation concern

Novel, male-produced aggregation pheromone of the cerambycid beetle Rosalia alpina, a priority species of European conservation concern

Preliminary Study on Novel Expedient Synthesis of 5-Azaisocoumarins by Transition Metal-Catalyzed Cycloisomerization

Urea‐Catalysed Access to Novel Spirooxindole Benzopyrans via Domino Multicomponent Cascade: Approach Towards Sustainability

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