An expedient synthesis of enantioenriched substituted (2-benzofuryl)arylcarbinols via tandem Rap–Stoermer and asymmetric transfer hydrogenation reactions

Kumaraswamy, Gullapalli; Ramakrishna, G.; Raju, Ragam; Padmaja, Mogilisetti

doi:10.1016/j.tet.2010.10.074

Cited by 25 publications

(10 citation statements)

References 29 publications

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“…(Scheme ). Meanwhile, benzofuran‐2‐carboxylic acid 4 was obtained by reacting salicylaldehyde with methyl bromoacetate and subsequent hydrolysis of the resulting ester. To obtain the corresponding 4‐chlorobenzofuran‐2‐carboxylic acid 6 , the reaction conditions were slightly modified (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…[29] (Scheme 2). Meanwhile, benzofuran-2-carboxylic acid 4 was obtained by reacting salicylaldehyde with methylb romoacetate [30] and subsequenth ydrolysis of the resulting ester.T o obtaint he corresponding 4-chlorobenzofuran-2-carboxylic acid 6,the reaction conditions were slightly modified (Scheme 3). 7-Methoxybenzofuran-2-carboxylic acid 7 was directly purchased and subsequently converted into the corresponding hydroxamic acid 7b.…”

Section: Chemistrymentioning

confidence: 99%

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Synthesis, Crystallization Studies, and in vitro Characterization of Cinnamic Acid Derivatives as SmHDAC8 Inhibitors for the Treatment of Schistosomiasis

et al. 2018

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Schistosomiasis is a neglected parasitic disease that affects more than 265 million people worldwide and for which the control strategy relies on mass treatment with only one drug: praziquantel. Based on the 3-chlorobenzothiophene-2-hydroxamic acid J1075, a series of hydroxamic acids with different scaffolds were prepared as potential inhibitors of Schistosoma mansoni histone deacetylase 8 (SmHDAC8). The crystal structures of SmHDAC8 with four inhibitors provided insight into the binding mode and orientation of molecules in the binding pocket as well as the orientation of its flexible amino acid residues. The compounds were evaluated in screens for inhibitory activity against schistosome and human HDACs. The most promising compounds were further investigated for their activity toward the major human HDAC isotypes. The most potent inhibitors were additionally screened for lethality against the schistosome larval stage using a fluorescence-based assay. Two of the compounds showed significant, dose-dependent killing of the schistosome larvae and markedly impaired egg laying of adult worm pairs maintained in culture.

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Section: Resultsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Synthesis, Crystallization Studies, and in vitro Characterization of Cinnamic Acid Derivatives as SmHDAC8 Inhibitors for the Treatment of Schistosomiasis

et al. 2018

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“…Among them, benzofuran structural functionality is present in many pharmacologically active natural products. The benzofurans were synthesized via Rap-Stoermer reaction of the linear dipeptide-like Ugi-4CR adducts under microwaves [103]. The aniline was reacted with salicyaldehydes in the presence of cesium carbonate under controlled microwave heating in acetonitrile for 15-30 min at 80-140 °C to directly provide benzofurans in 43-90% yields.…”

Section: Cesium Assisted Synthesismentioning

confidence: 99%

Applications of metal and non-metal catalysts for the synthesis of oxygen containing five-membered polyheterocylces: a mini review

et al. 2019

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The investigation of methods for the chemical synthesis is a growing area of interest due to increasing environmental issues. The use of catalysts in organic reactions has gained extensive interest. Metal and non-metal catalysts provided a new improved alternative to traditional methods in modern synthetic chemistry. The aim of present review is to focus on the applications of metals and non-metals for the synthesis of oxygen containing five-membered polyheterocylces.

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“…Natural and synthetic benzofuran derivatives are a class of important organic compounds with a broad range of biological activities, such as antioxidant, anti-inflammatory, antibacterial, antitumor, and so on [1,2,3,4,5,6,7,8,9,10,11]. Recently, benzofuran derivatives have attracted considerable interest for their versatile properties in chemistry and pharmacology.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Novel Benzofuran Derivatives Bearing N-Aryl Piperazine Moiety

Zheng

Gao

et al. 2016

Molecules

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A series of novel hybrid compounds between benzofuran and -aryl piperazine have been synthesized and screened in vitro for anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated RAW-264.7 macrophages and for anticancer activity against three human tumor cell lines. The results demonstrated that derivative not only had inhibitory effect on the generation of NO (IC = 5.28 μM), but also showed satisfactory and selective cytotoxic activity against human lung cancer line (A549) and gastric cancer cell (SGC7901) (IC = 0.12 μM and 2.75 μM, respectively), which was identified as the most potent anti-inflammatory and anti-tumor agent in this study.

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An expedient synthesis of enantioenriched substituted (2-benzofuryl)arylcarbinols via tandem Rap–Stoermer and asymmetric transfer hydrogenation reactions

Cited by 25 publications

References 29 publications

Synthesis, Crystallization Studies, and in vitro Characterization of Cinnamic Acid Derivatives as SmHDAC8 Inhibitors for the Treatment of Schistosomiasis

Synthesis, Crystallization Studies, and in vitro Characterization of Cinnamic Acid Derivatives as SmHDAC8 Inhibitors for the Treatment of Schistosomiasis

Applications of metal and non-metal catalysts for the synthesis of oxygen containing five-membered polyheterocylces: a mini review

Design, Synthesis, and Biological Evaluation of Novel Benzofuran Derivatives Bearing N-Aryl Piperazine Moiety

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