First Enantioselective Synthesis of Brosimacutins H and I

Ye, Ziping; Yang, Jinhui; Yao, Feng; Ma, Tao; Niu, Mingjie

doi:10.6023/cjoc201508021

Cited by 3 publications

(2 citation statements)

References 3 publications

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“…3.2.1. C-Isoprenylation Reaction of Compound 1 [46] 3,3-Dimethylallyl bromide (2.08 mL, 18 mmol) was slowly added to a stirred solution of β-resorcylaldehyde (1) (2.07 g, 15 mmol) and NaOH (0.6 g, 15 mmol) in methanol (20 mL) at 0 • C. The mixture was stirred for 12 h at room temperature and washed with water, extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure.…”

Section: Synthesis Of Licochalcone Cmentioning

confidence: 99%

Synthesis, Antibacterial Effects, and Toxicity of Licochalcone C

Ozanique,

Helena,

Menezes

et al. 2024

Pharmaceuticals

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Drug-resistant bacteria constitute a big barrier against current pharmacotherapy. Efforts are urgent to discover antibacterial drugs with novel chemical and biological features. Our work aimed at the synthesis, evaluation of antibacterial effects, and toxicity of licochalcone C (LCC), a naturally occurring chalcone. The synthetic route included six steps, affording a 10% overall yield. LCC showed effects against Gram-positive bacteria (MIC = 6.2–50.0 µg/mL), Mycobacterium species (MIC = 36.2–125 µg/mL), and Helicobacter pylori (MIC = 25 µg/mL). LCC inhibited the biofilm formation of MSSA and MRSA, demonstrating MBIC50 values of 6.25 μg/mL for both strains. The investigations by fluorescence microscopy, using PI and SYTO9 as fluorophores, indicated that LCC was able to disrupt the S. aureus membrane, similarly to nisin. Systemic toxicity assays using Galleria mellonella larvae showed that LCC was not lethal at 100 µg/mL after 80 h treatment. These data suggest new uses for LCC as a compound with potential applications in antibacterial drug discovery and medical device coating.

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Section: Synthesis Of Licochalcone Cmentioning

confidence: 99%

Synthesis, Antibacterial Effects, and Toxicity of Licochalcone C

Ozanique,

Helena,

Menezes

et al. 2024

Pharmaceuticals

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“…Furthermore, such dihydrochalcones like brosimacutins H and I can be prepared by the enantioselective synthesis of cheap starting materials: hydroxyl-acetophenone and hydroxyl benzene formaldehyde [57].…”

Section: Chemical Synthesis Of Dihydrochalconesmentioning

confidence: 99%

Dihydrochalcones: Methods of Acquisition and Pharmacological Properties—A First Systematic Review

2019

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Dihydrochalcones are a class of secondary metabolites, for which demand in biological and pharmacological applications is still growing. They posses several health-endorsing properties and, therefore, are promising candidates for further research and development. However, low content of dihydrochalcones in plants along with their low solubility and bioavailability restrict the development of these compounds as clinical therapeutics. Therefore, chemomicrobial and enzymatic modifications are required to expand their application. This review aims at analyzing and summarizing the methods of obtaining dihydrochalcones and of presenting their pharmacological actions that have been described in the literature to support potential future development of this group of compounds as novel therapeutic drugs. We have also performed an evaluation of the available literature on beneficial effects of dihydrochalcones with potent antioxidant activity and multifactorial pharmacological effects, including antidiabetic, antitumor, lipometabolism regulating, antioxidant, anti-inflammatory, antibacterial, antiviral, and immunomodulatory ones. In addition, we provide useful information on their properties, sources, and usefulness in medicinal chemistry.

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Biginelli reaction – an effective method for the synthesis of dihydropyrimidine derivatives (microreview)

Simurova

Майборода

2017

Chem Heterocycl Comp

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First Enantioselective Synthesis of Brosimacutins H and I

Cited by 3 publications

References 3 publications

Synthesis, Antibacterial Effects, and Toxicity of Licochalcone C

Synthesis, Antibacterial Effects, and Toxicity of Licochalcone C

Dihydrochalcones: Methods of Acquisition and Pharmacological Properties—A First Systematic Review

Biginelli reaction – an effective method for the synthesis of dihydropyrimidine derivatives (microreview)

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