Phenolic Compounds of Plants of the Scutellaria L. Genus. Distribution, Structure, and Properties

Information on flavones, flavanones, flavanonols, flavonols, chalcones, isoflavones, biflavonoids, lignoflavonoids, and lignane glycosides and stilbenes isolated from plants of the Scutellaria L. genus was systematized and reviewed. A list of 208 phenolic compounds was given according to flavonoid type with an indication of the plant sources, structures, and physicochemical properties and citations of the original articles.     

Novel organometallic chalcones functionalized with a crown ether fragment as optical ion chemosensors

We previously reported the synthesis and characterization of new organometallic chalcones derived from ferrocene, cyrhetrene and cymantrene functionalized with a benzo‐15‐crown‐5 fragment. The ferrocene and cyrhetrene chalcones have been investigated as chemosensors for metal ions with optical response in acetonitrile. Several metal ions were selected considering the diameter of the cavity and the charge‐to‐radius ratio of the cation. The stoichiometry of the complexes was determined using Job's method. It was found that Na⁺ and Ca²⁺ complexes have a 1:1 stoichiometry while a 2:1 (metaloligand‐to‐cation) stoichiometry was determined for Ba²⁺ and Pb²⁺ complexes. The association constants were calculated according to the stoichiometry of the complex and the results showed that they are directly affected by the electron‐withdrawing nature of the organometallic fragment. Moreover, complexes of ferrocenyl chalcone have larger association constants than those of the cyrhetrenyl analogue. This experimental observation is consistent with the electronic properties of the ferrocenyl fragment.     

An Efficient Synthesis of 1,5-Thiadiazepines and 1,5-Benzodiazepines by Microwave-Assisted Heterocyclization

A novel and efficient method for the synthesis of substituted thiazepines and diazepines has been developed. A simple one-pot reaction of chalcones 1a–f with 1-amino-2-mercapto-5-phenyl-1,3,4-triazole and o-phenylenediamine in the presence of a catalytic amount of sodium acetate under microwave irradiation gave 2-(3,8-diphenyl-7,8-dihydro[1,2,4]triazolo[3,4-b][1,3,4]thiadiazepin-6-yl)phenoles 2a–f and 2-(2-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-4-yl)phenoles 3a–f, respectively. The structure of all the synthesized compounds was elucidated on the basis of elemental analysis, IR, ¹H and ¹³C NMR, and mass spectral data.     

Iodine-Catalyzed Addition of Methyl Thioglycolate to Chalcones

Abstract

A series of novel β-mercapto carbonyl compounds (3a–z), methyl 2-(3-oxo-1,3-diarylpropylthio)acetate, were synthesized and characterized via iodine-catalyzed addition of methyl thioglycolate to chalcones (1a–z).

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.     

An efficient green procedure for the synthesis of chalcones using C-200 as solid support under grinding conditions

Abstract

A simple, rapid, efficient and environmentally benign procedure for the synthesis of chalcones has been achieved by grinding aryl aldehydes and acetophenones with anhydrous barium hydroxide (C-200) in the absence of any solvent. The use of organic solvent for extraction of compound is also avoided. This present method is highly useful for the synthesis of 2′-hydroxy chalcones, required intermediates for the synthesis of flavanoids.     

Regioselective A-Ring Chlorination of Benzodiazepine Analogues Using tert-Butyl Hypochlorite

Treatment of 2-phenyl-2,3-dihydro-1,4-benzodiazepin-5(4H)-one and a series of 1,4-benzoxazepinone analogues with tert-butyl hypochlorite affords products shown, by NMR and MS spectroscopy, to be chlorinated exclusively in the A-ring at positions 7 and/or 9.     

Simple and Efficient Synthesis of 2-Aryl-2,3-Dihydroquinolin-4(1H)-ones Using Silica Chloride as a New Catalyst Under Solvent-Free Conditions

A mild, efficient, and high-yielding method for the synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones from their corresponding 2-amino chalcones using silica chloride (SiO₂Cl) under solvent-free conditions is described. A series of 2-aryl-2,3-dihydroquinolin-4(1H)-ones containing both electron-donating and electron-withdrawing substituents were synthesized.     

Identification of a Prenyl Chalcone as a Competitive Lipoxygenase Inhibitor: Screening,Biochemical Evaluation and Molecular Modeling Studies

Cyclooxygenase (COX) and lipoxygenase (LOX) are key targets for the development of new anti-inflammatory agents. LOX, which is involved in the biosynthesis of mediators in inflammation and allergic reactions, was selected for a biochemical screening campaign to identify LOX inhibitors by employing the main natural product library of Brazilian biodiversity. Two prenyl chalcones were identified as potent inhibitors of LOX-1 in the screening. The most active compound, (E)-2-O-farnesyl chalcone, decreased the rate of oxygen consumption to an extent similar to that of the positive control, nordihydroguaiaretic acid. Additionally, studies on the mechanism of the action indicated that (E)-2-O-farnesyl chalcone is a competitive LOX-1 inhibitor. Molecular modeling studies indicated the importance of the prenyl moieties for the binding of the inhibitors to the LOX binding site, which is related to their pharmacological properties.     

Photophysical Study and Biological Applications of Synthetic Chalcone-Based Fluorescent Dyes

A chalcone series (3a–f) with electron push–pull effect was synthesized via a one-pot Claisen–Schmidt reaction with a simple purification step. The compounds exhibited strong emission, peaking around 512–567 nm with mega-stokes shift (∆λ = 93–139 nm) in polar solvents (DMSO, MeOH, and PBS) and showed good photo-stability. Therefore, 3a–f were applied in cellular imaging. After 3 h of incubation, green fluorescence was clearly brighter in cancer cells (HepG2) compared to normal cells (HEK-293), suggesting preferential accumulation in cancer cells. Moreover, all compounds exhibited higher cytotoxicity within 24 h toward cancer cells (IC₅₀ values ranging from 45 to 100 μM) than normal cells (IC₅₀ value >100 μM). Furthermore, the antimicrobial properties of chalcones 3a–f were investigated. Interestingly, 3a–f exhibited antibacterial activities against Escherichia coli and Staphylococcus aureus, with minimum bactericidal concentrations (MBC) of 0.10–0.60 mg/mL (375–1000 µM), suggesting their potential antibacterial activity against both Gram-negative and Gram-positive bacteria. Thus, this series of chalcone-derived fluorescent dyes with facile synthesis shows great potential for the development of antibiotics and cancer cell staining agents.     

Isolation and Characterization of Two Chalcone Derivatives with Anti-Hepatitis B Virus Activity from the Endemic Socotraen Dracaena cinnabari (Dragon’s Blood Tree)

Hepatitis B virus (HBV) infection is prevalent and continues to be a global health concern. In this study, we determined the anti-hepatitis B virus (HBV) potential of the Socotra-endemic medicinal plant Dracaena cinnabari and isolated and characterized the responsible constituents. A bioassay-guided fractionation using different chromatographic techniques of the methanolic extract of D. cinnabari led to the isolation of two chalcone derivatives. Using a variety of spectroscopic techniques, including ¹H-, ¹³C-, and 2D-NMR, these derivatives were identified as 2,4’-dihydroxy-4-methoxydihydrochalcone (compound 1) and 2,4’-dihydroxy-4-methoxyhydrochalcone (compound 2). Both compounds were isolated for the first time from the red resin (dragon’s blood) of D. cinnabari. The compounds were first evaluated for cytotoxicity on HepG2.2.15 cells and 50% cytotoxicity concentration (CC50) values were determined. They were then evaluated for anti-HBV activity against HepG2.2.15 cells by assessing the suppression of HBsAg and HBeAg production in the culture supernatants and their half maximum inhibitory concentration (IC₅₀) and therapeutic index (TI) values were determined. Compounds 1 and 2 indicated inhibition of HBsAg production in a dose- and time-dependent manner with IC₅₀ values of 20.56 and 6.36 μg/mL, respectively.