3-Hydroxy-2-phenyl-4(1H)-quinolinones as Promising Biologically Active Compounds

Abstract

2-Phenyl-3-hydroxy-4(1H)-quinolinones can be considered as aza-analogues of flavones, compounds which are known for the wide-range of their biological activity. These quinolinones were studied as inhibitors of topoisomerase, gyrase and IMPDH. They were tested for anticancer activity in-vitro and were also shown to possess immunosuppressive properties. This review is the first summarizing the synthesis and activity of the mentioned quinolinones.

Acid–base and coordination properties of 2-phenyl-3-hydroxy-4-quinolones in aqueous media

“…logK obs = logβ 111 -logβ 012 + pH (4) With stability constants given in Table 2 one obtains logK obs = 3.38 and 4.38 at pH 7.0 and 8.0 respectively, which are reasonably close to the experimental values in both aqueous and micellar solutions given in Table 3.…”

“…Chemical shifts (ppm) are relative to (CH 3 ) 4 Si. Infrared spectra were determined on an FTIR/FIR spectrometer 400 Perkin-Elmer 1600 series.…”

“…1 A particular group of these compounds constitute 3-hydroxy-4-quinolones, among which 2-heptyl-3-hydroxy-4-quinolone (PQS) serves as a quorum sensing signal molecule 2,3 and 2-phenyl-3-hydroxy-4-quinolones such as 1 and 2 are known to possess anticancer activity, immunosuppressive properties and to act as enzyme inhibitors. In particular 1 and 2 share common structural features with 3-hydroxyflavone (3) and 3-hydroxy-4-pyridinones such as Deferiprone (4). In particular 1 and 2 share common structural features with 3-hydroxyflavone (3) and 3-hydroxy-4-pyridinones such as Deferiprone (4).…”

Use of Mesoporous Molecular Sieves in the Production of Fine Chemicals: Preparation of Dihydroquinolinones of Pharmaceutical Interest From 2′‐Aminochalcones

“…2‐Aryl‐2,3‐dihydro‐4(1 H )‐quinolinones (or 2‐aryl‐1,2,3,4‐tetrahydro‐4‐quinolones) derivatives are six‐membered nitrogen heterocyclic compounds considered as aza‐analogs of flavanones. The synthesis of these compounds has generated continuous interest because of their wide range of biological activities, such as hypertensive, antibacterial, anti‐inflammatory, and as anticancer and immunosuppressive agents . They display significant cytotoxicity against a panel of human tumor cell lines and also have high activity toward multi‐drug resistant KB‐VIN, and ovarian 1A9 cell lines.…”

Solid-Phase Synthesis of 3-Hydroxy-6-Nitroquinolin-4(1H)-ones with Two Diversity Positions

“…Recently, the biological properties of hydroxyquinolinones have been reviewed. 11 In this article, we describe the solid-phase synthesis of novel hydroxyquinolinone derivatives using 4-chloro-2-fluoro-5-nitrobenzoic acid as an excellent multifunctional building block suitable for this purpose. After immobilization via substitution of the fluorine atom with polymer supported amines, the resulting 4-chloro-5-nitroanthranilic acid offers various transformations (Figure 1) based on the chlorine atom substitution with various nucleophiles, subsequent nitro group reduction, and another possible modification of the resulting o-phenylenediamines.…”