Synthesis of 2-alkenyl-3-hydroxyquinolin-4(1 H )-ones as promising antimicrobial and fluorescent agents

Horák, Radim; Kvapil, Lubomír; Motyka, Kamil; Slaninová, Ludmila; Grepl, Martin; Kořistek, Kamil; Urbášek, Miroslav; Hradil, Pavel; Soural, Miroslav

doi:10.1016/j.tet.2017.12.010

Cited by 8 publications

(6 citation statements)

References 22 publications

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“…The smooth hydrolysis of the [1,3]dioxolo[4,5‐ c ]quinoline scaffold (see compound 12 in Scheme ) indicated further applicability of the developed procedures in the field of 3‐hydroxyquinolin‐4(1 H )‐ones (3HQs). 2‐Aryl‐3HQs have been recently intensively studied as flavonol analogues, and their significant fluorescent and cytotoxic properties have been reported …”

Section: Resultsmentioning

confidence: 99%

“…Obviously, 2-aryl- [1,3]dioxolo [4,5-c]quinolines are not accessible from intermediates 5 or 6, but the set of dioxolo-quinolines was prepared from the corresponding 3HQs (15a-e), which were pre-synthesized using previously published procedures. [26,36] The formation of 2-aryl- [1,3]dioxolo [4,5-c] quinolines from 2-aryl-3HQs (Scheme 4) was applicable to a broad range of starting 2-aryl-3HQs; dichloroacetic acid and dichloroacetamide were also used to cyclize the dioxole scaffold to provide 16f and 16g (see structures in experimental section). To our delight, the solubility of compounds 16 compared to 3HQs 15 was significantly higher, and their hydrolysis with hydrochloric acid smoothly afforded the corresponding 2-aryl-3HQs.…”

Section: Resultsmentioning

confidence: 99%

“…In this regard, 2‐aryl‐[1,3]dioxolo[4,5‐ c ]quinolines may serve as suitable prodrugs with better solubility and better ability to release the parent 3HQ after administration in vivo. Obviously, 2‐aryl‐[1,3]dioxolo[4,5‐ c ]quinolines are not accessible from intermediates 5 or 6 , but the set of dioxolo‐quinolines was prepared from the corresponding 3HQs ( 15a‐e ), which were pre‐synthesized using previously published procedures . The formation of 2‐aryl‐[1,3]dioxolo[4,5‐ c ]quinolines from 2‐aryl‐3HQs (Scheme ) was applicable to a broad range of starting 2‐aryl‐3HQs; dichloroacetic acid and dichloroacetamide were also used to cyclize the dioxole scaffold to provide 16f and 16g (see structures in experimental section).…”

Section: Resultsmentioning

confidence: 99%

“…2-Aryl-3HQs have been recently intensively studied as flavonol analogues, and their significant fluorescent and cytotoxic properties have been reported. [29][30][31][32] It was proven that 2-aryl-3HQs interact with the elongation factor in the gamendazole binding site and that the 3-hydroxy-4-oxo moiety is directly involved in the structure of the pharmacophore. [33] On the other hand, 3HQs generally suffer from very low solubility resulting from an intermolecular hydrogen bond mediated by the 3-hydroxy group.…”

Section: Resultsmentioning

confidence: 99%

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Structural analogues of quinoline alkaloids: Straightforward route to [1,3]dioxolo[4,5‐c]quinolines with antibacterial properties

Horák

Kořistek

Šamšulová

et al. 2020

Journal of Heterocyclic Chem

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Compounds bearing [1,3]dioxolo‐quinoline scaffolds have been found in quinoline‐based natural products; the only exception is the [1,3]dioxolo[4,5‐c]quinoline moiety with a rare occurrence in both natural and synthetic derivatives. In this article, we report the preparation of diversely substituted and functionalized [1,3]dioxolo[4,5‐c]quinolines using [1,3]dioxolo[4,5‐c]quinoline‐4‐carbaldehyde (DQC) as the common intermediate. DQC was synthesized on a large scale from anthranilic acid and chloroacetone as the starting materials, with the rearrangement of acetonyl‐anthranilate as the key step. The developed method allows for the simple preparation of [1,3]dioxolo[4,5‐c]quinolines with various C2 substituents on the quinoline scaffold. Additionally, the synthetic route was successfully applied to the preparation of 3‐hydroxyquinoline‐4(1H)‐ones. The target compounds were tested against representative Gram‐positive/negative bacteria, and two derivatives exhibited submicromolar minimum inhibitory concentrations against Micrococcus luteus.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Structural analogues of quinoline alkaloids: Straightforward route to [1,3]dioxolo[4,5‐c]quinolines with antibacterial properties

Horák

Kořistek

Šamšulová

et al. 2020

Journal of Heterocyclic Chem

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“…To name some of them: shape measurement [1,2], vibration control [3], label-free analysis [4], quantitative biological samples phase imaging (QPI) [5], etc. DH techniques have a serious advantage for biological samples because many of them are transparent and, for visualization in conventional microscopy, coloring [6] or fluorescent agents [7] are often used which can be harmful especially for live objects [8]. DH allows a harmless introvision by reconstruction 3D complex-valued wavefront of transparent objects without additional preparations of samples [9].…”

Section: Introductionmentioning

confidence: 99%

Super-resolution microscopy for biological specimens: lensless phase retrieval in noisy conditions

Shevkunov

Katkovnik

Petrov

et al. 2018

Biomed. Opt. Express

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The paper is devoted to a computational super-resolution microscopy. A complexvalued wavefront of a transparent biological cellular specimen is restored from multiple intensity diffraction patterns registered with noise. For this problem, the recently developed lensless super-resolution phase retrieval algorithm [Optica, 4(7), 786 (2017)] is modified and tuned. This algorithm is based on a random phase coding of the wavefront and on a sparse complex-domain approximation of the specimen. It is demonstrated in experiments, that the reliable phase and amplitude imaging of the specimen is achieved for the low signal-to-noise ratio provided a low dynamic range of observations. The filterings in the observation domain and specimen variables are specific features of the applied algorithm. If these filterings are omitted the algorithm becomes a super-resolution version of the standard iterative phase retrieval algorithms. In comparison with this simplified algorithm with no filterings, our algorithm shows a valuable improvement in imaging with much smaller number of observations and shorter exposure time. In this way, presented algorithm demonstrates ability to work in a low radiation photon-limited mode.

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Synthesis and structural characterization of nano‐sized metal complexes of 3‐(1‐methyl‐4‐hydroxy‐2‐oxo‐1,2‐dihydroquinolin‐3‐yl)‐2‐nitro‐3‐oxopropanoic acid. XRD, thermal, 3D modeling, and antitumor activity studies

El-ghamry

El‐Shafiy

2021

Applied Organom Chemis

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New Co(II), Ni(II), Cu(II), Zn(II), and Fe(III) complexes of the ligand 3-(1-methyl-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-2-nitro-3-oxopropanoic acid (H 3 L) were synthesized and characterized by various analytical and spectroscopic techniques. The obtained data confirmed the formation of 1:1 (M:L) stoichiometry for Fe(III), Co(II) complexes and 2:1 (M:L) stoichiometry for Ni(II), Cu(II), Zn(II) complexes, and the ligand, H 3 L, acts as mono-, bi-, tribasic bis-, tris-and tetradentate towards the metal ions via the oxygen of quinolinonate, the enolic/ketonic of β-ketoacid, and carboxylate besides of the nitro groups. All complexes showed tetrahedral geometry, except Fe(III) complex which exhibited an octahedral geometry. The X-ray diffractograms of the ligand, H 3 L, and its metal complexes revealed a series of sharp and intense diffraction peaks which indicate their crystalline characteristic with the particle size in the nano-scale range. Geometrical optimizations of the ligand, H 3 L, and its metal complexes were performed at the B3LYP/6-311G(d, p) level using density functional theory (DFT) implemented in the Gaussian 09 program.The data obtained were correlated with the experimental results and suggested that the Zn(II) complex may exhibit extremely bio-efficiency than other compounds. The antimicrobial screening results showed enhancement in the efficiency of the free ligand, H 3 L, on coordination with the metal ions. The antitumor activity was evaluated in vitro against Hepatocellular carcinoma cell line (HepG-2 cells). The ligand, H 3 L, and its Zn(II) complex showed strong antitumor activities, especially nano-sized Zn(II) complex that exhibited IC 50 value (2.90 μg/ml) smaller than the well-known standard antitumor drug cisplatin (IC 50~3 .27 μg/ml), prominent it as an antitumor agent towards HepG-2 cells.

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Synthesis of 2-alkenyl-3-hydroxyquinolin-4(1 H )-ones as promising antimicrobial and fluorescent agents

Cited by 8 publications

References 22 publications

Structural analogues of quinoline alkaloids: Straightforward route to [1,3]dioxolo[4,5‐c]quinolines with antibacterial properties

Structural analogues of quinoline alkaloids: Straightforward route to [1,3]dioxolo[4,5‐c]quinolines with antibacterial properties

Super-resolution microscopy for biological specimens: lensless phase retrieval in noisy conditions

Synthesis and structural characterization of nano‐sized metal complexes of 3‐(1‐methyl‐4‐hydroxy‐2‐oxo‐1,2‐dihydroquinolin‐3‐yl)‐2‐nitro‐3‐oxopropanoic acid. XRD, thermal, 3D modeling, and antitumor activity studies

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