Quinolines as potent 5-lipoxygenase inhibitors: Synthesis and biological profile of L-746,530

Dubé, Daniel; Blouin, Marc; Brideau, Christine; Chen, Chan; Desmarais, Sylvie; Ethier, Diane; Falgueyret, Jean‐Pierre; Friesen, Richard W.; Girard, M. Fusco; Girard, Yves; Guay, Jocelyne; Riendeau, Denis; Tagari, Philip; Young, Robert N.

doi:10.1016/s0960-894x(98)00201-7

Cited by 269 publications

(79 citation statements)

References 14 publications

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“…The starting material 2-amino-4,5-dimethoxybenzaldehyde 1 was obtained by reduction of 4,5-dimethoxy-2-itrobenzaldehyde according to our previous procedure [6]. Our approach to the synthesis of 2 were based on the Friedländer condensation strategy.…”

Section: Resultsmentioning

confidence: 99%

“…We described a very efficient and environmentally friendly method for the synthesis of novel 9,10-dimethoxybenzo [6,7]oxepino [3,4-b]quinolin-13(6H)-ones 7a-p through the intramolecular Friedel-Crafts acylation, the hydrolysis, the Willamson reaction, the Wohl-Zeigler bromination and Friedländer condensation. The experimental procedure was very simple.…”

Section: Resultsmentioning

confidence: 99%

“…Quinoline-fused ring systems are a back-bone of many natural products and pharmacologically significant compounds and display a broad range of biological activities [1][2][3], including antiasthmatic [4][5][6], antibacterial [7,8], anti-inflammatory [9] and antihypertensive [10,11] properties. In addition to the medicinal applications, quinolines have been employed in the study of bioorganic and bioorganometallic processes [12].…”

Section: Introductionmentioning

confidence: 99%

“…

ABSTRACTA concise and efficient method for the synthesis of novel 9,10-dimethoxybenzo [6,7]oxepino[3,4-b]quinolin13(6H)-one and its derivatives 7a-p has been developed via the intramolecular Friedel-Crafts acylation reactions of 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylic acids 6a-p with polyphosphoric acid (PPA) as catalyst and solvent under mild conditions. The key intermediates 6a-p were prepared through the in situ formation of ethyl 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylates 5a-p followed by hydrolysis with aqueous ethanolic sodium hydroxide solution.

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confidence: 99%

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A Facile Synthesis of 9,10-Dimethoxybenzo[6,7]- ox-epino[3,4-b]quinolin-13(6H)-one and Its Derivatives

Yang¹,

Liang²,

Zuo³

et al. 2013

IJOC

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A concise and efficient method for the synthesis of novel 9,10-dimethoxybenzo [6,7]oxepino[3,4-b]quinolin13(6H)-one and its derivatives 7a-p has been developed via the intramolecular Friedel-Crafts acylation reactions of 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylic acids 6a-p with polyphosphoric acid (PPA) as catalyst and solvent under mild conditions. The key intermediates 6a-p were prepared through the in situ formation of ethyl 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylates 5a-p followed by hydrolysis with aqueous ethanolic sodium hydroxide solution. The novel synthetic method has the advantages of good yields, easy work-up, and environmentally friendly character, which may provide a novel highly efficient process for making quinoline and related azaheterocycle libraries.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…

…”

mentioning

confidence: 99%

See 2 more Smart Citations

A Facile Synthesis of 9,10-Dimethoxybenzo[6,7]- ox-epino[3,4-b]quinolin-13(6H)-one and Its Derivatives

Yang¹,

Liang²,

Zuo³

et al. 2013

IJOC

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“…From the available literature it's clear that the quinoline ring system and their fused derivatives are significant structural units and present as substructure in various alkaloids, therapeutics and synthetic analogues, which exhibit good biological activities (Larsen et al, 1996;Roma et al, 2000). Various quinolines derivatives are reported as anti-malarial, anti -inflammatory, antiasthmatic, antibacterial, anti-hypertensive and platelet derived growth factor receptor tyrosine kinase (PDGF-RTK) inhibiting agents (Dube et al, 1998). A large variety of quinolines are reported to exhibit substantial anti-cancer activities (Alkasomi et al, 2010) Quinoline derivative act as anti-cancer agents through a variety of mechanisms for example; cell cycle arrest in the G2 phase (Kim et al, 2005) inhibition of topoisomerase (Ching et al, 2008) and tubulin polymerization inhibition (Alkasomi., 2009) Another mechanism of action is the inhibition of tyrosine kinases (Mulvihill et al, 2008).…”

Section: Introductionmentioning

confidence: 99%

Chemical synthesis, docking studies and biological effects of functionalized 1,3-diaryl-2-propen-1-ones on human colon cancer cells

Zhu

Huang

2015

Bangladesh J Pharmacol

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Friedländer Synthesis of Quinolines Using a Lewis Acid‐Surfactant‐Combined Catalyst in Water

Zhang

2007

Adv Synth Catal

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In water, Friedländer annulation using Lewis acid-surfactant-combined catalyst provides a mild and efficient route for the synthesis of quinolines. Employing a catalytic amount of scandium tris(dodecyl sulfate) [Sc(O 3 SOC 12 H 25 ) 3 ], various polysubstituted and polycyclic quinolines were obtained in exellent yields.Keywords: Friedländer annulation; Lewis acids; quinoline; surfactant Lewis acid catalysis has attracted much attention in organic synthesis.[1] Recently, a new type of catalyst, "Lewis acid-surfactant-combined catalyst (LASC)", has shown high efficiency in various organic transformations. These reactions are promoted in water without organic cosolvents.[2] Proposed by Kobayashi, [3] this kind of catalyst acts both as a Lewis acid to activate the substrate molecules and as a surfactant to form emulsions in water. The high efficiency of LASC in reactions, as well as creation of environmentally benign processes promoted us to explore the possibility of methodological development in the scaffold construction of natural product-like compounds. The availability of a practical route for the generation of small molecules-based natural products is of utmost urgency and importance in biomedical research. As a privileged fragment, quinoline is a ubiquitous subunit in many quinoline-containing natural products with remarkable biological activities.[4] Members of this family have wide applications in medicinal chemistry.[4] Because of their importance as substructures in a broad range of natural and designed products, a significant effort continues to be given over to the development of new quinoline-based structures [5] and new methods for their construction. [6] As part of a continuing effort in our laboratory toward the development of new methods for the expeditious synthesis of biologically relevant heterocyclic compounds, [7] we became interested in the possibility of developing a novel and efficient method to construct the quinoline scaffold. It is well-known that the protocol reported by Friedländer is one of the most simple and straightforward methods for the synthesis of polysubstituted quinolines, although some methods such as Skraup, Doebner von Miller, and Combes reactions [8] are available. Brønsted acids like sulfamic acid, hydrochloric acid, sulfuric acid, p-toluenesulfonic acid and phosphoric acid were widely used as reagents or catalysts.[9] Recently, various Lewis acids have been reported to be effective for the synthesis of quinolines.[10] However, many of these procedures are complicated by harsh reaction conditions, low yields, difficulties in work-up, and the use of stoichiometric and/or relatively expensive reagents. And in some cases, high catalyst loadings had to be employed in order to obtain respectable yields. Since quinoline derivatives are increasingly useful and important in pharmaceuticals and industry, the development of a simple, eco-and environmentally benign protocol is still desirable. Inspired by the recent advances of "Lewis acid-surfactant-combined catalysts ...

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Quinolines as potent 5-lipoxygenase inhibitors: Synthesis and biological profile of L-746,530

Cited by 269 publications

References 14 publications

A Facile Synthesis of 9,10-Dimethoxybenzo[6,7]- ox-epino[3,4-<i>b</i>]quinolin-13(6<i>H</i>)-one and Its Derivatives

A Facile Synthesis of 9,10-Dimethoxybenzo[6,7]- ox-epino[3,4-<i>b</i>]quinolin-13(6<i>H</i>)-one and Its Derivatives

Chemical synthesis, docking studies and biological effects of functionalized 1,3-diaryl-2-propen-1-ones on human colon cancer cells

Friedländer Synthesis of Quinolines Using a Lewis Acid‐Surfactant‐Combined Catalyst in Water

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Quinolines as potent 5-lipoxygenase inhibitors: Synthesis and biological profile of L-746,530

Cited by 269 publications

References 14 publications

A Facile Synthesis of 9,10-Dimethoxybenzo[6,7]- ox-epino[3,4-&lt;i&gt;b&lt;/i&gt;]quinolin-13(6&lt;i&gt;H&lt;/i&gt;)-one and Its Derivatives

A Facile Synthesis of 9,10-Dimethoxybenzo[6,7]- ox-epino[3,4-&lt;i&gt;b&lt;/i&gt;]quinolin-13(6&lt;i&gt;H&lt;/i&gt;)-one and Its Derivatives

Chemical synthesis, docking studies and biological effects of functionalized 1,3-diaryl-2-propen-1-ones on human colon cancer cells

Friedländer Synthesis of Quinolines Using a Lewis Acid‐Surfactant‐Combined Catalyst in Water

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A Facile Synthesis of 9,10-Dimethoxybenzo[6,7]- ox-epino[3,4-<i>b</i>]quinolin-13(6<i>H</i>)-one and Its Derivatives

A Facile Synthesis of 9,10-Dimethoxybenzo[6,7]- ox-epino[3,4-<i>b</i>]quinolin-13(6<i>H</i>)-one and Its Derivatives