7-Chloro-4-phenylsulfonyl quinoline, a new antinociceptive and anti-inflammatory molecule: Structural improvement of a quinoline derivate with pharmacological activity

Pinz, Mikaela P.; Reis, Angélica S.; Oliveira, Renata L. de; Voss, Guilherme T.; Vogt, Ane G.; Sacramento, Manoela; Roehrs, Juliano A.; Alves, Diego; Luchese, Cristiane; Wilhelm, Ethel A.

doi:10.1016/j.yrtph.2017.08.014

Cited by 29 publications

(11 citation statements)

References 27 publications

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“…Quinoline and its benzo-fused derivative, benzoquinoline, are crucial scaffolds in medicinal chemistry and they have been reported to possess a large variety of biological activities which include antiplasmodial and antimalarial, antitubercular, antibacterial, antifungal, anti-HIV, anticancer, antinociceptive and anti-inflammatory, antipsychotic, analgesic, anti-Alzheimer's, antihypertensive properties, etc. [5][6][7][8][9][10][11][12][13][14][15][16][17]. Moreover, the quinoline pharmacophore has proved to be one of the most effective motifs used in antibacterial and antifungal therapy, and many of the existing drugs on the market incorporate a quinoline scaffold e.g., ciprofloxacin (antibacterial), bedaquiline (antitubercular), etc.…”

Section: Introductionmentioning

confidence: 99%

Benzoquinoline Derivatives: A Straightforward and Efficient Route to Antibacterial and Antifungal Agents

et al. 2021

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We report here the design, synthesis, experimental and in silico evaluation of the antibacterial and antifungal activity of some new benzo[f]quinoline derivatives. Two classes of benzo[f]quinolinium derivatives—(benzo[f]quinolinium salts (BQS) and pyrrolobenzo[f]quinolinium cycloadducts (PBQC)—were designed and obtained in two steps via a direct and facile procedure: quaternization followed by a cycloaddition reaction. The synthesized compounds were characterized by elemental and spectral analysis (FT-IR, 1H-NMR, 13C-NMR). The antimicrobial assay reveals that the BQS salts have an excellent quasi-nonselective antifungal activity against the fungus Candida albicans (some of them higher that the control drug nystatin) and very good antibacterial activity against the Gram positive bacterium Staphylococcus aureus. The PBQC compounds are inactive. Analysis of the biological data reveals interesting SAR correlations in the benzo[f]quinolinium series of compounds. The in silico studies furnished important data concerning the pharmacodynamics, pharmacokinetics and ADMET parameters of the BQS salts. Studies of the interaction of each BQS salt 3a–o with ATP synthase in the formed complex, reveal that salts 3j, 3i, and 3n have the best fit in a complex with ATP synthase. Study of the interaction of each BQS salt 3a-o with TOPO II in the formed complex reveals that salts 3j and 3n have the best-fit in complex with TOPO II. The in silico ADMET studies reveal that the BQS salts have excellent drug-like properties, including a low toxicity profile. Overall, the experimental and in silico studies indicate that compounds 3e and 3f (from the aliphatic series), respectively, and 3i, 3j and 3n (from the aromatic series), are promising leading drug candidates.

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Section: Introductionmentioning

confidence: 99%

Benzoquinoline Derivatives: A Straightforward and Efficient Route to Antibacterial and Antifungal Agents

et al. 2021

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“…[1,2] The significant pharmacological properties of quinoline moieties [3,4] have led to significant applications in the field of bioorganic, industrial, and synthetic organic chemistry, [1,5,6] and it is considered as an important pharmacophore and a privileged structure in medicinal chemistry. [7] There has been widespread interest in designing and developing efficient methods for the synthesis of quinoline derivatives [8,9] and in evaluating their biological activities as anticancer agents [5,10] as well as their antibacterial, [11] antineoplastic, [12] antimalarial, [13] anticonvulsant, [14] anti-inflammatory, [15] and other activities. [16] The development of new synthetic ways to enable the preparation of various quinoline skeletons remains a challenging task.…”

Section: Introductionmentioning

confidence: 99%

Decision making for promising quinoline‐based anticancer agents through combined methodology

Özcan

Ökten

Eren

2020

J Biochem & Molecular Tox

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During the development of effective drugs for the treatment of cancer, one of the most important tasks is to identify effective drug candidates having maximum antiproliferation and minimum side effects. This paper considers the problem of selecting the most promising anticancer agents, showing inhibition at low IC50 concentration and low releasing lactate dehydrogenase percentage (cytotoxicity). Recently, we prepared quinoline analogs bearing different functional groups and determined their anticancer potential against the HeLa, C6, and HT29 cancer cell lines using different anticancer assays. Experimentally, seven quinoline derivatives consisting of different substituents were determined as promising anticancer agents. We propose a multicriteria recommendation method to identify the most promising anticancer agents against all tested cell lines with an accurate prediction algorithm according to the available input data. A multicriteria decision‐making methodology (MCDM) was used for the solution of the relevant problem in this study. Both the experimental results and MCDM method indicated that 5,7‐dibromo‐8‐hydroxyquinoline (2) and 6,8‐dibromo‐1,2,3,4‐tetrahydroquinoline (6) are the most promising anticancer agents against the HeLa, HT29, and C6 cell lines.

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“…Quinolinescaffold has a special importance in the natural and synthetic organic compounds. [1] Quinoline derivatives are an important class of heterocycles due to their wide range of biological and pharmacological potentialities [2] such as anticancer, [3] antibacterial, [4] antiprotozoal, antiproliferative, [5] antitumor, [6] anti-inflammatory, [7] antifungal, antioxidant, antihypertensive, [8] antimalarial, [9] antitubercular, [10] anti-HIV agents. [11] Also, acridine derivatives have been known since the 19th century where they were first used as pigments and dyes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of benzo[h]quinolone and benzo[c]acridinone derivatives by Fe₃O₄@PS‐Arginine[HSO₄] as an efficient magnetic nanocatalyst

Karkhah

Kefayati

Shariati

2020

Journal of Heterocyclic Chem

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Fe 3 O 4 magnetic nanoparticles were synthesized and functionalized by propylsilan and after that arginine. The synthesized Fe 3 O 4 @PS-Arginine magnetic nanoparticles were modified to obtain Fe 3 O 4 @PS-Arg[HSO 4 ]. These nanoparticles were used as environmental friendly solidacid magnetic nanocatalyst for the synthesis of 2-amino-4-arylbenzo[h]quinoline-3-carbonitrile and 10,10-dimethyl-7-aryl-9,10,11,12-tetrahydrobenzo[c]acridin-8(7H)-one derivatives via the one-pot reaction of α-naphthilamine and aromatic aldehydes with malononitrile or dimedone. Simple operation, high reaction yields, reusability of catalyst for several times, short reaction time and easy separation from reaction mixture are the key advantages of using this catalyst.

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7-Chloro-4-phenylsulfonyl quinoline, a new antinociceptive and anti-inflammatory molecule: Structural improvement of a quinoline derivate with pharmacological activity

Cited by 29 publications

References 27 publications

Benzoquinoline Derivatives: A Straightforward and Efficient Route to Antibacterial and Antifungal Agents

Benzoquinoline Derivatives: A Straightforward and Efficient Route to Antibacterial and Antifungal Agents

Decision making for promising quinoline‐based anticancer agents through combined methodology

Synthesis of benzo[h]quinolone and benzo[c]acridinone derivatives by Fe₃O₄@PS‐Arginine[HSO₄] as an efficient magnetic nanocatalyst

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7-Chloro-4-phenylsulfonyl quinoline, a new antinociceptive and anti-inflammatory molecule: Structural improvement of a quinoline derivate with pharmacological activity

Cited by 29 publications

References 27 publications

Benzoquinoline Derivatives: A Straightforward and Efficient Route to Antibacterial and Antifungal Agents

Benzoquinoline Derivatives: A Straightforward and Efficient Route to Antibacterial and Antifungal Agents

Decision making for promising quinoline‐based anticancer agents through combined methodology

Synthesis of benzo[h]quinolone and benzo[c]acridinone derivatives by Fe3O4@PS‐Arginine[HSO4] as an efficient magnetic nanocatalyst

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Product

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Synthesis of benzo[h]quinolone and benzo[c]acridinone derivatives by Fe₃O₄@PS‐Arginine[HSO₄] as an efficient magnetic nanocatalyst