Identification of quinoline-chalcone hybrids as potential antiulcer agents

Sashidhara, Koneni V.; Avula, Srinivasa Rao; Mishra, Vaibhav; Palnati, Gopal Reddy; Singh, Lakhwant; Singh, Neetu; Chhonker, Yashpal S.; Swami, Priyanka; Bhatta, Rabi Sankar; Palit, Gautam

doi:10.1016/j.ejmech.2014.10.068

Cited by 82 publications

(34 citation statements)

References 52 publications

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“…The result indicates a possible cytoprotective activity. The concept of gastric cytoprotection signifies protection against mucosal injury by a mechanism other than inhibition of acid secretion (Robert, 1979;Sashidhara et al, 2014).…”

Section: Discussionmentioning

confidence: 99%

Gastroprotective and antioxidant potentials of ethanolic stem bark extract of Margaritaria discoidea (Euphorbiaceae) in rats

Sofidiya

Orisaremi

Sansaliyu

et al. 2015

Journal of Ethnopharmacology

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Section: Discussionmentioning

confidence: 99%

Gastroprotective and antioxidant potentials of ethanolic stem bark extract of Margaritaria discoidea (Euphorbiaceae) in rats

Sofidiya

Orisaremi

Sansaliyu

et al. 2015

Journal of Ethnopharmacology

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“…Quinoline derivatives have attracted considerable interest for many years due to their chemical reactivity and biological activity [1][2][3][4]. Literature surveys revealed that these derivatives possesses anti-inflammatory [5,6] antimicrobial [7,8], antimalarial [9,10], antioxidant [11,12], antitumor [13,14], antiprotozoal [15], antituberculosis [16,17] and antiulcer activity [18], as well as, A3 adenosine receptor antagonists [19]. On the other hand, pyrazole derivatives are known to exhibit diverse biological activities including anti-inflammatory [20], anticancer [21] and antimicrobial [22,23] activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Antimicrobial Activity of Some Novel Quinoline Derivatives Bearing Pyrazole and Pyridine Moieties

Amer

El‐Eraky

Mahgoub³

2018

Egypt. J. Chem.

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our efforts were directed towards the synthesis of new heterocyclic compounds containing quinoline ring bearing pyrazole and pyridine moieties with anticipated biological activities. Experimental General All melting points were determined in openglass capillaries and are uncorrected. IR spectra were recorded on a Bruker Vector 22 Germany spectrometer (KBr). 1 HNMR spectra were recorded on Bruker 400 MHz spectrometer using TMS as an internal reference. The Electron Impact mass spectrometry was obtained at 70 eV using Shimadzu QP-2010 Plus mass spectrometer. The reactions were monitored by thin-layer chromatography (TLC) on silica gel F254 aluminum sheets (Merck), and the spots were visualized by UV lamp at 254-365 nm. I N continuation of our interest in synthesis of novel quinoline derivatives with anticipated biological activity, we have synthesized new quinoline derivatives bearing pyrazole and pyridine moieties by formylation of quinoline hydrazones through the Vilsmeier-Haack reaction which is a common method for the synthesis of 4-formyl pyrazoles. Condensation of 2-hydrazinylquinoline 1 with 4-substituted acetophenone gave the corresponding hydrazones 2a-c which in turn underwent the Vilsmeier-Haack reaction in POCl 3 /DMF to furnish the corresponding 4-formyl pyrazole derivatives 3a-c. One-pot reaction of compounds 3a-c with malononitrile and thiophenol or ethyl mercaptan gave the 3,5-pyridine dicarbonitrile derivatives 11a-f. The synthesized derivatives were screened for their antimicrobial activities against Gram negative bacteria, Gram positive bacteria and Fungi. Most of compounds showed excellent antimicrobial activities compared to the reference drugs. All the newly synthesized compounds have been characterized by means of elemental analyses, IR, 1 H NMR and MS.

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“…They are significant as structural motifs among biologically active molecules and also for combinatorial assembly of heterocyclic scaffolds [2][3][4]. Chalcones containing several functional groups showed a wide spectrum of biological activities such as antileishmanial [5,6], antimalarial [5,7], anticancer [8,9], anti-HIV [10], antioxidant [11], inflammatory [12] antiprotozoal [13], antiulcer [14] and antimicrobial [15,16] activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Antiinflammatory Activity of Chalcone Derivatives Linked with Apocynin and 5-Nitrofuran Moiety

Reddy¹,

Kathale²

2018

Asian J. Chem.

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The present paper describes the synthesis of some new chalcone derivatives i.e. 1-[3-methoxy-4-(5-nitro-furan-2-ylmethoxy)-phenyl]-3-(substituted phenyl)-propenone derivatives (9A-9K) from furfural and apocynin as starting materials. Claisen-Schmidt reaction of 1-(4-((5-nitrofuran-2-yl)methoxy)-3-methoxyphenyl)ethanone (7) with aromatic aldehydes (8A-K) under solvent free conditions using solid NaOH as catalyst at room temperature resulted in the formation of chalcone derivatives (9A-9K) in 86-96 % yield. These compounds were characterized by 1 H NMR, Mass and IR spectroscopy and were evaluated for their anti-inflammatory activity.Keywords: Anti-inflammatory activity, Apocynin, Chalcones, Furfural, Synthesis.Asian Journal of Chemistry; Vol. 30, No. 2 (2018), 312-316 Merck pre-coated plates (silica gel 60 F254) were used and spots were visualized under UV light. Merck silica gel 60 (230-400 mesh) was used for flash column chromatography and the eluting solvents are indicated in the procedures. Melting point determinations were performed by using Mel-temp apparatus and are uncorrected. 1H NMR spectra were recorded in Varian MR-400 MHz instrument. The mass spectra were recorded on Agilent ion trap MS and infrared spectra were recorded on a Perkin Elmer FT-IR spectrometer. 5-Nitrofurfural diacetate (2):A premixed solution of concentrated nitric acid (8.6 mL, 12.2 g, 193.62 mmol) and concentrated sulphuric acid (0.06 mL, 1.1 g, 11.2 mmol) was added drop-wise into acetic anhydride (90 mL) at 0 °C with stirring. To the above reaction mixture, furfural (1) (freshly distilled, 10.4 mL, 12.06 g, 125.5 mmol) was added dropwise over a period of 45 min and stirred for 1 h at 0 °C. Water (100 mL) was added to the mixture and stirred at room temperature for 30 min to obtain a white precipitate. To the reaction contents, 10 % NaOH solution was added until the pH of the mixture reached about 2.5 and the mixture was heated at 50°C for 1 h. After cooling to room temperature, the white precipitate formed was filtered, washed with water, recrystallized from anhydrous ethanol and dried to obtain diacetate compound 2. Yield: 24.84 g, 82 %. 5-Nitrofurfural (3):A mixture of 5-nitrofurfural diacetate (2) (10 g, 41.12 mmol) and 50 % aqueous sulphuric acid (100 mL) was heated to 100 °C for 10 min. After completion of the reaction, checked by TLC, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (2 × 100 mL) and the organic layer was washed with water, brine solution and dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain 5-nitrofurfural 3. Yield: 5.10 g, 88 %. m.p.: 35-36 °C.(5-Nitrofuran-2-yl)methanol (4): To a stirred solution of 5-nitrofurfural (3) (5 g, 35.44 mmol) in methanol (100 mL), cooled to 0 °C, was added sodium borohydride (1.47 g, 38.98 mmol) portion-wise and continued to stirred for additional 30 min. After completion of the reaction, checked by TLC, the solvent was concentrated under reduced pressure and the residue was quenched with water (2...

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Identification of quinoline-chalcone hybrids as potential antiulcer agents

Cited by 82 publications

References 52 publications

Gastroprotective and antioxidant potentials of ethanolic stem bark extract of Margaritaria discoidea (Euphorbiaceae) in rats

Gastroprotective and antioxidant potentials of ethanolic stem bark extract of Margaritaria discoidea (Euphorbiaceae) in rats

Synthesis, Characterization and Antimicrobial Activity of Some Novel Quinoline Derivatives Bearing Pyrazole and Pyridine Moieties

Synthesis, Characterization and Antiinflammatory Activity of Chalcone Derivatives Linked with Apocynin and 5-Nitrofuran Moiety

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