The intense research work in the field of medicinal chemistry has enhanced the significance of Biphenyl moiety as pharmacologically important compound. Some of the compounds bearing Biphenyl moiety possess important medicinal properties like antihypertensive and calcium channel blocker, anti-inflammatory, diuretic, anti-diabetic activity, antipsychotic and anxiolytic activity. The present article describes the synthesis of novel benzohydrazides and 2-phenylacetohydrazides bearing Biphenyl moiety and vanillin hybrid. The synthesized compounds (31-40) were characterized by 1 H NMR, Mass and IR spectroscopic techniques and were evaluated for anti-inflammatory activity by carrageenan paw edema method. The results of the study revealed that compounds 39 and 40 (bearing 2-(4-nitrophenyl)acetohydrazide and 2-(2,3-dihydrobenzofuran-5-yl)acetohydrazide) showed maximum anti-inflammatory activity while the compounds 31, 32, 33, 34 and 38 bearing benzohydrazides displayed moderate anti-inflammatory activity.
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...
A novel series of hydrazide-hydrazone derivatives 39-50, linked with anacardic acid motif and 1,2,3-triazole ring were synthesized by reacting 4-(1-(2-methoxy-6-pentadecylbenzyl)-1H-1, 2, 3-triazol-4-yl)benzaldehyde with 2-phenyl-acetohydrazides and benzohydrazides. The structures of the newly synthesized hydrazide-hydrazone derivatives 39-50 were confirmed by 1 H NMR, MS and IR spectroscopic tools. These compounds were also evaluated for their anti-inflammatory activity by carrageenan paw edema method.
The present paper describes the synthesis and anti-inflammatory activity of some new hydrazide-hydrazone derivatives (4a-n) from commercially available vanillin as starting material in three synthetic steps.Step 1
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