Synthesis, antioxidant and $$\alpha $$-amylase inhibition activity of naphthalene-containing 2,4,5-trisubstituted imidazole derivatives

Abstract

A series of naphthalene ring containing 2,4,5-trisubstituted imidazole derivatives (2a-2l) were synthesized using one-pot multicomponent reaction. The reactions were carried out using naphthaldehyde and substituted benzil in the presence of ammonium acetate in acetic acid media. All newly synthesized imidazole derivatives were characterized by FT-IR, 1 H NMR, 13 C NMR and mass spectral analysis. Newly synthesized imidazole derivatives were screened for their in-vitro antioxidant activity by DPPH free radical scavenging assay method and α-amylase inhibition activity by DNS method. All the compounds showed excellent α-amylase activity at 10, 50 and 100 μg/mL and compounds 2d, 2g, 2k exhibited good antioxidant activity.

Recent Developments in the Synthesis of N‐Heterocyclic Compounds as α‐Amylase Inhibitors via In‐Vitro and In‐Silico Analysis: Future Drugs for Treating Diabetes

“…All the derivatives showed moderate amylase inhibition activity whereas derivative with methoxy substitution showed the best activity. [63][64][65] Figure 8 gives a comparison between all the most potential derivatives of series 2.4. The graph shows that compound 61 L has shown excellent inhibition potential among the whole series followed by 56 L. This means presence of sulphur and oxygen played very important role.…”

“…The naphthalene substituted imidazole derivatives were formed by reacting naphthaldehyde 62 and substituted benzyl 63 in the presence of ammonium acetate as shown in scheme 21. All the derivatives showed moderate amylase inhibition activity whereas derivative with methoxy substitution showed the best activity [63–65] …”

Simple practical method for synthesis of trisubstituted imidazoles: an efficient copper catalyzed multicomponent reaction

“…White solid; mp: 263–265 °C [Lit. 57 262–263 °C]; 1 H NMR (400 MHz, DMSO-d 6 ) δ 12.77 (s, 1H), 9.15 (d, J = 8.6 Hz, 1H), 7.97 (d, J = 7.9 Hz, 2H), 7.93 (d, J = 6.7 Hz, 1H), 7.61–7.52 (m, 7H), 7.43–7.20 (m, 6H) ppm; 13 C NMR (100 MHz, DMSO-d 6 ) δ 146.1, 137.6, 135.8, 134.2, 131.5, 130.8, 129.5, 129.2, 128.9, 128.8, 128.5, 128.3, 127.9, 127.7, 127.3, 127.1, 126.7, 125.8 ppm.…”

Fe3O4 Nanoparticles Catalyzed Tandem Synthesis of Fluorescent 3‐(4,5‐diaryl‐1H‐imidazol‐2‐yl) quinoline‐2‐amines: Solvatochromic, DFT and Biological Studies

“…[43] The compounds 6-(2-chloro-quinolin-3-yl)-imidazo[2,1-b] thiazol-5-yl] amines VII and 2-(2-chloro-quinolin-3-yl)-imidazo [1,2-a] pyridin-3-yl] amines VIII were tested against 15-lipoxygenase. [44] The quinoline clubbed with imidazole IX and X have shown good antibacterial and antioxidant activities as compared to Ciprofloxacin [45] as shown in Figure 2.…”