The reaction mixture of 2-(3′,5′-Dimethyl-4′-ethoxy carbonyl pyrrole)-1-phenyl-isosemi-carbazide (0.01 mol), monochloroacetic acid and (2 g) and anhydrous sodium acetate (2 g) in acetic acid (12 mL). The reaction mixture was refluxed for 8 h, cooled and poured over crushed ice with stirring. The solid was separated out, filtered, washed with water, dried and crystallized from methanol. Yield 62%, M.P. 215 °C: IR (KBr); 3350 (NH), 1660 (C O), 1480 (C N), 1320 (CH3), 1700 (COOC2H5), 826 (C–N); 1H NMR (300 MHz DMSO), Cobimetinib δ 4.58 (1H, pyrrole–NH), 2.1 (6H, w, 2 × CH3), 3.8 (5H, s, COOC2H5), 8.2 (4H, s, Ar–H), 7.1 (1H, s, CONH–N). Yield 74%, M.P. 247 °C: IR (KBr); 3450 (NH), 1630 (C O), 1420 (C N), 1320 (CH3), 1735 (COOC2H5) 829 (C–N); 1H NMR (300 MHz GSK1120212 DMSO), δ
4.9 (1H, pyrrole–NH), 2.2 (6H, w, 2 × CH3), 3.7 (5H, s, COOC2H5), 8.1 (4H, s, Ar–H) 7.3, (1H, s, CONH–N). Yield 52%, M.P. 260 °C: IR (KBr); 3250 (NH), 1690 (C O), 1430 (C N), 1332 (CH3), 1720 (COOC2H5), 839 (C–N), 738 (C–Cl); 1H NMR (300 MHz DMSO), δ 4.83 (1H, pyrrole–NH), 2.3 (6H, w, 2 × CH3), 3.5 (5H, s, COOC2H5), 8.1 (4H, s, Ar–H) 7.3, (1H, s, CONH–N). Yield 60%, M.P. 217 °C: IR (KBr); 3345 (NH), 1680 (C O), 1426 (C N), 1310 (CH3), 1720 (COOC2H5), 740 (C–Cl), 829 (C–N); 1H NMR (300 MHz DMSO), δ 4.9 (1H, pyrrole–NH), 2.5 (6H, w, 2 × CH3), 3.8 (5H, s, COOC2H5), 8.3 (4H, s, Ar–H) isothipendyl 7.9, (1H, s, CONH–N). Yield 50%, M.P. 291 °C: IR (KBr); 3360 (NH), 1620 (C O), 1438 (C N), 1320 (CH3), 1728 (COOC2H5), 1538 (C–NO2), 822 (C–N); 1H NMR (300 MHz DMSO), δ 5.1 (1H, pyrrole–NH), 1.98 (6H, w, 2 × CH3), 3.4 (5H, s, COOC2H5), 8.2 (4H, s, Ar–H) 7.6, (1H, s, CONH–N). Yield 40%, M.P. 274 °C:
IR (KBr); 3455 (NH), 1620 (C O), 1395 (C N), 1310 (CH3), 1722 (COOC2H5), 1570 (C–NO2) 842 (C–N); 1H NMR (DMSO–d6) 5.38 (1H, pyrrole–NH), 3.1 (6H, w, 2 × CH3), 3.9 (5H, s, COOC2H5), 8.2 (4H, s, Ar–H) 7.5, (1H, s, CONH–N). Yield 56%, M.P. 259 °C: IR (KBr); 3432 (NH), 1636 (C O), 1395 (C N), 1320 (CH3), 1775 (COOC2H5), 1565 (C–NO2), 827 (C–N); 1H NMR (300 MHz DMSO), δ 5.9 (1H, pyrrole-NH), 3.1 (6H, w, 2 × CH3), 4.1 (5H, s, COOC2H5), 8.9 (4H, s, Ar–H), 7.4, (1H, s, CONH–N). Comparative study of 3,5-dimethyl-2,4-diethoxy carbonyl pyrrole (1) and 2-substituted 1,2,4-triazole (4a–g), 4-oxadiazole (5a–g) and 4-oxazolidinones (6a–g) have been observed by using Norfloxacin and Griseofulvine as standards. The enhancement in biological activity of compound (1) as compared with the newly synthesized (4a–g), (5a–g), (6a–g) has been observed.