Abstract
Ethyl 5-acetyl-4-methyl-2-(phenylamino)thiophene-3-carboxylate (2) and there derivatives 3a-c, 4, 6a-c and 9a-f were synthesized. The structure of compound 2 was deduced by H-1-NMR, C-13-NMR, FT-IR, MS, microanalysis, and single-crystal X-ray crystallography. The compound crystallized in the monoclinic system, with space group P2(1)/c and cell coordinates a = 8.5752(16) angstrom, b = 21.046(4) angstrom, c = 8.2941(12) angstrom, = 101.131(6)degrees, V = 1468.7(4) angstrom(3), and Z = 4. Compounds 2, 3a-c, 4, 5a-c and 9a-f were subjected into in vitro antimicrobial activity tests. Compounds 3a and 3c were more potent than standard drug amphotericin B, showing MIC values of 23.8 +/- 0.42 and 24.3 +/- 0.68, respectively, against Aspergillus fumigatus while the standard drug MIC was 23.7 +/- 0.1. Compound 3c was also more potent (MIC 24.8 +/- 0.64) than the standard drug amphotericin B (MIC 19.7 +/- 0.2) against Syncephalastrum racemosum. Compounds 4 and 9f also showed promising anti-microbial activity. Molecular modeling was performed for the most active compounds.