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 1H-NMR, 13C-NMR, FT-IR, MS, microanalysis, and single-crystal X-ray crystallography. The compound crystallized in the monoclinic system, with space group P21/c and cell coordinates a = 8.5752(16) Å, b = 21.046(4) Å, c = 8.2941(12) Å, β = 101.131(6)°, V = 1468.7(4) Å3, 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.
Highlights
Heterocyclic compounds possessing the thiophene core have attracted tremendous interest in the field of medicinal chemistry due to their diverse and wide range of biological properties, including analgesic [1], antidepressant [2], anti-inflammatory [3], antimicrobial [4] and anticonvulsant activities [5–8]
With phenylamino (N1/C5-C10), ethyl carboxlyate (C11/O2/O3/C12-C13), methyl (C14), and acetyl (O1/C15-C16) substituents attached to the C1, C2, C3 and C4 atoms of the thiophene ring, respectively (Figure 1)
Pseudomoas aeruginosa and Escherichia coli for Gram-negative bacteria and Staphylococcus pneumonia and Bacillis subtilis for Gram-positive, and Aspergillus fumigates, Syncephalastrum racemosum, Geotricum candidum and Candida albicans for fungi
Summary
Heterocyclic compounds possessing the thiophene core have attracted tremendous interest in the field of medicinal chemistry due to their diverse and wide range of biological properties, including analgesic [1], antidepressant [2], anti-inflammatory [3], antimicrobial [4] and anticonvulsant activities [5–8]. Enaminones are key synthons for the synthesis of a wide variety of naturally occurring alkaloids [10,11], and nitrogen-containing heterocycles [12–15]. They have been employed as important intermediates for the synthesis of pharmaceutical drugs with antiviral, larvicidal [16] and anticonvulsant properties [17–19]. Due to their rich applications, many efficient approaches to these compounds have been developed. The antimicrobial activities of the synthesized compounds were examined and the molecular modeling of the most active products is discussed
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