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Molecules 2015, 20(5), 8712-8729; doi:10.3390/molecules20058712

Synthesis, In-Vitro Antibacterial, Antifungal, and Molecular Modeling of Potent Anti-Microbial Agents with a Combined Pyrazole and Thiophene Pharmacophore

1
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
2
Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia-21321 Alexandria, Egypt
3
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
4
Institut für Organische Chemie, Universitat Stuttgart, Pfaffenwaldring 55, Stuttgart 70569, Germany
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editor: Philippe Belmont
Received: 5 April 2015 / Accepted: 11 May 2015 / Published: 14 May 2015
(This article belongs to the Collection Heterocyclic Compounds)
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Abstract

Ethyl 5-acetyl-4-methyl-2-(phenylamino)thiophene-3-carboxylate (2) and there derivatives 3ac, 4, 6ac and 9af 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, 3ac, 4, 5ac and 9af 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. View Full-Text
Keywords: thiophene; enaminone; [2+3] cycloaddition; anti-microbial activity; molecular modeling thiophene; enaminone; [2+3] cycloaddition; anti-microbial activity; molecular modeling
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MDPI and ACS Style

Mabkhot, Y.N.; Kaal, N.A.; Alterary, S.; Al-Showiman, S.S.; Barakat, A.; Ghabbour, H.A.; Frey, W. Synthesis, In-Vitro Antibacterial, Antifungal, and Molecular Modeling of Potent Anti-Microbial Agents with a Combined Pyrazole and Thiophene Pharmacophore. Molecules 2015, 20, 8712-8729.

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