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Molecules 2017, 22(10), 1685; doi:10.3390/molecules22101685

Antibacterial and Antitubercular Activities of Cinnamylideneacetophenones

1
Laboratory of Green and Medicinal Chemistry, Department of Chemistry and Environmental Sciences, Institute of Biosciences, Humanities and Exact Sciences, São Paulo State University (Unesp), São José do Rio Preto, SP 15054-000, Brazil
2
Department of Pediatric Dentistry and Public Health, School of Dentistry, São Paulo State University (Unesp), Araçatuba, SP 16015-050, Brazil
3
Department of Biological Sciences, School of Pharmaceutical Sciences, São Paulo State University (Unesp), Araraquara, SP 14800-903, Brazil
4
Department of Biochemistry and Microbiology, Institute of Biosciences, São Paulo State University (Unesp), Rio Claro, SP 13506-900, Brazil
These two authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 30 August 2017 / Revised: 2 October 2017 / Accepted: 3 October 2017 / Published: 10 October 2017
(This article belongs to the Special Issue Emerging Drug Discovery Approaches against Infectious Diseases)
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Abstract

Cinnamaldehyde is a natural product with broad spectrum of antibacterial activity. In this work, it was used as a template for design and synthesis of a series of 17 cinnamylideneacetophenones. Phenolic compounds 3 and 4 exhibited MIC (minimum inhibitory concentration) and MBC (minimum bactericidal concentration) values of 77.9 to 312 µM against Staphylococcus aureus, Streptococcus mutans, and Streptococcus sanguinis. Compounds 2, 7, 10, and 18 presented potent effects against Mycobacterium tuberculosis (57.2 µM ≤ MIC ≤ 70.9 µM). Hydrophilic effects caused by substituents on ring B increased antibacterial activity against Gram-positive species. Thus, log Po/w were calculated by using high-performance liquid chromatography-photodiode array detection (HPLC-PDA) analyses, and cinnamylideneacetophenones presented values ranging from 2.5 to 4.1. In addition, the effects of 3 and 4 were evaluated on pulmonary cells, indicating their moderate toxicity (46.3 µM ≤ IC50 ≤ 96.7 µM) when compared with doxorubicin. Bioactive compounds were subjected to in silico prediction of pharmacokinetic properties, and did not violate Lipinski’s and Veber’s rules, corroborating their potential bioavailability by an oral route. View Full-Text
Keywords: cinnamaldehyde; cinnamylideneacetophenone; antimicrobial; antibacterial; antitubercular; Mycobacterium; Claisen-Schmidt reaction cinnamaldehyde; cinnamylideneacetophenone; antimicrobial; antibacterial; antitubercular; Mycobacterium; Claisen-Schmidt reaction
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Polaquini, C.R.; Torrezan, G.S.; Santos, V.R.; Nazaré, A.C.; Campos, D.L.; Almeida, L.A.; Silva, I.C.; Ferreira, H.; Pavan, F.R.; Duque, C.; Regasini, L.O. Antibacterial and Antitubercular Activities of Cinnamylideneacetophenones. Molecules 2017, 22, 1685.

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