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Article

Cinnamoyl-Oxaborole Amides: Synthesis and Their in Vitro Biological Activity

1
Faculty of Science, Department of Chemistry, Rhodes University, Grahamstown 6140, South Africa
2
Drug Discovery and Development Centre (H3-D), Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa
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MRC/NHLS/UCT Molecular Mycobacteriology Research Unit, Department of Pathology, University of Cape Town, Rondebosch 7701, South Africa
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Institute of Infectious Disease and Molecular Medicine, University of Cape Town, Rondebosch 7701, South Africa
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Faculty of Science, Department of Biochemistry and Microbiology, Rhodes University, Grahamstown 6140, South Africa
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Centre for Chemico- and Biomedicinal Research, Rhodes University, Grahamstown 6140, South Africa
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Foodborne Toxin Detection and Prevention Research Unit, Agricultural Research Service, United States Department of Agriculture, Albany, CA 94710, USA
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Department of Biological Sciences, University of the Pacific, Stockton, CA 95211, USA
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(8), 2038; https://doi.org/10.3390/molecules23082038
Received: 13 July 2018 / Revised: 6 August 2018 / Accepted: 7 August 2018 / Published: 15 August 2018
(This article belongs to the Section Medicinal Chemistry)
Due to the increased interest in their application in the treatment of infectious diseases, boron-containing compounds have received a significant coverage in the literature. Herein, a small set of novel cinnamoly-oxaborole amides were synthesized and screened against nagana Trypanosoma brucei brucei for antitrypanosomal activity. Compound 5g emerged as a new hit with an in vitro IC50 value of 0.086 μM against T. b. brucei without obvious inhibitory activity against HeLa cell lines. The same series was also screened against other human pathogens, including Mycobacterium tuberculosis, the causative agent of tuberculosis (TB), for which moderate to weak activity (10 to >125 μM) was observed. Similarly, these compounds exhibited moderate activity against the human protozoal pathogen Trichomonas vaginalis with no observed effect on common microbiome bacterial species. The cross-species inhibitory activity presents the possibility of these compounds serving as broad-spectrum antibiotics for these prevalent three human pathogens. View Full-Text
Keywords: benzoxaboroles; cinnamic acids; trichomoniasis; trypanosomiasis; Mycobacterium tuberculosis benzoxaboroles; cinnamic acids; trichomoniasis; trypanosomiasis; Mycobacterium tuberculosis
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MDPI and ACS Style

Gumbo, M.; Beteck, R.M.; Mandizvo, T.; Seldon, R.; Warner, D.F.; Hoppe, H.C.; Isaacs, M.; Laming, D.; Tam, C.C.; Cheng, L.W.; Liu, N.; Land, K.M.; Khanye, S.D. Cinnamoyl-Oxaborole Amides: Synthesis and Their in Vitro Biological Activity. Molecules 2018, 23, 2038. https://doi.org/10.3390/molecules23082038

AMA Style

Gumbo M, Beteck RM, Mandizvo T, Seldon R, Warner DF, Hoppe HC, Isaacs M, Laming D, Tam CC, Cheng LW, Liu N, Land KM, Khanye SD. Cinnamoyl-Oxaborole Amides: Synthesis and Their in Vitro Biological Activity. Molecules. 2018; 23(8):2038. https://doi.org/10.3390/molecules23082038

Chicago/Turabian Style

Gumbo, Maureen, Richard M. Beteck, Tawanda Mandizvo, Ronnett Seldon, Digby F. Warner, Heinrich C. Hoppe, Michelle Isaacs, Dustin Laming, Christina C. Tam, Luisa W. Cheng, Nicole Liu, Kirkwood M. Land, and Setshaba D. Khanye 2018. "Cinnamoyl-Oxaborole Amides: Synthesis and Their in Vitro Biological Activity" Molecules 23, no. 8: 2038. https://doi.org/10.3390/molecules23082038

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