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Open AccessArticle

Synthesis and Evaluation of N-(3-Trifluoroacetyl-indol-7-yl) Acetamides for Potential In Vitro Antiplasmodial Properties

1
Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, Private Bag X06, Florida 1710, South Africa
2
Institute for Research in Molecular Medicine (INFORMM), Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia
*
Author to whom correspondence should be addressed.
Molecules 2017, 22(7), 1099; https://doi.org/10.3390/molecules22071099
Received: 5 June 2017 / Revised: 21 June 2017 / Accepted: 28 June 2017 / Published: 2 July 2017
(This article belongs to the Section Bioorganic Chemistry)
A series of novel N-((2,5-diaryl-3-trifluoroacetyl)-1H-indol-7-yl)acetamides has been prepared via a successive and one-pot reaction sequence involving initial trifluoroacetic acid-mediated Beckmann rearrangement of the oximes derived from the 1-(2,5-diaryl-1H-indol-7-yl)ethanones, followed by trifluoroacetylation of the incipient N-(2,5-diaryl-1H-indol-7-yl)-acetamides with trifluoroacetic anhydride. The prepared compounds were evaluated for potential in vitro antiplasmodial properties. Preliminary results from antiplasmodial activity against the chloroquine-sensitive 3D7 strain of Plasmodium falciparum revealed that a combination of 2-(4-flurophenyl)- and 5-(4-fluorophenyl) or 2-(4-flurophenyl)- and 4-fluorostyryl groups in compounds 3(a,f) and 4(a,g), for example, is required for biological activity for both series of compounds. Their possible mode of action against the plasmodial parasite is explained theoretically through molecular docking of the most active compounds against the parasite lactate dehydrogenase (pLDH). These compounds were docked at the entrance of NAD+ in pLDH presumably hindering entry of lactate to cause the observed inhibition effect of pLDH. The four compounds were found to exhibit low toxicity against monkey kidney Vero cells at the highest concentrations tested. View Full-Text
Keywords: N-(2,5-diaryl-1H-indol-7-yl)acetamides; N-(3-trifluoroacetylindol-7-yl)acetamides; antiplasmodial activity; cytotoxicity; molecular docking N-(2,5-diaryl-1H-indol-7-yl)acetamides; N-(3-trifluoroacetylindol-7-yl)acetamides; antiplasmodial activity; cytotoxicity; molecular docking
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MDPI and ACS Style

Mphahlele, M.J.; Mmonwa, M.M.; Choong, Y.S. Synthesis and Evaluation of N-(3-Trifluoroacetyl-indol-7-yl) Acetamides for Potential In Vitro Antiplasmodial Properties. Molecules 2017, 22, 1099. https://doi.org/10.3390/molecules22071099

AMA Style

Mphahlele MJ, Mmonwa MM, Choong YS. Synthesis and Evaluation of N-(3-Trifluoroacetyl-indol-7-yl) Acetamides for Potential In Vitro Antiplasmodial Properties. Molecules. 2017; 22(7):1099. https://doi.org/10.3390/molecules22071099

Chicago/Turabian Style

Mphahlele, Malose J.; Mmonwa, Mmakwena M.; Choong, Yee S. 2017. "Synthesis and Evaluation of N-(3-Trifluoroacetyl-indol-7-yl) Acetamides for Potential In Vitro Antiplasmodial Properties" Molecules 22, no. 7: 1099. https://doi.org/10.3390/molecules22071099

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