2018
DOI: 10.21577/0103-5053.20180146
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Synthesis and Cytotoxicity Evaluation of a Series of 3-Alkenyl-2-Hydroxy1,4-Naphthoquinones Obtained by an Efficient Knoevenagel Condensation

Abstract: A modified and efficient Knoevenagel condensation procedure was developed to synthesize the title compounds using β-alanine and acetic acid as catalysts, showing good to excellent yields. We used lawsone with suitable aliphatic aldehydes including isobutyraldehyde, 3-methylbutyraldehyde, 2-ethylbutyraldehyde, phenylacetaldehyde, 2-phenyl-propionaldehyde, among others. These compounds were submitted to cytotoxic screening against three tumor cell lines presenting good to excellent cytotoxic profiles.

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Cited by 3 publications
(1 citation statement)
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“…Among all quinones, 1,4-NQ and its secondary products are of particular interest because of their occurrence as natural chemicals and/or products [12,13]. These compounds have diverse pharmacological properties, such as antimicrobial [14], antiviral [15], antiprotozoal and anthelmintic [16,17], also presenting cytotoxic effects on cancer cell lines [18]. Moreover, 2-hydroxy-1,4-naphthoquinone (lawsone) (2-OH-NQ), a photochemical reaction product of 1,4-naphthoquinones, can also be extracted from the leaves of Lawsonia inermis.…”
Section: Introductionmentioning
confidence: 99%
“…Among all quinones, 1,4-NQ and its secondary products are of particular interest because of their occurrence as natural chemicals and/or products [12,13]. These compounds have diverse pharmacological properties, such as antimicrobial [14], antiviral [15], antiprotozoal and anthelmintic [16,17], also presenting cytotoxic effects on cancer cell lines [18]. Moreover, 2-hydroxy-1,4-naphthoquinone (lawsone) (2-OH-NQ), a photochemical reaction product of 1,4-naphthoquinones, can also be extracted from the leaves of Lawsonia inermis.…”
Section: Introductionmentioning
confidence: 99%