Investigation of chemical reactivity of 2-alkoxy-1,4-naphthoquinones and their anticancer activity |
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Authors: | Manoj Manickam Pulla Reddy Boggu Jungsuk Cho Yeo Jin Nam Seung Jin Lee Sang-Hun Jung |
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Affiliation: | College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon 34134, Republic of Korea |
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Abstract: | To establish the structure-activity relationship of 5-hydroxy-1,4-naphthoquinones toward anticancer activity, a series of its derivatives were prepared and tested for the activity (IC50 in µM) against three cell lines; colo205 (colon adenocarcinoma), T47D (breast ductal carcinoma) and K562 (chronic myelogenous leukemia). Among them 2 (IC50: 2.3; 2.0; 1.4?µM), 6 (IC50: 1.9; 2.2; 1.3?µM), 9 (IC50: 0.7; 1.7; 0.9?µM) and 10 (IC50:1.7; 1.0; 1.2?µM) showed moderate to excellent activity. Our perception toward the DNA substitution of alkoxy groups at the C2 position of these naphthoquinones for the anticancer activity led us to investigate their reactivity of substitution toward dimethylamine as a nucleophile. The ease of the substitution of alkoxy groups at the C2 position with dimethylamine is strongly accelerated by hydroxyl group at C5 position and is well correlated with the found anticancer activity results. |
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Keywords: | 2-Alkoxy-5-hydroxy-1,4-naphthoquinone Anticancer activity Chemical reactivity |
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