Syntheses of 6-(2-hydroxy-6-phenylhexyl)-5,6-dihydro-2H-pyran-2-one derivatives and their cytotoxicities |
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| Institution: | 1. Research Unit of Environmental and Applied Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, P.O. Box 67, Dschang, Cameroon;2. Research Unit of Microbiology and Antimicrobial Substances, Department of Biochemistry, Faculty of Science, University of Dschang, P.O. Box 67, Dschang, Cameroon;3. Université de Reims Champagne Ardenne, CNRS, ICMR UMR 7312, 51097 Reims, France;4. Food Science, Department of Chemistry, Carleton University, Room 207D Steacie Building, 1125 Colonel by Drive, K1S 5B6 Ottawa, Canada;1. School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046, PR China;2. The Engineering and Technology Center for Chinese Medicine Development of Henan Province, Zhengzhou 450046, PR China;1. UMR 152 PharmaDev, Université de Toulouse, IRD, UPS, Toulouse, France;2. Laboratorios de Investigación y Desarrollo, Facultad de Ciencias y Filosofía, Universidad Peruana Cayetano Heredia, Lima, Peru;3. Institut de Chimie de Toulouse, ICT UAR 2599, Université Paul Sabatier-Toulouse III, Toulouse, France;1. Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, Hainan, 571158, People’s Republic of China;2. Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, Haikou, Hainan, 571158, People’s Republic of China;1. Postgraduate Program in Biological Chemistry, Department of Biological Chemistry, Regional University of Cariri (URCA), Crato, CE, Brazil;2. Department of Biological Sciences, Regional University of Cariri (URCA), Crato, CE, Brazil;3. Postdoctoral intern of the Laboratory of Microbiology and Molecular Biology (LMBM), Regional University of (URCA), Crato, CE, Brazil;4. Coordinator of the Laboratory of Natural Products Research, Regional University of Cariri (URCA), Crato, CE, Brazil;5. Coordinator of the Laboratory of Microbiology and Molecular Biology (LMBM), Regional University of Cariri (URCA), Crato, CE, Brazil;6. Postdoctoral advisor and permanent professor at the Graduate Program Rede Nordeste de Biotecnologia (RENORBIO-Nucleadora UECE), associate professor at the Universidade Estadual Vale do Acaraú, Sobral, CE, Brazil;7. Postdoctoral intern and coordinator of the Semiarid Bioprospecting Laboratory (LABSEMA), Regional University of Cariri (URCA), Crato, CE, Brazil;1. Laboratory of Cellular Immunology and Parasitology, Department of Biological Sciences, Central Washington University, Ellensburg, WA 98926, United States;2. Department of Chemistry, Central Washington University, Ellensburg, WA 98926, United States;3. Department of Chemistry, Western Washington University, Bellingham, WA 98225, United States |
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| Abstract: | The cytotoxicities against cancer cells (HL-60, HeLa) and insect cells (Sf9) of four stereoisomers of 6-(2-hydroxy-6-phenylhexyl)? 5,6-dihydro-2H-pyran-2-one (1) were evaluated, and then their structure-activity relationships examined. The 2′-dehydroxy derivative 5 of (6 R,2′R)- and (6 R,2′S)-1 showed the highest activity against HeLa cells (IC50 = 1.4 μM). To evaluate the effect of the 2′-hydroxy group of 1, 6R-and 6S-oxetane derivatives were also synthesized and their activities examined. Against HeLa and HL-60 cells, the activities of the less potent stereoisomers were enhanced 3–4-fold by the introduction of the oxetane moieties at the 2′-position. Against the insect cell line (Sf9), phenyl derivative 7 showed the highest activity with an IC50 value of 8.0 μM. |
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| Keywords: | Structure-activity relationship Cytotoxicity Oxetane |
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