Synthesis of triterpenoid triazine derivatives from allobetulone and betulonic acid with biological activities |
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| Institution: | 1. Molecular Design and Synthesis, Department of Chemistry, University of Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium;2. Rega Institute for Medical Research, University of Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium;1. Grupo Infección e Inmunidad, Facultad de Ciencias de la Salud, Universidad Tecnológica de Pereira, Pereira, Colombia;2. Grupo Polifenoles, Facultad de Tecnologías, Escuela de Química, Universidad Tecnológica de Pereira, Pereira, Colombia;3. Department of Chemistry, Universidad del Valle, Cali, Colombia;1. Department of Pharmacy, Faculty of Medicine, University of Latvia, 19 Raina Blvd., Riga, LV1586, Latvia;2. Department of Physical chemistry, Faculty of Chemistry, University of Latvia, 19 Raina Blvd., Riga, LV1586, Latvia;3. Department of Pharmacology, Faculty of Medicine, University of Latvia, 19 Raina Blvd, Riga, LV1586, Latvia;1. State Key Laboratory of Natural Medicines, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, PR China;2. Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, PR China;3. Department of Organic Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, PR China;4. Department of Microbiology, Immunology and Molecular Genetics, University of Kentucky College of Medicine, 800 Rose Street, Lexington, KY 40536, USA;5. College of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, PR China;1. Department of Histology and Embryology, Wroclaw Medical University, Cha?ubińskiego 6a, 50-368 Wroclaw, Poland;2. Department of Bioorganic Chemistry, Faculty of Chemistry, Wroclaw University of Technology, Wyb. Wyspiańskiego 27, 50-370 Wroclaw, Poland;3. Department of Medical Biochemistry, Wroclaw Medical University, Cha?ubińskiego 10, 50-368 Wroclaw, Poland |
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| Abstract: | The synthetic transformation and modification of natural products with the aim to improve the biological properties is an area of current interest. The triterpenoids betulin and betulinic acid are very abundant in nature and now are commercially available. In our study, starting from betulin and betulinic acid, we obtained allobetulone and betulonic acid in a few synthetic steps. The ketone function at the A-ring was used as the starting point for the synthesis of a series of 1,2,4-triazine-fused triterpenoids. The alkylation and Liebeskind–Srogl coupling were used for further substitution of 1,2,4-triazines, and the intramolecular hetero Diels–Alder reaction leads to interesting fused thienopyridine derivatives. All new compounds were tested for their cytostatic activities against murine leukemia L1210, human cervix carcinoma HeLa and human lymphoblast CEM tumor cells. The results show that some triterpenoid triazine betulonic acid derivatives have a promising cytostatic activity in vitro and could be used as potential leads for the development of new type of anti-cancer agents. Several compounds were also endowed with anti-HCMV activity in the low micromolar range. |
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| Keywords: | Triterpenoid triazine Diels–Alder reaction Murine leukemia Cervix carcinoma HeLa Lymphoblast CEM tumor cells |
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