STUDI SINTESIS CALKON TERPRENILASI
Flavonoids are known to have many biological activities. Due to their beneficial effects on human health, flavonoids are of particular interest as lead compounds for discovery of a new drug. There are some classes in flavonoid skeletons, including chalcone, flavanone, flavone, and flavonol. These co...
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| Format: | Final Project |
| Language: | Indonesia |
| Online Access: | https://digilib.itb.ac.id/gdl/view/16720 |
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| Institution: | Institut Teknologi Bandung |
| Language: | Indonesia |
| Summary: | Flavonoids are known to have many biological activities. Due to their beneficial effects on human health, flavonoids are of particular interest as lead compounds for discovery of a new drug. There are some classes in flavonoid skeletons, including chalcone, flavanone, flavone, and flavonol. These compounds show antioxidant, antitumor, antiimflammation, antibacterial, and antimicrobial activities. In particular, prenylation on flavonoids skeleton have an important role to strong activities and to the structure diversification of flavonoids. Due to differences in the prenylation position on the aromatic ring, various unit number of prenyl chain, and further modifications of the prenyl moiety, such as cyclization and hydroxylation, resulting in the occurrence of more than thousand prenylated flavonoids derivatives in plants. The interesting role of prenyl group on flavonoids have been atracted organic synthesis chemist to develop a methodolgy of prenylation for diversification of flavonoid structure which has the highest specific activity. In this research, we decided prenylated chalcone as a target molecule. Prenylated chalcone can be synthesized via Claisen-Schmidt condensation between an acetophenone and a benzaldehyde derivatives. We have succesfully synthesized two important intermediates for synthesis prenylated chalcone skeleton, including 2-O-prenyl-4,6-dimethoxyacetophenone and 4-O-TBDMS ethyl vanillin. The first compound 2-O-prenyl-4,6-dimethoxyacetophenone, was synthesized from 2-hydroxy-4,6-dimethoxyacetophenone and prenyl bromide under basic condition with 36% yields as a yellowish solid. The second compound, 4-O-TBDMS ethyl vanillin, was synthesized from ethyl vanillin and TBDMS-Cl under basic condition with 65% yield as a yellowish oil. Both of these compounds characterized using NMR, UV-Vis, MS, and FTIR spectroscopies. |
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