Abstract
An improved synthesis for the (Z)-14-methyl-9-pentadecenoic acid was developed based on the appropriate use of (trimethylsilyl)acetylene as the key reagent in the synthesis. The reported synthesis started with commercially available 8-bromo-1-octanol and furnished the desired acid in seven steps and in a 16% overall yield, a significant improvement over the previous reported synthesis for this fatty acid. The synthesis reported herein afforded sufficient amounts to study the acid topoisomerase I inhibitory potential and it was found that the title acid inhibits the human placenta DNA topoisomerase I enzyme at concentrations of 500 μM.
Highlights
There are several literature reports describing the inhibitory effects of fatty acids towards the topoisomerase I enzyme.[1,2,3,4,5,6,7,8,9]
Topoisomerase I is a key enzyme in the breaking and fixing of DNA strands and is involved in making the necessary topological changes to DNA for key cellular processes such as replication, transcription, and recombination.[1]
The bromo dihydropyranyl protected alcohol 3 was submitted to the first acetylide coupling reaction with the versatile reagentacetylene using n-BuLi in THF-HMPA affording the trimethylsilyl acetylenic derivative 4 in a 100% yield
Summary
There are several literature reports describing the inhibitory effects of fatty acids towards the topoisomerase I enzyme.[1,2,3,4,5,6,7,8,9] Topoisomerase I is a key enzyme in the breaking and fixing of DNA strands and is involved in making the necessary topological changes to DNA for key cellular processes such as replication, transcription, and recombination.[1].
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