122408-83-7Relevant academic research and scientific papers
2-(Fluoromethyl)-3-phytyl-1,4-naphthoquinone and its 2,3-epoxide. Inhibition of vitamin K epoxide reductase
Silverman,Oliver
, p. 2138 - 2141 (1989)
2(Fluoromethyl)-3-phytyl-1,4-naphthoquinone (7) was synthesized from the known compound 2-bromo-3-methyl-1,4-dimethoxynapthalene by N-bromosuccinimide bromination of the 3-methyl group, conversion to the corresponding 3-fluoromethyl compound with silver fluoride, attachment of the 3-phytyl substitutent via the lithium diaryl cuprate and phytyl bromide, and then silver oxide oxidation to 7. Epoxidation with basic hydrogen peroxide gave the corresponding 2,3-oxide (1) in a very low yield. Compound 1 was not a time-dependent inhibitor of beef liver microsomal vitamin K epoxide reductase, but it was a competitive, reversible inhibitor. It was not possible to determine if 1 was a substrate for the enzyme because the expected product of reduction, namely 7, rapidly decomposed under the assay conditions.
Synthesis of 2-Substituted-3-phytyl-1,4-naphthoquinone Epoxides
Ryall, Robert P.,Silverman, Richard B.
, p. 431 - 438 (2007/10/02)
Hydroxymethylation of 2-phytyl-1,4-naphthohydroquinone followed by epoxidation gives 2-hydroxymethyl-3-phytyl-1,4-naphthoquinone epoxide, which is converted to the corresponding 2-fluoromethyl-, 2-chloromethyl-, and 2-difluoromethyl- analogues.The latter compound is prepared from the 2-formyl analogue.
