RU2190591C1 - 2-methyl-3-phythyl-1,4-naphthoquinone highly labeled with tritium - Google Patents

Abstract

FIELD: organic chemistry, radiolabeled compounds. SUBSTANCE: invention describes the compound of the formula (I):

Description

 The invention relates to the field of organic chemistry and may find application in biology.

 When studying physiologically active compounds, their labeled analogues are required.

Данное соединение, получившее название "филлохинон", является фоточувствительным веществом и находит широкое использование в экспериментах, связанных с исследованием зеленых растений и бактерий K. Brettel et al., FEBS Letters 203, 220 (1986).Known 2-methyl-3-wick-1,4-naphthoquinone of the formula I:

This compound, called "phylloquinone", is a photosensitive substance and is widely used in experiments related to the study of green plants and bacteria K. Brettel et al., FEBS Letters 203, 220 (1986).

 However, tritium-labeled analogues of this known compound are not described.

 The technical result achieved by the present invention is to expand the range of labeled analogues of physiologically active compounds.

 The specified technical result is achieved by the fact that a new highly labeled with tritium 2-methyl-3-wick-1,4-naphthoquinone of the formula I is obtained.

 The following are examples of the implementation of the invention.

Example 1. In the reaction vial was placed 5 mg of phylloquinone supported on 50 mg of Lindlar catalyst based on 5% Pd / BaS0 ₄ . Then the ampoule was evacuated to a pressure of 0.1 Pa, filled with gaseous tritium to a pressure of 333 hPa and kept at 130 ^{° C. for} 20 minutes. Excess tritium was removed by evacuation. After cooling, the reaction products were dissolved in ethyl acetate (6 • 1 ml), the catalyst was filtered off, and the filtrates were evaporated several times with a mixture of ethyl acetate and methanol (9: 1) to remove labile tritium. The residue was purified by HPLC. The reaction mixture contained 1.6 mg (32%) of labeled phylloquinone, and the radiochemical purity was about 18%. After the first chromatography, 1.25 mg (25%) of labeled 2-methyl-3-wick-1,4-naphthoquinone with a radiochemical purity of 93% was isolated. After the second chromatography, the yield of the labeled preparation was 18-22%, the molar radioactivity was 60-65 Ci / mmol, and the radiochemical purity was 98-99%.

HPLC of preparative amounts of phylloquinone was carried out on a Kromasil C ₁₈ , 7 μm column, 4 • 150 mm, v - 0.8 ml / min, in the methanol-chloroform system (90:10), retention time - 12.77 min; Analytical data were obtained on a Kromasil 100 C ₁₈ , 6 μm, 2 • 80 mm column, v 0.1 ml / min, in a methanol-chloroform system (90:10), retention time 11.66 min.

 For reception and processing of chromatographic data, the MultiKhrom software and hardware complex (000 Ampersend, Russia) based on IBM PC / AT was used. Radioactivity was measured on a scintillation counter with a tritium detection efficiency of 30% in a dioxane scintillator.

Example 2. The synthesis was carried out as described in example 1, at a temperature of 100 ^o C. The output of the labeled drug is 25-30%, the molar radioactivity is 18-20 Ci / mmol.

 Thus, a new highly labeled tritium phyloquinone was obtained.

Claims (1)

Highly labeled tritium 2-methyl-3-wick-1,4-naphthoquinone of formula I