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<p>Various methods of introducing deuterium into compounds containing serotonin (5-hydroxytryptamine, 5-HT) and dopamine (DA) were considered. By deuteration of 6,7-dihydroxy-5,8-dimethoxy-2<i>H</i>-chromen-2-one (<b>1</b>) and the reaction of its reduction product 6,7-dihydroxy-5,8-dimethoxychroman-2-one (<b>2</b>) with 5-HT and DA in dioxane and DMF, compounds <b>3a,b</b>, which are deuterated analogues of 2,3-dimethoxy-5-methyl-<i>p</i>-benzoquinone containing moieties of biogenic amines, were obtained in yields of 25 and 20–30%, respectively. The technique of reduction of a double bond in compound <b>1</b> without the use of a solvent was worked out. This technique allows the reaction to be carried out at 100–200 °C, which results in an increase in the yield of the labeled product due to isotope exchange. The achieved yield of lactone <b>2</b> with the inclusion of 6–7 deuterium atoms was 60%. The benzyl protecting group was removed at 100 °C for 30 min in an atmosphere of gaseous deuterium. Deuterated compounds [D]<b>3a</b> and [D]<b>3b</b> contained 6–7 deuterium atoms in the quinone moiety. Condensation of [D]dopamine with lactone <b>2</b> gave compound <b>3b</b> containing ∼2.5 atoms of deuterium. By deuteration of unlabeled <b>3a,b</b>, isotopically labeled compounds containing 2.3 and 6.4 deuterium atoms were isolated in yields of 30 and 20%, respectively.</p>

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Introduction of deuterium into 2,3-dimethoxy-5-methyl-p-benzoquinone analogues containing serotonin and dopamine

  • 期刊论文

  • 发表日期：

    2026年2月1日

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  • V. P. Shevchenko,
  • I. Yu. Nagaev,
  • K. V. Shevchenko,
  • L. A. Andreeva,
  • N. F. Myasoedov,
  • O. I. Adaeva,
  • D. V. Demchuk,
  • V. V. Semenov

摘要

Various methods of introducing deuterium into compounds containing serotonin (5-hydroxytryptamine, 5-HT) and dopamine (DA) were considered. By deuteration of 6,7-dihydroxy-5,8-dimethoxy-2H-chromen-2-one (1) and the reaction of its reduction product 6,7-dihydroxy-5,8-dimethoxychroman-2-one (2) with 5-HT and DA in dioxane and DMF, compounds 3a,b, which are deuterated analogues of 2,3-dimethoxy-5-methyl-p-benzoquinone containing moieties of biogenic amines, were obtained in yields of 25 and 20–30%, respectively. The technique of reduction of a double bond in compound 1 without the use of a solvent was worked out. This technique allows the reaction to be carried out at 100–200 °C, which results in an increase in the yield of the labeled product due to isotope exchange. The achieved yield of lactone 2 with the inclusion of 6–7 deuterium atoms was 60%. The benzyl protecting group was removed at 100 °C for 30 min in an atmosphere of gaseous deuterium. Deuterated compounds [D]3a and [D]3b contained 6–7 deuterium atoms in the quinone moiety. Condensation of [D]dopamine with lactone 2 gave compound 3b containing ∼2.5 atoms of deuterium. By deuteration of unlabeled 3a,b, isotopically labeled compounds containing 2.3 and 6.4 deuterium atoms were isolated in yields of 30 and 20%, respectively.