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首页> 外文期刊>Chemistry: A European journal >Synthesis and structures of Se analogues of the antithyroid drug 6-n-propyl-2-thiouracil and its alkyl derivatives: Formation of dimeric Se-Se compounds and deselenation reactions of charge-transfer adducts of diiodine
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Synthesis and structures of Se analogues of the antithyroid drug 6-n-propyl-2-thiouracil and its alkyl derivatives: Formation of dimeric Se-Se compounds and deselenation reactions of charge-transfer adducts of diiodine

机译：抗甲状腺药6-正丙基-2-硫尿嘧啶及其烷基衍生物的硒类似物的合成与结构：二聚硒硒化合物的形成和二碘电荷转移加合物的脱硒反应

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Four selenium analogues of the antithyroid drug 6-n-propyl-2-thiouracil (PTU), of formulae RSeU, (R = methyl (Me) (1), ethyl (Et) (2), n-propyl (nPr) (3), and isopropyl (iPr) 4), have been synthesized. Reaction of 1-4 with diiodine in a 1:1 molar ratio in dichloromethane results in the formation of [(RSeU)I-2] (R = methyl (5), ethyl (6), n-propyl (7) and isopropyl (8)). All compounds have been characterized by elemental analysis, FT-Raman, FT-IR, UV/Vis, H-1-, C-13-, Se-77-1D and -2D NMR spectroscopy, and ESI-MS spectrometric techniques. Recrystallization of 4 from dichloromethane afforded (4 center dot CH2Cl2)- Crystals of [(nPrSeU)I-2] (7), a charge-transfer complex, were obtained from chloroform solutions, while crystallization of 6 and 7 from acetone afforded the diselenides [N-(6-Et-4-pyrimidone)(6-EtSeU)(2)] (9 center dot 2H(2)O) and [N-(6-nPr-4-pyrimidone)(6-nPrSeU)(2)] (10) as oxidation products. Recrystallization of 7 from methanol/acetonitrile solutions led to deselenation with the formation of 6-n-propyl-2-uracil (nPrU) (11). [(nPrSeU)I-2] (7) was found to be a charge-transfer complex with a Se-I bond. These results are discussed in relation to the mechanism of action of antithyroid drugs.
机译：式RSeU的抗甲状腺药6-正丙基-2-硫尿嘧啶（PTU）的四种硒类似物，（R =甲基（Me）（1），乙基（Et）（2），正丙基（nPr）（ 3）和异丙基（iPr）4）已经合成。 1-4与二碘在二氯甲烷中以1：1摩尔比反应导致形成[（RSeU）I-2]（R =甲基（5），乙基（6），正丙基（7）和异丙基（8））。所有化合物均已通过元素分析，FT-拉曼光谱，FT-IR，UV / Vis，H-1-，C-13-，Se-77-1D和-2D NMR光谱以及ESI-MS光谱技术进行了表征。从二氯甲烷中重结晶4，得到（4个中心点CH2Cl2）-[（nPrSeU）I-2]（7）的晶体从氯仿溶液中获得，同时从丙酮中结晶6和7，得到二硒化物。 [N-（6-Et-4-pyrimidone）（6-EtSeU）（2）]（9个中心点2H（2）O）和[N-（6-nPr-4-嘧啶酮）（6-nPrSeU）（ 2）]（10）作为氧化产物。 7从甲醇/乙腈溶液中重结晶导致脱硒，形成6-正丙基-2-尿嘧啶（nPrU）（11）。 [（nPrSeU）I-2]（7）被发现是具有Se-1键的电荷转移络合物。讨论了有关抗甲状腺药物作用机制的这些结果。

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