Kaul R, Hempel B, Schäfer W
Arzneimittelforschung. 1976 Apr;26(4):489-99.
The synthesis of 2-14C-1-allyl-3,5-diethyl-6-chlorouracil (2-14C-Aclu; Acluracil) is described. After application in rabbits, 2-14C-Aclu is biotransformed in one S-free major metabolite I and two S-containing minor metabolites II and III, which are more polar than Aclu. The metabolites have been isolated and purified by thick layer-, column- and gaschromatography. With the help of 1N-NMR- and mass spectroscopy, metabolite II could be identified as 1-allyl-3-ethyl-5-(2-hydroxy ethyl)-6-methylmercaptouracil and metabolite III as 1-allyl-3,5-diethyl-6-methylmercaptouracil. The introduction of methylmercapto group (-SCH3) in metabolites II and III represents a new biochemical pathway which to the best of our knowledge has not been reported in the literature up to now.
本文描述了2-¹⁴C-1-烯丙基-3,5-二乙基-6-氯尿嘧啶（2-¹⁴C-Aclu；阿氯尿嘧啶）的合成。将其应用于兔子后，2-¹⁴C-Aclu会生物转化为一种不含硫的主要代谢物I以及两种含硫的次要代谢物II和III，它们的极性均强于Aclu。这些代谢物已通过薄层色谱、柱色谱和气相色谱进行了分离和纯化。借助¹H-NMR和质谱，代谢物II可被鉴定为1-烯丙基-3-乙基-5-(2-羟乙基)-6-甲基巯基尿嘧啶，代谢物III可被鉴定为1-烯丙基-3,5-二乙基-6-甲基巯基尿嘧啶。在代谢物II和III中引入甲基巯基（-SCH₃）代表了一种新的生化途径，据我们所知，迄今为止文献中尚未报道过。
