1-(2’-烷硫基乙氧基)甲基尿嘧啶及其氧化物的合成  

Synthesis of 1-(2'-Alkylthioethoxyl)methyl Uracil and Its Oxidation Products

作　　者：刘学军[1] 陈茹玉[1] 

机构地区：[1]南开大学元素有机化学所

出　　处：《高等学校化学学报》2000年第10期1501-1505,共5页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金!(批准号 :2 9972 0 2 1)资助

摘　　要：采用 3 0 %H2 O2 /DEAD的试剂组合 ,用于将硫醚及亚砜的衍生物氧化成砜类物质的反应 ,合成了1 ( 2 烷硫基乙氧基 )甲基尿嘧啶及其氧化物 ,产物结构经元素分析、1HNMR和IR进行表征 。As a continuation to our projects of searching for new anticancer and antiviral agents, the series of novel 1 (2 alkylthioethoxy)methyl uracils have been synthesized in overall yields of 70.4%_74.9% in three steps from uracil, and they have been smoothly oxidized into corresponding sulfoxides in yields of 88.5% _ 94.4% by NaIO 4 in ethanol/water. Corresponding sulfones were obtained in yields of 86.2% _ 93.5% from sulfides and sulfoxides by means of 30% H 2O 2 /DEAD(diethyl diazodicarboxylate) as oxidation reagent in methanol or THF. All the new compounds have been characterized by 1H NMR, IR spectrum and elemental analysis. The literature procedure of synthesizing the key intermediate(1,4 bistrimethylsilyluracil) was improved by hexamethyldisiylazane(HMDS)/trimethyl chloride(TMSCl) as substituent of HMDS/(NH 4) 2SO 4, and reaction time was shortened so much from 12 h to 3 h in new procedure. The experimental results indicated that the conversion of sulfides and sulfoxides to the corresponding sulfones was very slow and in low yields(42.5% and 47.3%), when only 30% H 2O 2 was used as the oxidation reagent. After addition of DEAD into the reaction mixture, the reaction could be considerably accelerated, and conversion rates of the reaction were raised (86.2%_93.5%). The anticancer and antiviral activities of the compounds 4, 5, 6 are being testing. [WT5HZ]

关 键 词：尿嘧啶衍生物 亚砜 砜 合成 抗癌活性 

分 类 号：O626.41[理学—有机化学]