摘要
以豆腐果苷为原料,与盐酸羟胺缩合反应生成4-β-D-吡喃阿洛糖苷-苯甲醛肟(2),2与次氯酸叔丁酯发生取代反应生成4-β-D-吡喃阿洛糖苷-α-氯苯甲醛肟(3);再将3与Schiff碱通过1,3-偶极环加成生成一系列3-(4-β-D-吡喃阿洛糖苷-苯基)-4-芳基-5-芳基-1,2,4-噁二唑啉(5a～5h).3和5a～5h共9个化合物均未见文献报道,其结构经1HNMR,IR和MS(HRMS)加以确认,并对5a～5h进行了药理活性筛选.结果表明,部分化合物具有良好的镇静活性.其中,化合物5g(200,100mg?kg-1)和5h(200,100mg?kg-1)与豆腐果苷相比较具有更强的活性.
Using helicid as a starting material, 4-β-D-allopyranosyloxy-benzaldehydeoxime （2） has been synthesized by the condensation reaction with hydroxyamine hydrochloride. Novel 4-β-D-allopyranosyloxy-a- chloro-benzaldehydeoxime （3） was synthesized by substitution reaction of 2 with t-BuOCl, and novel 3-（4-β-D-allopyranosyloxyphenyl）-4-aryl-5-aryl-l,2,4-oxadiazoline derivatives （5a-5h） have been synthesized by 1,3-dipolar cycloaddition reaction of 3 with Schiff bases 4a--4h. The new compounds 3 and 5a-5h were established by ^1H NMR, IR, and MS （HRMS） spectra. The preliminary bioassay test of 5a-5h showed that some of such compounds have good calm activity. For example, compounds 5g （200, 100 mg·kg^-1） and 5h （200, 100 mg ·kg^-1） were better than the parent helicid.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2008年第2期348-352,共5页
Chinese Journal of Organic Chemistry
