含磺胺嘧啶结构单元β-氨基酮的合成及其生物活性

doi:10.11944/j.issn.1000-0518.2015.11.150070

摘要/Abstract

摘要：

通过原子经济的Mannich反应实现了磺胺嘧啶、1-萘乙酮与芳香醛三组分的连接,直接合成了16个含有磺胺嘧啶结构单元的未见报道的β-氨基酮;所得化合物经¹H NMR、¹³C NMR、HRMS和MS等技术手段确证其结构。生物活性测试结果显示,在17.04~19.69 nmol/L浓度范围内,所有目标分子的α-葡萄糖苷酶抑制活性很弱,但部分目标分子的过氧化物酶体增殖物激活受体反应元件(PPRE)激动活性较好,最高达到了52%。

关键词: 糖尿病, 过氧化物酶体增殖物激活受体反应元件(PPRE), α-葡萄糖苷酶, Mannich反应, β-氨基酮, 磺胺嘧啶

Abstract:

Sixteen new β-amino ketones containing sulfadiazine moiety have been directly synthesized through atom-economic Mannich reaction of sulfadiazine with 1-acetonaphthone and some aromatic aldehydes. The chemical structures of these obtained compounds were identified by ¹H NMR, ¹³C NMR, and HRMS. The biological assay results show that all obtained compounds in the concentration range of 17.04~19.69 nmol/L possess very weak α-glucosidase inhibitory activities, while some compounds can activate peroxisome proliferator-activated receptor response element(PPRE) moderately, of which one exhibits the strongest activity(52%).

Key words: diabetes mellitus, peroxisome proliferator-activated receptor response element(PPRE), α-glucosidase, Mannich reaction, β-amino ketones, sulfadiazine

唐雪梅, 范莉, 赵琴, 杨大成. 含磺胺嘧啶结构单元β-氨基酮的合成及其生物活性[J]. 应用化学, 2015, 32(11): 1231-1239.

TANG Xuemei, FAN Li, ZHAO Qin, YANG Dacheng. Synthesis and Bioactivities of β-Amino Ketones Containing Sulfadiazine Moiety[J]. Chinese Journal of Applied Chemistry, 2015, 32(11): 1231-1239.

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