引用本文:
张映霞, 晏菊芳, 范莉, 张蔚瑜, 苏小燕, 陈欣, 唐雪梅, 周祖文, 杨大成. 4-(3-(4-羟基苯基)-3-氧代-1-芳基丙氨基)-N-(5-甲基异噁唑-3-基)苯磺酰胺的合成及其抗糖尿病活性[J]. 应用化学,
2010, 27(9): 1026-1031.
doi:
10.3724/SP.J.1095.2010.90506
Citation: ZHANG Ying-Xia, YAN Ju-Fang, FAN Li, ZHANG Wei-Yu, SU Xiao-Yan, CHEN Xin, TANG Xue-Mei, ZHOU Zu-Wen, YANG Da-Cheng. Synthesis and Preliminary Evaluation of Antidiabetic Activity of 4-(3-(4-Hydroxyphenyl)-3-oxo-1-arylpropylamino)-N-(5-Methylisoxazol-3-yl) Benzenesulfonamide[J]. Chinese Journal of Applied Chemistry, 2010, 27(9): 1026-1031. doi: 10.3724/SP.J.1095.2010.90506
Citation: ZHANG Ying-Xia, YAN Ju-Fang, FAN Li, ZHANG Wei-Yu, SU Xiao-Yan, CHEN Xin, TANG Xue-Mei, ZHOU Zu-Wen, YANG Da-Cheng. Synthesis and Preliminary Evaluation of Antidiabetic Activity of 4-(3-(4-Hydroxyphenyl)-3-oxo-1-arylpropylamino)-N-(5-Methylisoxazol-3-yl) Benzenesulfonamide[J]. Chinese Journal of Applied Chemistry, 2010, 27(9): 1026-1031. doi: 10.3724/SP.J.1095.2010.90506
4-(3-(4-羟基苯基)-3-氧代-1-芳基丙氨基)-N-(5-甲基异噁唑-3-基)苯磺酰胺的合成及其抗糖尿病活性
摘要:
由磺胺甲噁唑、对羟基苯乙酮和芳香醛反应直接合成了13个未见报道的β-氨基酮,反应选择性发生在羰基α位。产物结构通过1HNMR、13CNMR、MS进行了表征。生物活性试验显示,低浓度范围,所得化合物不仅对蛋白质酪氨酸磷酸酶1B(PTP1B)和α-葡萄糖苷酶有一定抑制活性,而且对过氧化物酶体增殖物激活受体反应元件(PPRE)具有中等强度的激动活性,8个化合物的激动活性超过40%,其中化合物11的活性达到72.7%。
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关键词:
- α-葡萄糖苷酶
- / 蛋白质酪氨酸磷酸酶1B
- / 过氧化物酶体增殖物激活受体反应元件
- / 对羟基苯乙酮
- / 磺胺甲噁唑
- / β-氨基酮
- / Mannich反应
English
Synthesis and Preliminary Evaluation of Antidiabetic Activity of 4-(3-(4-Hydroxyphenyl)-3-oxo-1-arylpropylamino)-N-(5-Methylisoxazol-3-yl) Benzenesulfonamide
Abstract:
Thirteen new β-amino ketones were designed and synthesized directly through the Mannich reaction of sulfamethoxazole,4-hydroxyacetophenone and aromatic aldehydes in good yields.The reaction selectively occurred at the α-position of the carbonyl group of 4-hydroxyacetophenone. Their chemical structures were confirmed by means of 1H NMR,13C NMR and MS.Biological activity tests showed that in the rage of low concentrations,these title compounds displayed a certain inhibitory activity against protein tyrosine phosphatase 1B (PTP1B) and α-glucosidase.Moreover,some could activate the peroxisome proliferator-activated receptor response element(PPRE) moderately.The PPRE agonist activity of eight compounds was over 40%,among them compound 11 showed the highest activity(72.7%),which deserved further study.
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