4-(2-(2-(3,4-dihydroxyphenyl)acetoxy)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-(2-(3,4-dihydroxyphenyl)acetoxy)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide
• 英文别名: 2-[[4-(Benzenesulfonyl)-5-oxido-1,2,5-oxadiazol-5-ium-3-yl]oxy]ethyl 2-(3,4-dihydroxyphenyl)acetate；2-[[4-(benzenesulfonyl)-5-oxido-1,2,5-oxadiazol-5-ium-3-yl]oxy]ethyl 2-(3,4-dihydroxyphenyl)acetate
• 化学式: C₁₈H₁₆N₂O₉S
• 分子量: 436.399
• InChiKey: KOEBAZMIXHPQEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  170
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3,4-二羟基苯乙酸 在 4-二甲氨基吡啶 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 4-(2-(2-(3,4-dihydroxyphenyl)acetoxy)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide
  参考文献：
  名称：

  Phenylsulfonylfuroxan NO-donor phenols: Synthesis and multifunctional activities evaluation

  摘要：

  Phenylsulfonyfuroxan nitric oxide (NO)-donor phenols were designed, synthesized and evaluated. The compounds were designed through a symbiotic approach using selected phenols and phenylsulfonylfuroxan NO-donor. The antioxidant activities of the hybrid compounds T-2-T-6 showed to be good in vivo. Compounds T-4 and T-6 revealed excellent yeast alpha-glucosidase inhibitory activity and anti-glycosylation activity. All of the compounds exhibited strong NO releasing activity and significant anti-platelet aggregation activity. The inhibition of platelet aggregation was more than 50% at low concentration (1.5 mu M) and 95% at higher concentration (15 mu M and 150 mu M). The vasodilatation experiment demonstrated that the six compounds under test exhibited definite vasodilation activity (pIC(50) ranged from 5.698 to 6.383), especially compound T6 (pIC(50) was 6.383) which was similar to sodium nitroprusside (pIC(50) was 6.786). Both anticoagulant and vasodilatation effects were correlated with their NO releasing activities. These hybrid phenylsulfonyfuroxan-based NO-donor phenols offer a multifunctional prodrug design concept for the development of therapeutic or preventive agents for metabolic syndrome. (C) 2017 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2017.06.023

文献信息

• Phenylsulfonylfuroxan NO-donor phenols: Synthesis and multifunctional activities evaluation
  作者：Yundong Xie、Yaping Yang、Sen Li、Yanhong Xu、Wenfang Lu、Zizhang Chen、Guangde Yang、Yiping Li、Yongxiao Cao、Xiaoli Bian

  DOI：10.1016/j.bmc.2017.06.023

  日期：2017.8

  Phenylsulfonyfuroxan nitric oxide (NO)-donor phenols were designed, synthesized and evaluated. The compounds were designed through a symbiotic approach using selected phenols and phenylsulfonylfuroxan NO-donor. The antioxidant activities of the hybrid compounds T-2-T-6 showed to be good in vivo. Compounds T-4 and T-6 revealed excellent yeast alpha-glucosidase inhibitory activity and anti-glycosylation activity. All of the compounds exhibited strong NO releasing activity and significant anti-platelet aggregation activity. The inhibition of platelet aggregation was more than 50% at low concentration (1.5 mu M) and 95% at higher concentration (15 mu M and 150 mu M). The vasodilatation experiment demonstrated that the six compounds under test exhibited definite vasodilation activity (pIC(50) ranged from 5.698 to 6.383), especially compound T6 (pIC(50) was 6.383) which was similar to sodium nitroprusside (pIC(50) was 6.786). Both anticoagulant and vasodilatation effects were correlated with their NO releasing activities. These hybrid phenylsulfonyfuroxan-based NO-donor phenols offer a multifunctional prodrug design concept for the development of therapeutic or preventive agents for metabolic syndrome. (C) 2017 Published by Elsevier Ltd.