(E)-4-(2-((3-(4-hydroxy-3-methoxyphenyl)acryloyl)oxy)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide | 1257641-95-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-4-(2-((3-(4-hydroxy-3-methoxyphenyl)acryloyl)oxy)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide
• 英文别名: (E)-2-(4-(phenylsulfonyl)-1,2,5-oxadiazol-3-yloxy)ethyl 3-(4-hydroxy-3-methoxyphenyl)acrylate；2-[[4-(benzenesulfonyl)-5-oxido-1,2,5-oxadiazol-5-ium-3-yl]oxy]ethyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 1257641-95-4
• 化学式: C₂₀H₁₈N₂O₉S
• 分子量: 462.437
• InChiKey: LHGROPWCRJCPGZ-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  159
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (2E)-3-{4-[(ethoxycarbonyl)oxy]-3-methoxyphenyl}acrylic acid 在 4-二甲氨基吡啶 、 C.I.酸性橙108 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (E)-4-(2-((3-(4-hydroxy-3-methoxyphenyl)acryloyl)oxy)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide
  参考文献：
  名称：

  设计和合成新型NO-供体-阿魏酸杂交体作为潜在的抗动脉粥样硬化药物候选物a

  摘要：

  通过使用阿魏酸和三个不同的NO供体基团（例如硝酸酯​​，4-羟基-3-苯基呋喃喃和4-羟基甲基-3-苯基磺酰呋喃喃）通过共生方法设计和合成了新型NO供体-阿魏酸杂交体。抗氧化剂，一氧化氮释放和血管舒张剂的性能研究表明，目标苯磺酰呋喃喃14（尤其是14c）在保持抗氧化剂活性的同时，显示出比硝酸异山梨酯（ISDN）更高的NO释放活性和血管舒张活性。因此，14c可能被认为是一种新型的有效抗动脉粥样硬化药物。Drug Dev Res 72：405–415，2011.©2011 Wiley‐Liss，Inc.

  DOI：

  10.1002/ddr.20442

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.
• Design and synthesis of novel NO-donor-ferulic acid hybrids as potential antiatherosclerotic drug candidatesa
  作者：Nian-Guang Li、Rong Wang、Zhi-Hao Shi、Yu-Ping Tang、Bao-Quan Li、Zhen-Jiang Wang、Shu-Lin Song、Li-Hua Qian、Li Wei、Jian-Ping Yang、Li-Juan Yao、Jun-Zuan Xi、Jia Xu、Feng Feng、Da-Wei Qian、Jin-Ao Duan

  DOI：10.1002/ddr.20442

  日期：——

  Novel NO‐donor‐ferulic acid hybrids were designed and synthesized through a symbiotic approach using ferulic acid and three different NO‐donating groups, such as nitric ester, 4‐hydroxyl‐3‐phenylfuroxan, and 4‐hydroxymethyl‐3‐phenylsulfonylfuroxan. Antioxidant, nitric oxide release, and vasodilator properties studies showed that the target phenylsulfonylfuroxan 14, especially 14c, while keeping the

  通过使用阿魏酸和三个不同的NO供体基团（例如硝酸酯​​，4-羟基-3-苯基呋喃喃和4-羟基甲基-3-苯基磺酰呋喃喃）通过共生方法设计和合成了新型NO供体-阿魏酸杂交体。抗氧化剂，一氧化氮释放和血管舒张剂的性能研究表明，目标苯磺酰呋喃喃14（尤其是14c）在保持抗氧化剂活性的同时，显示出比硝酸异山梨酯（ISDN）更高的NO释放活性和血管舒张活性。因此，14c可能被认为是一种新型的有效抗动脉粥样硬化药物。Drug Dev Res 72：405–415，2011.©2011 Wiley‐Liss，Inc.