4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl 3-methoxy-4-((4-(nitrooxy)butanoyl)oxy)benzoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl 3-methoxy-4-((4-(nitrooxy)butanoyl)oxy)benzoate
• 英文别名: [4-(5-Sulfanylidenedithiol-3-yl)phenyl] 3-methoxy-4-(4-nitrooxybutanoyloxy)benzoate；[4-(5-sulfanylidenedithiol-3-yl)phenyl] 3-methoxy-4-(4-nitrooxybutanoyloxy)benzoate
• 化学式: C₂₁H₁₇NO₈S₃
• 分子量: 507.566
• InChiKey: BHIJHQCPBYSLLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  200
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  香草醛 在 4-二甲氨基吡啶 、 sodium chlorite 、 potassium dihydrogenphosphate 、 双氧水 、 silver nitrate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 32.0h， 生成 4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl 3-methoxy-4-((4-(nitrooxy)butanoyl)oxy)benzoate
  参考文献：
  名称：

  Synthesis and anti-cancer potential of the positional isomers of NOSH-aspirin (NBS-1120) a dual nitric oxide and hydrogen sulfide releasing hybrid

  摘要：

  We recently reported the synthesis of NOSH-aspirin, a novel hybrid compound capable of releasing both nitric oxide (NO) and hydrogen sulfide (H2S). In NOSH-aspirin, the two moieties that release NO and H2S are covalently linked at the 1, 2 positions of acetyl salicylic acid, i.e., ortho-NOSH-aspirin. Here we report on the synthesis of meta-and para-NOSH-aspirins. We also made a head-to-head evaluation of the effects of these three positional isomers of NOSH-aspirin on colon cancer cell kinetics and induction of reactive oxygen species, which in recent years has emerged as a key event in causing cancer cell regression. Electron donating/withdrawing groups incorporated about the benzoate moiety significantly affected the potency of these compounds with respect to colon cancer cell growth inhibition. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.08.023

文献信息

• Synthesis and anti-cancer potential of the positional isomers of NOSH-aspirin (NBS-1120) a dual nitric oxide and hydrogen sulfide releasing hybrid
  作者：Federica Vannini、Andrew C. MacKessack-Leitch、Erin K. Eschbach、Mitali Chattopadhyay、Ravinder Kodela、Khosrow Kashfi

  DOI：10.1016/j.bmcl.2015.08.023

  日期：2015.10

  We recently reported the synthesis of NOSH-aspirin, a novel hybrid compound capable of releasing both nitric oxide (NO) and hydrogen sulfide (H2S). In NOSH-aspirin, the two moieties that release NO and H2S are covalently linked at the 1, 2 positions of acetyl salicylic acid, i.e., ortho-NOSH-aspirin. Here we report on the synthesis of meta-and para-NOSH-aspirins. We also made a head-to-head evaluation of the effects of these three positional isomers of NOSH-aspirin on colon cancer cell kinetics and induction of reactive oxygen species, which in recent years has emerged as a key event in causing cancer cell regression. Electron donating/withdrawing groups incorporated about the benzoate moiety significantly affected the potency of these compounds with respect to colon cancer cell growth inhibition. (C) 2015 Elsevier Ltd. All rights reserved.