S-(3-nitrooxypivaloy)-thiophenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: S-(3-nitrooxypivaloy)-thiophenol
• 英文别名: S-phenyl 2,2-dimethyl-3-nitrooxypropanethioate
• 化学式: C₁₁H₁₃NO₄S
• 分子量: 255.295
• InChiKey: CZRSWPXILIHXDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯硫酚 、 2,2-二甲基-3-(硝基氧基)丙酸 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以28%的产率得到S-(3-nitrooxypivaloy)-thiophenol
  参考文献：
  名称：

  NO-Donors, part 3: nitrooxyacylated thiosalicylates and salicylates – synthesis and biological activities##For part 2 see [1]

  摘要：

  Organic nitrates release nitric oxide when incubated with thiosalicylic acid. S-Nitrooxyacylated esters and amides of thiosalicylic acid, together with the corresponding salicylates, were synthesized in order to perform a first in vitro evaluation of these new nitrate-thiol-hybrid prodrugs. These prodrugs might release NO in vivo after biotransformation without the use of endogenous reductives. None of these prodrugs released NO spontaneously when dissolved in buffer solution, but they did activate soluble guanylyl cyclase and induced vasodilatation of phenylephrine-pretreated male Wistar rat aorta in a potency range between that of isosorbiddinitrate and glycerole trinitrate. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(99)00110-5

文献信息

• NO-Donors, part 3: nitrooxyacylated thiosalicylates and salicylates – synthesis and biological activities##For part 2 see [1]
  作者：Stefan Endres、Andreas Hacker、Eike Noack、Georg Kojda、Jochen Lehmann

  DOI：10.1016/s0223-5234(99)00110-5

  日期：1999.11

  Organic nitrates release nitric oxide when incubated with thiosalicylic acid. S-Nitrooxyacylated esters and amides of thiosalicylic acid, together with the corresponding salicylates, were synthesized in order to perform a first in vitro evaluation of these new nitrate-thiol-hybrid prodrugs. These prodrugs might release NO in vivo after biotransformation without the use of endogenous reductives. None of these prodrugs released NO spontaneously when dissolved in buffer solution, but they did activate soluble guanylyl cyclase and induced vasodilatation of phenylephrine-pretreated male Wistar rat aorta in a potency range between that of isosorbiddinitrate and glycerole trinitrate. (C) 1999 Editions scientifiques et medicales Elsevier SAS.