3-Bromopropane-1,2-diol dinitrate | 179677-64-6

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: 3-Bromopropane-1,2-diol dinitrate
• 英文别名: 1,2-dinitrooxy-3-bromopropane；3-bromo-1,2-dinitrooxypropane；(1-Bromo-3-nitrooxypropan-2-yl) nitrate
• CAS: 179677-64-6
• 化学式: C₃H₅BrN₂O₆
• 分子量: 244.986
• InChiKey: UEOWKLNIPHWZJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-Bromopropane-1,2-diol dinitrate 在 sodium thiosulfate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以65%的产率得到sodium 2,3-dinitrooxypropane-1-thiosulfonate
  参考文献：
  名称：

  Synthesis of novel organic nitrate esters: guanylate cyclase activation and tissue relaxation

  摘要：

  报告了四种新型含硫硝酸酯的合成以及鸟苷酸环化酶激活和组织松弛的数据。

  DOI：

  10.1039/p19960001073
• 作为产物：
  描述：

  3-溴-1,2-并二酚 在 硫酸 、 硝酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以45%的产率得到3-Bromopropane-1,2-diol dinitrate
  参考文献：
  名称：

  Synthesis of novel organic nitrate esters: guanylate cyclase activation and tissue relaxation

  摘要：

  报告了四种新型含硫硝酸酯的合成以及鸟苷酸环化酶激活和组织松弛的数据。

  DOI：

  10.1039/p19960001073

文献信息

• Chimeric Nitrate Esters and Use of the Same in a Treatment for Depression
  申请人：Thatcher Gregory R.J.

  公开号：US20090182011A1

  公开（公告）日：2009-07-16

  Chimeric nitrate esters and their use in the treatment of depression are disclosed. The chimeric nitrate esters also are useful in the treatment of depression and comorbidity associated with aging.

  混合硝酸酯类化合物及其在治疗抑郁症中的应用被披露。这些混合硝酸酯类化合物也在治疗与衰老相关的抑郁症和共病中具有用途。
• Synthesis of novel organic nitrate esters: guanylate cyclase activation and tissue relaxation
  作者：Kexin Yang、Jennifer D. Artz、Jodi Lock、Cristina Sanchez、Brian M. Bennett、Amy B. Fraser、Gregory R. J. Thatcher

  DOI：10.1039/p19960001073

  日期：——

  The syntheses of four novel sulfur-containing nitrate esters are reported, together with data for guanylyl cyclase activation and tissue relaxation.

  报告了四种新型含硫硝酸酯的合成以及鸟苷酸环化酶激活和组织松弛的数据。
• Nitrate Esters as Nitric Oxide Donors:  SS-Nitrates
  作者：Sergei I. Zavorin、Jennifer D. Artz、Adina Dumitrascu、Adrian Nicolescu、Dan Scutaru、Stefanie V. Smith、Gregory R. J. Thatcher

  DOI：10.1021/ol007022a

  日期：2001.4.1

  The important biological secondary messenger NO can be generated from exogenous nitrovasodilators and NO donors, Nitrate esters are nitrovasodilators and NO mimetics, believed to be biotransformed to NO in vivo. On the basis of a mechanistic hypothesis, nitrates have been synthesized that release NO at significant rates in neutral aqueous solution in the presence only of added thiol. The novel masked beta -mercaptonitrates reported (SS nitrates), provide information on possible sulfhydryl dependent biotransformation mechanisms for nitrates in clinical use.
• Inhibition of Lipid Peroxidation in Synaptosomes and Liposomes by Nitrates and Nitrites
  作者：Adrian C. Nicolescu、Sergei I. Zavorin、Nicholas J. Turro、James N. Reynolds、Gregory R. J. Thatcher

  DOI：10.1021/tx025529j

  日期：2002.7.1

  NO is produced endogenously from arginine by the action of NO synthase, and exogenously by nitrovasodilators, including organic nitrates and nitrites. NO has been proposed as a cytotoxic and cytoprotective agent. There is strong evidence that NO acts as an apparent antioxidant in inhibiting lipid peroxidation, via chain termination, and interestingly lipid nitrates and nitrites have been proposed to be products of this chain termination. Both pro- and antioxidant mechanisms may be drawn for nitrates and nitrites; therefore, their effects on lipid peroxidation were measured in two systems, using tocopherol, thiol, and an NO donor for comparison: (1) rat cerebrocortical synaptosomes with Fe(II)-induced lipid peroxidation measured by thiobarbituric acid reactive substances (TBARS), and (2) phospholipid liposomes with an azo-initiator induction system, quantified by a fluorescent probe of peroxide formation. In contrast to the classical nitrate nitroglycerin, novel nitrates which release NO on reaction with thiols and two novel nitrates which spontaneously generate NO in aqueous solution inhibited lipid peroxidation. i-Amyl nitrite inhibited lipid peroxidation, and its properties were further studied with ESR spectroscopy. The data show that classical nitrites and novel nitrates are not prooxidants, but inhibit lipid peroxidation.