3-(2-formylphenoxy)propyl nitrate | 141534-60-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(2-formylphenoxy)propyl nitrate
• CAS: 141534-60-3
• 化学式: C₁₀H₁₁NO₅
• 分子量: 225.201
• InChiKey: JVNVVQYKWYDZPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2-formylphenoxy)propyl nitrate 在 potassium permanganate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 10.5h， 生成 3-[2-[(1-butyl-3-oxo-1H-2-benzofuran-5-yl)carbamoyl]phenoxy]propyl nitrate
  参考文献：
  名称：

  Synthesis and biological evaluation of nitric oxide releasing derivatives of 6-amino-3-n-butylphthalide as potential antiplatelet agents

  摘要：

  A series of novel nitric oxide releasing derivatives of 6-amino-3-n-butylphthalide were designed, synthesized and evaluated as potential antiplatelet agents. Compound 10b significantly inhibited the adenosine diphosphate (ADP)-induced platelet aggregation in vitro, superior to 6-amino-3-n-butylphthalide, 3-n-butylphthalide (NBP) and ticlopidine. Meanwhile 10b released moderate levels of NO, which could be beneficial for improving cardiovascular and cerebral circulation. Furthermore, 10b had an enhanced aqueous solubility relative to NBP. These findings may provide new insights into the development of novel antiplatelet agents for the treatment of thrombosis-related ischemic stroke. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.035
• 作为产物：
  描述：

  2-(3-溴丙氧基)苯甲醛 在 silver nitrate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 3-(2-formylphenoxy)propyl nitrate
  参考文献：
  名称：

  Synthesis and biological evaluation of nitric oxide releasing derivatives of 6-amino-3-n-butylphthalide as potential antiplatelet agents

  摘要：

  A series of novel nitric oxide releasing derivatives of 6-amino-3-n-butylphthalide were designed, synthesized and evaluated as potential antiplatelet agents. Compound 10b significantly inhibited the adenosine diphosphate (ADP)-induced platelet aggregation in vitro, superior to 6-amino-3-n-butylphthalide, 3-n-butylphthalide (NBP) and ticlopidine. Meanwhile 10b released moderate levels of NO, which could be beneficial for improving cardiovascular and cerebral circulation. Furthermore, 10b had an enhanced aqueous solubility relative to NBP. These findings may provide new insights into the development of novel antiplatelet agents for the treatment of thrombosis-related ischemic stroke. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.035

文献信息

• (Nitrooxyacyloxy)methyl Esters of Aspirin as Novel Nitric Oxide Releasing Aspirins
  作者：Loretta Lazzarato、Monica Donnola、Barbara Rolando、Konstantin Chegaev、Elisabetta Marini、Clara Cena、Antonella Di Stilo、Roberta Fruttero、Stefano Biondi、Ennio Ongini、Alberto Gasco

  DOI：10.1021/jm900587h

  日期：2009.8.27

  A series of (nitrooxyacyloxy)methyl esters of aspirin were synthesized and evaluated as new NO-donor aspirins. Different amounts of aspirin were released in serum from these products according to the nature of nitrooxyacyloxy moiety present, In the aromatic series, there is a rather good linear correlation between the amount of aspirin released and the potencies of the products in inhibiting platelet aggregation induced by collagen. Both the native compounds and the related nitrooxy-substituted acid metabolites were able to relax rat aorta strips precontracted with phenylephrine, in keeping with a NO-induced activation or the sGC as a mechanism that underlies the vasodilator effect. The products here described are new improved examples of NO-donor aspirins containing nitrooxy groups. They could represent all alternative to the use of aspirin ill a variety of clinical applications.
• THIAZOLIDIN DERIVATIVES
  申请人：CEDONA PHARMACEUTICALS B.V.

  公开号：EP0547104A1

  公开（公告）日：1993-06-23
• US5385922A
  申请人：——

  公开号：US5385922A

  公开（公告）日：1995-01-31
• [EN] THIAZOLIDIN DERIVATIVES
  申请人：CEDONA PHARMACEUTICALS BV

  公开号：WO1992004337A1

  公开（公告）日：1992-03-19

  (EN) Compounds of general formula (I) wherein the substituents and symbols have the meanings as given in the specification, are new compounds with marked cardiovascular activity.(FR) Les composés répondant à la formule générale (I), dans laquelle les substituants et symboles ont les singifications précisées dans la description, sont des nouveaux composés présentant une activité cardio-vasculaire importante.
• Synthesis and biological evaluation of nitric oxide releasing derivatives of 6-amino-3-n-butylphthalide as potential antiplatelet agents
  作者：Xiaoli Wang、Linna Wang、Zhangjian Huang、Xiao Sheng、Tingting Li、Hui Ji、Jinyi Xu、Yihua Zhang

  DOI：10.1016/j.bmcl.2013.02.035

  日期：2013.4

  A series of novel nitric oxide releasing derivatives of 6-amino-3-n-butylphthalide were designed, synthesized and evaluated as potential antiplatelet agents. Compound 10b significantly inhibited the adenosine diphosphate (ADP)-induced platelet aggregation in vitro, superior to 6-amino-3-n-butylphthalide, 3-n-butylphthalide (NBP) and ticlopidine. Meanwhile 10b released moderate levels of NO, which could be beneficial for improving cardiovascular and cerebral circulation. Furthermore, 10b had an enhanced aqueous solubility relative to NBP. These findings may provide new insights into the development of novel antiplatelet agents for the treatment of thrombosis-related ischemic stroke. (C) 2013 Elsevier Ltd. All rights reserved.