4-(3'-nitrooxypropoxy)-benzaldehyde | 1144618-39-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3'-nitrooxypropoxy)-benzaldehyde
• 英文别名: 3-(4-formylphenoxy)propyl nitrate
• CAS: 1144618-39-2
• 化学式: C₁₀H₁₁NO₅
• 分子量: 225.201
• InChiKey: CBUFNFFKVFAOIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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：

  4-(3'-nitrooxypropoxy)-benzaldehyde 在 potassium permanganate 作用下， 以 丙酮 为溶剂， 以81%的产率得到4-[3-(nitrooxy)propoxy]benzoic acid
  参考文献：
  名称：

  (Nitrooxyacyloxy)methyl Esters of Aspirin as Novel Nitric Oxide Releasing Aspirins

  摘要：

  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.

  DOI：

  10.1021/jm900587h
• 作为产物：
  描述：

  对羟基苯甲醛 在 potassium carbonate 、 silver nitrate 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 3.0h， 生成 4-(3'-nitrooxypropoxy)-benzaldehyde
  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

• α-Aryl-<i>N</i>-alkyl Nitrones, as Potential Agents for Stroke Treatment: Synthesis, Theoretical Calculations, Antioxidant, Anti-inflammatory, Neuroprotective, and Brain–Blood Barrier Permeability Properties
  作者：Mourad Chioua、David Sucunza、Elena Soriano、Dimitra Hadjipavlou-Litina、Alberto Alcázar、Irene Ayuso、María Jesús Oset-Gasque、María Pilar González、Leticia Monjas、María Isabel Rodríguez-Franco、José Marco-Contelles、Abdelouahid Samadi

  DOI：10.1021/jm201105a

  日期：2012.1.12

  heteroaryl-N-alkyl nitrones as potential agents for stroke treatment. The majority of nitrones compete with DMSO for hydroxyl radicals, and most of them are potent lipoxygenase inhibitors. Cell viability-related (MTT assay) studies clearly showed that nitrones 1–3 and 10 give rise to significant neuroprotection. When compounds 1–11 were tested for necrotic cell death (LDH release test) nitrones 1–3, 6, 7, and

  我们报告了合成，理论计算，抗氧化剂，抗炎和神经保护特性，以及穿越（Z）-α-芳基和杂芳基-N-烷基硝酮作为潜在药物的血脑屏障（BBB）的能力。用于中风治疗。大多数硝酮与DMSO竞争羟基自由基，其中大多数是有效的脂氧合酶抑制剂。细胞活力相关（MTT法）的研究清楚地表明，硝1 - 3和10产生显著的神经保护作用。当化合物1 - 11为坏死性细胞死亡（LDH释放试验）硝酮进行了测试1 - 3，6，7和9被证明是神经保护剂。在所选择的硝酮的BBB渗透的体外评价1，2，10，和11使用PAMPA-BBB实验表明，所有的人都穿过BBB。渗透性喹啉硝酮2和3具有强大的抗氧化和神经保护作用，因此可以被认为是在潜在卒中治疗的特定测试中进一步开发的新的先导化合物。
• NEW NO-DONOR ASPIRIN DERIVATIVES
  申请人：Fruttero Roberta

  公开号：US20100210694A1

  公开（公告）日：2010-08-19

  The present invention refers to new NO-donors aspirin derivatives, a process for their preparation and pharmaceutical compositions containing them.

  本发明涉及一种新的NO供体阿司匹林衍生物，其制备方法和包含它们的药物组合物。
• [EN] NEW NO-DONOR ASPIRIN DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS D'ASPIRINE DONNEURS NO
  申请人：NICOX SA

  公开号：WO2009049961A3

  公开（公告）日：2009-06-25
• (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.
• Porphyrins containing nitric oxide donors: Synthesis and cancer cell-oriented NO release
  作者：Wukun Liu、Chaozhou Liu、Changjun Gong、Weiying Lin、Cancheng Guo

  DOI：10.1016/j.bmcl.2009.02.005

  日期：2009.3

  Four novel porphyrins containing nitric oxide (NO) donors were synthesized, and the structures of all the products were characterized by IR, UV-vis, H-1 NMR, and elementary analysis. Interestingly, these new compounds not only were able to release NO, but also showed cancer cell-oriented accumulation. Higher accumulation of these new porphyrins containing NO donors in BEL-7402 liver cancer cells than in L-02 liver normal cells was corroborated by UV-vis spectroscopy. The biological activity of these porphyrins against BEL-7402 liver cancer cells was tested with a MTT assay. The studies indicated that they had more effective killing of BEL-7402 liver cancer cells than that of L-02 liver normal cells, and they had similar activity against MCF-7 breast cancer cells when compared to 5-fluorouracil in the absence of light. (C) 2009 Elsevier Ltd. All rights reserved.