3-(3-formylphenoxy)propyl nitrate | 1184723-01-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(3-formylphenoxy)propyl nitrate
• CAS: 1184723-01-0
• 化学式: C₁₀H₁₁NO₅
• 分子量: 225.201
• InChiKey: IBDGYZADKGPVDP-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：

  3-(3-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-[3-[(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：

  间羟基苯甲醛 在 potassium carbonate 、 silver nitrate 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 3.0h， 生成 3-(3-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

• A green multicomponent synthesis of tocopherol analogues with antiproliferative activities
  作者：Mariana Ingold、Rosina Dapueto、Sabina Victoria、Germán Galliusi、Carlos Batthyàny、Mariela Bollati-Fogolín、David Tejedor、Fernando García-Tellado、José M. Padrón、Williams Porcal、Gloria V. López

  DOI：10.1016/j.ejmech.2017.11.003

  日期：2018.1

  A one-pot efficient, practical and eco-friendly synthesis of tocopherol analogues has been developed using water or solvent free conditions via Passerini and Ugi multicomponent reactions. These reactions can be optimized using microwave irradiation or ultrasound as the energy source. Accordingly, a small library of 30 compounds was prepared for biological tests. The evaluation of the antiproliferative

  通过Passerini和Ugi多组分反应，在无水或无溶剂条件下，开发了一种一锅高效，实用且环保的生育酚类似物合成方法。可以使用微波辐射或超声波作为能源来优化这些反应。因此，准备了一个包含30种化合物的小型文库用于生物学测试。对人实体瘤细胞系A549（肺），HBL-100（乳腺），HeLa（子宫颈），SW1573（肺），T-47D（乳腺）和WiDr（结肠）的抗增殖活性的评估提供了先导化合物带有GI 50值介于1和5μM之间。还讨论了结构与活动的关系。研究的化合物之一有望成为开发有效的模拟生育酚的癌症治疗药物的未来候选者。
• (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.
• 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.