3-amino-1-propanol nitrate | 2153-94-8

• 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-amino-1-propanol nitrate
• 英文别名: 3-aminopropyl Nitrate
• CAS: 2153-94-8
• 化学式: C₃H₈N₂O₃
• 分子量: 120.108
• InChiKey: TWSSISIQGXNDOT-UHFFFAOYSA-N

物化性质

• 沸点：
  178.6±23.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丙半胱氨酸 、 3-amino-1-propanol nitrate 在 焦碳酸二乙酯 作用下， 生成 3-[[(4R)-2-oxo-1,3-thiazolidine-4-carbonyl]amino]propyl nitrate
  参考文献：
  名称：

  Synthesis and collateral dilator activity of nitroxyalkylamides having direct or latent sulfhydryl moieties

  摘要：

  To develop an orally active, long-acting nitrate that does not induce tolerance, nitroxyalkyl compounds were prepared and their activities evaluated by the use of carotid collaterals in anesthetized dogs. A compound having a favorable pharmacological profile, that is, long-lasting collateral vasodilatation and little hypotension, and lack of nitrate tolerance, was chosen for further evaluation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00199-9
• 作为产物：
  描述：

  N-(3-nitrooxypropyl)phthalimide 在 甲胺 作用下， 以 四氢呋喃 为溶剂， 生成 3-amino-1-propanol nitrate
  参考文献：
  名称：

  第二代α-生育酚类似物一氧化氮供体：合成，物理化学和生物学表征。

  摘要：

  报道了一系列具有NO释放能力的α-生育酚模拟物的合成，物理化学和生物学特性。所选的NO供体部分是硝基氧基和呋喃喃。测试了所有产品的体外NO释放能力，血管舒张特性和哺乳动物细胞毒性活性。还评估了所有产品的亲脂-亲水平衡。一种新的杂氧呋喃杂酚衍生物，苯酚衍生物17，具有足够的研究性质。

  DOI：

  10.1016/j.bmc.2007.06.019

文献信息

• Synthesis and biological evaluation of NO-donor containing photosensitizers to induce ferroptosis of cancer cells
  作者：Xiuhan Guo、Haoze Yu、Wanjie Shen、Rui Cai、Yueqing Li、Guangzhe Li、Weijie Zhao、Shisheng Wang

  DOI：10.1016/j.bioorg.2021.105355

  日期：2021.11

  that the new NO-donor containing photosensitizers (PS-NO) exhibited more potent photodynamic activity than chlorin e6, and the introduction of NO donor moieties to chlorin e6 increased the level of NO and ROS in cells. The addition of Ferrostatin-1, a ferroptosis inhibitor, markedly reduced the photodynamic activity of PS-NO as well as the level of NO and ROS in cells. Mechanism studies further showed

  光动力疗法 (PDT) 是一种通过在光照射下激发光敏剂 (PS) 产生细胞毒性活性氧 (ROS) 来治疗肿瘤的非侵入性治疗方法。然而，肿瘤组织附近的低氧浓度限制了PDT的治疗效果。在此，我们合成了六种含有 NO 供体的二氢卟酚 e6 衍生物，以通过 ROS 和 NO 的协同作用增强其抗肿瘤活性。结果表明，新的含 NO 供体的光敏剂 (PS-NO) 表现出比二氢卟酚 e6 更强的光动力活性，并且将 NO 供体部分引入二氢卟酚 e6 可增加细胞中 NO 和 ROS 的水平。Ferrostatin-1（一种铁死亡抑制剂）的加入显着降低了 PS-NO 的光动力活性以及细胞中 NO 和 ROS 的水平。
• 具有光、声敏活性的二氢卟吩硝酸酯类化合物、制备方法与应用
  申请人：大连理工大学

  公开号：CN111423446B

  公开（公告）日：2022-07-08

  本发明提供了一类具有光、声敏活性的二氢卟吩硝酸酯类化合物、制备方法与应用，属于化学医药技术领域。本发明所述的二氢卟吩硝酸酯类化合物制备方法简便，通过引入硝酸酯基团作为NO的供体，提高活性氧的产率，增强光、声敏化合物的活性。在体外抗肿瘤活性评价中对人宫颈癌细胞系Hela细胞具有不同程度的抑制作用，光、声活性要高于作为对照的Chlorin e6。可用于肿瘤的光动力治疗及声动力治疗中的光敏剂及声敏剂的制备。
• Amodiaquine analogues containing NO-donor substructures: Synthesis and their preliminary evaluation as potential tools in the treatment of cerebral malaria
  作者：Massimo Bertinaria、Stefano Guglielmo、Barbara Rolando、Marta Giorgis、Cristina Aragno、Roberta Fruttero、Alberto Gasco、Silvia Parapini、Donatella Taramelli、Yuri C. Martins、Leonardo J.M. Carvalho

  DOI：10.1016/j.ejmech.2011.02.029

  日期：2011.5

  The synthesis and physico-chemical properties of novel compounds obtained by conjugation of amodiaquine with moieties containing either furoxan or nitrooxy NO-donor substructures are described. The synthesised compounds were tested in vitro against both the chloroquine sensitive, 010 and the chloroquine resistant, W-2 strains of Plasmodium falciparum (P falciparum). Most of the compounds showed an antiplasmodial activity comparable to that of the parent drug. By comparing the activities of simple related structures devoid of the ability to release NO, it appears that the contribution of NO to the antiplasmodial action in vitro is marginal. All the compounds were able to relax rat aorta strips with a NO-dependent mechanism, thus showing their capacity to release NO in the vessels. A preliminary in vivo study using Plasmodium berghei ANKA-infected mice showed a trend for prolonged survival of mice with cerebral malaria treated with compound 40, which is potent and fast amodiaquine-derived NO-donor, when compared with amodiaquine alone or with compound 31, a milder NO-donor. The two compounds showed in vivo antiplasmodial activity similar to that of amodiaquine. (C) 2011 Elsevier Masson SAS. All rights reserved.
• WO2006/99058
  申请人：——

  公开号：——

  公开（公告）日：——
• Carnosine analogues containing NO-donor substructures: Synthesis, physico-chemical characterization and preliminary pharmacological profile
  作者：Massimo Bertinaria、Barbara Rolando、Marta Giorgis、Gabriele Montanaro、Elisabetta Marini、Massimo Collino、Elisa Benetti、Pier Giuseppe Daniele、Roberta Fruttero、Alberto Gasco

  DOI：10.1016/j.ejmech.2012.04.032

  日期：2012.8

  The synthesis, physico-chemical, and biological characterisation of a short series of carnosine amides bearing NO-donor nitrooxy functionalities are described. The NO-donor carnosine analogues and their des-NO derivatives display carnosine-like properties, differing from the lead for their high serum stability. The newly-synthesised compounds are able to complex Cu2+ ions at physiological pH, displaying significant copper ion sequestering ability, and protect LDL from oxidation catalysed by Cu2+ ions. All products show moderately-potent HNE quenching activity. The NO-donor compounds 7c-f relaxed rat aorta strips via an NO-dependent mechanism. In vivo evaluation of organ protection in a model of cerebral ischaemia/reperfusion injury, using the selected NO-donor 7e and its des-NO analogue 7a, showed that both derivatives protect from hypoxia-induced brain damage, at lower concentrations than carnosine: 7e also decreased serum TNF-alpha levels. This class of NO-donor carnosine amides is worthy of further study as potential tools for treating a wide range of chronic vascular and neurodegenerative diseases in which NO-bioavailability is reduced. (C) 2012 Elsevier Masson SAS. All rights reserved.