2,2-dimethoxy-3-(nitrooxy)propan-1-ol

• 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: 2,2-dimethoxy-3-(nitrooxy)propan-1-ol
• 英文别名: 2,2-dimethyl-3-(nitrooxy)propan-1-ol；(3-hydroxy-2,2-dimethylpropyl) nitrate
• 化学式: C₅H₁₁NO₄
• 分子量: 149.147
• InChiKey: GJZIQWDDCYOUOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 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：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-dimethoxy-3-(nitrooxy)propan-1-ol 、 托灭酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以70%的产率得到
  参考文献：
  名称：

  Nitric oxide releasing derivatives of tolfenamic acid with anti-inflammatory activity and safe gastrointestinal profile

  摘要：

  Tolfenamic acid esters with nitrooxyalcohols are synthesized. They are anti-inflammatory agents reducing carrageenan rat paw edema, with low gastrointestinal and general toxicity. In vitro, they are nitric oxide donors, inhibitors of lipoxygenase and cyclooxygenases. A two to three carbon chain between carboxylic and nitric ester groups seems optimal for activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.049
• 作为产物：
  描述：

  2,2-二甲基-1,3-丙二醇 在 硝酸 、 乙酸酐 、 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 生成 2,2-dimethoxy-3-(nitrooxy)propan-1-ol
  参考文献：
  名称：

  一氧化氮供体作为COX-2抑制剂的新型二茂铁-吡唑衍生物的设计，合成和生物学评价

  摘要：

  设计，合成和生物学评估了一系列新的含一氧化氮供体作为COX-2抑制剂的二茂铁-吡唑衍生物。其中，化合物7升对COX-2（IC显示的最有效的抑制50  = 0.82μM）和针对Hela细胞的抗增殖活性（IC 50  = 0.34μM）塞来昔布进行比较（IC 50  = 0.38和7.91μM）。进一步的机理研究表明，7l可以通过线粒体去极化诱导Hela细胞凋亡，而7l的抗增殖活性与Hela细胞内细胞内NO释放水平呈正相关。最值得注意的是7公升可以显着抑制异种移植Hela细胞肿瘤模型中的肿瘤生长。总之，化合物7l可能是用于癌症治疗的有希望的候选物。

  DOI：

  10.1016/j.ejmech.2018.08.048

文献信息

• Nitrosated glutamic acid compounds, compositions and methods of use
  申请人：Garvey S. David

  公开号：US20070037821A1

  公开（公告）日：2007-02-15

  The invention describes novel nitrosated glutamic acid compounds and pharmaceutically acceptable salts thereof, and novel compositions comprising at least one nitrosated glutamic acid compound, and, optionally, at least one nitric oxide donor and/or at least one therapeutic agent. The invention also provides novel kits comprising at least one nitrosated glutamic acid compound, and, and, optionally, at least one nitric oxide donor compound and/or at least one therapeutic agent. The invention also provides methods for (a) treating cardiovascular diseases; (b) treating renovascular diseases; (c) treating diabetes; (d) treating diseases resulting from oxidative stress; (e) treating endothelial dysfunctions; (f) treating diseases caused by endothelial dysfunctions; (g) treating cirrhosis; (h) treating pre-eclampsia; (j) treating osteoporosis; (k) treating nephropathy; (l) treating diseases resulting from elevated levels of gamma-glutamyl transpeptidase and (m) the targeted delivery of compounds and nitric oxide to organs, cells or tissues containing the enzyme gamma-glutamyl transpeptidase.

  该发明描述了新型的硝化谷氨酸化合物及其药学上可接受的盐，以及包含至少一种硝化谷氨酸化合物，和/或至少一种一氧化氮供体和/或至少一种治疗剂的新型组合物。该发明还提供了包含至少一种硝化谷氨酸化合物，和/或至少一种一氧化氮供体化合物和/或至少一种治疗剂的新型试剂盒。该发明还提供了治疗心血管疾病、肾血管疾病、糖尿病、氧化应激引起的疾病、内皮功能障碍、内皮功能障碍引起的疾病、肝硬化、先兆子痫、骨质疏松症、肾病、γ-谷氨酰转移酶水平升高引起的疾病以及将化合物和一氧化氮有针对性地输送到含有γ-谷氨酰转移酶的器官、细胞或组织的方法。
• [EN] NITROSATED GLUTAMIC ACID COMPOUNDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSES D'ACIDE GLUTAMIQUE NITROSES, LEURS COMPOSITIONS ET PROCEDES D'UTILISATION
  申请人：NITROMED INC

  公开号：WO2005030135A3

  公开（公告）日：2005-06-16
• Design, synthesis and biological evaluation of novel ferrocene-pyrazole derivatives containing nitric oxide donors as COX-2 inhibitors for cancer therapy
  作者：Shen-Zhen Ren、Zhong-Chang Wang、Dan Zhu、Xiao-Hua Zhu、Fa-Qian Shen、Song-Yu Wu、Jin-Jin Chen、Chen Xu、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2018.08.048

  日期：2018.9

  A series of novel ferrocene-pyrazole derivatives containing nitric oxide donors as COX-2 inhibitors for cancer therapy were designed, synthesized and biologically evaluated. Among them, compound 7l displayed the most potent inhibitory against COX-2 (IC50 = 0.82 μM) and antiproliferative activities against Hela cells (IC50 = 0.34 μM) compared with Celecoxib (IC50 = 0.38 and 7.91 μM). The further mechanistic

  设计，合成和生物学评估了一系列新的含一氧化氮供体作为COX-2抑制剂的二茂铁-吡唑衍生物。其中，化合物7升对COX-2（IC显示的最有效的抑制50  = 0.82μM）和针对Hela细胞的抗增殖活性（IC 50  = 0.34μM）塞来昔布进行比较（IC 50  = 0.38和7.91μM）。进一步的机理研究表明，7l可以通过线粒体去极化诱导Hela细胞凋亡，而7l的抗增殖活性与Hela细胞内细胞内NO释放水平呈正相关。最值得注意的是7公升可以显着抑制异种移植Hela细胞肿瘤模型中的肿瘤生长。总之，化合物7l可能是用于癌症治疗的有希望的候选物。
• Nitric oxide releasing derivatives of tolfenamic acid with anti-inflammatory activity and safe gastrointestinal profile
  作者：George N. Ziakas、Eleni A. Rekka、Antonios M. Gavalas、Phaedra T. Eleftheriou、Karyofillis C. Tsiakitzis、Panos N. Kourounakis

  DOI：10.1016/j.bmc.2005.07.049

  日期：2005.12

  Tolfenamic acid esters with nitrooxyalcohols are synthesized. They are anti-inflammatory agents reducing carrageenan rat paw edema, with low gastrointestinal and general toxicity. In vitro, they are nitric oxide donors, inhibitors of lipoxygenase and cyclooxygenases. A two to three carbon chain between carboxylic and nitric ester groups seems optimal for activity. (c) 2005 Elsevier Ltd. All rights reserved.