2,3-bis(nitrooxy)propylammonium nitrate

• 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: 2,3-bis(nitrooxy)propylammonium nitrate
• 英文别名: 3-amino-1,2-propanediol 1,2-dinitrate nitrate；1-amino-2,3-bis-nitryloxy-propane; nitrate；1-Amino-2,3-bis-nitryloxy-propan; Nitrat；(1-Amino-3-nitrooxypropan-2-yl) nitrate;nitric acid
• 化学式: C₃H₇N₃O₆*HNO₃
• 分子量: 244.118
• InChiKey: HNGZXIYRAZMQBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.62
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  202
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3-bis(nitrooxy)propylammonium nitrate 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 生成 3-aminopropane-1,2-diol 1,2-dinitrate
  参考文献：
  名称：

  Unusual reaction of 4-[(3-carboxypropyl)amino]-6-chloro-5-nitrobenzofuroxan with 3-aminopropane-1,2-diol 1,2-dinitrate

  摘要：

  Reaction of 4-[(3-carboxypropyl)amino]-6-chloro-5-nitrobenzofuroxan with 3-aminopropane-1,2-diol 1,2-dinitrate yielded 6-chloro-5-nitro-4-(2-oxopyrrolidin-1-yl)benzofuroxan instead of the expected 6-chloro-5-nitrobenzofuroxan amino derivative.

  DOI：

  10.1134/s1070363214080192
• 作为产物：
  描述：

  3-氨基-1,2-丙二醇 在 硝酸 、 乙酸酐 作用下， 反应 2.0h， 生成 2,3-bis(nitrooxy)propylammonium nitrate
  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

• Nitroanandamide, nitroprostamides E2 and F2α , and their analogs
  作者：I. V. Serkov、N. M. Gretskaya、V. V. Bezuglov

  DOI：10.1007/s10600-010-9718-y

  日期：2010.11

  Synthetic methods were developed for nitrates of the natural bioactive lipids anandamide and prostamides E2 and F2α in addition to their analogs that contained nitrates of ethanolamine and 3-amino-1,2-propanediol as the NO-generating fragment.

  开发了合成方法，用于天然生物活性脂质安安酰胺以及前列腺素E2和F2α的硝酸盐，以及含有乙醇胺和3-氨基-1,2-丙二醇的硝酸盐作为NO生成片段的类似物。
• Barbiere, Bulletin de la Societe Chimique de France, 1944, vol. <5>11, p. 473
  作者：Barbiere

  DOI：——

  日期：——
• Synthesis and Pharmacological Characterization of New H2-Antagonists Containing NO-Donor Moieties, Endowed with Mixed Antisecretory and Gastroprotective Activities
  作者：Massimo Bertinaria、Giovanni Sorba、Claudio Medana、Clara Cena、Maristella Adami、Giuseppina Morini、Cristina Pozzoli、Gabriella Coruzzi、Alberto Gasco

  DOI：10.1002/(sici)1522-2675(20000119)83:1<287::aid-hlca287>3.0.co;2-2

  日期：2000.1.19

  Synthesis, structural characterization, and pharmacological profile of a series of Hz-antagonists able to release nitric oxide (NO) are reported. These compounds were obtained by using appropriate spacers to join H-2-antagonistic pharmacophoric groups related to lamtidine and tiotidine to different NO-donor moieties such as esters of HNO3, nitrosothio groups, and benzenesulfonyl-substituted furoxans. All of the compounds were tested for their NO-donor properties. Furthermore, the hybrid structures synthesized, together with some selected reference compounds, were tested for their H-2-antagonistic properties, both in vitro and in vivo, and for their gastroprotective effects. Only the hybrid compounds were able both to antagonize histamine effects on guinea-pig papillary muscle and to display in vivo antisecretory and gastroprotective action. The best results were obtained with the lamtidine/furoxan hybrid structure.
• 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。
• Unusual reaction of 4-[(3-carboxypropyl)amino]-6-chloro-5-nitrobenzofuroxan with 3-aminopropane-1,2-diol 1,2-dinitrate
  作者：E. A. Chugunova、R. E. Mukhamatdinova、I. V. Serkov、S. V. Kharlamov、A. B. Dobrynin、A. R. Burilov

  DOI：10.1134/s1070363214080192

  日期：2014.8

  Reaction of 4-[(3-carboxypropyl)amino]-6-chloro-5-nitrobenzofuroxan with 3-aminopropane-1,2-diol 1,2-dinitrate yielded 6-chloro-5-nitro-4-(2-oxopyrrolidin-1-yl)benzofuroxan instead of the expected 6-chloro-5-nitrobenzofuroxan amino derivative.