O2-(2,4-dinitrophenyl) 1-[4-(propargyloxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate | 1163704-74-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: O2-(2,4-dinitrophenyl) 1-[4-(propargyloxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate
• 英文别名: RN-1-37；(2,4-dinitrophenoxy)imino-oxido-(4-prop-2-ynoxycarbonylpiperazin-1-yl)azanium
• CAS: 1163704-74-2
• 化学式: C₁₄H₁₄N₆O₈
• 分子量: 394.301
• InChiKey: WVSIGFHCHWUGJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  166.72
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  O2-(2,4-dinitrophenyl) 1-[4-(propargyloxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate 、 5,5-di(azidomethyl)-2-phenyl-1,3-dioxane 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 以72%的产率得到[OA-1-136]
  参考文献：
  名称：

  “Click” Reaction in Conjunction with Diazeniumdiolate Chemistry: Developing High-Load Nitric Oxide Donors

  摘要：

  The use of Cu(I)-catalyzed "click" reactions of alkyne-substituted diazeniumdiolate prodrugs with bis- and tetrakis-azido compounds is described. The "click" reaction for the bis-azide using CuSO4/Na-ascorbate predominantly gave the expected bis-triazole. However, CuI/diisopropylethylamine predominantly gave uncommon triazolo-triazole products as a result of oxidative coupling. Neither set of "click" conditions showed evidence of compromising the integrity of the diazeniumdiolate groups. The chemistry developed has applications in the synthesis of polyvalent and dendritic nitric oxide donors.

  DOI：

  10.1021/ol101645k
• 作为产物：
  描述：

  炔丙基氯甲酸酯 、 (2,4-dinitrophenoxy)imino-oxido-piperazin-4-ium-1-ylazanium;chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到O2-(2,4-dinitrophenyl) 1-[4-(propargyloxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  Synthesis and evaluation of piperazine and homopiperazine analogues of JS-K, an anti-cancer lead compound

  摘要：

  Here we report a number of novel JS-K structural analogues with sub-micromolar anti-proliferative activities against human leukemia cell lines HL-60 and U937; JS-K is the anti-cancer lead compound O-2-(2,4-dinitrophenyl) 1-[(4-ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate. The ability of these compounds to generate intracellular nitric oxide correlated well with their observed anti-proliferative effects: analogues that had potent inhibitory activity against leukemia cells formed elevated levels of intracellular nitric oxide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.115

文献信息

• Synthesis and evaluation of piperazine and homopiperazine analogues of JS-K, an anti-cancer lead compound
  作者：Rahul S. Nandurdikar、Anna E. Maciag、Michael L. Citro、Paul J. Shami、Larry K. Keefer、Joseph E. Saavedra、Harinath Chakrapani

  DOI：10.1016/j.bmcl.2009.03.115

  日期：2009.5

  Here we report a number of novel JS-K structural analogues with sub-micromolar anti-proliferative activities against human leukemia cell lines HL-60 and U937; JS-K is the anti-cancer lead compound O-2-(2,4-dinitrophenyl) 1-[(4-ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate. The ability of these compounds to generate intracellular nitric oxide correlated well with their observed anti-proliferative effects: analogues that had potent inhibitory activity against leukemia cells formed elevated levels of intracellular nitric oxide. (C) 2009 Elsevier Ltd. All rights reserved.
• “Click” Reaction in Conjunction with Diazeniumdiolate Chemistry: Developing High-Load Nitric Oxide Donors
  作者：Oyebola A. Oladeinde、Sam Y. Hong、Ryan J. Holland、Anna E. Maciag、Larry K. Keefer、Joseph E. Saavedra、Rahul S. Nandurdikar

  DOI：10.1021/ol101645k

  日期：2010.10.1

  The use of Cu(I)-catalyzed "click" reactions of alkyne-substituted diazeniumdiolate prodrugs with bis- and tetrakis-azido compounds is described. The "click" reaction for the bis-azide using CuSO4/Na-ascorbate predominantly gave the expected bis-triazole. However, CuI/diisopropylethylamine predominantly gave uncommon triazolo-triazole products as a result of oxidative coupling. Neither set of "click" conditions showed evidence of compromising the integrity of the diazeniumdiolate groups. The chemistry developed has applications in the synthesis of polyvalent and dendritic nitric oxide donors.