O(2)-(3,4,6-tri-O-acetyl-N-acetyl-β-D-glucosaminyl) 1-[N-(2-carboxymethyl)-N-methylamino]diazen-1-ium-1,2-diolate | 1202358-01-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O(2)-(3,4,6-tri-O-acetyl-N-acetyl-β-D-glucosaminyl) 1-[N-(2-carboxymethyl)-N-methylamino]diazen-1-ium-1,2-diolate
• 英文别名: RN-2-32
• CAS: 1202358-01-7
• 化学式: C₁₇H₂₆N₄O₁₂
• 分子量: 478.413
• InChiKey: BLOMFRGDKUDXCQ-NHMWIVBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.53
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  205.43
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  O(2)-(3,4,6-tri-O-acetyl-N-acetyl-β-D-glucosaminyl) 1-[N-(2-carboxymethyl)-N-methylamino]diazen-1-ium-1,2-diolate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以91%的产率得到O(2)-(N-acetyl-β-D-glucosaminyl) 1-[N-(carboxymethyl)-N-methylamino]diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  Glycosylated PROLI/NO Derivatives as Nitric Oxide Prodrugs

  摘要：

  GlcNAc-PROLI/NO prodrugs that are activated by N-acetylglucosaminidase to release nitric oxide (NO) are described. A classical acid-amine coupling is used to bifunctionalize these PROLI/NO prodrugs, which on activation generate up to 4 mol of NO, a peptide residue, and an N-acetylglucosamine residue. Many of the prodrugs synthesized are efficient sources of intracellular NO.

  DOI：

  10.1021/ol902481s
• 作为产物：
  描述：

  O(2)-(3,4,6-tri-O-acetyl-N-acetyl-β-D-glucosaminyl) 1-[N-(2-hydroxyethyl)-N-methylamino]diazen-1-ium-1,2-diolate 在 sodium periodate 、 ruthenium(III) chloride trihydrate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以54%的产率得到O(2)-(3,4,6-tri-O-acetyl-N-acetyl-β-D-glucosaminyl) 1-[N-(2-carboxymethyl)-N-methylamino]diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  Glycosylated PROLI/NO Derivatives as Nitric Oxide Prodrugs

  摘要：

  GlcNAc-PROLI/NO prodrugs that are activated by N-acetylglucosaminidase to release nitric oxide (NO) are described. A classical acid-amine coupling is used to bifunctionalize these PROLI/NO prodrugs, which on activation generate up to 4 mol of NO, a peptide residue, and an N-acetylglucosamine residue. Many of the prodrugs synthesized are efficient sources of intracellular NO.

  DOI：

  10.1021/ol902481s

文献信息

• “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.