(S)-3-(3-(hydroxymethyl)quinoxalin-2-yl)propane-1,2-diol | 32781-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (S)-3-(3-(hydroxymethyl)quinoxalin-2-yl)propane-1,2-diol
• 英文别名: 3-(3-hydroxymethyl-quinoxalin-2-yl)-propane-1,2-diol；(2S)-3-[3-(hydroxymethyl)quinoxalin-2-yl]propane-1,2-diol
• CAS: 32781-21-8
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: CZURFOKIGDYUPJ-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.5
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  邻苯二胺 生成 (S)-3-(3-(hydroxymethyl)quinoxalin-2-yl)propane-1,2-diol
  参考文献：
  名称：

  TAKAGI, MASANOSUKE;DAIDO, YOSHIYUKI;KURIYAMA, MASAO;MORITA, NAOFUMI, ANAL. SCI., 6,(1990) N, C. 529-534

  摘要：

  DOI：

文献信息

• Qualitative Profiling of Polyglucose Degradation Products in Peritoneal Dialysis Fluids
  作者：Sabrina Gensberger、Carina Knabner、Reiner Waibel、Jochen Huppert、Monika Pischetsrieder

  DOI：10.1021/acs.analchem.5b00665

  日期：2015.6.16

  Heat sterilization of peritoneal dialysis (PD) fluids leads to partial degradation of the osmotic agent to form reactive carbonyl structures, which significantly reduce the biocompatibility of PD fluids and impair long-term PD therapy. Hence, it is important to know the exact composition of the degradation products to improve biocompatibility of PD fluids. Our study conducted targeted screening for degradation products in polyglucose (icodextrin)-containing PD fluids (pGDPs) by applying o-phenylenediamine (OPD) to form stable derivatives, which were analyzed by ultrahigh-performance liquid chromatography with hyphenated diode array tandem mass spectrometry (UHPLC–DAD–MS/MS). For the first time, specific degradation products of polyglucose, namely, 4-deoxyglucosone (4-DG) and 3,4-dideoxypentosone (3,4-DDPS), could be identified in PD fluids. Further, a reaction product of 5-hydroxymethylfurfural (5-HMF) and OPD could be characterized to be (5-(1H-benzo[d]imidazol-2-yl)furan-2-yl)methanol. Additionally, 3-deoxyglucosone (3-DG) and 3-deoxygalactosone (3-DGal), both known to be present in glucose-based PD fluids, were also detected in polyglucose-containing fluids. Trapping a hitherto unknown degradation product with OPD yielded 1,4-bis(1H-benzo[d]imidazol-2-yl)-3,4-dihydroxybutan-1-one, which was present in heat- as well as filter-sterilized PD fluids.

  腹膜透析液的加热灭菌会导致渗透剂部分降解，形成活性羰基结构，从而大大降低腹膜透析液的生物相容性，影响腹膜透析的长期治疗。因此，了解降解产物的确切成分对改善透析液的生物相容性非常重要。我们的研究通过邻苯二胺（OPD）形成稳定的衍生物，有针对性地筛选了含聚葡萄糖（糊精）的PD液（pGDPS）中的降解产物，并采用超高效液相色谱-二极管阵列串联质谱法（UHPLC-DAD-MS/MS）对其进行了分析。研究人员首次在腹膜透析液中发现了聚葡萄糖的特定降解产物，即 4-脱氧葡糖酮（4-DG）和 3,4-二脱氧戊酮（3,4-DDPS）。此外，5-羟甲基糠醛（5-HMF）与 OPD 的反应产物可以确定为（5-(1H-苯并[d]咪唑-2-基)呋喃-2-基）甲醇。此外，在含多聚葡萄糖的液体中还检测到了 3-脱氧葡萄糖酮（3-DG）和 3-脱氧半乳糖酮（3-DGal），这两种物质已知都存在于以葡萄糖为基础的 PD 液体中。用 OPD 捕获一种迄今未知的降解产物，得到了 1,4-双（1H-苯并[d]咪唑-2-基）-3,4-二羟基丁-1-酮，它存在于加热和过滤灭菌的 PD 流体中。