D-木糖肟 | 36722-82-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: D-木糖肟
• 英文名称: D-xylose oxime
• 英文别名: D-Xylose-oxim；Xylose-oxim；Xylose-Oxime；(2R,3R,4S)-5-hydroxyiminopentane-1,2,3,4-tetrol
• CAS: 36722-82-4
• 化学式: C₅H₁₁NO₅
• 分子量: 165.146
• InChiKey: OKDOWAAKOUUJPX-VPENINKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  114
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D-木糖肟 在 platinum(IV) oxide 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、310.27 kPa 条件下， 生成 (2'S,3'R,4'R)-5,6-dihydro-6-(2',3',4',5'-tetrahydroxypentyl)-5,11-dioxo-11H-indeno[1,2-c]isoquinoline
  参考文献：
  名称：

  醇、二醇和碳水化合物取代的茚并异喹啉作为拓扑异构酶 I 抑制剂：研究涉及立体化学、氢键和生物活性的关系

  摘要：

  DNA松弛酶拓扑异构酶I（Top1）可以被杂环化合物如吲哚并咔唑和茚并异喹啉抑制。碳水化合物和含羟基的侧链对于吲哚并咔唑的生物活性是必不可少的。目前的研究调查了如何将相似的功能“转化”到茚并异喹啉系统，以及立体化学和氢键如何影响生物活性。本文描述了用短链醇、二醇和碳水化合物取代的茚并异喹啉的制备和测定。几种化合物（包括那些来自糖的化合物）显示出有效的 Top1 中毒和抗增殖活性。二醇取代的茚并异喹啉的 Top1 中毒活性取决于立体化学。虽然效果惊人，由于配体和 Top1-DNA 复合物之间类似的计算相互作用以及结合模式的模糊性，分子建模和对接研究没有表明活性差异的任何原因。还观察到碳水化合物衍生的茚并异喹啉具有立体化学依赖性。尽管在其他类别的 Top1 抑制剂中观察到了类似的趋势，但这种效应的确切性质尚未阐明。

  DOI：

  10.1021/jm101338z
• 作为产物：
  描述：

  D-木糖 在 盐酸羟胺 、 sodium methylate 作用下， 生成 D-木糖肟
  参考文献：
  名称：

  新型碳水化合物取代的茚并异喹啉拓扑异构酶 I 抑制剂的合成和生物学评价以及实验性抗癌剂 Indotecan (LMP400) 和 Indimitecan (LMP776) 的改进合成

  摘要：

  碳水化合物部分被策略性地从吲哚并咔唑拓扑异构酶 I (Top1) 抑制剂类转移到茚并异喹啉系统，以寻找结构新颖且有效的 Top1 抑制剂。报告了 20 种新型茚并异喹啉糖基化的线性和环状糖基的合成和生物学评价。2,3-二甲氧基-8,9-亚甲二氧基或3-硝基的芳环取代对抗增殖和Top1抑制活性有很强的影响。虽然碳水化合物侧链的长度与抗增殖活性明显相关，但立体化学和生物活性之间的关系不太清楚。12 种新茚并异喹啉表现出等于或优于喜树碱的 Top1 抑制活性。

  DOI：

  10.1021/jm401814y

文献信息

• Two New Cytotoxic Disulfated Holostane Glycosides from the Sea Cucumber<i>Pentacta quadrangularis</i>
  作者：Hua Han、Qiang-Zhi Xu、Yang-Hua Yi、Wei Gong、Bing-Hua Jiao

  DOI：10.1002/cbdv.200800324

  日期：2010.1

  Two new disulfated triterpene glycosides, pentactasides B and C (1 and 2, resp.), were isolated from the sea cucumber Pentacta quadrangularis collected from the South China Sea. Their structures were elucidated by extensive spectral analysis (2D-NMR and MS) and chemical methods. The compounds 1 and 2 possess the same tetrasaccharide moieties with two sulfated groups, but are different in the side chains

  从南海采集的海参四角蓬中分离出两个新的二硫化三萜糖苷，五倍体糖苷B和C（分别为1和2）。通过广泛的光谱分析（2D-NMR和MS）和化学方法阐明了它们的结构。化合物1和2具有相同的带有两个硫酸基团的四糖部分，但是三萜糖苷配基的侧链不同。五齿asB和C（分别为1和2）对不同的人类肿瘤细胞系表现出明显的细胞毒性（IC（50）0.09-2.30 microM）。
• Antioxidant activity of a water-soluble polysaccharide purified from Pteridium aquilinum
  作者：Wentao Xu、Fangfang Zhang、YunBo Luo、Liyan Ma、Xiaohong Kou、Kunlun Huang

  DOI：10.1016/j.carres.2008.10.021

  日期：2009.1

  A water-soluble crude polysaccharide, obtained from fern Pteridium aquilinum, was fractionated by DEAE-Sepharose Fast-Flow column chromatography, and purified by Sephacryl S-400 HR column chromatography. The average molecular weight (M-w) of the purified polysaccharide (PLP) is 458,000 Da. The monosaccharide components of PLP were characterized by gas chromatography (GC), and the majority of the monosaccharide components was glucose (relative mass 58.1%) with low levels of galactose, mannose, rhamnose, and arabinose (relative mass 18.7%, 6.8%, 10.2%, and 6.1%, respectively). The Fourier-transform infrared spectra (FTIR) of PLP revealed typical characteristics of polysaccharides. On the basis of the ferric-reducing antioxidant power assay (FRAP), DPPH radical-scavenging, the superoxide radical assay, and self-oxidation of 1,2,3-phentriol assay, the antioxidant activities of PLP were investigated. The purified polysaccharide was demonstrated to have strong reductive power (FRAP value: 827.6 mu mol/L), moderate scavenging activities against DPPH radicals (83.1%) and superoxide radicals (60.5%), and moderate inhibiting power for self-oxidation of 1,2,3-phentriol (52.4%). (C) 2008 Elsevier Ltd. All rights reserved.
• Five furostanol saponins from fruits of <i>Tribulus terrestris</i> and their cytotoxic activities
  作者：Jue Wang、Xuyu Zu、Yuyang Jiang

  DOI：10.1080/14786410902940990

  日期：2009.10.15

  Two new furostanol saponins, terrestroside A, 3-O--D-xylopyranosyl-(1 3)-[-D-xylopyranosyl(1 2)]--D-glucopyranosyl(1 4)-[-L-rhamnopyranosyl(1 2)]--D-galactopyranosy}-26-O--D-glucopyranosyl-L-5a-furost-20(22)-en-(25R)-3,26-diol (1) and terrestroside B, 3-O--D-xylopyran-osyl(1 3)-[-D-xylopyranosyl(1 2)]--D-glucopyranosyl(1 4)-[-L-rhamnopyranosyl-(1 2)]--D-galactopyranosy}-26-O--D-glucopyranosyl-5a-furostan-12-one-(25R)-22-methoxy-3,26-diol (2), together with three known compounds, chloromaloside E (3), terrestrinin B (4) and terrestroneoside A (5) were isolated from the dry fruits of Tribulus terrestris. Furthermore, the inhibitory effects of the compounds on tumour cells were evaluated, and compounds 1-5 showed potential anti-tumour activity.
• New Dammarane-Type Saponins from the Roots of<i>Panax notoginseng</i>
  作者：Li Qiu、Yang Jiao、Gui-Kun Huang、Ji-Zhao Xie、Jian-Hua Miao、Xin-Sheng Yao

  DOI：10.1002/hlca.201300155

  日期：2014.1

  AbstractThree new dammarane‐type triterpenoid saponins, 1–3, were isolated and identified as (20S)‐20‐O‐[β‐D‐xylopyranosyl‐(1→6)‐β‐D‐glucopyranosyl‐(1→6)‐β‐D‐glucopyranosyl]dammar‐24‐ene‐3β,6α,12β, 20‐tetrol (1), (20S)‐6‐O‐[(E)‐but‐2‐enoyl‐(1→6)‐β‐D‐glucopyranosyl]dammar‐24‐ene‐3β,6α,12β,20‐tetrol (2), and (20S)‐6‐O‐[β‐D‐xylopyranosyl‐(1→2)‐β‐D‐xylopyranosyl]dammar‐24‐ene‐3β,6α,12β,20‐tetrol (3) from the roots of Panax notoginseng (Burkill) F.H.Chen (Araliaceae). Their structures were elucidated on the basis of spectroscopic analyses, including 1D‐ and 2D‐NMR techniques and HR‐ESI‐MS, as well as by acidic hydrolysis.