(3R,4R,5R)-N-(10-chloro-9-anthracenemethyl)-3,4-dihydroxy-5-hydroxymethylpiperidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (3R,4R,5R)-N-(10-chloro-9-anthracenemethyl)-3,4-dihydroxy-5-hydroxymethylpiperidine
• 英文别名: N-(10-chloro-9-anthracenemethyl)isofagomine；N-(10-chloro-9-anthracenemethyl) isofagomine；(3R,4R,5R)-1-[(10-chloroanthracen-9-yl)methyl]-5-(hydroxymethyl)piperidine-3,4-diol
• 化学式: C₂₁H₂₂ClNO₃
• 分子量: 371.864
• InChiKey: JAKCAYIMYYRPCK-WHIIXXIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  10-氯-9-蒽甲醛 、 (3R,4R,5R)-5-(羟基甲基)哌啶-3,4-二醇盐酸盐 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 28.17h， 生成 (3R,4R,5R)-N-(10-chloro-9-anthracenemethyl)-3,4-dihydroxy-5-hydroxymethylpiperidine
  参考文献：
  名称：

  β-葡糖苷酶†中异黄酮质子化的荧光研究

  摘要：

  制备N-（10-氯-9-蒽甲基）异黄酮5和N-（10-氯-9-蒽甲基）-1-脱氧野oji霉素6，并测定其对杏仁β-葡萄糖苷酶的抑制作用。发现异黄花碱衍生物5是有效的抑制剂，而1-脱氧野oji霉素衍生物6在所研究的浓度下没有显示出抑制作用。杏仁β-葡萄糖苷酶在不同pH值下的5的荧光光谱显示，抑制剂氮与酶结合时不会质子化。对pH抑制数据的分析证实了5作为胺结合到酶的非质子化二羧酸盐形式。这是与文献中异黄花胺和其他亚氨基糖所观察到的根本不同的结合方式。

  DOI：

  10.1039/c5ob00624d

文献信息

• Synthesis and Chemistry of Noeuromycin and Isofagomine Analogues
  作者：Huizhen Liu、Vinni H. Lillelund、Jens Andersch、Xifu Liang、Mikael Bols

  DOI：10.1081/car-200030070

  日期：2004.12.29

  Several N-substituted analogues of noeuromycin ((2RS,3S,4R,5R)-2,3,4-trihydroxy-5 -hydroxymethylpiperidine) and isofagomine ((3R,4R,5R)-3,4-dihydroxy-5-hydroxymethylpiperidine) were synthesised. The isofagomine analogues (3RS,4RS,5RS)N-(2-phosphonoethyl)-3,4-dihydroxy-5-hydroxymethyl-piperidine, (3SR,4SR,5RS)-N-(2-phosphonoethyl)-3,4-dihydroxy-5-hydroxy-methylpiperidine, and (3R,4R,5R)-N-(10-chloro-9-anthracenemethyl)-3,4-dihydroxy-5-hydroxy-methylpiperidine were synthesised by direct alkylation of the corresponding azasugar. N-Substituted noeuromycin derivatives could not be made in this straightforward manner, but were made by modification of a synthesis intermediate. By this method (2RS,3S,4R,5R)-N-(4-methoxyphenyl)-2,3,4-trihydroxy-5-hydroxymethylpiperidine and (2RS,3S,4R,5R)-N-nonyl-2,3,4-trihydroxy-5-hydroxymethylpiperidine were synthesised. The stability of noeuromycin was studied and was found to depend on stereochemistry and pH. The L-fuco isomer ((2RS, 3R,4R,5R)-2,3,4-trihydroxy-5-methylpiperidine) was observed to undergo a particularly facile Amadori rearrangement at neutral pH to the 3-ketopiperidine. A noeuromycin analogue, that could not undergo the Amadori rearrangement, was synthesised.
• A fluorescence study of isofagomine protonation in β-glucosidase
  作者：Emil Lindbäck、Bo Wegge Laursen、Jens Christian Navarro Poulsen、Kristine Kilså、Christian Marcus Pedersen、Mikael Bols

  DOI：10.1039/c5ob00624d

  日期：——

  N-(10-Chloro-9-anthracenemethyl)isofagomine 5 and N-(10-chloro-9-anthracenemethyl)-1-deoxynojirimycin 6 were prepared, and their inhibition of almond β-glucosidase was measured. The isofagomine derivative 5 was found to be a potent inhibitor, while the 1-deoxynojirimycin derivative 6 displayed no inhibition at the concentrations investigated. Fluorescence spectroscopy of 5 with almond β-glucosidase at different pH

  制备N-（10-氯-9-蒽甲基）异黄酮5和N-（10-氯-9-蒽甲基）-1-脱氧野oji霉素6，并测定其对杏仁β-葡萄糖苷酶的抑制作用。发现异黄花碱衍生物5是有效的抑制剂，而1-脱氧野oji霉素衍生物6在所研究的浓度下没有显示出抑制作用。杏仁β-葡萄糖苷酶在不同pH值下的5的荧光光谱显示，抑制剂氮与酶结合时不会质子化。对pH抑制数据的分析证实了5作为胺结合到酶的非质子化二羧酸盐形式。这是与文献中异黄花胺和其他亚氨基糖所观察到的根本不同的结合方式。