N-(p-tolyl)-β-D-mannopyranosylamine | 2871-14-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(p-tolyl)-β-D-mannopyranosylamine
• 英文别名: N-(4-Methylphenyl)-I(2)-D-mannopyranosylamine；(2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-(4-methylanilino)oxane-3,4,5-triol
• CAS: 2871-14-9
• 化学式: C₁₃H₁₉NO₅
• 分子量: 269.298
• InChiKey: SCLFETMCMRCGEO-NAWOPXAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  102
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(p-tolyl)-β-D-mannopyranosylamine 在 四氢呋喃 、 吡啶 、 甲醇 、 aluminum (III) chloride 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 11.25h， 生成 (Z)-1-(β-D-mannopyranosyl)-5-methyl-3-[3-oxobenzo[b]selenophen-2(3H)-ylidene]indolin-2-one
  参考文献：
  名称：

  Synthesis and antiproliferative activity of selenoindirubins and selenoindirubin-N-glycosides

  摘要：

  通过将异喹啉和异喹啉-N-糖苷与3-乙酰氧基苯并[b]硒苯反应，分别制备了硒代吲哚红及其N-糖苷。尽管之前没有报道硒代吲哚红-N-糖苷，但已有三种非糖苷化的硒代吲哚红被报道，然而没有给出数量、产率、规模、实验细节和光谱数据。此外，我们的研究无法再现以获得纯产品。本文包含了一种优化的硒代吲哚红合成程序及其完整的表征。无论是硒代吲哚红还是硒代吲哚红-N-糖苷，在肺癌细胞系中均显示出抗增殖活性。在黑色素瘤细胞中，抗增殖效应进一步伴随着与死亡配体TRAIL结合诱导的凋亡。

  DOI：

  10.1039/c3ob40603b
• 作为产物：
  描述：

  甘露糖 、 乙烷,三氯氟- 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 N-(p-tolyl)-β-D-mannopyranosylamine
  参考文献：
  名称：

  Molecular and crystal structures of N-aryl-β-d-glycopyranosylamines from mannose and galactose

  摘要：

  The molecular and crystal structures of 12 N-aryl-beta -D-glycopyranosylamines have been determined by X-ray crystallography. Six of these are mannose derivatives, the N-p-bromophenyl (1), N-p-tolyl (2), N-m-chlorophenyl (3), N-p-methoxyphenyl (4), N-o-chloroyhenyl (5), and N-o-tolyl (6) derivatives that are formed by reaction with the corresponding substituted anilines. The remaining six are galactose derivatives, the N-phenyl (7), N-p-chlorophenyl (8), N-p-bromophenyl (9), N-p-iodophenyl (10), N-p-nitrophenyl (11) and N-p-tolyl (12), derivatives prepared similarly. Compounds 1 3 assume the same packing arrangement. Compounds 4, 5, and 6 assume unique packing an arrangements, although that assumed by 4 is closely related to that assumed by 1-3. Compounds 7-11 assume the same packing arrangement; that assumed by 12 is closely related to that assumed by 7-11. That the same packing arrangements can be maintained in spite of substantial changes in the electronic and steric nature of the substituent on the aryl ring reflects the strength of the hydrogen bond network connecting the monosaccharide portions of the molecules in the solid state. A hydrogen bonding motif found in all six mannose structures is a mutual interaction between translationally related molecules involving 0-3-(HO)-O-...-5 and O-6-(HO)-O-...-4 hydrogen bonds. The recurrence of this motif throughout this group of mannosylamines suggests that it is an especially favorable interaction that might be expected to occur also in related macromolecular systems. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00117-3

文献信息

• Synthesis and characterization of N-tolyglycosylamines
  作者：R. I. Kublashvili、M. O. Labartkava、K. P. Giorgadze、D. Sh. Ugrekhelidze

  DOI：10.1007/s10600-008-9095-y

  日期：2008.7

  N-Tolylglycosylamines were synthesized from o-, m-, and p-toluidines and aldoses (D-glucose, D-galactose, D-mannose, L-rhamnose, D-xylose, and L-arabinose). The anomeric and isomeric compositions of the synthesized products were established using 13C NMR methods.

  N-甲苯基糖胺由邻-、间-和对-甲苯胺和醛糖（D-葡萄糖、D-半乳糖、D-甘露糖、L-鼠李糖、D-木糖和L-阿拉伯糖）合成。使用 13 C NMR 方法确定合成产物的异头和异构组成。
• Quantitative analysis of selective glycosylation of saccharides with aromatic amines
  作者：Toshihiko Hanai、Keiko Shimada、Nobuhiro Koyama、Yukio Nohara

  DOI：10.1016/j.carres.2020.108171

  日期：2020.12

  Glycosylation, a part of the Maillard reaction, occurs non-enzymatically in food and biological processes. The selectivity of N-glycosylation was analyzed based on the reactivity of monosaccharides with aromatic amines, including aromatic amino acids, and the degree of molecular interaction (MI) measured using liquid chromatography. Furthermore, the chemical structures of reaction products were determined

  糖基化是美拉德反应的一部分，在食品和生物过程中以非酶促方式发生。N-糖基化的选择性基于单糖与芳香胺（包括芳香氨基酸）的反应性以及使用液相色谱测量的分子相互作用 (MI) 程度进行分析。此外，使用 X 射线晶体学和/或 NMR 确定反应产物的化学结构。使用不同构象的优化能量值在计算机中估计可能的反应产物。使用模型相的计算机分析计算氨基和糖类的 MI 能量值。具有较大 MI 值的糖类容易产生稳定的 N-糖苷晶体。葡萄糖（一种能量糖）的反应速度很慢，它很容易产生 Amadori 化合物。芳香胺与糖类反应性的研究、单糖在色谱中氨基相保留的测量以及 N-糖苷的合成以确定其结构将为候选药物的修饰提供有关选择性糖基化的有用信息以提高它们的水溶性。
• Synthesis and antiproliferative activity of selenoindirubins and selenoindirubin-N-glycosides
  作者：Friedrich Erben、Dennis Kleeblatt、Marcel Sonneck、Martin Hein、Holger Feist、Thomas Fahrenwaldt、Christine Fischer、Abdul Matin、Jamshed Iqbal、Michael Plötz、Jürgen Eberle、Peter Langer

  DOI：10.1039/c3ob40603b

  日期：——

  Selenoindirubins and selenoindirubin-N-glycosides were prepared by the reaction of isatins and isatin-N-glycosides with 3-acetoxy-benzo[b]selenophene, respectively. While selenoindirubin-N-glycosides have not been reported before, three non-glycosylated selenoindirubins were previously reported, but without quantities, yields, scales, experimental details and spectroscopic data. In addition, the work could, in our hands, not be reproduced to prepare pure products. The present paper includes an optimized procedure for the synthesis of selenoindirubins and their complete characterization. Both selenoindirubins and selenoindirubin-N-glycosides showed antiproliferative activity in lung cancer cell lines. In melanoma cells, antiproliferative effects were further accompanied by induced apoptosis in combination with the death ligand TRAIL.

  通过将异喹啉和异喹啉-N-糖苷与3-乙酰氧基苯并[b]硒苯反应，分别制备了硒代吲哚红及其N-糖苷。尽管之前没有报道硒代吲哚红-N-糖苷，但已有三种非糖苷化的硒代吲哚红被报道，然而没有给出数量、产率、规模、实验细节和光谱数据。此外，我们的研究无法再现以获得纯产品。本文包含了一种优化的硒代吲哚红合成程序及其完整的表征。无论是硒代吲哚红还是硒代吲哚红-N-糖苷，在肺癌细胞系中均显示出抗增殖活性。在黑色素瘤细胞中，抗增殖效应进一步伴随着与死亡配体TRAIL结合诱导的凋亡。
• Molecular and crystal structures of N-aryl-β-d-glycopyranosylamines from mannose and galactose
  作者：Charles R Ojala、Joanne M Ostman、Summer E Hanson、William H Ojala

  DOI：10.1016/s0008-6215(01)00117-3

  日期：2001.6

  The molecular and crystal structures of 12 N-aryl-beta -D-glycopyranosylamines have been determined by X-ray crystallography. Six of these are mannose derivatives, the N-p-bromophenyl (1), N-p-tolyl (2), N-m-chlorophenyl (3), N-p-methoxyphenyl (4), N-o-chloroyhenyl (5), and N-o-tolyl (6) derivatives that are formed by reaction with the corresponding substituted anilines. The remaining six are galactose derivatives, the N-phenyl (7), N-p-chlorophenyl (8), N-p-bromophenyl (9), N-p-iodophenyl (10), N-p-nitrophenyl (11) and N-p-tolyl (12), derivatives prepared similarly. Compounds 1 3 assume the same packing arrangement. Compounds 4, 5, and 6 assume unique packing an arrangements, although that assumed by 4 is closely related to that assumed by 1-3. Compounds 7-11 assume the same packing arrangement; that assumed by 12 is closely related to that assumed by 7-11. That the same packing arrangements can be maintained in spite of substantial changes in the electronic and steric nature of the substituent on the aryl ring reflects the strength of the hydrogen bond network connecting the monosaccharide portions of the molecules in the solid state. A hydrogen bonding motif found in all six mannose structures is a mutual interaction between translationally related molecules involving 0-3-(HO)-O-...-5 and O-6-(HO)-O-...-4 hydrogen bonds. The recurrence of this motif throughout this group of mannosylamines suggests that it is an especially favorable interaction that might be expected to occur also in related macromolecular systems. (C) 2001 Elsevier Science Ltd. All rights reserved.