N-phenyl-2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranosylamin | 34246-08-7

• 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: N-phenyl-2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranosylamin
• 英文别名: N-(2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranosyl)aniline；2,3,4,6-tetra-O-acetyl-1-deoxy-1-(phenylamino)-d-glucopyranose；[(2R,3R,4S,5R)-3,4,5-triacetyloxy-6-anilinooxan-2-yl]methyl acetate
• CAS: 34246-08-7
• 化学式: C₂₀H₂₅NO₉
• 分子量: 423.42
• InChiKey: BUWRELKHEYDARI-QUIYGKKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-phenyl-2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranosylamin 在 三氯化铝 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 5.5h， 生成 (3Z)-3-(3-oxo-1H-indol-2-ylidene)-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]indol-2-one
  参考文献：
  名称：

  First synthesis of indirubin N-glycosides (red sugars)

  摘要：

  The first indirubin N-glycosides were prepared by reaction,of isatine N-glycosides with indoxyl acetate under basic conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.024
• 作为产物：
  描述：

  苯胺 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 36.0h， 生成 N-phenyl-2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranosylamin
  参考文献：
  名称：

  Synthesis and bioactivity of N-glycosylated 3-(2-oxo-2-arylethylidene)-indolin-2-ones

  摘要：

  通过将异喹啉-N-糖苷与取代的乙酰苯甲酮反应制备了N-糖基-3-烷基亚甲基氧吲哚和N-糖基化的3-(2-氧代-2-芳基乙基亚甲基)吲哚-2-酮。

  DOI：

  10.1039/c4ra14301a

文献信息

• Synthesis and antiproliferative activity of N-glycosyl-3,3-diaryloxindoles
  作者：Dennis Kleeblatt、Christoph A. Cordes、Philipp Lebrenz、Martin Hein、Holger Feist、Abdul Matin、Rabia Raza、Jamshed Iqbal、Omar Munshi、Qamar Rahman、Alexander Villinger、Peter Langer

  DOI：10.1039/c4ra02627f

  日期：——

  N-Glycosylated 3,3-diaryloxindoles were prepared by Lewis acid catalyzed reaction of acetylated N-glycosylisatins with various benzene derivatives and subsequent deprotection. Some of the products showed antiproliferative activity against malignant cutaneous melanoma cells HT-144 (ATCC HTB-63) and lung carcinoma (H157) cell lines (ATCC CRL-5802).

  N-糖基化的3,3-二芳基氧化吲哚是通过乙酰化N-糖基异噻啉与各种苯衍生物在路易斯酸催化下反应，随后脱保护制备而成。部分产物对恶性皮肤黑色素瘤细胞HT-144(ATCC HTB-63)和肺癌细胞系H157(ATCC CRL-5802)表现出抗增殖活性。
• Synthesis of Thia-Analogous Indirubin<i>N</i>-Glycosides and their Influence on Melanoma Cell Growth and Apoptosis
  作者：Manfred Kunz、Katrin M. Driller、Martin Hein、Stephanie Libnow、Ina Hohensee、Robert Ramer、Burkhard Hinz、Anja Berger、Jürgen Eberle、Peter Langer

  DOI：10.1002/cmdc.200900506

  日期：2010.4.6

  by condensation of N‐glycosylisatines with thiaindane‐3‐one and subsequent deprotection, were tested for their activity against malignant melanoma cells. These indirubin‐N‐glycoside thia‐analogues are active against melanoma cells, inducing growth arrest, apoptosis and inhibition of intracellular signal transduction.

  遏制癌症！测试了通过将N-糖基尿素与Thiaindane-3-one缩合并随后脱保护而制备的靛玉红N-糖苷的硫代类似物对恶性黑色素瘤细胞的活性。这些靛玉红N-糖苷硫代类似物对黑色素瘤细胞有活性，诱导生长停滞，凋亡和抑制细胞内信号转导。
• Esswein, Angelika; Schmidt, Richard R., Liebigs Annalen der Chemie, 1988, p. 675 - 678
  作者：Esswein, Angelika、Schmidt, Richard R.

  DOI：——

  日期：——
• Synthesis of indirubin-N′-glycosides and their anti-proliferative activity against human cancer cell lines
  作者：Stefanie Libnow、Karen Methling、Martin Hein、Dirk Michalik、Manuela Harms、Kristian Wende、Anke Flemming、Martin Köckerling、Helmut Reinke、Patrick J. Bednarski、Michael Lalk、Peter Langer

  DOI：10.1016/j.bmc.2008.04.003

  日期：2008.5

  The first indirubin-N'-glycosides were prepared based on reactions of isatin-N'-glycosides with indoxyls. The products show a significant anti-proliferative activity against various human cancer cell lines. Good results were observed for an indirubin-N'- mannoside which was shown to have medium to high anti-proliferative activity against all investigated cell lines. The highest activities and selectivities against the MCF-7 breast cancer cell line were observed for indirubin-N'-rhamnosides. (C) 2008 Elsevier Ltd. All rights reserved.