Acetic acid (3R,4R,5S,6S)-4,5-diacetoxy-6-methyl-2-phenylamino-tetrahydro-pyran-3-yl ester | 913057-17-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (3R,4R,5S,6S)-4,5-diacetoxy-6-methyl-2-phenylamino-tetrahydro-pyran-3-yl ester
• CAS: 913057-17-7
• 化学式: C₁₈H₂₃NO₇
• 分子量: 365.383
• InChiKey: UMWQLRRZUVXRGX-HATYWHASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  100.16
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (3R,4R,5S,6S)-4,5-diacetoxy-6-methyl-2-phenylamino-tetrahydro-pyran-3-yl ester 在 aluminum (III) chloride 、 六乙基亚磷酸胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 1,1′-di(2,3,4-tri-O-acetyl-β-L-rhamnopyranosyl)isoindigo
  参考文献：
  名称：

  Synthesis of N,N′-diglycosylated isoindigos

  摘要：

  第一种N,N′-二糖苷化的异靛蓝通过P(NEt2)3介导的乙酰保护N-糖苷-5-烷基异靛的二聚化制备而成。随后的去乙酰化反应生成了相应的去保护的N,N′-二糖苷化异靛蓝。含有未取代或烷基取代的杂环基团和β-D-甘露糖和β-L-鼠李糖构型的糖类取代基的异靛酮-N-糖苷成功转化为相应的异靛蓝。相比之下，具有β-D-葡萄糖或β-D-木糖构型取代基的异靛酮未能得到预期产物。

  DOI：

  10.1039/c2ob25866h
• 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 Acetic acid (3R,4R,5S,6S)-4,5-diacetoxy-6-methyl-2-phenylamino-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis and antiproliferative activity of N-glycosyl-3,3-diaryloxindoles

  摘要：

  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。

  DOI：

  10.1039/c4ra02627f

文献信息

• 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。
• Synthesis and bioactivity of N-glycosylated 3-(2-oxo-2-arylethylidene)-indolin-2-ones
  作者：Dennis Kleeblatt、Martin Becker、Michael Plötz、Madeleine Schönherr、Alexander Villinger、Martin Hein、Jürgen Eberle、Manfred Kunz、Qamar Rahman、Peter Langer

  DOI：10.1039/c4ra14301a

  日期：——

  N-Glycosyl-3-alkylideneoxindoles, N-glycosylated 3-(2-oxo-2-arylethylidene)indolin-2-ones, were prepared by reaction of isatin-N-glycosides with substituted acetophenones.

  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。
• 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。
• First synthesis of indirubin N-glycosides (red sugars)
  作者：Stefanie Libnow、Martin Hein、Dirk Michalik、Peter Langer

  DOI：10.1016/j.tetlet.2006.07.024

  日期：2006.9

  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.
• 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.