(2S,3R,4R,5R)-2-methyl-6-(phenylamino)tetrahydro-2H-pyran-3,4,5-triol | 27136-83-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5R)-2-methyl-6-(phenylamino)tetrahydro-2H-pyran-3,4,5-triol
• 英文别名: (2S,3R,4R,5R)-2-Methyl-6-phenylamino-tetrahydro-pyran-3,4,5-triol；(3R,4R,5R,6S)-2-anilino-6-methyloxane-3,4,5-triol
• CAS: 27136-83-0
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: BYMXFRHOUVRVTJ-HLZWTVFNSA-N

物化性质

• 熔点：
  128 °C
• 沸点：
  450.9±45.0 °C(Predicted)
• 密度：
  1.379±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  82
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R)-2-methyl-6-(phenylamino)tetrahydro-2H-pyran-3,4,5-triol 在 吡啶 、 aluminum (III) chloride 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 37.67h， 生成 3,3-bis(4-methoxyphenyl)-1-(β-L-rhamnopyranosyl)indolin-2-one
  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
• 作为产物：
  描述：

  L-rhamnopyranose 、 苯胺 以 乙醇 为溶剂， 反应 12.0h， 生成 (2S,3R,4R,5R)-2-methyl-6-(phenylamino)tetrahydro-2H-pyran-3,4,5-triol
  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 N,N′-diglycosylated isoindigos
  作者：Dennis Kleeblatt、Baraa Siyo、Martin Hein、Viktor O. Iaroshenko、Jamshed Iqbal、Alexander Villinger、Peter Langer

  DOI：10.1039/c2ob25866h

  日期：——

  The first N,N′-diglycosylated isoindigos were prepared by P(NEt2)3-mediated dimerization of acetyl protected N-glycosyl-5-alkylisatins. Subsequent deacetylation yielded the corresponding deprotected N,N′-diglycosylated isoindigos. Isatine-N-glycosides containing an unsubstituted or alkyl-substituted heterocyclic moiety and β-D-manno- and β-L-rhamno configured carbohydrate substituents were successfully transformed into the corresponding isoindigos. In contrast, isatins with β-D-gluco- or β-D-xylo configured substituents failed to give the desired products.

  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。
• 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。
• Synthesis of 3-arylamino-2-polyhydroxyalkyl-substituted indoles from unprotected saccharides and anilines
  作者：Jilai Wu、Likai Zhou、Song Xie、Chao Wei、Xiaoliu Li、Hua Chen

  DOI：10.1039/d3gc04440h

  日期：2024.2.19

  protocol has been developed for the synthesis of 3-arylamino-2-polyhydroxyalkyl-substituted indoles by using unprotected sugars and aromatic amines. The protocol is simple to carry out with high yields under mild reaction conditions, and has atom economy with a good substrate scope and functional group tolerance, providing a new alternative route for the synthesis of structurally diverse indole derivatives

  开发了一种简单高效的一锅合成方案，用于使用未保护的糖和芳香胺合成 3-芳基氨基-2-多羟基烷基取代的吲哚。该方案操作简单，反应条件温和，收率高，且具有原子经济性、良好的底物范围和官能团耐受性，为结构多样的吲哚衍生物的合成提供了新的替代路线。