1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indoline-2,3-dione | 53382-96-0

• 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: 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indoline-2,3-dione
• 英文别名: N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)isatine；1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)isatin；1-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyl)-isatin；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(2,3-dioxoindol-1-yl)oxan-2-yl]methyl acetate
• CAS: 53382-96-0
• 化学式: C₂₂H₂₃NO₁₁
• 分子量: 477.425
• InChiKey: RKPWDQYPWYNDFD-QKYBYQKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indoline-2,3-dione 、 对硝基苯乙酮 在 甲基磺酰氯 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 以71%的产率得到(E)-3-(2-(4-nitrophenyl)-2-oxoethylidene)-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indolin-2-one
  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
• 作为产物：
  描述：

  1-(β-D-glucopyranosyl)indoline 在 吡啶 、 chromium(VI) oxide 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 38.0h， 生成 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indoline-2,3-dione
  参考文献：
  名称：

  Synthesis and antiproliferative activities of diversely substituted glycosyl-isoindigo derivatives

  摘要：

  in the course of structure-activity relationship studies, diversely substituted 1-(beta-(D)-glucopyranosyl)-isoindigo derivatives were prepared from commercially available indolines. Their antiproliferative activities were evaluated toward a panel of human solid cancer cell lines (PC 3, DLD-1, MCF-7, M4Beu, A549, PA 1), a murine cell line (L929) and a human fibroblast primary culture to get an insight into the substitution pattern required for the best biological potencies. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.10.004

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 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。
• Synthesis of 6H-indolo[2,3-b]quinoxaline-N-glycosides and their cytotoxic activity against human ceratinocytes (HaCaT)
  作者：Katrin Marie Driller、Stefanie Libnow、Martin Hein、Manuela Harms、Kristian Wende、Michael Lalk、Dirk Michalik、Helmut Reinke、Peter Langer

  DOI：10.1039/b812308j

  日期：——

  N-Glycosides of 6H-indolo[2,3-b]quinoxalines were prepared and structurally characterized. The synthesis relies on the cyclocondensation of isatine-N-glycosides with 1,2-diaminobenzenes. Some products exhibit weak cytotoxic activity against human ceratinocytes (HaCaT).

  制备了 6H-吲哚并[2,3-b]喹喔啉的 N-糖苷并进行了结构表征。该合成依赖于靛红-N-糖苷与 1,2-二氨基苯的环缩合。一些产品对人角质形成细胞 (HaCaT) 表现出弱的细胞毒活性。
• Synthesis and antiproliferative activities of isoindigo and azaisoindigo derivatives
  作者：Fadoua Bouchikhi、Fabrice Anizon、Pascale Moreau

  DOI：10.1016/j.ejmech.2007.05.012

  日期：2008.4

  In the course of structure-activity relationship studies, diversely substituted 1-(beta-D-acetylatedglucopyranosyl)isoindigoderivatives were prepared from indolines. New 7'-azaisoindigo analogues were also synthesized by coupling a glycosylated isatine and a 7-azaindolin-2-one derivative. Compounds containing a 7'-azaisoindigo framework have never been described before. To get an insight into the substitution pattern required for the best biological potencies, their antiproliferative activities were evaluated toward a human buccal carcinoma cell line (KB) and two human myeloid leukaemia cell lines (K562, HL60). (c) 2007 Elsevier Masson SAS. All rights reserved.