N-(2,3,4-tri-O-acetyl-β-L-rhamnopyranosyl)isatine | 913057-19-9

• 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-(2,3,4-tri-O-acetyl-β-L-rhamnopyranosyl)isatine
• 英文别名: N-(2,3,4-tri-O-acetyl-β-L-rhamnopyranosyl)isatin；1-(2,3,4-tri-O-acetyl-β-L-rhamnopyranosyl)isatine；[(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-(2,3-dioxoindol-1-yl)-2-methyloxan-3-yl] acetate
• CAS: 913057-19-9
• 化学式: C₂₀H₂₁NO₉
• 分子量: 419.388
• InChiKey: CKFKRJTZJGZZSA-WZHKTHIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-(2,3,4-tri-O-acetyl-β-L-rhamnopyranosyl)isatine 、 对硝基苯乙酮 在 甲基磺酰氯 、 三乙胺 作用下， 以 乙醇 为溶剂， 以78%的产率得到(E)-3-(2-(4-nitrophenyl)-2-oxoethylidene)-1-(2,3,4-tri-O-acetyl-β-L-rhamnopyranosyl)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：

  苯胺 在 吡啶 、 aluminum (III) chloride 作用下， 以 乙醇 为溶剂， 反应 37.5h， 生成 N-(2,3,4-tri-O-acetyl-β-L-rhamnopyranosyl)isatine
  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 (Z)-1-glycosyl-3-(5-oxo-2-thioxoimidazolidin-4-ylidene)indolin-2-ones and (Z)-3-(2-glycosylsulfanyl-4-oxo-4,5-dihydro-thiazol-5-ylidene)indolin-2-ones
  作者：Friedrich Erben、Dirk Michalik、Holger Feist、Dennis Kleeblatt、Martin Hein、Abdul Matin、Jamshed Iqbal、Peter Langer

  DOI：10.1039/c3ra44362k

  日期：——

  The reaction of N-glycosylated isatines with imidazolones and thiazolones afforded N-glycosylated (Z)-1-glycosyl-3-(5-oxo-2-thioxoimidazolidin-4-ylidene)indolin-2-ones. The reaction of S-glycosylated thiazolones with isatines gave S-glycosylated (Z)-3-(2-glycosylsulfanyl-4-oxo-4,5-dihydro-thiazol-5-ylidene)indolin-2-ones. These molecules represent hybrids of pharmacologically important moieties, including carbohydrates, isatines, 2-thiohydantoin, pseudo-thiohydantoin and rhodanine. The products show a good and selective activity against lung carcinoma cell lines H157. The best activity was obtained for 3-(5-oxo-2-thioxoimidazolidin-4-ylidene)indolin-2-ones containing a glucose moiety.

  N-糖苷化的异靛蓝与咪唑酮和噻唑酮的反应生成N-糖苷化的(Z)-1-糖苷-3-(5-氧-2-硫喹唑啉-4-亚基)吲哚-2-酮。S-糖苷化的噻唑酮与异靛蓝反应生成S-糖苷化的(Z)-3-(2-糖苷硫酰基-4-氧-4,5-二氢噻唑-5-亚基)吲哚-2-酮。这些分子代表了药理学上重要的混合结构，包括碳水化合物、异靛蓝、2-硫脲、伪硫脲和罗丹宁。产品对肺癌细胞系H157表现出良好且选择性的活性。含有葡萄糖基团的3-(5-氧-2-硫喹唑啉-4-亚基)吲哚-2-酮具有最佳活性。
• 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。
• 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.