(5R,6S)-5-acetoxy-6-methyltetrahydro-2-pyranyl acetate | 871567-63-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (5R,6S)-5-acetoxy-6-methyltetrahydro-2-pyranyl acetate
• CAS: 871567-63-4
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: AZPGXVLAQVGXDQ-WNHALPOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (5R,6S)-5-acetoxy-6-methyltetrahydro-2-pyranyl acetate 在 palladium on activated charcoal indium(III) chloride 、 二氯二茂铪 、 4 A molecular sieve 、 氢气 、 silver perchlorate 、 sodium hydride 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 65.0h， 生成 7-fluoro-2-((2S,5R,6S)-5-((2S,5S,6R)-5-benzyloxy-6-methyl-tetrahydropyranyloxy)-6-methyltetrahydro-2-pyranyl)-1,5,8-trimethoxynaphthalene
  参考文献：
  名称：

  迭代苯并呋喃环加成反应：对ent-Sch 47554和ent-Sch 47555的总合成的研究。

  摘要：

  [反应：见正文]由1,4-二氟-2,5-二甲氧基苯与Diels-Alder环加成呋喃的锂化和苯炔形成而制备的7-氟-5,8-二甲氧基-1-萘酚依次为C在Suzuki条件下被糖基化，并使用二-O-乙酰基-L-鼠李糖基被O-糖基化以提供相应的β-萘基C，O-二糖。进一步锂化，形成苯并形成并与呋喃进行环加成反应，生成氧杂桥联的1,4-二氢蒽基C，O-二糖，这是与Sch 47555的总合成有关的模型化合物。

  DOI：

  10.1021/ol061007+
• 作为产物：
  描述：

  (E)-4-O-acetyl-2,3,6-trideoxy-aldehydo-L-erythro-hex-2-enose 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 (5R,6S)-5-acetoxy-6-methyltetrahydro-2-pyranyl acetate
  参考文献：
  名称：

  迭代苯并呋喃环加成反应：对ent-Sch 47554和ent-Sch 47555的总合成的研究。

  摘要：

  [反应：见正文]由1,4-二氟-2,5-二甲氧基苯与Diels-Alder环加成呋喃的锂化和苯炔形成而制备的7-氟-5,8-二甲氧基-1-萘酚依次为C在Suzuki条件下被糖基化，并使用二-O-乙酰基-L-鼠李糖基被O-糖基化以提供相应的β-萘基C，O-二糖。进一步锂化，形成苯并形成并与呋喃进行环加成反应，生成氧杂桥联的1,4-二氢蒽基C，O-二糖，这是与Sch 47555的总合成有关的模型化合物。

  DOI：

  10.1021/ol061007+

文献信息

• Syntheses and biological activities of daunorubicin analogs with uncommon sugars
  作者：Lizhi Zhu、Xianhua Cao、Wenlan Chen、Guisheng Zhang、Duxin Sun、Peng George Wang

  DOI：10.1016/j.bmc.2005.06.053

  日期：2005.12

  It suggests that the sugar structure in daunorubicin plays a critical role in determining its anticancer activity. In the compounds with various sugars, the 4'-OH of the sugar is an important determinant for their activity, while the axial-3'-substituent in the sugar interferes with the binding of daunorubicins to DNA. Therefore, 2,6-dideoxy sugars are a better choice for generating biologically active

  为了研究糖结构对蒽环类抗癌细胞活性的影响，合成了六种含有不同罕见糖的柔红霉素类似物。通过MTS分析测试了它们对结肠癌细胞的细胞毒性。结果显示，不具有糖部分的糖苷配基对癌细胞的活性比具有各种不常见糖的柔红霉素衍生物低70-100倍。这表明柔红霉素中的糖结构在确定其抗癌活性中起关键作用。在具有各种糖的化合物中，糖的4'-OH是其活性的重要决定因素，而糖中的轴3'-取代基会干扰柔红霉素与DNA的结合。因此，2
• Syntheses and Biological Activities of 3‘-Azido Disaccharide Analogues of Daunorubicin against Drug-Resistant Leukemia
  作者：Guisheng Zhang、Lanyan Fang、Lizhi Zhu、Yanqiang Zhong、Peng George Wang、Duxin Sun

  DOI：10.1021/jm050916m

  日期：2006.3.1

  Anthracyclines, such as daunorubicin (DNR) and doxorubicin (Dox), are widely used for cancer therapy but are limited by drug resistance and cardiotoxicity. To overcome drug resistance, we synthesized a novel class of disaccharide analogues of DNR against drug-resistant leukemia. In these disaccharide analogues (1-6) the first (inner) sugar in the carbohydrate chain is a 3-azido-2,3,6-trideoxy-L-lyxo-alpha-hexopyranose; the second (outer) sugars that are linked via alpha(1 -> 4) to the first sugar are a series of uncommon sugars. Their cytotoxicities were examined in drug-sensitive leukemia cells K562 and doxorubicin-resistant K562/Dox cells by MTS assay. In drug-sensitive cells, compounds 1-6 were found to be active against leukemia K562 cells with IC50 in the nanomolar range (200-1100 nM), while compounds 2-5 with 2,6-dideoxy sugars showed better activity than compounds 1 and 6 with 2,3,6-trideoxy sugars. In doxorubicin-resistant K562/Dox cells, compounds 1, 3, and 5 exhibited much better activities (with IC50 between 0.29 and 2.0 mu M) than DNR (with IC50 > 5 mu M). Compound 3 emerged as the most active compound, showing at least 17-fold higher activity against drug-resistant cells than parent compound DNR. The IC50 values of compound 3 in both drug-sensitive and drug-resistant cells are identical, which indicates that compound 3 completely overcomes drug resistance. Structure-activity relationship (SAR) studies showed that the substitution and orientation of the 3-OH group in the second sugar significantly influence its activity against drug-resistant leukemia. These results suggest that sugar modifications of anthracyclines change their activity and overcome drug resistance.
• WO2006/124720
  申请人：——

  公开号：——

  公开（公告）日：——